Be Unapologetically Fierce About Pursuing Your Dreams

Never let anything get in the way of pursuing your dreams. If you do, you will regret it. As I wrote in my Wall Street Journal bestseller, Buy This, Not That, “You will regret more of the things you don't do than the things you try!

Remember that annoying kid in school who made fun of you for getting a good grade? The goal was to make you feel bad at doing well so he wouldn't feel so terrible about himself.

I had plenty of encounters with such kids growing up at my public high school. In the end, I brushed their mockery aside. I decided to be the best student possible to have as many opportunities as possible.

The Kids Who Teased You Continue To Do So As Adults

I thought the mockery would slow down as I got older. However, it seems to have amplified due to the internet. Most recently, I was criticized for my idea of starting and keeping a family business going. My idea was to provide options for my children when they graduate from school. The world is a harsh and competitive place.

Andrew from Vancouver, who is 29 with no kids said I was “obsessed.” Another guy named Li from somewhere in Asia, who is also 29 with no kids, called me “crazy” over e-mail.

I'm not sure why people without kids feel like they know about the pressures parents face. But it's a curious phenomenon I've observed since I became a father.

Why is planning ahead and offering an idea to help other concerned parents considered obsessive and crazy? Besides, what kind of fool would sell a cash cow that is enjoyable to run in a low-interest rate environment?

In my mind, it is stupid not to plan for the future. Globalization increases competition for jobs while technology reduces the number of jobs required to produce. My decision to potentially give up on early retirement and go back to work due to inflation and economic uncertainty is logical. Yet, you'll read tons of comments making fun of me for the move. How strange.

Paradoxically, life is getting easier and harder at the same time. As parents, we must fight for our children until they can independently fight for themselves.

Always Keep Pursuing Your Dreams

There are a lot of dreamers who read this site looking for a better life. But due to the fear of being ridiculed, they hesitate to pursue something different. Or they are too afraid to put themselves out there for the world to judge. What a shame!

Even Andrew, my critic, decided to shut down his website after I visited it. I just wanted to understand where he was coming from. It's probably a good idea. His employer would be none too pleased reading his article about how laziness was helping him reach retirement sooner.

It's OK to be obsessed with the things you care about. It doesn't matter how whacky your goals may be. The people criticizing you are too afraid to try themselves. They wished they had your courage. They're fearful that one day you might succeed, making them regret their lack of effort.

It takes courage to get out of suboptimal situations. Just know your financial independence number is not real if nothing changes.

Finding New Motivation To Continue

I'm revisiting this topic because the pandemic really put a damper on my energy and motivation. For example, no longer do I prepare a post the night before after a long day with the kids. Instead, I wake up later and take my sweet time. Toward the end of the pandemic, I really burned out because I spent so much effort marketing my book.

As you grow older, there's generally a natural decline in motivation. You've accumulated more wealth, achieved more goals, and are more aligned with your life philosophies. The quiet quitting movement becomes more appealing.

However, I've found that criticism helps recharge my motivation battery. Therefore, if you are a naysayer, I'm asking you to lob some new criticism my way! It will help prevent me from slacking off too much. After all, I'm a father of two young children. I need to stay in shape and provide for them until the year 2037!

Here are five examples where I was given the thumbs down. However, due to an unwavering desire to keep going, I was able to prove my detractors wrong. I hope at the end of the post, you share some examples of how you overcame criticism as well.

Pursuing Your Dreams By Overcoming The Naysayers

1) Getting Benched In Tennis

In 2010, there was an arrogant, overweight guy named Chris who captained a USTA 4.5 level team I was on. He seldom let me play because he thought I wasn't good enough. This was even though I was beating the other starters on the team. Every time we'd get on the court for practice he would make fun of any mistakes I made.

One day, I had enough and told him to play me in a singles match or shut up. He accepted the challenge and I ended up beating him 6-4, 4-6, 6-3 on a cool evening over two-hours. The next day he went to the hospital for pneumonia and stopped playing for five months.

During the district playoffs, he decided not to put me in the lineup. He put his buddies in instead and we lost. Given I didn't receive the playing time I thought I deserved, I joined a different team a year later. My new team and I ended up beating Chris' team during the playoffs. No victory tasted so sweet. I credit Chris for keeping me motivated to keep practicing and keep eating right.

Today, he's still a 4.5 level player while I got bumped up to 5.0 for five years. Fight on!

2) Making Fun Of My Blogging Endeavors

Back in 2009, I told one of my work colleagues, Robert, about my new blogging endeavor. At the time, I was writing a daily investment newsletter recapping the markets and really enjoyed the process. Maybe blogging might be a natural next step for me after finance? I was hopeful.

Instead of being supportive about pursuing my dreams of doing something new, he made a funny face. H then started typing on an air keyboard in mockery. I was taken aback because we were at a team bonding dinner and he was my junior.

What kind of emotional dummy makes fun of a senior colleague's hopes? Further, I was to be interviewed by the promotion committee to help determine his upcoming promotion.

Not only did he not get promoted that year or the next year, but the firm also shipped him off to NYC to a different department. The department later downsized due to the rise of electronic trading. He's still at the same firm doing the same miserable job, but for less pay.

This site, which he made fun of, is now the best thing I've ever done financially. It earns at least 2X more than his job with 70% less work and 90% less stress.

If I one day want to sell it and do something new, I can for a nice chunk of change. If he wants to sell himself one day, he can't, unless he wants to try the black market for body parts.

His air keyboard mockery was one of the best fuel that has kept me going.

Related: The 10 Best Reasons To Start An Online Business

3) Writing A Severance Negotiation Book

When I first published, How To Engineer Your Layoff in 2012, I heard an endless cacophony of doubters. Readers and other bloggers said the idea was stupid. The most frequent things mentioned were, “why would anybody pay you to get laid off,” and “that sounds sketchy and not something I'd do to my company.” 

Today, I still hear the doubters even though quitting your job and leaving your colleagues in a bind is selfish. It is dumb to not try and negotiate a severance from a job you planned to quit anyway. If you plan to retire early, then all the more reason to try and negotiate a severance.

Eleven years later, I've received countless personal e-mails from readers telling me how the book helped liberate them from a bad job situation. One woman told me this summer she walked away with a $65,000 severance. She would have been fine quitting with nothing.

Another guy told me he not only walked away with over $100,000 in severance because he was a co-founder of the company that got acquired. He also sent me a glowing article an online publication wrote about his transition to angel investing. Nice work Eric!

One doubter confessed he was let go with only two months of severance after eight years of work. I had to break it to him that his two months of severance was not severance. It was actually mandatory WARN Act pay. He sadly got zero severance and would have known this had he read my book.

The book generates a steady stream of passive income to the tune of $40,000+ a year. The book is in its 6th edition and is a passive income generation workhorse!

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

Related posts:

The Inside Scoop On How One Man Negotiated His Freedom (a reader's story)

How To Negotiate A Severance As A High-Performing Employee (the detailed story of how I helped my wife negotiate a six figure severance at 34 as well)

4) Seeking Early Retirement

The natural transition after negotiating a severance is to take some time off, find a new job, change industries, start a business, or retire. I decided to permanently leave corporate America at 34 and focus on my writing. Writing is what I've loved to do ever since I was a middle schooler writing international pen pal letters while living in Malaysia.

Of course I had my doubters. Leaving a high-paying job before your highest earning years sounds foolhardy. But the funny thing is, many people in the finance industry back then wanted out as well. They just didn't have the courage or the plan to leave. If I later realized I needed more money, I could have just gone back to work.

Given it was my financial well-being I was putting at risk, I was my biggest naysayer. You can see every early retirement stone I turned over in the post, The Dark Side Of Early Retirement.

However, thanks to publishing this post two years before making a move, I was able to face my fears and gain some perspective from hundreds of people who had made the same move.

If Andrew and Li were around back in 2010, they'd probably also think this amount of planning was obsessive and crazy. But this amount of self-reflection is what gave me the courage to change my life for the better.

