Perpetual Failure: The Reason Why I Continue To Save So Much

One of the reasons why I continue to save so much is that I'm a perpetual failure. I've made so many mistakes in my life that I need a financial buffer to constantly bail me out. A landmine-filled upbringing has also embedded in me the necessity to save.

If it's not an investment mistake, it's a career mistake. If it's not a career mistake, it's a lifestyle mistake. Now that I'm in my mid-40s, random health issues are slowly popping up. Gotta save!

Over time, the self-inflicted mistakes have declined in frequency. However, I know they will still keep coming now that I'm a father to two young children. Parenting is tough.

Even after negotiating a severance and leaving Corporate America in 2012, I still save most of my passive income and online income each month.

It feels like eventually, this dreamworld my wife and I have been living in will come crashing down on us. Need to save.

Always Question The Sustainability Of Your Good Luck

Whenever things are going well for an extended period of time, I begin to worry. Where did all the bad luck go? Something must be wrong

I'm not sure why life has turned out OK for me when there are plenty of smarter, more deserving people out there who still struggle. Maybe the exhausted fumes of good karma from a past life?

The longer you live, the longer you realize nothing good lasts forever. Something bad is bound to happen – a break of an ankle, a bad investment, a friend who disappoints, a boss who lies, a disease that debilitates, a black swan global event, etc.

This is part of the scarcity mindset at work that's hard to break. But this is also adopting a “tragic optimism” mindset, which actually helps people bounce back from bad events and feel happier.

Sudden Bad Luck With The Pandemic

The pandemic began just months after our daughter was born. Then, preschools shut down. Then, stocks crashed in March 2020. If there's one thing 2020 taught us, it's that anything and everything can happen!

Instead of waiting for disappointment, I sometimes like to seek out failure to knock some reality back into my life. Getting rejected is also a great way of keeping the ego under control.

Most of our wealth is mainly due to luck. To start thinking our wealth is mostly due to hard work and skill will likely set you up for disappointment in the future. Don't be fooled into thinking you're a wunderkind.

Why We Rationally Save So Much: Unknown Failure

Ever since I got my first paycheck in 1999, I’ve saved over 50% of my after tax income. I didn't care about living in a studio with another fella the first two years out of college because I needed to save. I wanted to achieve financial independence even on a modest income.

Over the years, people have asked me why be so frugal? Work to live, especially while young, right?

They asked whether I thought extreme savings was learned, or part of one’s DNA. I always responded that extreme savings is due to circumstance.

When you know you won’t be able to last in a brutal work environment for an extended period of time, you save. When you know tax cuts are temporary, you save to pay for the inevitable hike. If you believe it is your duty to not only take care of your children, but also your parents, you save and save some more.

When life is good, the tendency is to not save as much.

There's no need to prepare for the unknown. The good life is the reason why the savings rate is so low in America. We've got a stable government, fresh air, the internet, cheap electronics, an abundance of food and water, Social Security, manageable inflation, and accessible education for all.

Why bother saving more than you have to? Move to India or China, and the national savings rate zooms over 20% because life is much harder!

And then we see what happens when hard times do come. Out of nowhere, a pandemic hit and the U.S. personal savings rate reached an all-time high in 2020. Life got tough, so Americans decided to save more.

U.S. personal savings rate

We rationally save more to improve our chances of survival. The harder your life, the more you will try to save. The easier your life, the opposite will likely be true. It's time to look deep inside to figure out why your saving rate is at the rate that it is.

Now, in 2023, the personal saving rate in America is back down to about 3%. That's no good as consumers are lulled into complacency when a recession could hit the economy hard.

Meet The King Of Perpetual Failure

Here are all my failures since college. There are many more than listed in this post.

Failure #1: No Job Offer After College

When I graduated from public school at William & Mary, I had no official job offer. How embarrassing it was to have nobody believe in me after four years of studying and working at internships.

I told the Economics department I got an offer at Goldman Sachs just so I could have an employer's name next to my name in the graduation booklet. This was even though I was still in the middle of interviews. It wasn't until a month after graduation that GS finally welcomed me in. I must have been the last person to get an offer in my Equities class.

I thought the job offer was a fluke because it came in e-mail form while I was visiting my girlfriend in Tokyo. So I decided to save like crazy just in case they made a mistake.

After all, William & Mary wasn't a target school. I didn't have rich parents as private wealth clients to hook me up. And I got into trouble with the law while I was in high school. GS never did retract the offer. But I certainly wasn't a prized analyst like others.

Related: This Financial Move I Made Is Something Everyone Can Do

Failure #2: On The Chopping Block Two Years Later

Because the dotcom bubble burst in 2000, I knew my job was at risk. I overheard a conversation my supervisor had with another Managing Director about how I probably was going to be let go in the next round of layoffs. As a result, I frantically interviewed with a competing firm in San Francisco and left the firm before they could let me go!

At my new shop, I began saving even more than 50% of my paycheck partly because San Francisco was cheaper than Manhattan. But the main reason for saving more was because I felt like I had escaped a firing squad back East.

Two years after I left, only about 25% of my analyst class remained. Further, surely my new firm would soon discover I wasn’t any good and retrench me during the next Last In First Out layoff round. After all, I was just a 24-year-old kid who wasn’t bringing in any business, yet.

What I was experiencing in my early 20s was “The Impostor Syndrome.” I was making decent money, but felt I really didn't know what I was talking about. Why the hell would/should older, more experienced clients listen to me about investing in international equities?

One client called me “green as a gourd” when I traveled with him to India. Another client asked if my senior colleague could cover her instead. Confidence shaken. So, I saved and saved some more.

Failure #3: Could Not Get Promoted

When I failed to make Managing Director in 2012 after four years as a Director and three years as a VP I decided to create my own luck by leaving. I didn't want to navigate another 1-3 years of corporate bureaucracy partially because I knew I probably would never get promoted.

My overall income immediately took a 80% dive, and once again, despite having negotiated a severance package, I found myself worried about my financial future. I started saving my passive income and severance income like mad because I was so uncertain of the future.

Failure #4: My Severance eBook Didn't Take Off

One of my ideas after leaving Corporate America was to write a bestselling book. I dreamed my book would help millions of Americans who disliked their jobs to negotiate a severance and find freedom to do what they really wanted.

I entitled the book, “How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye.” Given there weren't any books out there about the topic, and there still aren't, I thought my book would be a runaway success!

After all, who doesn't want to walk away from a job with more financial security during a time of great uncertainty? 11 years later and multiple revisions to incorporate the best severance negotiation strategies, I'm still only selling about 40 books a month. But that's about $4,500 a month, so not too shabby.

How To Engineer Your Layoff Ebook New Edition
Get The eBook Now button

Failure #5: Online Advertisement Network

In 2013, I attempted to create a personal finance advertisement network. I brought on a partner and we gave it a go for six months. Her goal was to bring in the advertisers. My goal was to bring on the bloggers. She ended up finding full-time employment and I realized brokering transactions was a supreme PITA! The project was shut down a couple months later.

Failure #6: Considered Going Back To Work Full-Time

In 2015, I started having doubts about whether being unemployed longer than three years in my 30s was a good idea. I had failed at creating an advertising network business. Further, I didn't think having my existing retirement income and online income from Financial Samurai was good enough to support a family.

As a result, I decided to look for full-time work again. If Financial Samurai was a runaway success, I wouldn’t have needed to entertain going back to Corporate America. Working for yourself is pretty amazing despite the loneliness of being a solopreneur. But my site's growth rate slowed.

Let's look at some more failures from 2015 alone, when I originally first wrote this post. At the time, I was really wondering whether I should go back to work because my wife had just negotiated her own severance. That was an interesting moment in time as another safety net finally got removed.

Now I've stated I'm sadly giving up on early retirement by 2024. This is not so much failure, but a desire to be more productive now that both my children will attend school full time.

Lots More Failures In Just One Year

Perpetual failure is the reason why I save

* Didn’t get the job I spent 10 hours interviewing for at a fintech consumer lending company. They decided the scope of the work was too narrow for me, and they didn't have the capacity or desire to pay more. That company turned out to be Upstart, which ended up going public and increasing in value by at least 15X!

* Interviewed at a buddy's firm for an hour, and the person didn't even bother to e-mail back or follow up with any closure after I thanked him for meeting up. I have no plans to inquire further as I'd rather not mix friendship w/ business. Funny enough, in 2021, I decided to invested money is his new venture capital fund. Strange how we forget bad things so easily.

* I lost the remaining three years of stock options promised to me as an advisor to a company after our agreement was terminated in November. At least I get to vest 1.5 years worth of options that should be in the money. Holy crap, the company was sold in 2020, and I would have made at least $150,000 more if I had been able to keep my other options.

* Didn't get into a startup fellowship program after spending ~3.5 hours on the application. Yes, there were 6,500 applicants for 22 spots, but still, there was a chance!

And The Disappointment Continued…

* An advertising client decided to suddenly terminate our business arrangement, despite having a contract in place. While another just shutdown and decided not to pay for the work I did for them. But they paid their employees for the month. How is that fair?

* Got rejected from a local incubator program after spending five hours filling out the application and another couple hours going down to Redwood City and giving the pitch. This one particularly hurt because I thought I sold my value proposition well.

But now that I see who got in, it's clear that incubators no longer incubate ideas. Instead, they incubate companies that have already been around for years and have received funding. For example, one company that got in already raised over $1.2 million and has a viable product for years already.

More Setbacks

In 2017, I damaged my health by working too much. 2017 was the time to finally relax because my son was born in April. However, I was overly worried about being able to provide for my family as someone who still didn’t have a day job.

My wife didn’t have a day job either. Therefore, I decided to work more at the expensive of my happiness, sleep, and relationship with my wife. This was truly a failure of not being able to let go of the endless chase for money.

Between 2017 – 2019, we applied to seven preschools. We got rejected by six of them. Luckily, we were accepted by our neighborhood preschool out of chance since we kept bumping into one of the teachers at the science museum. We did end up getting off the waitlist for two more schools. But by then, it was too late.

Getting rejected by so many preschools is likely a harbinger for plenty more school rejections in the future. These rejections may eventually translate into my children not being able to get a secure job. Merit-based rewards is declining. Therefore, I will save and invest for them.

Bought A House A Year Before The Pandemic!

In early 2019, I bought another house because I thought I got a great deal. However, then the pandemic hit just 10 months later, leaving me wondering whether my home purchase was a wise one.

For several months, I questioned whether this was me buying near the top of the market again, like I did in 2007. Thankfully, the real estate market held up well.

Then I learned from a reader in 2H2020, that he felt like I left $655,000 on the table. I sold my rental property in 2017 via a pocket listing rather than though the MLS.

Today, I'm sure the house I sold has appreciated by at least $500,000. However, at least I reinvested the proceeds and the money has grown.

Looking Ahead Past Failure

2021 and 2022 were exhausting years as I kept up my regular writing cadence and simultaneously finished writing a 300-page book, Buy This, Not That: How To Spend Your Way To Wealth And Freedom. The book is now out and it became a #1 Amazon Bestseller and a Wall Street Journal Bestseller!

It's nice to know I'm not a failure in everything. Buy This, Not That is going to help a lot of people get straight with their money and make more optimal decisions.

Buy This Not That Book Reviews

Now that my book is out, I want to re-retire in 2023 and take it easy again. But that feels like a letdown when I have two young kids and a wife depending on me to survive. But I'm so exhausted from all the hustle that I just need a break.

I admire parents who can keep on working hard at work while trying to raise children. Please teach me how! The endurance needed to do both is Herculean.

Wanting To Let Go Of The Grind

Today, my continued main disappointment is not being able to completely let go of the desire to make more money. I'm trying to understand why I'm not more satisfied with what I have. That said, I have entered the decumulation phase of my life and have begun to spend more freely and give more to charities.

I've crunched the numbers over and over again. We should have enough, especially after the surprise surge in investments since 2020. Yet, I'm still grinding away more than I like. It is a befuddling problem that needs to be resolved. I think the source of all our stress is giving a damn!

Failure Makes Not Trying A Tempting Path

Rejection hurts. Failure is embarrassing.

It's often easier to not try so we can avoid this pain. If I think about the rejections too much, it will make me mad. I know I can run circles around my competition. I just needed a chance. But feeling the pain of failure and rejection is exactly what I want so I never take anything for granted.

Look, I know it's not all bad. I've got my health and my family who are always supportive. The Financial Samurai community is still rocking after more than 12 years. However, it’s the unknown I’m trying to prepare for.

Having money is all about having the freedom to choose. A large cash cushion is what will help us get through the inevitable dip. Even better is having F You Money so you can do what you want!

Seek Rejection To Get Yourself Motivated

The next time you start feeling a little too good about yourself, perhaps seek out rejection from a person or an organization. Better yet, spend hours of your time trying to create something of your own only to realize nobody gives a damn.

When I hit my 10-year mark, there weren't any fireworks but I kept on going: The Secret To Your Success: 10 Years Of Unwavering Commitment

You'll feel bad at first when you get hit with rejection. But after a couple days, your motivation meter to save and work harder will explode through the roof! Put your hopes and dreams in you.

Life continues to be uncertain today. Therefore, our saving rate will continue to stay at around 50%, as it has been for 20 years. But as soon as we’re fully back to normal, my saving rate will decline.

For those of you who are feeling down on your luck, things will get better if you keep on going. Just continue to always build your savings buffer. It is the perfect counterweight for a mysterious future.

How much money do you need to feel financially free? (What is your FU money amount?)

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What Should My Net Worth Or Savings Be By Income?

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For more nuanced personal finance content, join 65,000+ others and sign up for my free weekly newsletter. In the newsletter, we'll discuss how to make more money and utilize our money to live more free. Perpetual Failure is a FS original post.

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159 thoughts on “Perpetual Failure: The Reason Why I Continue To Save So Much”

  1. HI Sam!
    Have been reading you for years but never responded because I am not good on this technology thing or how to remain anonymous.

    Anyway – just want to say your post on failures really hit home for me and my esteem for you grew even more. It takes a great person to admit “mistakes” and the fact that you took those learning moments and grew, adapted and prospered by them is a great primer in the road to success. And the fact that you shared them with all of us is a gentle reminder that all of us stumble and no one has a gilded path.

    Thank you again for sharing. I truly appreciate your posts!


  2. John Wycliffe

    “What good is it for someone to gain the whole world, yet forfeit their soul?” Mark 8:36

    “For the love of money is a root of all kinds of evil. Some people, eager for money, have wandered from the faith and pierced themselves with many griefs.” 1 Timothy 6:10

  3. Sam,
    I read your newsletters. I like them. Not only because they are short, but because they are honest.

    You wrote about how people did not want to talk about their failures. I am an educational psychologist (did my graduate work at Columbia and Indiana, a professor at Tennessee now) and I focus on design, specifically design *failures*.

    Do you know that research articles that highlight failure on the part of designers are cited more than twice as often as articles that celebrate success!? Nevertheless, it is often difficult to get authors to write and explain how they failed.

    Explaining the logical thinking that led to misconceptions is what our reviewers love to read, but authors are very reluctant to write about it.

    Failure and how we discuss it is a full-on area of study in Educational Psychology because it is so tied to learning. Oftentimes when we succeed, we *think* we succeed for a reason that is not the actual reason we credit for our success.

    We may have gotten it right, but we don’t know *how* we got it right. Failure is different. We think a whole lot about WHY we failed. We take it apart. We analyze where we went wrong. We are more critical about the reasons we failed.

    I remember that you’re writing a book. I’ve written a couple myself. A section on failures, even if they are drawn from your readers’ others you’ve encountered, would be a very, very valuable section and make your book more effective. Of course, your own will have value as well. But one person can only remember so much.

    Keep up the excellent writing and I look forward to your book,

  4. Absent eternal perspective which fuels contentment, there will never be enough. King Solomon’s book of Ecclesiastes is a testimony of this futile chase. And yet, he was arguably the richest man at the time. i suspect on par with Musk, Bezos, etc. I’d encourage you to Keep in mind that you are just passing through.

    too much of the mindset of the 30-40 somethings today is built on a plan to build wealth as quickly as possible which isn’t practical for most. the vast majority of healthy household balance sheets (including my own, and many of my peers) became that way slowly. For me, 40 years of living below means and investing the difference in the equity markets has produced margin i never imagined i would carry . . . at least not when i was 35 when kids and careers consumed all we had both time and energy (and at times.$).

    cheering you on,

    1. Thanks for the reminder. Recently, I have been searching for answers to, “Is this all there is to life? Work, pay debts, save, invest, rinse and repeat.” I also noticed that poor people have more drive/will to live than people with money which is quite ironic. When I was struggling as a single mom, I was very motivated to make more money so we can get out of poverty. But now that I have enough to cover the essential things in life and some wants, I lost all motivation to earn more money.

  5. Talk about failure – I bought a 1br condo in SF in 2019 and then had to move to another city in 2021. If I sold it today, I would be down at least $50k, and it’s still bleeding money even though it’s rented out.
    I also turned down a generous offer from a software company in 2018 that has more than 10x-ed since then in favor of another company that went nowhere.
    You’re not alone friend :)

  6. Fear of failure is one of the greatest motivators of achievers. However, at one point, when you have reached your goals, you have to start to look beyond this fear and see what is next. My biggest fear when I was younger was to be poor. I was born in one of the poorest and most dangerous slums in the world, so I know what poverty looks like up close. At a younger age, I did everything in my power to NOT be poor. I ended up out-performing, out-saving, and overachieving financially due to this fear of poverty. To this day, I still run the numbers in my head to triple check I will never fall into poverty (I am 50, have 12-15M net worth, have 200K annual passive income plus 1M business income). In fact, I used to check my social security benefits just to feel more “secure” but it is all irrational because it is time to move on. I think we get into this psychological state because that is what we needed to survive/succeed. But now, I am trying to let go of these irrational fears and look for the next chapter in life. I feel like an athlete who has trained all his life to win a gold medal, now that I have won it, I need to make a plan so I can grow and evolve as a person, otherwise, life will be just about that “gold medal”. In essence, I am trying to progress to the “self-actualization” stage in Maslow’s hierarchy of needs, and how that looks, is completely different for every person unlike a financial goal of 1, 5, or 10 million.

    I’d highly recommend looking into the expectations of 80-year-olds in Quora. I think that will give people here who are in mid-life some perspective. At the end of the day, money serves an important purpose, but there is a lot more to life than making or saving a lot of money, or worrying about it after having more than enough to spare.

    1. Good luck on your quest for self actualization. Finding something to do that helps other people is very rewarding. What is it that you do that earns you $1 million a year?

      Working til 50 is great. Maybe it’s time to move on to something new? I’ve enjoyed my second chapter since 2012. My main focus is on my children now. You have kids?

    2. Lance I amnot

      “Poor man wanna be rich
      Rich man wanna be king
      And a king ain’t satisfied till he rules everything”…Bruce Springsteen.

    3. You have the immigrant advantage, which, in my opinion, is the greatest advantage anyone in America can have (growing up dirt poor in America would be second). Congratulations on your success.

  7. Sam, this seem like proof-positive that you are now very rich!

    Early in my career I was a fund raiser for several children’s charities and that put me in the company of a lot of wealthy people, a few of whom were worth north of $500 million. All were self-made.

    Once you got them in their comfort zone, I found that instead of talking about their successes they preferred to talk about their failures. At the time, I assumed they did so because it put their successes in even sharper relief.

    Since then I’ve found this capacity in non-rich but self-secure people. People who are secure in themselves, whatever their net worth, can talk about all the things in their life that fell flat.

  8. Dear Sam –
    I have been listening to your thoughts on financial freedom via your podcasts for a couple of years now. Recently, I started reading some of your blog posts as well.

    You have attributed saving so much to being a perpetual failure and asked why you weren’t more satisfied with what you had.

    Here are some of my thoughts for you to consider. From what you’ve said, and what I’ve observed:

    1. You are driven. Once you’ve achieved a goal that you’ve set, you raise it and keep going.
    2. You don’t allow yourself to take credit for the accomplishments that you’ve achieved.
    3. You strive to provide more for your family at the expense of your own health, even if you and your family can do very well with what you already have.
    4. Your insecurity of losing what you’ve amassed drives you to be ultra conservative in your investing style.

    I would argue that all of these traits are likely due to the Asian values that your parents have instilled in you. It is your cultural upbringing and not your perpetual failures or other environmental influences that cause you to save and not be satisfied with what you have. The failures in your life are just incidental to your core values. Since these values are ingrained in you, it’s a never ending cycle of always wanting and achieving more.