Thinking about the negatives of early retirement was the catalyst for coming up with the idea to negotiate a severance. Negotiating a severance package that paid for five to six years of living expenses enabled me to try new things without fear of financial ruin.

Not a day goes by where I'm not thankful for extricating myself and my wife from the matrix. If I had listened to people who told me I would be stupid to leave banking, I'd probably be incredibly unhealthy, stressed, and unhappy right now.

Pursuing your dreams is worth it. After retiring early in 2012, I look back and smile at all the things I tried.

Related post: How A Couple Can Retire Early

5) Overcoming The Internet Retirement Police

About 18 months after I retired from the finance world, I no longer said I was retired. It felt stupid and disingenuous to say so. I wanted to consult part-time for a couple of fintech startups in San Francisco to see what all the fuss was about.

After getting my taste of what the startup world was like for a couple of years, I set my sights on becoming a teacher. I've always enjoyed mentoring kids and young adults. When a high school tennis coaching position opened up for $1,100/month I decided to interview for the position.

After two years of coaching, we won the Northern California Sectionals championship for our division. This was the first time in the school's 50-year history. It was a proud moment and a wonderful feeling being a part of the teaching community.

Remember, when people doubt you, just keep winning!

The Internet Retirement Police Trying To Arrest Me

After winning, I sent out a tweet wondering if there were other teachers who wanted to share their financial journey story on Financial Samurai. My goal was to help bring more awareness and respect to the teaching community since we were relatively underpaid. In the tweet, I also mentioned I was a teacher.

This is when the Internet Retirement Police tried to bash down my door and say that I wasn't a teacher. They tried to pigeonhole me as something else, even after two years of coaching. In the end, I utilized their criticism to write more interesting posts. We won another Northern California Sectionals championship the next year! It's interesting, but the IRP tend to mostly be the most privileged people around!

I'm not sure why people feel the need to tell others who they are and what they should do. But I'm appreciative of their criticism because it enabled me to become a nice part of the school's history. Maybe, when my boy turns 13 and is applying to high schools, my school might look upon him favorably. After all, he's already ben a part of the family for so long.

Related: Sweet Dreams Of Becoming A Millionaire Again

You Will Regret More Of The Things You Don't Do

The #1 reason why more people don't do the unorthodox is that society has a terrible way of accepting the unusual. People who are able to freely pursue their interests are the luckiest people on Earth. It's sad pursuing your dreams is often faced with ridicule. But that's society.

Conversely, people who not only don't pursue their interests, but also try to take others down, are the saddest people who will forever wonder why they never tried.

To all the dreamers out there who want to do something different, please go for it! Don't let the naysayers deny your progress. Be unapologetically fierce about pursuing your dreams!

Make Better Decisions And Reach Financial Independence Sooner

You’ve only got one life to live. So you might as well arm yourself with as much knowledge as possible! My new Wall Street Journal instant bestsellerBuy This, Not That is here to help you build more wealth so you can better live the life you want.

Not only will you learn how to achieve financial freedom sooner, you’ll also learn how to make better choices using my 70-30 decision-making framework. Start reading it today!

Buy this not that Wall Street journal bestseller

Once You Have F You Money, It's Hard To Tell Others To F Off

For A Better Life, Be The 1% In Something, Anything

Three White Tenants, One Asian Landlord: A Story About Opportunity

Overcoming The Trough Of Sorrow: Defeating An Emptiness Inside

Reader Questions And Suggestions

Readers, what makes you stop pursuing your dreams? Given many things today were once whacky and new, why don't more people experiment with different things? What became of those annoying kids in grade school who made you feel bad about your efforts? Why is pursuing your dreams so hard?

Listen and subscribe to The Financial Samurai podcast on Apple or Spotify. I interview experts in their respective fields and discuss some of the most interesting topics on this site. Please share, rate, and review!

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98 thoughts on “Be Unapologetically Fierce About Pursuing Your Dreams”

  1. Mike from NH


    Like you, I won’t apologize for my success I worked hard to become the best I could be in my field of employment. My wife and I lived below our means while raising two beautiful girls. We spent money on the things we valued, educating our kids as an example, and eliminated meaningless spending.

    My wife decided give up her career to be a stay at home mom. I’m forever grateful

    When our income increased over time we didn’t fall into the “keeping up with Jones” trap. Saved and invested wisely

    Retired at 55 and laughing everyday. Life’s Good

  2. I’m not sure why you get trolled sometimes. Probably because you have strong opinions that sometimes go against conventional wisdom. However you are always respectful, always back up your opinions with facts or personal experiences and are kind to your commenters. But lets face it, you are very successful and very talented and that makes you a target for jealousy. That is a sweet tennis victory. I was dropped off a tennis team that had “too many” players. I joined another team and my partner and I smoked my former team’s best two players in a match. They did try to take credit by saying they had taught me how to play better!

  3. There is no shortage of opinionated people with big mouths trying to tell you what to do these days. It could be friends, family, teachers, bosses/ supervisors etc. You have to keep believing in yourself no matter what these people try to tell you. I’ve had a few unfair situations happen to me that ended up working out well for me after the fact. And to see those responsible get their payback through karma was definitely sweet! Appreciate your efforts with the blog Sam.

  4. Have you ever heard the “crab in a basket” analogy?
    I don’t want to type it all out right now but I’ve seen it time and again.
    A guy I worked with is exactly what you describe here. Always a victim, always squelched. Even my genuine attempts to help him in his career (i was a consultant he was fte) were taken as threats.
    The times I had to restrain my laughter came when a new widget was introduced to market and I’d have to listen to him all day about how he thought if that years ago and his idea was stolen.
    He exerted more energy than anything I observed to:
    -trying to find weed,
    -sharing racial slurs at the office as humor,
    -and undermine others as his moving-up strategy.
    Applied appropriately, selfishness is actually a virtue, but so few can get their one dimensional mindset around that.

    Great post, Sam. I’ll tell you more about the analogy over an ale sometime. Bummed I didn’t get a chance to meet you when I was living there.

  5. Since forever i knew normies wont never understand how the game is played. They dont have “hardware“ to even think for themselves.

    So i keep me first — always — and my dreams in my heart with action and use all laughs as fuel.

    I guess i’m doing good for the last 15 yrs. Sleeping and making dough online. Meanwhile normies still waking in the morning to for the men.

  6. Haters are gonna hate. Agree 100%

    If you keep thinking about something you want to do, there’s no reason not to do it.

    I’ve never regretted anything I’ve actually done, it’s always the things I didn’t do. Vacations/travel/sporting events included.

  7. It just sucks that you HAVE to deal with things like this. I remember in my rotational class, I told everyone how retiring early is totally possible, as young as in your 20’s or 30’s. This one guy would publicly mock me and laugh at the idea of early retirement.

    Saying things like “hahahaha you think early retirement is possible, look at you!”. It sucks that factually incorrect statements like that are legally allowed to be said.

  8. pakithebanker

    Great post! I really enjoyed this read and it made me think about my dreams and passions. Unfortunately, I have been living to the expectations of others (friends, parents, etc.) and find myself in a depressed and miserable banking job.

    I took a step back after reading this article, and do not have any passions or dreams anymore. I am 28 years old and feel depressed about my future. I have no idea what my passions are or what I can do to find a fulfilling career path.

    Any advise? Anything would be helpful. Thank, Samurai.

    1. David @ Filled With Money

      Are you at least pursuing FIRE or have you thought of taking off a month away from work?

  9. Read Teddy Roosevelt’s “Man In the Arena” speech if you haven’t already. It’s perfect for this conversation.

  10. Hello Financial Samurai,

    I’ve been following your site for a few years now. The fact that you kept your head above the ground and followed your dreams is obviously what’s provided you and your a family a lifestyle that many people can never fathom. There will always be naysayers in all that any of us do, but unfortunately some would rather put someone down than do the work to improve upon their lives. I’m certainly not up to your pedigree, but I can honestly say that the information that I’ve gained from your site has been an integral part of changing my financial outlook.