    You actually recounted this when you spoke about your FIRE budget targets changing from $100k to $300k/yr as your family situation changed. You knew that if you worked more, you could achieve the inflated lifestyle at the expense of spending less time with your kids. What you might not have considered is that your family would adjust just fine to your current lifestyle budget without inflating it.

    In a lot of ways, you remind me of myself when I was younger. My Indian parents also instilled similar values in me. However, I broke free from that never ending cycle of wanting and doing more by realizing that I could take pride in my accomplishments and didn’t need to inflate my lifestyle in the quest for satisfaction. Yes, it is a choice that can be made — and once I made it, I started feeling a sense of calmness like never before!

    You always have a choice, and you can always choose to fit the family needs into your current budget. For example, send your kids to the lottery system public schools instead of private, eat-in more, spend less on vacations, or get the higher deductible health plan since you never reach the deductible limit anyway. The continual inflation of your lifestyle bar will never allow you to be truly happy or satisfied with what you already have.

    As far as I can tell, you’re already in the top 2% of accumulated net worth individuals in the US. You’ve already “made it” by all standards. But, you don’t need to compare yourself with others. You should feel proud of what you’ve already accomplished!

    The truth is, as long as you are withdrawing less than you effective rate of return for the year (i.e., total return % minus inflation) your investments will automatically grow over time and provide even greater returns in the future.

    One way to amplify your income without working more is by slightly increasing your equity exposure up to 50% (which is still very conservative for your age). As a result, you would simultaneity need to reduce your extremely heavy bond and real estate exposure. Yes, your overall portfolio risk would increase by these changes and you would need to learn to be comfortable with that.

    Remind yourself that your investment horizon is much greater than any short term volatility. Over time, the average investment return would be higher and the passive returns would continue to grow. This would allow you to inflate your lifestyle while continuing to spend more time with family or hobbies. Bes of all, you won’t need to work more to achieve this — which is all that you claim to want. However, your cultural values are getting in the way because you aren’t satisfied with what you have and continue to strive for more to keep up with the lifestyle inflation by working more.

    In my case, I’ve achieved partial FIRE, still continuing to work part-time — just like you. My first son was born last year. My wife retired after her maternity leave ended. I transitioned to part time after my paternity leave ended.

    I’m in a position where I could fully retire, but choose to continue to work at my W-2 job because of the excellent benefits — 70% off my health insurance premium costs, ability to max out a 401k contributions, company match, paid time off etc. I don’t have any of pressure that I used to and my responsibilities have been significantly scaled back as compared to when I was working full time. It’s a trade that I’m happy that I took. I really enjoy the extra time that I have to spend with my son.

    As for you, I would say don’t kid yourself to think that circumstance is the reason you save so much and aren’t satisfied. I would say it’s all due to the Asian value system that has been passed on to you by your parents. Weather you’re satisfied with what you have is entirely a choice that you can make.

    And I would say… choose to be satisfied! You have every right to be!


  9. With the mindset of saving and investing to get to that magical number for the last 30 years it is extremely hard to change that way of thinking.
    I will hit that magic number sometime in 2023. I will be 57 and I know I will have a hard time adjusting.

    As most people, FEAR of the unknown has a way of creeping into the decision making process.

    * FEAR of running out of money
    * FEAR of a huge correction in the market in the first couple years of retirement
    * FEAR of Inflation
    * FEAR of future Health Issues

      1. Great article. Fear is both a motivating factor and can also be debilitating if you let it take over.

        Overcoming Fear has been critical to my journey.

        In 2004, I decided to give up a 150K job (good money back then), to start my own business from scratch. Investing every saved penny I had.

        The Fear of making the wrong decision and taking the path of least resistance is was the hardest combination for me to overcome.

        All the research and business planning told me that this was the right move, however in the back of my mind the voice always said “You’re nuts for leaving a good job and what if you FAIL. You will lose everything”

        Once my business was successful people who knew me always asked me “how did you make that call?” I likened it to making a Leap of Faith. You have to believe in yourself and your plan.

        However, that FEAR of Failure motivated me to work ungodly hours for the first 3 years and taking on tasks that were outside my comfort zone. Now 16 years later I am setting it all up for sale.

  10. Money Ronin

    I’ve been reading your site since 2013 when I was laid off. I never returned to a full-time job. Financial freedom is an elusive goal, perhaps even a fallacy.

    I felt financially free in 2013 when I was being laid off. I had enough saved up to not work indefinitely but not forever. My wife still had her W-2 job to keep us afloat. I had two young kids starting private school, and looked forward to spending more time with them. I was optimistic about trying new things.

    8 years later, my NW has skyrocketed but I don’t feel any financially freer. Mo’ money, mo’ problems. — Notorious B.I.G.

  11. “I admire parents who can keep on working hard at work while trying to raise children. Please teach me how! The endurance needed to do both is Herculean.”

    Most people do this out of necessity/constant survival mode. I am not discounting their herculean efforts, but they really don’t have much of a choice. You have discovered financial freedom (or at least mostly freedom), which really starts to change your views about work and money, as I have also started to experience even though I am not quite there yet. I never considered that my motivation/drive might decrease once I started smelling the roses, but admittedly it has to a certain extent. I sometimes feel guilty about not being constantly motivated (which seems like where you might be too), but have considered that maybe I need to give myself the opportunity to take a breath and eat a steak and then give myself some time to kick it into high gear again.

  12. Colorado Lawyer

    Longtime reader, first time writer . . . This was such a lovely, vulnerable, accurate article. And you definitely learn so much more from setbacks. And I appreciate the nod to the folks like me who took the other path. I am a partner in a large law firm. I have looked at your story before and viewed it as you living the dream. But running your business is still a different version of the same struggle. When I had kids, I shifted, coached soccer for my kids, exercised and tried to balance it all. Of course, that meant my career and income suffered, but it was worth it. Perhaps most importantly, I always saved, didnt spend the way some of my peers did, and now, at 48, with kids nearing college and launching, I have more time to invest in career, if I want to. But there is this feeling now that I can loosen the purse strings a little, and I do struggle with the question of what now? The problem for me is, I like the challenge and have a nagging fear from my childhood of never having “security” I never had growing up. I talk about retirement, but its hard to imagine what to do with myself and its hard to turn that fear off. And yet, I ask daily how much more one can save, and for what purpose? Building something sounds more interesting than just looking to walk away.

  13. Sam, I appreciate your posts and their honest and authentic nature. Regarding this comment “Today, my continued main disappointment is not being able to completely let go of the desire to make more money. I’m trying to understand why I’m not more satisfied with what I have.”

    This is a very real struggle for many people, and oftentimes the best way to get to the bottom of it is to speak to a psychologist. You can look at them as your brain/mind health guy – that can help you further improve and be satisfied with every facet of your life. For too long there has been a stigma to doing this, but I see it as being no different than working with a personal trainer at the gym. This is a personal trainer for your mind – and what could be more important than that?!

    Hope you find this helpful and that you find that answer (peace/solace) soon!

    1. Thanks! Any recommendations? I don’t think there’s a stigma at all to seeking professional mental help.

      If you have been able to overcome the desire to make money to provide for your family, can you share some tips on how you did it? I am always looking for examples of people Who were able to quit their jobs and be 100% present with their children while they are still at home.

      I really wonder if being a provider is inherent in our DNA once we have children. How old are your children?


    2. JC this is wonderful advice. Sam, it doesn’t sound like fun living inside your head! You have accomplished so much and have the gift of a loving partner and family. There will always be someone who has more than you. Let it go. You have proved over and over again that when the chips are down you rally and provide. Removing fear as your primary driver will free your mind up to experience so much more. Peace, endless gratitude, consistent joy. Try to stop hoarding and just start giving more. Mostly of your time and from your heart. I became independently wealthy in 2009 and had the same mindset you seem to have for many years after. A family event changed my mindset in 2019. These past two years have been the happiest of my life. When the market crashed in 2020 I didn’t blink. All I could think of was how what I had was still more than enough and how blessed I was to have more than 99% of the people in this world. You do too.

      1. Hi Jocelyn,

        It’s not about having more to have more than someone. It’s about being a father and have enough to always be able to take care of my family, even after I’m gone.

        When your children were little, did you not have this inherent drive to do better for them even though you may have been doing OK? I feel like this is an evolutionary drive that is hard to shake to help our species survive.

        How much more do you think I should give? How do I actually remove the fear of not being able to take care of my family?

        Congrats for reaching financial independence in 2009 and no longer having any fear or worry. I truly do want to learn from enlightened people like you. All tips welcome! What do your children do now?



  14. Sam,

    Certainly a courageous post to publicly discuss your failures and shortcomings. I tend to be hesitant and calculated when pursuing things, as I want to be certain that I will succeed. Then, when I do commit, I put all of my effort behind my intentions. While I cannot say I am successfully at everything – that would be a lie – I feel good knowing I gave it my all. Starting my blog has been a huge creative outlet that I would have never realized I needed. When I want to share my opinions or just get lost in an activity, writing has been a blessing. All the best!

    Olaf, the Mile High Finance Guy

  15. The Social Capitalist

    This is one of my two favorite wealth accumulation websites precisely because of articles like this. This country has been stuck in a Boomer Me, Me, Me mentality selfishly overspending and not enough selfishly oversaving for too long – too many grasshoppers and not enough ants.

    Interestingly, FS, your failures lead you to a great success/asset – your mindset. The key to recognizing failure though is that it must come from a place of success – there are no tragedies without great falls – and one only fails after having been successful. So, the reflection on these failures likely leads you back to the path of your success – hard work.

    Finally, the point about luck is overwhelmingly true. Which is why we must support those who are not. Sometimes it’s as simple as paying taxes and sending kids to public schools (invest in your community), sometimes it requires more – time, treasures, and talent as my old pastor said. But in order for luck to remain in a society it must be stable, law abiding and respectful (not accommodating to) of dissent. I worry that if these things continue to erode we all may run out of good fortune and our fortunes.

  16. I love this mindset and this post.

    Also, hope you find the perfect balance between working hard and enjoying the fruits of your labor as you go further down your retirement life.

    By the way, I’d love to read your thoughts on inflation and where you think inflation will go in the future.

    1. Hi Jeff – I’ve been a long proponent of low interest rates for a long time, and I think low interest rates will continue for the rest of our lives. Hence, I think an uptick in inflation will be temporary… no more than one more year from now as supply issues alleviate the pressure.