  11. “society has a terrible way of accepting the unusual. People who are able to freely pursue their interests are the luckiest people on Earth.”


  12. Sam

    This post is reflective of my comment to you about how if you want to get even/revenge with an enemy/naysayer just be more successful than they are!

    Clearly you have done well at placing those individuals in their rightful resentful place!

    Good on you for doing so, everyone should dream big and act on it, or wallow in mediocrity and self pity!

    I used to regularly council Marines on this very topic!

    “Misery Loves Company”, Author Unknown!

    Marines trying to go to college at night in the late 80’s were routinely harassed to go out drinking rather than focusing on their college courses!

    It was clear to me that they were more interested in your failure so they could continue to say they knew better than to try!

    I learned early in life that most people are extremely lazy but for some reason want higher accolades and organizational standing than those willing to actually work hard to earn them!

    It’s like my previous postings that describe how wealthier people will always interject their family standings as the benchmark others have to achieve prior to being allowed at the table of discussion!

    I grew up poor and am now wealthier than the majority of my colleagues who still look down upon me because my wealth came from blue collar labor work and personal discipline and theirs came from pedigreed parents thereby allowing them to imagine themselves as deserving a hierarchical/societal position above myself!

    Truly it’s comical talking to entitled idiots who want blue collar workers to pay for their student loans!

    What a disgusting group of educated idiots to even imagine that their acceptance of incurred debt for an education that allows them access to best paying jobs in the country should be forgiven by having the less fortunate who could not even imagine going to college pay for it!

    Only a Dumocrat or a Communist could come up with this for an actual debatable discussion!

    I would rather the government pay for outstanding home loans than outstanding student loans!

    Your message is Spot On!

    Above Average people carve out their own path and usually it goes straight through the thickets and thorn bushes of naysayers and evil doers (Just got to Love George Bush jr.) Which this reminds me I earned my first $20.00 at 10 years old, cutting out a massive thorn bush near one of my childhood friends dad’s home.). One of the other boys who did not work as hard only got $5.00.


  13. Woohoo! You got me cheering for you reading this post. Way to go! Some people get completely crushed from naysayers and critics. So I love how you use them as fire to fuel your motivation and prove them wrong.

    I also couldn’t stop laughing when I read your line on that air keyboard naysayer, “If he wants to sell himself one day, he can’t, unless he wants to try the black market for body parts.” You sure proved that guy wrong!

    When I was growing up, I used to get really defeated when people were mean to me or said rude things. Slowly, I started to grow out of that as I gained confidence. Developing a bit of a competitive streak helped me work harder as well.

    It is interesting when you say your biggest naysayer was yourself. I definitely struggled with this a lot. And still do sometimes now. I love my mom, but she has always had a defeatist mentality. So often she would say things like, “Oh no, I can’t do that,” “I’m not smart enough,” I don’t understand xyz” etc. It really rubbed off on me subconsciously so that sometimes I automatically think that too when I’m facing a challenge or something new. Now that I’m aware of this, I’m trying to break out of this default and really help my kids grow up believing they can do anything with enough practice, time, and dedication.

    1. Hi Untemplater. I am seeing that the women of my mother’s generation (I think me and you are similar ages, 35) grew up in this weird era of gender shifts. They were supposed to be independent, but not really. Yes, free love, but really… a traditional marriage was still the norm.

      Many, like my mother, were left divorced, when they were raised in a world with so few divorces… “In 1958, the [divorce] rate even slumped to 2.1 [per 1000 Americans], with 368,000 divorces. ” The divorce rates then went to 5.1 per 1000 Americans by 1979. And “TIME reports that older generations continue to get divorced, but the decline [ to a rate of 2.9 Americans/1000 in 2017] is due to the smaller amount of millennials getting married.” (in the fifties )

      So, what I mean is, they were conditioned to expect to be married, then they have been divorced and left, and I often hear the narrative for that generation of women being “I don’t know how to do something.” My mom is 65. From my observations, I do not see that mentality from women who are 55 and Under. (I am not sure about the gradation in confidence from 55 to 65). And I am not saying that your mom is divorced, though she may or may not be.

      I think it’s more of an idea of gender stereotypes that women were born with, and the immense change that our society has gone through in their lifetime. And my main comment is just to agree with you. I hear my mother (and other of my friends’ moms) sound just like yours. And it makes me bristle, and also think about why.

      And also, you nail on what could be a solution: Teach your kids they can do anything. And also, open their minds to think big and take action. Good luck to you!

    2. Untemplater,

      My mother said the same thing all the way up until her death this past October!

      But she was interviewed by Barbara Walters and testified before Arlan Specter and other congressional leaders in a hearing that eventually led to Juvenile Justice reform across the country!

      Dropped out of high school at 15, had 6 kids before 21, during the winter of 1977 left with all 6 kids in tow an abusive disgusting husband/father, got hired as a prison guard, got her GED, took some college while working 2/3 jobs and spent every dollar she ever made on her children, grand children and great grandchildren up to her last breath!

      Only ever preached/lived with Integrity regardless of the fact that every monster (Male and Female) within a 4 county radius attacked and took advantage of her and all of her/our family!

      She may have feigned weakness and ignorance but she is by far the most amazing person of strength, intelligence and dignity I have ever even dreamed or imagined could exist, let alone actually met!

      She is absolute proof that God exists and that he loves the World immensely as there can be no other answer for his creation of her!

      I reflect daily on my weaknesses and talk to the man in the mirror about taking actions to correct my failings!

      It’s amazing the character flaws you can change once you acknowledge and take concrete actions to correct them!

      One must have faith in thyself as no one not even your siblings wish you more success than themselves!

      “Dream Big, Take Action, Succeed!”

      Good luck in all that you wish to accomplish!


    3. Thanks! Yes, our parents actions and attitudes really do rub off on us.

      We must be careful how we act around our children. They are always watching and observing, even if we don’t think they are!

  14. LazyGardener

    Steven Pinker and Judith Harris say parenting has almost no influence (0 to 10%) in shaping children’s behavior. Rather, genes and chance events in life have far more influence in an individual’s personality. If this is true, which I agree to large extent based on my own experience, parents should just relax at night and not worry too much about teaching them lessons or morality.

    What do you think?

    Steven Pinker – Parental Influence On Personality

    Radio Interview with Judith Rich Harris

    1. I think nurture is closer to 50%, based on my experience getting nurtured and seeing how the nurture affects my attitudes and thoughts today. My drive is driven by seeing a friend die at the age of 15. He was the most popular kid in school and had so much potential. I think about him all the time and realize that every day I live is an opportunity to do some good he never got a chance to do. His death made me appreciate life and NOT WASTE time or my abilities. If I can, I must.

      What happened in your experience that makes you believe parenting has no affect?

      It would be interesting to see how being an absentee parent is and see what becomes of the kids. But are you willing to be absent and take that risk?

    2. LazyGardener

      I would have to agree with Sam on the 50% unless the child’s college is funded by their parents, then you are probably right about it being 10%.

      My mother had her son/my brother arrested for theft of a $5.00 toy when he was 15. He hung himself in his jail cell that night.

      A few years later I was 14 and stole a bike, I was scared the police were going to come to the house as the boys who I gave the bike to had gotten caught with it and “Ratted me out”!

      When I told my mother she just got mad and said she hoped they would come and take me to jail and that she wasn’t going to stop them!

      I “sobbed” myself to sleep that night and have never stolen again!

      Once when I was 15 my mother woke me up in the morning around 2 am and asked me if I was smoking Marijuana!

      I couldn’t see straight because I was blinded by the light. I told her that I had not been smoking Marijuana and she just said that she wasn’t going to to tell me not to smoke it but that she would just hope that I wouldn’t!