  17. Lawrence Ayson

    I grew up in an environment where everything revolved around money. From an early age (in Asia), there was constant emphasis on wealth among cousins and friends. Since we were not wealthy, it was a constant struggle. My kids are completely different.

    Being raised in a very comfortable household where they have everything they need, they don’t think of money the same way I did growing up. Anyway, you asked what would I do to address this. Well, it’s a constant struggle.

    Moderation doesn’t help because I tend to have an “all or none” mentality. I find that the only thing that helps is to focus on other things. New hobbies, new things to obsess over. For example, when I got into triathlons, I didn’t think about money. I was focused on something else. It gave me my identity.

    But those things are fleeting, you eventually go back to the money addiction coz that’s where you get your self worth and identity from. The temporary fix is to find new things to obsess over coz again, moderation doesn’t work.

  18. Thanks for sharing so many personal experiences. It’s wild how we can face so many obstacles in a lifetime but they can really shape our motivations and influence the subsequent decisions we make. I can relate to how failure, competition, and survival are huge motivators. I’ve used all three at various points in my life. It’s also true that America can easily make us soft when we get too comfortable. I haven’t traveled abroad in a long time, but the times I visited third world countries were really eye opening. Those folks work so hard, save every single extra penny they have, and don’t waste anything. Even when times are hard here, we really have so much more opportunity in the US than a lot of people realize.

  19. The problem is most people including Sam are primarily saving in deteriorating worthless “dirty fiat” as USD, Euro, Yen, Peso’s, etc. Bitcoin allows people to save in a way that preserves and increases their purchasing power over time. Had you invested in Bitcoin at any point in the last 12 years, you would have more purchasing power over time, and it’s still early. I expect and believe Bitcoin to hit $300k to $500k next year. I know it’s hard to believe but many old time financial guru’s including my Chase investment advisor shares the same outlook. Study these people: Plan B, Willie Woo, Pomp, and you will soon see how many intelligent and successful people agree with my outlook. Bitcoin has given me life changing wealth and the ability to stop worrying about having enough money to retire, yet I still enjoy being an active entrepreneur in multiple side hustles to be able to keep saving dollars to keep buying more bitcoin and not have to spend down my savings anytime soon, until I decide to really retire. I’m 46 now so still got motivation to keep up the hustle especially since it’s pretty easy to continue my established businesses. Meanwhile gold/silver have performed pretty horrible in keeping up with inflation for the past 15 years, I know as I’m still sitting on some around the same price I paid long ago. It’s too manipulated by the paper markets. Bitcoin is a truly finite scarce supply with an open ledger that anyone can see.

    1. I love cryptocurrency, but I intend to buy heavy only after the Tether fraud ends. Has every red flag of a scam waving strongly. “Every Tether coin is backed by a dollar of currency.” “Sweet, let a third party audit you.” “No.”

  20. Saving is a long time saving habit I will never break. While not saving to your extent my wife and I are in our early 70s and we save some from each and every one of our income sources every month, without fail.

  21. Because I’ve made choices that allow me to do so. Wife and I will both retire early come summer with two great pensions and a very comfortable diversified portfolio.

    Our problem will be flipping the switch from contributing to withdrawing. Our pensions will cover everything by far, so it will be interesting to see how much we increase our standard of living with our drawdowns.

    My kids have been briefed that minus any unforeseen circumstances a windfall will be enjoyed with them not by them.

  22. I loved this article because I can so easily relate to it and similar things that have happened in my own life. The difference is I have about 20 years on you.

    One thing that always stuck with me that I have to keep reminding myself is this:

    A baseball hitter who winds up in the Hall of Fame only succeeds 3 out of 10 times or put another way, fails 70% of the time. The key to his success? He continues stepping up to the plate and taking his swings for a long period of time, regardless of the outcome.

    Keep swinging Sam, you’re doing just fine!

  23. Chuck Sarahan II

    You remind me of family members who grew up during the Great Depression. Not a bad thing. Some are natural born savers and yes since you don’t a retirement package that is someone else’s responsibility to manage, yes…you do worry about money. I see nothing wrong in your approach. After all, you are responsible for you and the family. That is a load in and of itself.

    I am a saver but my wife not so much. I would love to save 25% of my income but not gonna happen. So, I continue to work and deal with it. Working up to 20% right now. My wife’s health is a bit precarious so that will impact me as well.

    I like the honesty of your articles. You may be a bit too tough on yourself but the analysis is first rate. Too few people do that including members of my family.

    1. Good luck! You are acting rationally by working more because your current saving rate doesn’t make you feel secure enough.

      If I went back to work, I might ironically decrease my saving rate bc I would feel more secure with a steady income, health insurance, benefits, and a growing network.

      But bc I don’t have those things, I must save to make up for the uncertainty.

      It’s actually good to not feel like you have to save much money at all. That means that life is pretty good and there aren’t many worries or responsibilities.

    2. It’s nice to know you have the some of the same uncertainty and anxiety that we all have in this world. Prospectively, as we age the world looks increasingly risky. In retrospect, we see our errors and hope that the balance of good decisions to mistakes is positive. There are many, many risks in this life that are neither prevented or mitigated by more money. There’s nothing better than a margin of safety, particularly if your current lifestyle is leveraged by mortgages, other assets depending on future appreciation to deliver the benefit of current ownership.
      You were extraordinarily fortunate, according to your own disclosure of your business/earning history. Most of us get there more slowly, with longer intervals of hard work. The best lesson I have learned is to live modestly, save generously and plan to bequeath the excess when it is no longer meaningful.
      There are SO MANY good things in this American life that don’t cost tons of money to enjoy. They are out there to be discovered. Good research identifies the diminishing return on investment in happiness during the pursuit of wealth. If “more” is the only measure of success, it’s equally the guarantee of failure. Many people would say that defining happiness in terms of how much you have given in your life is a more reliable measure than how much you have received or acquired. There isn’t necessarily a dollar figure attached to that, because the one thing that is truly allotted to us in this life is a measure of time.

        1. I left a career that was deeply satisfying in one sense and highly lucrative but was made increasingly intolerable due to a deteriorating environment in which to do the work (another story). I took a 2 year stroll through entrepreneurial pursuits, learned a lot, including the understanding that I didn’t have the motivation to deal with all of the mundane details of growing hobbies into businesses. Then, the pandemic gave the opportunity for a true sabbatical, from which I am only now emerging. I’m going back to work; as an employee rather than an owner/operator, at 70-80% of what I used to do. I want to be useful to others, want the social interaction, satisfaction of the work itself and reasonable compensation. I spent over 30 years saving like mad and also went through a period of lifestyle creep, then realized I was born with dirt between my toes and really preferred to get back there, so that’s exactly what we did. My understanding of “enough” is to pay expenses with my own labor with just enough work until age/health/motivation intervenes, having lots more fun along the side, and allow our growing retirement assets slowly and increasingly support us into our twilight years. There will come a time when the work no longer lights up my eyes, but it’ll probably be another decade or so.

          1. Awesome Nathan! So glad you were able to take time off and find a new job that still pays well.

            I’m kinda going in reverse and working hard now until sometime in 2022, if and when tax rates go up. Then I plan to re-retire and take it easier,

            Hopefully by 2022, there will be more covid treatments and less sickness. Then it’s time to travel and explore again!

  24. Mike Hensley

    FS, appreciate your introduction to Fundrise and Crowdstreet platforms.

    While Fundrise’s 10% (roughly) compounded return is good, it seems that I have to give up another 6-10% which I can make thru Crowdstreet. Investing with the developers as opposed to those that purchase the stabilized properties offers significant upside potential.

    I am early in my r/e investing on these two platforms so I will have to wait 3-4 years before I can support my initial thoughts with results.

    I never thought I would need 10mm to retire comfortably. I never thought I could reach that goal. If we can quit having things like the IT crash, the Great Recession, the Chinese Pandemic, etc…maybe us little people can get ahead!!

  25. Lawrence Ayson

    No disrespect but I think you have a money addiction. I have the same issues. No matter how much I have, it doesn’t seem to be enough. I’m 49 and actually have more than enough to retire and just take it easy but I’m too addicted to accumulating for the wrong reasons. Even though I have more than enough, my thoughts, my inability to spend and constant fear of not having enough feels horrible. I envy those that have less and are perfectly content.

    1. I, for SURE have an obsessive focus on money, after all, I’ve published 3 posts related to money every week since 2009. These obsessions/habits are hard to quit. Hence, I’m looking for solutions on how to decrease this addiction. If you have kids, I’m especially curious on how you deal? I’m always looking for suggestions from readers and those who’ve been where I’m going.

      Related posts with some solutions:

      Stop Frugality Disease From Causing Lifestyle Deflation

      It’s Revenge Spend Time! Time To Spend To Get Back At Life

      Helping Your Lifestyle Inflation Keep Up With Your Investment Inflation

      Now, back on sabbatical!

  26. I’ve had many failures in my life as well…but often success is born out of failure. So the more I fail the better my chances are to succeed, at least that’s how I see it.

    Also, luck is often where opportunity meets hard work…or something like that:)

      1. Okay! Some Failures…

        1. Not trying at all in school until my Junior Year in College because I found school extremely boring leading people to believe that I was lazy (which I was!!!).

        2. Wasting a huge amount of time and money early on (until early-mid 20’s) because I didn’t learn anything about how to handle/treat it from my parents…aka not taking personal responsibility.

        3. Wasting a ton of time on useless pursuits (video games).

        Of course, all of this led to some of my greatest accomplishments which include…
        1. Cashflowing grad school and maintaining the top rank in my class while working full time
        2. Learning about money so that my wife and I can be equal partners in our marriage and share the responsibility of providing for our family (budgeting, planning, etc…)
        3. Putting down the video game controller for fitness pursuits.

        1. Good stuff! Thanks for sharing. I remember being into video games as a middle Schooler. But for some reason, I never got into it afterwards. It just took too much time and I wanted to play sports.

          As a creator, I want to create, not consume as much.

  27. Squirrels save nuts for winter. They just don’t save 1,000 tons of nuts. Enough is enough. If it isn’t, move to a nice cheap place with territorial taxation where the sun still shines, it still rains, and they actually have food to eat. You’re getting neurotic.

    1. Hi Cody – I appreciate the tough love attitude. As someone who is older than me, any specific action steps you can recommend to reduce the worry and neuroticism? If you have kids, what are some steps you did to ensure they were OK?