      I probably smoked Marijuana about 15-20 times prior to my 18th birthday but that interaction when I was 15 eventually weighed on me enough to quit for good! Allowing me to make it into the Marine Corps and staying clean the rest of my life!

      My mother once worked three jobs at one time and for most of my childhood life she had two jobs!

      Her dedication to work hard in order to feed 6 ungrateful derelict children became my mantra for life! At 16 I took my first job on a horse farm at $4.00 an hour for 75+ hours a week I continue to work 50-75 hours a week without flinching or complaint.

      She only ever preached to not lie, cheat or steal!

      Something you will see by my postings I continue to preach as a path to success and eternal salvation!

      A parent has more influence if they are not so wrapped up in their own interest than the development of their children!

      Lazy parents have 10% influence and out of guilt they pay for their children to continue being childlike in adulthood!

      Adult children incapable of personal responsibility and sacrifice for others are now living at home at the highest percentage in American history because of cowardly parenting that accepts defeat of societal liberalism!

      Collective Cowards accept the defeatist norms that make up the majority of lazy parents, capitalist individuals are the exceptional parenting achievers!

      I do not have children so who am I to say which parents are nasty and which ones are exceptional?


    3. Amanda L Gant

      I agree with Sam. My mother taught me how to read, and she read with me from birth until, well, forever. I could read before I have memories, and definitely before the age of three when I do have memories. That opened up so many avenues of success for me. I was learning about places from around the world at the age of 4 by reading encyclopedias and any book that I wanted. We were not rich, I could not have any toy that I wanted, but I could have any book! I do think the brain is open very early on, and that if parents (or any caretakers) give true attention and love to the kid, that the kid will react to their highest potential, and that kind of confidence follows the kid.

  15. Definitely, many people will frown upon your dreams. Part of it is that since they feel that they can’t accomplish it, you can’t either (or shouldn’t – that way you don’t rise above them). It’s the crabs in a bucket sort of thing. Just imagine how many people’s dream were crushed through this way and how many unfulfilled potential went to waste.

    I am not a great writer, but I started a blog anyways on the advice of Sam. It’ll probably never be big nor gain much traction, but if I can help just even a few people on their path to FI, I feel it’s a worthwhile pursuit. My hopes for myself is that I can become a better writer and be able to come up with focused ideas.

    Never knew how difficult it is to come up with original content for a post until now. Don’t know how you keep doing it Sam! Thanks for the motivation and your work.

    1. If you can speak forever, you can write forever! Good luck with your blogging journey. Just got to make it through the first year with a consistent schedule, and things get better over time. The question you have to ask yourself is: how much are you willing to sacrifice in the short term to earn X amount of side income or never have to work for anybody ever again?

  16. Matt Carter

    Be obsessed or settle for average results. If you want extraordinary results regarding the things you care most about you have to be obsessed with them. The only reasons people will criticize obsession are people who were obsessed with something and it detracted from other areas of their life and they want you to avoid that negative result. The issue was not their obsession but their lack of obsession in the other areas of their life that were negatively impacted. The other reason you described perfectly, they don’t want to see you succeed and feel bad about their lack of effort.

    Great post Sam.

  17. Love this post!! I am from Sweden where an incredible consensus-seeking stay-in-your-cubicle type mentality prevails that makes no one even able to start thinking about retiring early, much less try to actively do it.
    Reading this motivates me even further to follow my ambition and let nothing stop me on my way to retire in 7 years from now, so thanks a lot!!

  18. I have two young kids and your article spurred some conversation about starting a business with the main intent to educate and train my kids about business and finance. Experience in the real world in combination with traditional education is a great formula for success.

    Your article was thought provoking, inspirational, and helpful.

    I’m shocked that people would waste their most precious resource of time to speak negatively about your work.

    Thanks for the great content, please keep it coming.

  19. Sam,
    Thank you for helping to remember to dream!Our culture is filled with people that will tell you ” you want to do what”.

  20. Ok, now I’m ready to go out there and crush it!!!

    People will always be jealous and try to bring you down. I love this idea of channelling negativity into greater drive! I have also learned that sometimes I do better when I only tell my “crazy” goals to friends I know will be supportive.

  21. Lisa;Michelle

    This is very calming.
    I thought it was awesome of you to share how to negotiate severance pay when you'd worked out how to do it for yourself. – No reason for disbelief – you're the example!
    No financial successes to speak of here.
    Almost go in on the local property ladder a few months before the market almost doubled, and kept growing. A relative very knowledgeable in real estate I asked for advise told me, as a single person such a thing wasn't possible / to hard. I just needed to know how to fill in firms and do the process – see if, with finances available to me I could buy my first place to eventually either rent out or borrow against for the next and next and next. My plan being to be out of the 40 hr a week workforce by 45 as, I couldn't handle being around the people you describe here. I come across so many and they crush dreams and increase darkness. Sometimes you can't brush their effects off and life goes bad because they are humans that crap all over other people's dreams — even small ones.
    I am retired at 45 . Have been since 36 when I got fired due to chronic lateness for a chronic illness I was getting medical attention on ( finally!!) the very next fortnight in my annual holidays.
    No real estate financed income – I fell in a dark hole after my relative wouldn't help. Threw the money away gambling, thought there was no point to anything and was suicidal for a long time.
    Some good and bad things happened since then.
    Got granted a disability pension as, it turned out many of my sore body parts we're and actual illness! Can't be cured other than with death , managed most days with medication a good diet enough sun and exercise…… And, a good an ongoing dose of positivity and serves of how to look at the bright/er side of whatever is on my mind.
    Which is why I read You and a collection of other people blogs, doing what works for them and sharing it, here in internet land.
    The real estate thing makes me sad. It was 2 hrs tops out of that persons life and they couldn't be bothered to answer my questions. Now they are old, hopefully won't need to use retirement homes, but if they do, I won't be able to help out as I otherwise would of as, I have no sums of money I could give.
    I'm fortunate I got a council flat a few years ago. This improved my health greatly after about a year of being here. My previous place was full of black mould and my health had deteriated to the point I couldn't keep up with the cleaning of keeping it at bay.

    So now, it's working on my attitude. Friends have just bought themselves a new place and, I had to face all my anger over this history anew and push it aside so I could be there to help my friend. 80%succeeded.

    Keep at all the ventures that work for you Jim and if they don't, round them up, pass them on and try something else. It is very interesting to learn about even if I can't put knowledge to practice


  22. This is great. I read your blog many years ago and some how I started reading it again. You Probably got me hooked when I found out you are a tennis player like I am and worked in the financial industry like I do (former college and now play 5.0 leagues, and teach on the side as a side hustle). You are a true inspiration to some of us. You keep it real and are probably one of the most authentic bloggers on the FIRE Community. Tennis question: what string do you use to save money?

  23. Happy Thanksgiving, Sam.

    Your posts really helped shape many of my own personal financial decisions.

    Continue being yourself and writing great posts.

    Like they say… live and learn and only get stronger….

  24. Sam,
    Your successful story touched and inspired many people like me. One of the ways America is great is that, each of us can pursue our own dreams. Believe in ourselves, work hard, the good results will come eventually. Thank you for sharing the story.

  25. LikeToBeAnonymous

    Hey Sam,

    I have a question. I’m a fairly young minority going through life and dealing with (at times) racist remarks and I consider myself fairly successful so I’ve attracted some criticism in the past. I know that you’ve told readers to be unapologetically successful and I agree, you should fiercely follow your path as long as you don’t hurt innocent people along the way and you do it legally.

    My question is, how do you grow a thick skin while pursuing success? I know that’s the right way to go about it but man, it still doesn’t sting any less, especially when done face to face (which is better than talking behind my back but still). Insight would be appreciated :)

    1. You can build a thick skin several ways:

      1) Aggressively increase your knowledge. The more you know, the more confident you will be. A lot of times, I’m able to simply brush off arguments because I know others have not done their homework.

      2) Learn martial arts / self defense skills. If you know how to strike and defend, you will also have confidence. A lot of people will talk crap behind your back or over the internet. But if they do in your face, you know you can spar.