      Here’s a post I wrote for parents: Career Insurance: The Guaranteed Way To Prevent Unemployment

      I haven’t met anybody in their 60s+ who decided to start a personal finance site and sell online courses. Usually, they’re deciding to take it easier. So I’m interested in hearing your reasons why you did on top of your day job. If you need some advice, let me know.

      1. Lance I Amnot

        Warren Buffett is 91 years old. Is still very vibrant. Loves his work. And, goes to work everyday and works a full day, as he has since he was probably 10 y.o. Oh, and he has a net worth of over $100 billion. I don’t know Mr. Buffett, but he seems very happy even though he still drags his butt out of bed everyday and into the office and grinds away in Omaha, Nebraska.

        What does Warren Buffett know about the joy of life that the rest of us do not? What’s his secret? Where does he find the drive or meaning or purpose?

          1. Lance I Amnot

            Buffet knows that true happiness is not found in achieving financial independence, or an endless life of ease.

            Being financially independent and being able to retire is great, but financial independence that ensures a life without challenges, stresses, risks, successes and failures is not really life, is it?

  28. Brutally honest post, Sam. I like it. A lot of people in this space don’t admit their failures even though we all have many.

    Thanks for the great content. Every post I read gives me more motivation to save save save.

  29. Frugal Bazooka

    What you’re describing as failure is actually just participating in life with its ups and downs. In the US the average college educated person will have a ratio of 1 success for every 10 tries. We take it in stride because failure is never really failure, it’s education, trial and error and part of the game of life. It’s baked into our positive attitude about the future. No matter how hard the media tries to tell us that the world is bad we know most of the time our world is an amazing place to be and most of us would never want to be anywhere else. There’s a very good reason why so many poor people continue to immigrate to the US, it’s not because it’s the land of failure. As far as people being greedy and wanting more, it’s only logical that people who are good at making money would continue to do so just like a baker who is good at baking bakes until he’s 100. Mick Jagger isn’t touring at 78 because he wants another 200 million dollars.

    1. Lance I Amnot

      And, Warren Buffet at the age of 91 isn’t going to work everyday because he needs another $100 billion.

  30. Key factors that make the national personal savings rate higher are a fast growing economy with a young average age. That means that older people are dissaving much less than young people are saving, raising the average savings rate. Other factors of course depend on how much the government provides for retirement through the tax system etc. Also, if corporations save so that investors get capital gains rather than pay out dividends then that reduces the personal savings rate. Investors get capital gains rather than have to save their dividends. Only when all these are taken into account can you start talking about preference for saving vs spending varying across countries.

  31. IndianRipper

    Excellent piece that I could identify a bit with. Especially when you say “my main failure is being unable to let go of the desire to make more money”. Being a first generation immigrant that grew up in India, all I saw around me during childhood was people’s lives being ruined because of debts, lack of good salaried jobs and illnesses that could have been treated better if one had money to spend. Though it is crystal clear the probability of those events are much smaller given my current state, this past learning is so hard-wired that any thought of ‘not working’ creates instant insecurity for me.

  32. IN 1967 when starting my first job I thought a million dollars would be all I would need but when I got there a million dollars is considered as nothing,

  33. Memento mori

    The hardest thing for a man is to sit still while his friends are getting rich.
    It totally corrodes your brain.
    Why we always want more?
    Some people are greedy indeed and wealth for its own sake provides meaning to their life. But most people aren’t, especially the poor, as soon as they get some money usually they will stop working and do other things.
    Witness how hard is to get people back to work nowadays.
    That’s why they are usually a happy bunch and don’t stress as much as the rich.
    Most work is a chore and has been so throughout human history.
    Last 200 years is an exception with the Protestant ethics.
    But people who do hard work know it and they will quit doing so given the opportunity.
    The origin of the word work in most countries comes from the Latin tripalium which is basically a torture instrument.
    But that’s not the issue here.
    The problem you face when you think you saved enough money to stop working is threefold:
    First, you finally meet yourself and discover it’s an empty shell, freedom is hard to tolerate and boredom is it’s child.
    When people are free, they usually tend to imitate each other.
    We hate freedom because it implies responsibility. No one likes responsibility.
    Second, if you are somehow educated, you spend a lot of time thinking about the meaning of life and happiness and come to the conclusion that you were happier when you were working.
    The thinking behind such conclusions is that people are happy when their desires are fulfilled. But we only desire what we lack.
    When your desire is satisfied, the element of lack disappears, so you don’t desire it anymore, hence it’s impossible to be happy because what you desired isn’t lacking anymore. Boredom inevitably follows. Happiness is impossible.
    Third, you can always count on the government to continuously devalue your savings.
    No matter how much money you save, this continuous stealth devaluation will increase your anxiety proportionally and either force you into speculative investment with its own stress or you can silently suffer watching your cash diminish like a “peau de chagrin” . People don’t know that at most during medieval ages , taxes were no more than 10%. We have the most oppressive government in history, but we are comforted because we vote them in, but the crux of democracy is to rule not vote.
    And, government doesn’t want idle people.

    1. I disagree about inflation. Stocks and RE are tied to inflation, they don’t lose value. Insecurity has more to do with children who have constant and future expenses such as college, etc which is out pacing inflation. I imagine those without children have much less anxiety than Sam.

      1. Memento Mori probably doesn’t have kids. It would be great if he actually shares something about himself. Most people who say what he says is usually a loner.

        1. Interesting comment. It sounds like MM hit a little too close to home for comfort. The thoughts are valid (kids or not).

          In as communication vehicle such as this, providing one’s life story in a comments section is not really necessary.

          Accurate and insightful thoughts MM. btw – I have kids :)

      2. Memento mori

        Timing is critical for all investment.
        It’s impossible to get the timing right.
        Sam is correct, luck plays a big part in striking gold.
        Stocks can also perform poorly during inflation, look at the 70s.
        Real estate is a better bet but you will be taxed accordingly. You can’t hide it and it’s an easy target plus it deteriorates.
        There is no way to escape the wealth destruction that counterfeiting of currency by the government will cause no matter what you do.
        Read Thomas Mann on how inflation destroys and the fabric of society and demoralizes the people.
        Anxiety and insecurity doesn’t come from children.
        Au contraire, they are source of hope and regeneration.
        Look at the Fed’s self imposed mandate of 2% inflation per year.
        You lose by decree 50% of the purchasing power in a generation. (25 to 30years) while your wages never keep up.
        Why is it acceptable that your money which represents years of saved labor be devalued arbitrary?
        It’s impossible to reasonably plan for the future when government can nullify your effort instantly.
        That is the source of your economic anxiety.

        1. No failure means you are not trying. There is no perfect path. Sharing setbacks helps others learn. If they don’t think so , they are being judgy. (I know that is not a word)

          I have had many investment failures. I learned what to do and not do. As far as children and health, like investments, you can only control so much. Stuff happens, Enjoy it all. Life is interesting. People who say their life is free from worry are liars. They haven’t gone through enough yet, most likely.

          Lastly,” Getting rejected is also a great way of keeping the ego under control, and sounding like a braggart is not the way”
          Nobody likes a braggart – terrible quality. Rejection and failure equals growth and character; if you are paying attention.

          Oprah said hard work and good luck equals success – it is a bit of both.

          You are a writer too – don’t let people influence too much what you are compelled to write. And you will know when enough is enough for you.

  34. I think a lot of your “failures” are actually successes .. the fact u made it to director level is a huge succsss. I wouldn’t call #1 a failure either – unfortunately society has framed for us what is failure vs what’s not. You landed an awesome job right out of school so that success negates the failure of not having it lined up while in school.

    I’ve learned from you not to care what others are doing. Forgo prestige and ego. You mentioned that you’re “Now I’m motivated more than ever to prove my detractors wrong!” I personally think you’ll be much happier if u don’t care. They are just a few of what are 7 billion people in the world. You’re a huge success and you should enjoy life more. In terms of wealth you’re in the top 1% and yes the sky could fall but you’ll likely be fine. Go enjoy life bro and work less and keep up your health – it’s the only true wealth.

  35. I loved your comment on how a construction worker cost you $1000 in revenue. I think it’s inspiring to be able to quantify ROI or in this case missed out on ROI, which is also important. Great content on just hard quantifying mistakes. I hope you don’t focus too much on the mistakes in detriment of the good, let’s say there’s also the emotional ROI to consider…

  36. Hey Sam,
    I have been reading your blog for about the last 2-3 years. I don’t comment much just because that’s my thing. In any case remind your yourself that you have helped a great many people. Me included. Since reading your comments I have almost become debt free, retired at 49 and now have a nice, not great, SAVINGS account that has provided more peace of mind and freedom that I thought was possible. Just thought you would like to know.


    1. Wonderful to hear Martin! Thanks for letting me know. It’s motivating for me to keep on going. Thanks for also sharing my articles with other folks.

      Got to LOVE the feeling of financial security!


      1. I second that , you churn out great articles on a weekly basis unlike most blogs . I have quadrupled my networth thanks to your weekly blogs . I can’t thank you enough

  37. I liked how open you were with this article. Everybody has failures, and as I can see in the comments, it’s all about how you look at them.

    Regarding your concerns about your website, have you thought about making different products? I bought your layoff eBook, and have read pretty much every one of your posts. I think that if you were to create another product, many people would consider buying it.

    My favourite posts are those that contain the numbers and age brackets, such as net worth, your 1/10th rule for car buying, income, savings amounts, and so on. Perhaps you could put together an eBook that puts these kinds of articles all together, and do some kind of general analysis on each age bracket? E.g. “this is what I recommend your income/savings/etc… to be like at age 25/30/35/40, here’s what to do if it isn’t there yet”.

    I’m struggling to improve the income on my own website so I know the feeling.

    Just a thought :) Either way, keep up the good work, and enjoy the break.

    1. Thanks for buying my book and reading my articles Ben.

      I think I’ll try to create a new product once a year so that after five years I should have a stable of new products. Thanks for the encouragement!

  38. First off, bad luck and failure, you can both stay all the way over there. I’ll be over there.

    *Sigh* If only.

    My failures. I don’t have time to list them all because that would take days of continuous, uninterrupted writing. But for this year alone?

    1) Attempted to transition from banking into a law enforcement career. Did not work out. Did not work out HARD.

    2) Tried to go to a different, higher paying credit union after that didn’t work out. Ended up crawling back to the bank I was so excited to leave and promising that I was now there for the long haul. If it weren’t for the concept of unemployment, that would have been the worst case scenario.