      3) Be financially independent. See: How does it feel to be financially independent. When you have nobody to report to, you can do whatever you want without fear. Nothing scares a bully more than telling their institution you’ll be having a talk with them.

  26. One thing there will never be a shortage of is naysayers. People with the sole purpose of trying to tear you down. This one time a guy told me I wouldn’t be a professional baseball player, and you know what…he was right. I guess that’s a bad example.

    It would be great if everyone out there offered encouragement but I think some people are too insecure for that.

    I started my website after reading yours for years. So you helped build me up without even trying.

    If anyone out there needs encouragement about an endevour, then I’m your guy!

    Mr. Widget

  27. Sam-

    Just wanted to say thanks for this as it’s huge and a great way to enforce “Sticking to your Guns!” regardless of what others think. For example, some people shun others for non-linear thinking (i.e. blogging vs i.banking, Buy Utility Rent Luxury, etc.) whilst the non-linear achieves overarching goals at a faster rate. Thus the non-linear also receives all the ammo possible to fuel their goal achievement!!

    Also, keep up the audio cast. Love it!

  28. Thank you for sharing your struggles with us. I faced doubts myself over my short career but I didn’t let that define me. Instead, I took doubts as a motivation and work hard to get better.

  29. Paper Tiger

    Sam, this is a great article and resonated with me in many ways. One of the things I’ve noticed about you as I have followed your writings over this past year is that you strike me as an “early bloomer.” In other words, you’ve gained tremendous wisdom and put it to good use at a young age. I, on the other hand, am a classic late bloomer. It just seems like I always figured stuff out later in life before I took action.

    A few years ago I “retired” (forced layoff) at 57 and for the last 3 years have become very active in early-stage investing and becoming a co-founder in my own startup business. It is obviously a much riskier venture than my traditional roles of the past but this is my dream that I now choose to follow and I’m “financially equipped” to take it on so that even if it fails, we will still be OK.

    My Millionaire Interview (#27) was just published on ESI Money in case you’d like to check it out and learn more about my life journey to this point. As always Sam, it is a pleasure reading and commenting on your work!

    1. Hi PT,

      Yes, I think you’re right. I’ve always hung out with older friends and wanted to do what they did ever since I was a kid. The b-school director asked me the same thing when I was applying for the PT program at age 26, “Why apply now?” when the average age was 30-31. I told her, “Why not leverage my degree for a longer period of time in my career?”

      I’ll check out your interview. Thanks!


  30. Hey Sam, I have been a reader for a few years now. While I don’t always agree with you I have always loved how direct you are. I remember one of the first posts I read of yours was the 10% of your salary for your new car. After I had just paid cash for a car that was 25% of my salary I was pretty pissed reading your article saying I spent 2.5 times too much. I thought you gotta be kidding I work hard and have a good job but you are telling me I can’t even drive $10,000 car? I didn’t type any comment but I was definitely on the side of all the haters you got on that one.

    Well fast forward a few years and that was actually some fantastic advice that I wish I would have followed before buying my car. I wasn’t a big asshole four years I was just ignorant with an ego. Tough combo.

    Now, my wife is trying to leave her job to pursue her dreams and stay home with our now one year old daughter. While I don’t fully understand how it is possible to have some pay you to quit we are going to buy your book and give it a go. I certainly hope I’m wrong about this one too.

    1. Hi Grant – Glad you weren’t an asshole about the post then! Folks can disagree. Just do so in a way you’d speak to someone face to face is all I ask. With the way some people comment on the internet, they would get a good ‘ol fashion BEAT DOWN in real life.

      I wonder though, is there something in the water that makes so many 20-something year olds think they know everything and disrespect their elders? I would say about 80% of the haters are always 20-something year olds who have no idea of what it’s like to grind for decades, be a parent, go through a recession, start a business etc.

      I took a completely different approach in my 20s. I recognized I knew little-to-nothing, so I sought out as many mentors as possible who had been where I want to go and listened.

      Just know that EVERYTHING is negotiable when it comes to work and business. Your wife will be fine if she knows how to identify what her employers want and make a smooth transition.

  31. So true we are obsessed about our children future but we want to give them options, my daughter is in law school and told me she wants to own Real Estates rental and be a landlord! therefore she can increase and manage our real estate holdings!

  32. I think your own drive is incredibly strong, Sam. If you were leading a startup venture, I’d give strong consideration to backing you (even though I know the odds for startups to succeed is really dismal). You have a nice balance of optimism, curiousness, adaptability, persistence, empathy and intelligence.

    It’s good to see you paying it forward with your son and the blogging community.


  33. Wait, I thought you said you were getting LESS haters the longer you blog, not more?

    Besides being called crazy by “friends” and family, I’ve also gotten racist e-mails, sexiest comments, all sorts of crap. I just delete them. When people lash out, it really says more about them than it does about you. Happy people don’t need to put other people down. Happy people are too busy being happy!

    Beside, it’s good to be called crazy every now and then. Otherwise, how do you know you’re pushing the status quo? I mean, who wants to be sane and normal. BORING!

    I love this line “You Will Regret More The Things You Don’t Do” because it’s SO true. Whenever I get scared of doing something, I realize it’s my brain training to protect me from failure and ridicule. So unless it’s actually life-threatening, I just do it. If you don’t do it, you fail by default.

    1. The percentage declines, but the absolute number increases as the size of FS increases, and the new topics. Now that I’m writing about family finances, it feels like when I first started writing about investing, real estate, etc. There are more naysayers in the beginning, and then over time, they realize… oh shit, he’s still at it, and oh shit, what he said makes sense now that I’m older, etc.

  34. Hi Sam,

    My daughter, who is a senior in high school, will be attending their schools senior retreat next week. The school asked the parents to write a letter to their child sharing what the parents think is the best qualities of their child. My kid has a 3.8gpa average in all honors classes. She actually takes 2 extra online college classes above and beyond her normal schedule in order to enter college as a sophomore. She made it to state as a 5″1 pole vaulter as well as making it to state on her soccer team as the starting middle defender. At 14 years old she hiked the Teton mountains for 2 weeks as part of a NOLS trip. They had to wipe their butts with rocks and leaves for f…k sake. She does charity and community work above and beyond what there school requires.

    Regardless of all her success, in my letter I told her the thing I’m most proud about is here desire and determination to fulfill her dreams and not listen to all the naysayers who think she is crazy.

    She basically can go to college anywhere in the world and has the grades and our finances to cover it. Her decision is to attend college in Alaska even though she doesn’t know a single person at the college. She loves whales, sea life and the outdoors. Her dream is to be a research scientist or marine biologist and she feels getting on the ground experience along with making local connections will help her achieve her goals. I have no doubt she will be successful.

    Myself, I’m either to comfortable, lazy or to scared to ever take big chances or that matter not a hell of a lot of smaller chances either.

    I believe parents have a huge influence on whether we succeed in achieving our dreams or not. I ingrained in my daughter from a very young age that the key to happiness is pure suing your dreams. I figured if she does what she loves money becomes less important because she’s happy. I was poor growing up so I figured money was the key to happiness. I’ve since learned money does make things easier but it doesn’t ensure happiness.

    Thanks, Bill

    1. Thanks for sharing Bill! Gone up to visit her yet in Alaska? I went once for a week, and it was amazing. Just breathing in the fresh air everyday made me happy.

      “in my letter I told her the thing I’m most proud about is here desire and determination to fulfill her dreams and not listen to all the naysayers who think she is crazy.” – I will definitely keep this in mind for my son.

      And yes, money not only doesn’t ensure happiness, it doesn’t make us happy after a certain sustainable point that’s FOR SURE. I hope everybody makes a bunch money so they can realize this.

  35. One of the better posts here recently Sam. Succinct, to the point, and although a lot of us can relate to you (having a family, some insecurities here and there), probably few people see the tenacity you have in going after what you want. That’s what makes people like “Andrew” and “Li” weak. They lack the ability to unleash their inner animal.



  36. Sam this is one of my favorite posts. I left a cushy State Job for Entrepreneurship and EVERYONE thought I was CRAZY. I was ALWAYS motivated and worked my tale off to get ahead at this job. I even had some of the lifer employees tell me “you should slow down as you are making the rest of us look bad”. One blamed me for the reason why our department was underfunded (his view not mine) as apparently you need to run a State job in the red in order to apply for more funds the following year. Shame on me for being efficient, concise, and on budget. I remember clearly that one of the Employees when I left to start my consulting business was mocking me and said I should give him stock. Like that made sense I should give him stock in something that he didn’t value. What is funny is I still keep in contact with some of the people I hired in my department at the State Entity I worked at and they are still in the same position. Honestly besides the equity I have built in the business I take home 6X what I made when I left there. One of the reasons why I left was because I hit my ceiling at in my position after 3 years and realized if I was going to work this hard I should do it for myself. The other reason was that I felt like this job was going to corrupt my soul and make me a slacker. I have two kids one 14 and one 9 and they see me hustle and I have been able to provide private school and other things I would never had an option had I stayed at the previous job. Aim for the stars and you will reach the sky. It is a great view from here.

  37. In my sixties I’m proud to hang in as a lowly 4.0 tennis player. You 5.0 guys are like gods or at least demigods to me! I played on another town’s team a couple of years ago and they never gave me a decent partner (seniors tennis is doubles only) and we struggled to be competitive. I knew I was one of the best players on their team because I’m an endurance runner and much more fit than most of them, but they didn’t think so. I changed teams last year and was partnered with another guy who was right at my level and we played my former team in a match. We drew their number one team and beat them like a drum. My former teammates just couldn’t stop talking about how much I had improved! Really, I was the same guy playing the same game. It was karma and I have to say I really enjoyed the win.

    1. 4.0 is a great level, especially in your 60s! I hope to hang at 4.0 in my 60s as well.

      Matchups and great partners is key. I did terrible my last season at 5.0, but I partnered with a 4.5 playing against two 5.0s the entire season. But I didn’t care that I kept on losing, I just wanted to compete.

      The only problem is, USTA won’t bump me down to 4.5, so I plan on appealing. Not too many 5.0 guys I know, and I want to play with my 4.0-4.5 buddies.

  38. When I purchased a rental property, my colleague friends mocked me. When I invested in online crowdfunding, they mocked me some more. I stopped talking about my dreams and plans to them shortly afterwards. Instead, I found a bunch of like-minded people online and they’ve been an incredible source of knowledge and support. The naysayers are usually people who think they know everything and don’t want to learn or try anything new. Deep down, it’s rooted in insecurity.
    When I started a blog not too long ago, I was filled with fear and insecurity. But I knew if I didn’t at least try, I’d always live with regret.
    Regarding having a backup plan for your children- there is nothing wrong with that and I applaud you for thinking about it. But I do want my two boys to forge their own path and find their own way. Struggle and failure will be almost certain and it will be hard to watch from the sidelines. But they need to go through it to eventually succeed. I will not protect them from every little setback in life. They are young but I’m trying to teach to them to be self-sufficient. If they want a toy, they have to earn it. If they fail to turn in their homework they have to face the consequence and talk to the teacher themselves. I enroll them in sports. If they don’t fight for the ball, no one will give it to them. If they don’t try hard enough, they might lose. Boy scouts teach them a lot of life lessons too. If they don’t set up the tent, they don’t sleep. If they don’t cook they don’t eat. In the future, I will keep teaching them about being responsible for their own actions. It’s not easy and I’m still finding my way with my kids. I tell my kids-” Your mom and I have a lot, but you have nothing. If you want nice things when you grow up, you’ll have to work hard for it. We will help you.” Thanks for the great post.

  39. Sam – not sure how to send you a PM, so am posting here. Want to thank you for your severance negotiation book. It’s helped me get a minimum $450K severance package (with potential for up to $750K, but am still negotiating). Appreciate the details on how to negotiate and set myself up to be best positioned to get the most possible to start the next chapter of my life. I did have one question that I was hoping to run past you live. I have used an attorney (declined to take him on retainer given costs), but would appreciate your thoughts on my situation.

    Think you do some consulting work, but also not sure how to best connect there. Please let me know.

    Will check back on the the sites comments section for your response (am choosing to stay anonymous for obvious reasons).


  40. Adam Sandler’s character in The Water Boy uses his naysayers as “tackling fuel” on the football field and proves to everyone that he can play football. It’s a silly movie but I love it and it has a similar theme that the naysayers and bullies get nowhere in life and that one can do anything he/she strongly believes in and loves.

    Great job sticking with what you believe in and going against the grain. You’ve definitely proven your naysayers wrong and had many successes in life. You’re a great inspiration to us all. Keep it up!

  41. There are thousands of captains like Chris in this world, and I’ve found I don’t want to be on their USTA teams, even if it means playing for a team that loses. Good for you for showing him up. Here’s to improving in 2018!

  42. A former boss once told me that the biggest obstacle to success at entrepreneurial ventures is the next million people that will tell you why you are stupid. Success comes when you able to ignore all of them.

  43. Two thoughts…

    First, tennis. You are a team coach now, and have to deal with dynamics and personalities. Chris, as player-coach, had to compete with you for position, as well as sort the lineup for maximum team performance. Tennis players are thin-skinned, vicious, selfish, deluded egomaniacs, who would watch a baby-buggy roll into traffic before missing a minute of court time, or admitting they lost because the other player is better.

    Um. Maybe I’m projecting. Nevertheless!

    As a coach you will now have to place value on things like loyalty, seniority, showing up to practice, potential, etc. You might get a top player just parachute in one season, and when that happens you will have to deal with all the egos on the team that have put in time and effort, and have expectations. At some level, Chris knew you were a threat to his spot, authority, and self-image. Five months off the court showed you both how the ‘Chrises’ of the world deal with threat and loss.

    Second, think about why your air-typing colleague acted as he did, by mocking your efforts to try something new. You may have shared your reason for starting the blog (that you were depressed at how the financial world, and prospects, had been blown up in 2009). My armchair ‘blink’ is that he saw your sharing a personal goal and interest as a chance to make a passive-aggressive attack on you. Why? Because while you showed vulnerability by sharing a non-work-related pursuit, and maybe make a friend or find that he shared your interest, he only saw that you are his superior and showing a potential weakness or failure. Because it involved non-work-related subject, he felt he could state his opinion without consequence. And if you called him on it, he could fall back on the passive-aggressive “hey man, I’m just joking, don’t be so sensitive!”, as if you are the one with the problem. It was a chance for him to ‘get over’ on you, and he took it; says far more about him, than it does about you and your ambition.

    That reminded me of another story you have mentioned, about the subordinate who really pushed boundaries to get you to reveal your compensation range. Without you realizing it, he was ‘competing’ with you. Just as the mocking colleague was. Just as Chris was. These guys aren’t hard to understand; they don’t care about your goals, or even your merit. They only care about their own. I say all this, to share some wisdom I could have used 40 years ago.

    “The game is always on. Always. Whether you play the game or not, it’s always on. There’s always winners. There’s always losers.” – Ed Latimore

    1. As always, good insights. USTA league tennis is kinda crazy indeed. So many prima donnas, it’s nuts. You’re right. Of course Chris put himself in the starting line up always. It was sad when I saw him and a friend partner up in the playoffs last year. It was 2-2 and down to their doubles match to win. They were playing my buddy’s team, and they lost in the tie-breaker. So much of the game is mental, and they choked. I was ecstatic for my friend’s team, have to admit.

      The other thing about Robert, air keyboard man, is that we were about the same age, but he was 4-5 years behind on the promotion track. Even though I started at the firm 5 years earlier, and got poached from a big shop, I don’t think it sat well with him. He was Robert XXX III who went to boarding school and private university.