    3) Failed to negotiate a higher salary after I was promoted.

    4) Have performed horrendously since my promotion kicked in. Didn’t meet my sales quotas last quarter and have no leads or anything in the pipeline for investment products (I’m the only person in my branch that is qualified to sell them, so much of the branch’s profitability falls directly on me). I’m completely failing to motivate the branch staff in sending me qualified referrals as well. Pretty much, every function and responsibility entailed by my new position is one that I’m not even close to performing well at.

    5) Wanted to earn $5,000 in dividends for 2015. Off by about $1,000.

    6) Wanted to be earning at least $100/month from Google Adsense revenue by the end of the year. Not. Even. Close.

    7) My overall plan to retire at 35? After some back-of-the-napkin calculations, it seems like if I try, work, save, and invest REALLY hard, I might retire by 45. Barely. I don’t want to work for another 15 years. I don’t even want to go to work today.

    And like I said, that’s just for 2015. That’s not even the full 2015 list either! That’s just what I’m willing to put on here.

    But you know what? While I can’t say I have no regrets, I don’t have nearly as many as that list seems to imply.

    At least I’ll never wonder “What if?” when it came to a career change.

    At least I HAVE a website. I showed it to a friend of mine recently who I hadn’t seen in over a year (he’s away at school). I always had a reputation for not knowing computers well, so when he said “This website is pretty interesting. Who made it?”, I was very proud to tell him it was me.

    I got my job back. My manager pulled strings to get me back and then gave me an in-branch promotion. So I can’t be too bad at my job. Plus, my recent Year End Performance Assessment shows that he disagrees with me on my own view of how things are going there for me, as it was a glowing review. Plus, I made my first fixed annuity sale last month! No referrals, nothing. It was 100% me.

    And despite not making my dividend goal this year, it’s partially because I set the bar arbitrarily high for myself. I made $1800 in my first full year and this is my second. It was a number I was aiming for because it seemed like a large but reasonable step forward, and it was hopefully one that could be replicated each year. If I tripled my dividend income each year, I’d be happily retired by 35. Of course, that’s pretty unrealistic (entailing a six figure dividend income in five years. Where is that money coming from!?), but I was aiming to get a good early start so that compounding, dividend growth, and dividend reinvestment would pick up the slack for my lack of consistent fresh capital.

    And to retire between 45 and 50 (possibly)? How many people in this country will be retiring at 62? 67? I wonder how many people in my generation will be able to retire at all?

    Failure is one of those things that we have to accept if we are going to do anything, well, at all. Bad luck I can’t stand when it’s pointless nonsense with no potential to move me forward, but anything good in life comes with the risk of failure and setbacks. I’d just like to get past those parts already. I want my successes to outweigh my failures.

    Sam, it seems like you’ve reached that point already. You’ve achieved financial freedom and are able to do what you love whenever you want. And good for you; you’ve worked hard and earned it. You’ve had–and still have–many failures, but your successes have outweighed them immensely. Be proud.

    Pyrrha: “Wait, Jaune, stop. Do you feel that?”
    Jaune: “Soul-crushing regret?”
    –RWBY Volume 1

    ARB–Angry Retail Banker

    1. Thanks for sharing! That’s a really healthy dividend income stream based on your day job income, so nice work! Also, it is great you do have a site. What do you think is keeping it from growing as fast as you want? Are you posting 3X a week consistently?

      It took me well over a year to get $100/month in Adsense fyi. But after 2.5 years or so, things started really taking off. Hang in there!

      1. I wish I was posting that often. Between 50-60 hours a week at two jobs (not including commute, getting ready, compliance modules that I have to do at home, etc.), I’ve been falling asleep at seemingly random points during the day. I wanted to do some work and get some writing done when I got home from the bank yesterday, and I ended up eating dinner and falling asleep instead.

        I’ve got to learn how to focus more. It feels like I’m moving from task to task without a definitive conclusion to anything. I’m looking to turn some of my 2015 failures into 2016 successes.

  39. In my line of work failure is part of the game. As an academic I am constantly submitting my work for peer review. I get rejected more times than I get accepted even with a publication record that is pretty good for my field. For me it acts as motivation. Best advice I ever got was: 1) Get the results and stick it in a drawer for a couple of days. 2) Then pull out the results. Read them. Spend 2 days being angry; 3) Spend 2 days being sad; 4) Then sit down, shut up, and do the work. Works for me.

  40. Sam, while I agree that failure makes us into better and tougher people, I think there’s also an issue of perception at play here. Not having a job out of college could seem a mark of failure, but you also passed the yardstick of getting the degree (that not all people do; side note: Go Tribe!). Additionally, you left corporate work to try your hand at something else, and were financially able to do so. That it didn’t play out the way you expected it to is no more a failure than the decision to undertake it: it’s just a fact of the experience. I have no doubt that you’ll move on to a new success, and it will likely happen soon given your history.

    I was in the depths myself last year when I got passed over for a new post at my job, especially because I’m looking for the next big ‘thing’ in my career. But it does mean I just keep looking, and I’ve done enough in my current position to realize that I’ve got it pretty good.

  41. Sam, have you read this –

    It’s an interesting read if you haven’t! :)

    But on the post, your successes kill your failures. And success and failure goes hand in hand right?

    Failure is like weight training for your resolve!

    Mr Z

      1. I’m only part way through at the moment. But it’s about adapting from failures rather than aiming for success per say.

        Also a big comparison between evolution and business success or failure. Which is cool. But scary, as it suggests that more of success is random than we think (especially when we consider large businesses)

        Pretty interesting. But I do like to pretend I have some semblance of control!

  42. The only failure in my opinion that is of any real significance is the failure of one’s financial independence. I don’t personally understand the desire to overcome comparatively frivolous “failures” when compared to one’s ability to abstain from active employment.

    The fear of losing it all only keeps one from never really retiring at all. Not that “retirement” is everything.

    The truth is, the worse case scenario is never really that bad. I’d rather not worry about insignificant failures when I know I’m already in great shape. Should shit ever hit the fan, I know I’m a resourceful individual that will make it work and maybe even come back stronger. The need for reaffirmation that I “still got it” just isn’t enough for me to care about such relatively small failures. That’s just me though. I can see both sides.

    The only thing that would keep me up at night with regards to failing is the desire to have more in life. I already have way more than I could ever want, so there is no motivation to acquire more money at all. I’m more interested in intellectual pursuits that will probably inevitably lead to more money. But if I fail – I’m not necessarily more motivated to try harder simply for the money.

    1. I am very impressed that you have no motivation to acquire more money at all. If your desire is just on intellectual pursuits, then all you’ve got to do is really read, hear, an watch a lot from people who provide intellectually stimulation information!

      When do you think your complete motivation for money stopped?

      1. The motivation stopped as soon as I had enough and a comfortable lifestyle and realized that acquiring more things or being in a different place wasn’t worth working any longer unless it’s something I’m passionate about.

        I do definitely consume a lot (reading, movies, etc.), but plan on creating my own things in the future – I’m just now settling into this lifestyle. Being free from having to work for money gives you the ability to think about what you really want to do and not have any fear of ever not making money from it.

  43. Been following your blog for a while and really enjoying the content. I noticed that you’ve been looking at roles within fintech. Shoot me an email if you’d like to chat; not a recruiter but we’re hiring as we grow, and I’m happy to refer

  44. Great post. One of your best! I think dwelling on failures/setbacks can take you down a slippery slope. (I’ve done it myself.) We’re all quarterbacks in life that are one play from throwing an interception. In some respects you gotta have short term memory and look to the next play. Don’t be too hard on yourself. You have a lot to be proud of. We’ve all made mistakes and missed opportunities.

    1. I try not to dwell. I try to just be frank and remember so I don’t take anything for granted. Now, I can look back to this post whenever things feel too good to be true.

  45. I agree with your attitude and I think it’s fair to describe those things as failures. I also tend to set myself up for small failures in the sense that I set lofty goals that I can’t always meet. The danger in this approach is that it can leave you vulnerable to psychological wounds from never feeling good enough, but the older I get, the easier it is to look back and feel satisfied with what I’ve accomplished rather than focus on the “failures”. And yes, having a large savings rate certainly eases the anxiety that comes from more significant financial failures. Peace of mind is very valuable!

  46. Wow! That’s a lot of failures to cramp into one blog post and even though it was amusing to see list go on and on, I wondered why you’re even thinking of getting a day job when you run one of the most famous financial blogs in the world. Maybe you’re trying to aim higher and higher, and there’s nothing wrong with that, but for all the failures you have listed, this is one major successful venture that could set them off! I do fully support the idea of saving because you simply don’t know what the future holds for you, so save, save, save all you can.

    1. Is FS one of the most famous blogs in the world? I’m not so sure, but that would be kinda cool if it was!

      I really feel like I should be doing a little bit more with my life on the professional front. It’s like my time for working hard over yet, as a result, might as well do some extra work while I still have the energy. I know my energy will eventually fade, so I want to pack in this much stuff as possible before that day happens.

      1. It has to be one of the most visited financial blogs because your site is in the top 5 results on many common financial Google searches.

        1. SEO is neat b/c I know the fundamentals of SEO, but I don’t use any hacks/tricks to try to rank well for particular search terms. The most important way to rank well is to just think logically about search and write something worth reading.

  47. quantakiran

    Varsity and personal problems burnt me out and when I started at work, I had the worse case of “The Impostor Syndrome.” (very accurately christened by the way!). In hindsight, it’s a good thing, because I don’t have the arrogant attitude that some of my co-workers have.

    I save because I know my job is at risk (since 2008 really), I live in a 3rd world country and I want to live a rocking awesome life full of travel and a comfortable home somewhere safe in my old age.

    So in short I save because I want to live!

    1. Sounds like a great reason to say to me! I think if you come to the United States, you’ll wonder why everybody isn’t a very well-off person because life is so easy here compared to other places 。But I also think you realize that because life is so easy here there is in this intense desire to save as much as in other countries.

  48. Gen Y Finance Guy

    Failure is what makes Success feel so good!

    Failures are the stepping stones to success!

    Failure is not Futile!

    You can’t have the sweet with out the bitter. We need contrast in our lives to fully appreciate.

    I think Failure is Fantastic!

    If you want to win you just have to fail faster than the people you are competing with. You get to determine how many at bats you get…and you just might hit a home run instead of another strike out.

    You got this Sam.

    Have to love the self deprecation.

    I hope we get a chance to meet in person one of these days.

    Enjoy Hawaii.



    1. Hi Dom! I wouldn’t go so far as to say that failure is fantastic, but I do believe failure is a healthy part of being a better person. Come on up to San Francisco one day and we’ll go grab a beer!

  49. Funny how failure is really in the eye of the beholder – I would struggle to classify many of these as failures at all. Some are achievements that might have fallen short of a very high benchmark you’ve set yourself, or simply things that have happened over which you have minimal control.

    But we all set our own expectations and goals, and I guess if it feels like a failure to you, then it is. I do appreciate the point about seeking rejection though, to keep you motivated. When life is good, I really try and be grateful for it, and recognize that things can change at any moment – although it can be hard to stay motivated just by being grateful and it’s easy to grow ‘soft’. But I’m definitely not as much of a glutton for punishment as you Sam…

    1. Everything is relative, I agree. But failure to me feels the same and is the same as failure to anybody else with goals that are not achieved. And so I say, hang a lantern on it. Shine your failures as Bright as possible so that you never forget how hard and takes to get to where you want to go. So that when you ultimately succeed, you will savor the success and appreciate the victory that much more.

  50. These tie into “lack of education,” but I think deserve their own focus. In the “Why don’t Americans save question” I think some of the largest factors include:

    1. Perceptions of successful people as apart or different. It took meeting some very successful people and witnessing the lack of anything overwhelmingly different for me to change from “That’s not me,” to “Why not me?” Americans mythologize famous entrepreneurs and have lost the spirit of entrepreneurship that is embodied in the successful.

    2. Perceived inability to save. The idea of saving $10 a month would be scoffed at by most. I think most people who have tried to learn to be frugal start small to establish good habits, and this leads to successful saving of larger and larger sums. The first thing most people do when they get some breathing room is expand their spending. And one trip on that hamster wheel and they are screwed.

    3. Lack of ambition or drive. I don’t want to point a finger at a whole generation, but at 25 years old, I think most of my peers are pleased to have a decent job. Most wouldn’t consider bailing on one for a riskier but potentially more lucrative career.

    4. Not lack of education, but downright misinformation is pumped into the cultural consciousness. I get a big chuckle from broke movie characters living in chic flats in the ehart of America’s most expensive cities, or the drone of go to college but college isn’t for everyone (which is more about holding up how important it is for anyone of worth to attend college then it is about validating tradesman work or independent business). Public school teachers land in the goldilocks zone of comfort vs. risk when it comes to employment. Most of those responsible for educating millennials have no idea what it takes in todays job market or financial world.

    I don’t want to sound too doom and gloomy though. As much as millennials get looked down on when it comes to the employment and financial side of things, I think much of these woes can be attributed to the learning curve we didn’t expect to encounter, rather than laziness or unwillingness to work.

    1. On the bright side, if much of these woes can be attributed to the learning curve, and all it takes is more and more awareness for people savings rates and savings amounts to go up!

  51. Because people here take everything granted….my Cousin bough 27k second hand lexus just because he like cars..WTH…he can barely afford it but who cares, he likes car so he should get lexus……this mentality is killing america

  52. Perpetual Failure Equals Whatever Meaning YOU Assign.

    “Nothing in life has any meaning, except the meaning we choose to give it”.
    — Tony Robbins

    I followed a similar path…

    1) Age 20 – Lost girlfriends to drugs and other guys – learned to select better girlfriends.
    2) Age 25 – Lost money on credit card interest – learned how to budget w/ no debt.
    3) Age 30 – Lost money on stock tips – learned how to invest properly.
    4) Age 35 – Lost money when associates stole from me — learned to work for myself.
    5) Age 40 – Lost job when boss lied about me — learned to be financially independent.

    6) Age 41 – Lost desire to work in corporate America — learned to be retired at 42.

    Thank you for the lessons, – what a blessing!!

    Choose your meaning carefully or society may choose something for you!

    1. I agree with your belief. And I do believe that all the failures I’ve listed are indeed failures. There is no sugarcoating around them. I think it’s great to write down the ones failures to remind themselves how they are not good enough and how they can get better. Because as the saying goes, if you’re coasting, you’re going downhill !

    2. quantakiran

      Hmm two apply to me
      5) Age 31 – Lost promotion when boss lied about me — learned to be financially independent.
      6) Age 31 – Lost desire to work in unsafe work environment — saving to retire.

  53. It is super important not to let fear of failure rule over your brain and everyday thinking. I try to create the overall wealth game-plan based on a little fear, but live day to day as carefree as possible! And when I really think about it, as long as I have food, a few great friends, and I’m growing personally I will be happy. Since I have already got these things, the worst-case scenarios seem a lot less scary. And if you aren’t happy living a modest lifestyle, you won’t be very much happier living a lavish one. Money just buys security for me, not happiness.

    That said, I continuously save 75%+ of my income based on a little fear! Fear of running out of money and fear of having to work forever. In some ways, I think a healthy amount of fear can make you much more wealthy in the long run. I am a little afraid of getting laid off from my day job, so I work hard there and try to shine during those 40 hours. I am afraid because my day job will never bring the financial freedom I want quickly enough, so I hustle on the side with a blog or a small business. Constant fear of failure drove me to diversify my income streams as much as I could. It is probably some sort of survival instinct for this new digital age.

    1. A 75% savings rate is fantastic! How long have you been saving at this rate and how much do you need to say to be able to take the risk and find a new job that you like?

      1. I have only been saving 75% for around 1.5 years, after reading blogs like Financial Samurai and Mr. Money Mustache. I’m lucky I found your website while I am still young (25). Bless the exploding volcano of helpful information we call the internet.

        I currently have a fantastic, entrepreneurial friend and business partner, so instead of looking for a new W-2 job, we are trying to create our own company or side business. If any one of our ventures was looking promising and started to demand more time, I would probably quit my day job and pursue that. Partly inspired by a few close friends who are successful entrepreneurs, and a few of your articles like Bankers, Techies, and Doctors never getting rich.

  54. Interesting post Sam. I feel that I was very similar in your outlook. I saved because I was sure that at some point I’d find myself out of work and I wanted a financial cushion if it happened. Well, it did happen and every day I thank my paranoid self. People who push themselves generally are doing it by thinking themselves into a discontented state. It wouldn’t be hard to reframe and focus on the positives of your experiences. But I don’t think that’s your intent here.

    1. There are definitely positives from all the failures. But I really want to focus on the failures and not sugarcoat them to remind me that nothing good lasts forever. I’ve had enough post about wins before. I thought it be nice to Show a different side of the story.

  55. Adam @

    In an era when social media encourages nothing but perfect filtered photos, amazing vacations, flawless homes, and all AWESOME all the time, it’s nice to read somebody’s honest list of failures and shortcomings.

    I’ve certainly got plenty myself. I’m not at the level of career I’d hoped so far and while I think the quality of my blog is decent, it hasn’t seen the traffic levels I hoped to get to this year.

  56. I like your approach to aggressively saving because nothing’s ever guaranteed to last forever. I think however you do not mention the possibility to be flexible. Surely, there are lots of things one could do to lower their expenses way below $100’000 a year, in particular if they have their house paid.

    Thanks for sharing your failures. I think you and I had this discussion a few days ago that one could learn a lot from the people who failed. Your a person who succeeded, but with failure along the way, that’s good enough ;)

  57. Like Jim said, I like to think of things like this as setbacks instead of failures. Much better to think positively too :)

    We save a great deal of money because we have no idea what the future holds for us. I’d rather be prepared so that I can worry less later!

  58. I can’t wait to see where you go next, Sam. You are 100% right about failures knocking you down, but then motivating you to try harder afterward. I didn’t realize it until you said it.

    After college, I was out looking for a fun or meaningful job with a decent salary, and was disappointed by what I found. I always wanted to be a writer for Road & Track or Car & Driver, but even my mediocre path toward that career (copywriting for an internet-based home automation company) fizzled out when they laid me off. None of the other job options were good (outside sales jobs with no base salary), and I ended up managing an inbound call center by default. It was torture. I still hate to hear the phone ring.

    I had wanted to be a lawyer previously, but got burned out in school, and gave up and decided to just get a “normal” job. I thought that being a college grad from a pretty good UC school would give me some good options, but it was really depressing to see that that wasn’t the case. Fortunately, it kicked me in the ass and made me decide to take the LSAT to see what would happen. I studied hard and ended up scoring in the 97% percentile, which not only got me into law school but landed me a 50% scholarship my first year.

    If I had gotten a mediocre-to-good job, I probably would have passed on the law school opportunity, and my life would be much worse today. Being kicked down and having to pull yourself back up is a really great motivator.

      1. Tell you what, the first one of us to get hired at R&T has to promise to get the other one a job there, too. :)

  59. I like to think of negative events as setbacks, rather than failure. Failure means it’s done for good, setback just means it’s temporary… because it is. Losing stock options, quitting before you get fired, selling only 30-40 books a month instead of hundreds — merely setbacks.

  60. One way I deal with failure by saving is the following. If I have an unusual expense such as a plumbing failure that for example costs $1,000 I will think of a way to save that extra $1,000 in order to be at least back to even. So basically small failures lead me to save more.

  61. Lance @ HealthyWealthyIncome

    Too many folks try and avoid all types of failure and all that does is ensure that you never put yourself in a place to achieve anything significant because you are never around risk that will pay off. Play it safe and you always wonder “what if” and live a life of regrets. I hate failure too, but every time I get rejected I just chalk it up to that business has no interest in really being successful. Lots of opportunity these days and tomorrow is another day. Companies have never fulfilled me, but the opportunity to grow and build on ideas fulfills my goals.

    1. Not experiencing the “what if” is right up there with the main reason I want to try. I knew if I didn’t try online entrepreneurship FT in 2012 I would always wonder what if! Now, I can rest better going back to work if I want.

  62. We’ve all had tons of failures, so try not to beat yourself up. I got rejected for a promotion I wanted and really deserved, have been rejected from well over a hundred job applications, failed at scholarship applications and music competitions, and the list goes on and on.

    You’ve had a huge list of accomplishments, which is awesome. And while failure does suck, it’s good that you are able to use it as motivation and to continually find ways to improve and learn new things. That in itself is a huge success!

  63. A few thoughts about people not saving enough (in addition to all the reasonable ones mentioned in the article):

    – Capital is cheap and relatively easy to access in the US and developed countries. Why save up to afford the things you want when you can easily tap your future earnings with credit today?