      I don’t miss office politics one bit. Lucky nobody has really messed with me. Because if they did, it would be game over with their careers at least.

      1. Blog posts like this one, on ‘pursuing your dreams’, is why I enjoy the PF community and your blog so much. These stories are amazing, yet relatable. Reading them makes me feel like I am ‘not the Lone Ranger’ and that this stuff only happens to me.:-)

        One of the things I admire about you, FS, is that you recognized a lifestyle and work environment that was not what you wanted. And, unlike most of us, you actually did something about it! You have freed yourself from unpleasant people who add zero value. Continued success, and Happy Thankgiving!(nntr)

  44. Absolutely awesome article, Sam! Thank you for being an inspiration for those who want to “feel the fear and do it anyway!” People like you – those who take the risk – encourage the rest of us to never give up on our own dreams and to continuously search for ways to make those dreams come true. Please stay true to yourself and please, please, please continue to keep this website going for a long, long time.

    1. Will do my best Camille. Hopefully for 18 – 24 years! :)

      I have this mindset: if you can speak forever, you can write forever. So I’m giving myself over a 50% chance this site will be around for a while.

  45. Damn Millennial

    I think those that tend to put down others on the internet are just showing jealousy through their anger. Why someone would take the time to read about what you or anyone else is doing and then comment in a negative way is bizarre. Why not channel that anger into something that will actually better their own position?

    I have been reading your blog consistently for 4 years and find value in it and appreciate your posts. I feel like I can relate to a lot of the things you have already gone through and learn from what you did both good and bad. Isn’t that the whole point?

    I have listened to your advice on the possibilities of blogging and started giving it a shot myself!

    We all will regret the things we don’t do in the end, and putting down someone else for working on themselves is a losers game.

    Good read.

  46. Hi Sam! Unlike the haters, I do have a kid – well, she’s a 20 yo college student now, so not really a kid anymore. I do understand you want the very best for your son. I really do. I have some thoughts though, based on a sort of theme I’ve gotten from various items you’ve written in the past about what you want to provide for him.

    There is an unsettling phenomenon happening now around parenting. Parents – particularly those who became first time parents later in life – are making their children the center of the universe for themselves and everyone else. I’ve seen it in my own circle and in those of my family members. Things that used to be done easily by one parent who also held down a full time job now take 1 full time parent plus a nanny, or 2 full time parents – for ONE kid, often one infant. I know someone who gave away her dog she’d had for 8 years because she couldn’t handle one healthy infant and a well-trained dog at the same time. People buy all the things. People stop all other interaction and hobbies. Grown adult humans rearrange their lives so that there is no one and nothing but the child and giving everything to the child. I could give you countless other anecdotal instances of the same sort of semi-obsessive behavior.

    I find this trend troubling for all parties, but mostly for the children. In my opinion, it indicates to the child from the jump that they are the center of the galaxy. Their needs trump everyone and everything else. No sacrifice is too great, no amount of time or money is too much, there is no anything without them being happy. It also doesn’t allow them what you had – the character building exercise of trying and failing. Their parents take care of everything for them so that precious never has to be upset or angry or sad or not have something they want.

    Our lives and character are not built in the wins and the easy that we obtain. They’re built in the struggle – made in the space of having to figure out things on our own and the confidence we gain in ourselves when we do so. Too many parents now seem to be stealing those experiences from their children so that they can feel good as parents.

    It’s HARD to see your child struggle. You want to do everything for them. It’s always a judgement call between helping and enabling them. I won’t pretend for one.single.minute that I have all the answers. I will say though that even though I don’t know you, I don’t think you want your son to grow up under the helicopter experience. Those kids want for nothing materially, but they are generally obnoxious, entitled and no fun to be around at all. There is among them a depressing lack of empathy and understanding for others that does not bode well for our shared future.

    Best of luck as you navigate the rocky shoals of parenthood. It’s not easy and it’s not always fun, but it’s worth it if in the end you have helped guide a person who will give something to the world beyond what you were able to.

    1. Thanks for sharing your thoughts as a parent. Empathy and an indomitable spirit are the two things I hope to teach my son, and I have several ideas how. Related:

      Parenting is an interesting one bc so many parents think their way is a better way than others. It’s almost like personal finance. There’s just no exact right way beyond the fundamentals of love, care, and time spent, only the way that fits your lifestyle and your child’s personality and your personality the best. And in the end, the results are apparent by the happiness of your child.

      What does your daughter want to do after college? And do you have specific suggestions on how to “moderate” the amount of care to your child in order to make them better people? What were some of the things you did to make her a success growing up? Finally, what are the negatives of developing a backup plan in case college becomes a big waste of time and money in the future?




    2. The toughest thing as a parent is seeing other acquaintances and friends who are able to stay home and take care of their little one. Because we all know that spending more time with our children is better than spending less time. So if we see a couple able to stay home and work from home, that brings about the biggest guilt in ourselves for not doing the same.

    3. As the father of a four year old, I totally agree with this post. While I am fortunate to have early retired and be able to provide all that she needs, I force myself to take a step back and make mistakes on her own and plan to do more and more of this as she grows up. Our children need to make mistakes and learn. She is going to do her own work when she is in school, even if it means she can’t get into the Stanfords and Harvards of the world because she is competing against kids with helicopter parents.

      A Stanford dean agrees with this approach:

    4. Sara, I agree with you. My parents, and especially my mom, took this approach, and it was an almost unbearable amount of pressure when I was a teenager. My mom gave up a career, social life, hobbies. I was a competitive athlete and she drove me to practice at 430 am 5 days a week. And I had 2 siblings who were also busy with their own activities. Her day started at 4 am and ended at 9 pm. It was 100% child centric. I felt an immense amount of pressure to succeed in my sport, school, music, etc. I think it led to some less than stellar life choices in my early twenties when I went to college and was “free”, and I saw the same thing in my younger sibling. In the end, we all are doing good now and maybe going through a period of rebellion and overcoming it made us better people today, or maybe there is an easier way. I am forever grateful to my parents and especially my mom, but I also find myself reflecting on this constantly now that I’m a parent and trying to do things differently.

  47. Hey, Sam. I’ve been very fortunate. No real detractors in my life. I’m not saying that all my family, friends, and co-workers agreed with everything I did to advance my career and financial prospects, but no one was ever negative or douchebaggy about it. Just the luck of the draw, I guess. But you make an excellent point about naysaying adults. And the only difference between naysaying adults and naysaying children is the degree of sophistication. Naysaying children are wont to belittle their successful peers with crude mocks (i.e., geek, nerd, brainiac, etc.) or a punch to the arm. Naysaying adults, however, are wont to to belittle their successful peers by saying their success is largely the result of “privilege.” (Thank you academia for providing negative and douchebaggy adults with a patina of learnedness!) Either way, though, the naysaying is pretty sad. Awesome post, my friend.

    1. Ah, you are lucky then! When you start your career in Manhattan and then move to San Francisco, there is an ENDLESS environment of super type A, competitive folks out to eat your lunch.

      It’s one of the reasons why I moved to the western part of SF, and why I’m now thinking of moving to Hawaii within the next 3-5 years.

  48. “You Will Regret More The Things You Don’t Do”.

    That’s why we’ll be selling our paid off McMansion and moving to a triplex on the Outer Banks, NC next summer! Oh, and leaving our well-paying jobs in the process. And leaving one of the best school districts in the state. And… you get the idea… Everyone we told seems to think we’ve lost our minds and comes up with a hundred things that can go wrong, so I can totally relate. I’ve ran the numbers a thousand times and it should work out just fine. If it doesn’t, well I guess we can always come back and plug back in. At least we’ll know we gave it a go.

  49. I currently make $200k as a senior non-profit leader of a national organization. I’m less than 40 yrs old and so in a peak earning period of my life. Yet I’ve been contemplating quitting to do my PhD. Every prof that I’ve talked to says that I’m too old to go the tenure track route, which is fine by me. I want to teach, lead a research center, and consult with non-profits and government. I could likely do this without a PhD but also like the idea of 3-4 years in grad school to explore my interests and spend more time with family. My current plan is to keep working for a few more years to payoff a HELOC and then try to start a program when I’m about 40. But I’m still hesitant to do it! The crazy thing is that I’ve been thinking about doing this for almost 20 years – way back to my senior year of college when my dad talked me in to going into strategy consulting out of college. So it’s a dream to be in a practitioner professor role for a while but I’m still hesitant. The good news is that my net worth just cracked $1M so I’m feeling more ready to take a risk!

    1. I left public education when I was in my highest earning years as an administrator after earning my Ed.D. (doctorate of Education) at 43. I taught at the college level and took a few tenure track jobs, but then decided I’d rather not be held to doing all the work I didn’t want to do (I just wanted to teach!) I took a huge pay cut (down to $55K) worked less than half the time I did as an administrator. Some of my best professors were folks who were in the field for a long time before coming to academia. Now I just consult and pick up adjunct jobs when I want to and when I find something interesting. I’m glad I pursued it – and even more glad I had a good mentor to push me when I thought of stopping part way through.

  50. Great article. It is so true that you always regret not pursuing your dreams. A current dream I’ve been pondering over is whether to invest in a real estate property in a city I’m about move from for a new job in another city. I’ve lived in this current city for six years and am more familiar with this city than the next city I’ll be moving to. Everyone I’ve told about this situation almost always suggests to not do it, but I’m convinced to pursue my dreams of owning a real estate property by taking action now instead of possibly regretting waiting years down the line.

    1. Hi Phil – With real estate, definitely run the numbers, and model out THREE scenarios (bear market, neutral, and bull market) to make sure you will be OK.

      I’d spend at least 6 months getting to know the city and checking out open houses before buying. There is no rush at this point in the cycle.


  51. I really don’t regret trying anything and it’s true that there is more regret when you don’t try something. Some people in my family don’t understand still what blogging is so I don’t really try to explain much to them.
    On my bucket list to learn how to play guitar in the next few years but I may push that up :-)
    A new guitar store opened up five minutes from my home; maybe it’s a sign!

  52. Haters gonna hate.

    At the end of the day you can pander to them or you can just ignore it and keep on doing what you think is best for you and your family. At the end of it all when you look at who’s happier and in a better spot, I’m putting my money on the person who isn’t criticizing someone else’s life when they’re making clearly productive decisions.

  53. Great article Sam. I work in a highschool currently (teacher) and it is very easy to see the haters vs the innovators. Love the fact that you use the doubt as fuel for this blog, reminds me of how Jordan used to look for any reason to go out and play his best.

    Thanks again for the inspiration:)

    1. Hi Clint, so cool you are a high school teacher. I wanted to be one after I left work in 2012 as well, but didn’t have the patience with the additional schooling and SF bureaucracy. I’d love to hear some stories about your teacher-student interactions one day. I’m still seeking some of my own as a HS tennis coach.

  54. I knew you were going to get flack for that post! I just knew it. I want the same thing for my kids (maybe it’s an Asian thing) someday and people look at me like I’m crazy.

    It’s pretty logical to me. I’m “sorry” I plan so far out. I just want them to be OK and with ___ that I’ll leave them, I can make the odds better in their favor. It’s partial love combined with utility.

    (Thanks for the update on Robert. I was curious what exactly became of Mr. Braggart.)

  55. Oh, where to begin…

    – Elementary / Middle School: They called me Stay Puft (Marshmallow Man from Ghostbusters); I couldn’t run and play sports very well. I wanted to try football and swim and got made fun of ridiculously in that really tight speed-o. One or two years later, I began beating the same kids in games and races.

    – High School: I wanted to play running back in football but had never played in the position because I always weighed too much and was restricted to playing a defensive or offensive lineman position. In high school, the weight restrictions by position didn’t exist. I eventually became a starter and played extensively later on.

    – College: I wanted to major in liberal arts, so I did. Toward the end of sophomore year, I realized I wanted to go into business but didn’t want to change my majors or prolong school. I minored in Econ, joined a professional business fraternity and took business electives. Peers scoffed at me when I said I was not in the “management” school; interviewers asked the same questions of why I didn’t major in business (valid question). By senior year, I was president of the professional business fraternity and had a job offer by September of senior year.

    – First couple years in the workplace. I wanted to try client service / relationship management as well as project management. I started in operations or “back office”; colleagues said I didn’t have the educational background (didn’t come from an ivy league school) or practical experience (couldn’t argue there). I couldn’t change where I went to school (and an ivy league degree was NOT required), so I got the experience within my role: I volunteered for additional assignments, I project-managed process improvements without the title of project manager, I built relationships with clients and the heads of the “front office”. Within a few years, I (1) ran my group area within the “back office”, (2) expanded the role of the group to include process change / project management, and (3) respectfully turned down an offer to formally join the “front office”. I gradually evolved my role to what I wanted it to become.

    -Today: TBD :)

    Overall, I don’t think there has been one particular event that sticks out. It’s been a series of small events.

    1. Nice progress Mike. Sounds like you’re happy with where you are. So many things stick out in my life, and I’m not sure if it’s b/c I’ve ruffled too many feathers or have a default fierce spirit.

      Thanks for sharing.

  56. I think the biggest naysayer is really yourself. Everyone is afraid of failing and looking like a fool. It’s difficult to take a chance and make a big life change. It’s much easier to criticize other people and belittle them. It took me a long time to realize that to succeed, you have to take some chances.

    You’re a huge inspiration to many people. Keep it up!

  57. Glad you turned your back on those Negative Nelly’s and persevered toward your goals. As I read your post, I discern disguised jealousy as well. It’s rampant in our world and it is really tiresome and unproductive. People don’t have the courage to do interesting but risky things….but they are threatened when others try it. I absolutely love your enthusiasm and ingenuity towards the life you created. It is extremely motivating for myself and countless others. Best regards from Vancouver (we’re not all “Andrew’s” ) C

  58. I went to my reunion about 8 years back and found most of those nay sayers jobless during the downturn. Others were making due as cashiers and waiters. In some ways it was satisfying, but others it was depressing as I wish everyone success.

    The reality is, the biggest block to anyones success is to just start. No one else other then your family really cares. Your family may have concerns but I’m sure they will ultimately support your endeavor if it’s thought out. As for the rest, well no one else truly matters. Also many of them will forget about you next week or next year, let alone your decision.

    I may disagree with some of your positions and provide constructive counter positions, Sam, but I respect the decisions you make as yours.

  59. Chris Nichols

    Fantastic article, Sam. Thank you very much. How does someone balance honesty along with avoiding the appearance of the type of negativity you discuss in your article?

    Honesty is one of the principles of bushido, the ethics of the samurai. Have you written articles on bushido or business ethics in general? I would love to read more of your thoughts on these topics.

    Thanks again.

    1. Honesty is pretty straightforward. You just tell it as it is. It’s really easy to write when you write from experience and fact. It’s a joy to talk to random folks b/c there’s inevitably a story that can be told.

  60. Thanks for being so open about the challenges you’ve faced, Sam! I’ve realized over the years that those who want to put me down or explain about any outcomes I’ve achieved are those who are just insecure about themselves.

    I’ve had plenty of failures in my life and at many times was tempted to explain away people’s success to feel better about myself, but I tried not it. The reason is simple. It won’t change the fact that many people are successful. Now that I’m 30, I I just think it’s silly and immature to make fun of other people for doing well at something.

    The Andrew and Li guys you mentioned above don’t have kids, so they don’t know what it’s like to worry about our children. I also feel that some parents are shamed for having plans for their kids. I guess in a way it makes other parents feel bad about not being so prepared. I know because I tend to feel that way sometimes. But people’s feelings are just not relevant in many cases. Our actions do.

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