    – Savings is a bit of a catch 22 in the sense that I personally choose to save and invest for all the reasons commonly mentioned on this site. BUT… I would prefer (reductio ad absurdum) if everyone else in the entire world spent everything they made and more since consumer purchasing is what drives the value of my investments over the long run.

  64. 1 million buys you 25K? how do you get that number?

    The way i see it,

    A 4% withdrawal rate is 40K which if you only take from 401K up to the 15% tax bracket and the rest from investments you get it without paying taxes.

    Unless I’m missing something…

  65. I’ve been failing upwards my entire life..due to feeling inadequate. It’s strangely been leading to some really great opportunities. I keep thinking I’m not “good enough” to do X Y and Z, and then those opportunities pop up. But it all started because I’ve always felt inadequate. I do think if you start off having to work for everything, you do have sort of a chip on your shoulder that makes you hustle harder. I have a friend who is a multi-millionaire who told me he never received much help when he was starting out, and was sort of an outcast (always got into trouble growing up), and just hustled and made it happen. So I think there is definitely truth in what you are saying.

    1. +1

      Early adversity is a common thread in a lot of real-life Horatio Alger or business success stories. Adversity can be a gift. It puts things into perspective and provides motivation.

  66. “I have not failed. I’ve just found 10000 ways that won’t work.” – Thomas A. Edison

    I’m not sure everyone would agree with some of your “failures” Sam. I mean, growing a site only 50% a year after 120% growth in previous years is not really considered failure in the corporate world (growth has to slow eventually). It sounds more like type-A overachieving not quite reaching the outrageous goals you set for yourself.

    But you’re right, any goal not achieved feels like failure regardless of how successful you are compared to others.

    1. Accepting a 50% growth rate from a 120% growth rate the year before is a slippery slope. Because once you accept 50%, then you’ll accept 20% the next year, 0% the following year, negative, and then a complete loss one day. Complacency is what kills progress.

      That said, it’s also important to ask how much progress one really needs. Further, it’s about what you compare progress towards. These are challenges I face at least every year when I review my year’s performance and plan for the future.

      BTW, nobody has ever said I’m a type-A overachiever, so thanks! All have said type-B, hang loose guy on the courts (someone said this yesterday wondering why I always seem so relaxed and saying that I looked lazy on the court), and at work (clients always wondered why I wasn’t more stressed, especially hedge funds).

      The one thing I love is a challenge. The more something or someone can kick the shit out of me, the better. I admire high performers. And I love to compete and get things done. Doesn’t everyone?

      1. I think most businesses have taken a hit since last year. My sales drop probably 40% which is huge when I have over 20k in rents. Anyways, sometimes you gotta grind and make things happen. Is not accepting, because if you are working the same or harder and you still went down it may not be entirely about you it could be the market or it may be time to navigate into to other adventures. Who knows! 100+ year businesses go under, what makes you think they want that to happen or that they let go? its market change and as a person you can make a drastic change, when is a corporation it will go under.
        People are making money on the internet today like people were making money in stores in the 1900s. All smaller channels that we see today people making money on the internet will start to make less and less in the upcoming years. Just like Brick and mortal today. My reasoning behind is lets say for example, you sell clothes online and you make good profits 100k a month! right now there are thousands making 100k a month selling clothes online right? lets say 2000 in the world ( it may be a small number but w/e) whats going to happen when 200k people start the same business? those 100k a month become 10k a month ( which is still a good number) but hey the market will continue to expand ( how about 2 million people selling clothes online?) thats whats happening to retail. In my city of 70-80k people there was 1 walmart 3 years ago, now we have 3 of them, can we have 4 or 5 yes! but, sales will continue to drop the more they open. And mom and pop stores are almost extinct noways. hmm Dollar stores in my city alone there were like 2 total 10 years ago, now they are like 15 between dollar tree, dollar general, general dollar etc.. Population growth?60K to maybe 70k-80k now…

        So, yes! If you need more you do what you gotta do and get more! there is always more out there! Btw, my comment wasnt negative is just something thats happening! I now own 7 stores, I know in 3 years I need 12 stores to make the same money as today! so, don’t be scared the internet is still booming for the next 20 years! enjoy.

  67. There’s an old quote, not certain who said it first, that the easiest way to not fail is to never try. So you’ve failed. At least you tried! Hold your head up! You’ve accomplished more than 90% of America!

    1. But what about that other 9% to 99%? :)

      I’ve always had a goal to try to get to the top 1% for things I care about eg income, tennis, blogging, etc. Might as well if I’m going to try!

    2. Try. There is no try. It is do or do not. Try is the mantra of those that do not see the true value in their failures and do not fully learn from them. From failure you learn what not to do and possibly learn what to do better next time. Try is for those that quit and choose not to continue. If you want something bad enough you will get to it. Try is the ” it could have been me”s of the world that eventually give in or give up. This may come across as harsh but I am more of an all or nothing kinda guy. You give it your all and continue to do so until you get what you are truly and honestly looking for. Otherwise try is you not knowing what you truly want in the first place. Try is you just wanted the experience of the effort and not the actual end goal. I see this often. People think they know what they want but are not willing to commit to it and risk it all. By nature we avoid pain. Pain is inevitable. Make pain part of your reward. That may sound crazy but it is a badge of your success.

  68. Good stuff, Sam. I look around at folks coasting through life (ignorantly) wondering how they sleep at night. Most would consider me very successful, but I’m always working. Sure I take a break when I feel like it, take a nap when I want, but I’m always hustling. While most people were enjoying doing absolutely nothing the last 4 days of Thanksgiving weekend, I put in probably 30+ hours. I did it with a smile, too, knowing my wife and I are set if we keep hustling for 7 more years (I’m 48)… and I’ve been hustling since 16.

    Keep hustling, Sam, and keep on encouraging others to hustle.

  69. And on failure. . .

    This isn’t universally true, but as a coach and investor, I want entrepreneurs who have experienced failure. It’s a myth that successful business leaders never fail. It’s the ability to deal with failure, learn and find an alternate route to success that defines character and improves the probability of success. I don’t want an entrepreneur to experience failure for the first time on my watch. I love the Lean LaunchPad process of customer/peer discovery before operational launch. The guru’s talk about moving from faith-based to fact-based market insight. I call it, “non-destructive business model testing” (c) because the alternative of guessing and getting it wrong is destructive of time, money, energy and relationships. Otherwise known as failure.

    1. +1

      If you haven’t failed, you aren’t trying hard enough.

      When I interview people for anything – business, personal, etc. – I want to hear about people’s failures. It shows me their ambitions, and it shows me their strengths and weaknesses. When you can fail, and tell me why you failed and what you learned from it, you’re someone I want to invest time in learning more about, and likely someone I want to invest my money in.

      Failure teaches us our most important lessons.

  70. Interesting observations on the changing nature of incubators/accelerators. These broad terms cover a variety of practices, objectives, virtues and sins.

    Venture Capital money in many areas of the country is looking for proof of market traction rather than just cultivating an idea. Angels and crowdfunding are options to VC money, but early key customers are often more important than early equity to startup success. This means bootstrapping and cultivating customers has to be considered rather than just running after investors.

    A few hot spots like Silicon Valley still seem focused on scale (e.g., traffic or eyeballs) with a willingness to figure out monetization later.

    Incubators with a real estate focus (fill my building, cover the incubator’s overhead) judge by a “startup’s” ability to pay rent. Ability to pay generally requires current cash or cash flow.

    Accelerators applying the Eric Reis’ Lean Startup methodology like National Science Foundation’s Lean LaunchPad (Steve Blank, Bob Dorf et al.) look to cultivate market insight as the foundation for getting the business model correct, before worrying about writing a business plan. You can write a great business plan for a terrible business model if you’re not careful.

    Competitive selection models do tend to consider evidence of prior success, whether awards, grants or investors.

    If you’ve gone to the work to prepare a pitch, develop a business model canvas, or business plan, and you strike out on your first try, there are a multitude of venues to keep trying. It’s like a bank, just because the first one says, “No,” doesn’t mean the next one won’t say, “Yes.”

    You do want to match your business to the history and interests of the incubator/accelerator program. Their connections and insight are as important as their money. An incubator that is an expert cultivator in med tech may not have as much insight into online marketing to consumers.

    In fair disclosure, I am a certified Lean LaunchPad instructor and teach and coach startups for the NIACC John Pappajohn Entrepreneurial Center and the University of Iowa’s, Tippie School of Business, Iowa Venture School (an NSF I-Corps accelerator). One of my mantras for startup clients is that success is not about who you know, but who you get to know. (Stolen from LBJ’s secrets of political success.)

    1. It’s hard to blame the incubators for accepting and “incubating” already proven businesses. The incubators don’t want to fail or look bad either.

      The only area of bullshit I see is one company who got into the program I applied, and then they joined another incubator the next year, taking the spot of a company that has never gotten the same tutelage. To the company, it’s free money so why not. To the incubator, I think it’s a gutless move.

      But again, fear of failure is a great driver to just accept as late an established early stage company as possible. Like adopting a 17 year old!

  71. I was laid off from my first job out of college. And I was probably better off not spending the next few years earning less than $30K at a record label. But that failure has stuck with me for every job I’ve held since. And I save because I know I’m never safe. I pick up side jobs for added financial security.

    I can definitely empathize with your mindset, Sam. But I think you’re being overly hard on yourself. I hope the time in Honolulu gives you a chance to clear your mind and recharge.

    1. I wrote this post right after I found out I got dinged by the incubator. When emotions are high, it’s best to write. Such a cathartic and healthy exercise.

      Thanks for sharing your failure!

  72. John C @ Action Economics

    Recent Failures:
    1. Failed to secure a perfect 6 figure job that was local. I was overconfident that between my experience, education, and connections I would be a sho-in, but I didn’t even get an interview, I found out a month after applying that the position was filled internally.

    2. Failed to negotiate a meaningful raise at my current position, but on the bright side I still have a decent job

    3. Failed to hit my earnings goal for my blog…

    But with failures, you also need to look at the successes:

    1. I exceeded my savings rate goal for the year, bringing me in at over 33%.
    2. I increased my total income by over 25%, mostly by working more
    3. I increased total traffic to my blog by 500% (roughly 1,000 page views/mo to 5,000 page views/ mo)

    All in all the good balances out the bad! Thanks for sharing, we all have failures and set backs, but for the most part we tend to advertise our wins much more than our losses.

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