What If You Take A Leap Of Faith And Your Dreams Don’t Come True

Sometimes you take a leap of faith with and your dreams don't come true. That’s OK because at least you won't regret never trying!

In this article, taking a leap of faith means trying your hand at entrepreneurship. Entrepreneurship means leaving the comfort of a steady paycheck and benefits to make money from an idea.

Entrepreneurship is scary because you're responsible for everything. There is nowhere to hide if something goes wrong. The more years of education you have, the greater the opportunity cost to become an entrepreneur.

But when things go right in entrepreneurship, there might be no better feeling professionally. No promotion or raise comes close when reward is perfectly correlated to merit.

Technically, I've been an entrepreneur since I launched Financial Samurai in July 2009. This site earns enough to provide for a family of four in San Francisco. However, it wasn't always this way.

What If Your Business Doesn't Go According To Plan?

A reader asked, “What do you think you’d be doing now if FS hadn’t worked out so well for you? Back to the IB grind, real estate tycoon, build a tennis school…other? Might be an interesting article unto itself. I know you’d get at least one interested reader.

I've technically been an entrepreneur since 2009 when I started Financial Samurai. The site might have made $250 in advertising revenue its first year. I didn't have a goal of making lots of money online. Instead, I wanted a creative outlet to share my thoughts and commiserate with others during the global financial crisis.

Not everything worked out as planned. But when you have little-to-no expectations for making money from a new endeavor, any money that is made feels like gravy!

Since leaving my job in 2012, I haven't thought much about what I would have done if Financial Samurai had failed. But this is a good thought experiment to ponder.

I'm sure some of you might be wondering what if you take a leap of faith and things don't work out either. Like with all big decisions, pre-mortem planning is a must!

A Time Limit On Your Crazy Idea

You've got about three years to gain traction in your business or crazy idea before society writes you off. Nobody will bat an eye if you disappear for one or two years. Plenty of eager beavers go off to business school for two years and re-enter the workforce with no problem.

But after three years, people will start wondering what you were doing with all that time. They'll start questioning your judgment to take a leap of faith. They'll wonder whether you were too delusional or too stubborn to realize your endeavor wasn't a good idea.

Once they start to think these things, your chances of getting hired at a comparable job you left for comparable pay diminishes precipitously.

Two or three years is also a perfect amount of time for a rational entrepreneur to decide whether their product or service can generate a minimum livable income stream. During this time period, you can probably pivot one or two times as well.

If you aren't generating a livable income stream after 36 months, or you haven't raised capital from outside investors, then you should probably get a job.

My Entrepreneurial Time Limit Was Two Years

According to FINRA regulations, the Series 7 license expires after an employment lapse of two years. The test is six hours long and contains 260 questions. There was no way I was taking that puppy again if I decided to rejoin the financial services industry!

Taking A Leap Of Faith And Retiring On My Own Terms

Therefore, I gave myself two years to see if I could generate momentum on Financial Samurai. I published three times a week and saw progress. My back was against the wall!

During this two-year period, I hedged my bets by going on interviews with several financial firms. But I just didn't feel the same excitement about working in finance as I did in my 20s. Instead, my excitement was 100% targeted towards my online business.

It was a scary moment to let my Series 7 license expire in June 2014, but it also allowed me to burn my boat and only look forward.

If you plan to take a leap of faith, check on any license expirations and set a three-year time limit, whichever comes first before you go back to work. To help your cause, consider freelancing in your old industry to stay relevant just in case.

Scenarios If Financial Samurai Failed

It's easy to see a scenario where Financial Samurai would have stayed stagnant or disappeared.

I could have lost my motivation to write consistently each week. Search engines like Google may have never decided to rank my content. Larger media publications may have never decided to highlight my work. Disruptors like artificial intelligence writers could have gotten me down.

Since 2009, the vast majority of personal finance sites have either shut down, gotten sold, or stopped publishing. If I couldn't gain momentum after two years, I would have done the following in order of likelihood.

1) Return to investment banking at age 37 (2014). 

Instead of working at a bulge bracket firm, I would have elected to work at a boutique bank with better hours, lower expectations, and less stress. This way, it would have been easier to keep Financial Samurai going as a secret side hustle.

After three years of aggressively saving most of my salary and bonuses, I would have tried to take a leap of faith again at age 40. Three years of bull market returns would probably have given me more confidence and security.

With three more years of content, I'm also confident Financial Samurai would have been able to generate a livable online income stream by then. The combination of more passive investment income, a potential severance check, and additional online income would have been more than enough to leave traditional employment for good after age 40.

2) Move to Honolulu and say to hell with it by age 38 (2015).

Failure is on a spectrum. Failure also depends on your expectations. If I expected Financial Samurai to make $1 million a year after three years of full-time dedication, but it only generated $250,000 a year, I'd feel like a failure. But my expectations were for a modest $12,000 a year in online income.

My wife and I planned a simple, child-free lifestyle living off of ~$100,000 in Hawaii. $88,000 would come from passive investment income and $12,000 would come from online income. We'd reinvest 100% of our severance checks into stocks and real estate.

Then, for three months, we'd move in with my parents to buy us time to find a place of our own. We'd either find a decent two-bedroom apartment for $3,000 or look to buy a two or three-bedroom house.

With no job and a lackluster lifestyle business, I would have been highly tempted to sell my primary residence in SF before moving to Hawaii. If I did in 2014 or 2015, I would have given up ~$500,000 in gains given I sold it in 2017.

Hawaii Is My Alternate Universe That Could Still Happen

Now that I think about it, I probably would have purchased a single-family home in Honolulu for up to $1.5 million ($1.25 million cheaper home). If so, the house would have appreciated by at least $300,000 since 2015.

While in Hawaii, I would continue to write on Financial Samurai and probably focus more on lifestyle, travel, entrepreneurship, and minimalism. We'd probably also do some online freelance work as well.

The amazing thing about Hawaii is that our favorite activities, going to the beach and hiking, are both free. It doesn't cost much to live there once your housing costs are taken care of.

With a more easy-going and family-friendly lifestyle in Hawaii, my wife and I would most likely want to start a family.

3) Get a job at a financial technology company until age 40. 

The fintech space has grown tremendously since 2012. I ended up consulting part-time with firms like Personal Capital and Motif Investing for two years. It was a lot of fun understanding the industry, meeting new people, and learning/advising a lot about online marketing.

The only downside with fintech is its much lower base pay compared to investment banking. We're talking 40% less on average.

After at most four years of working in fintech (37 to 40), I'd leave. Three-to-four years is how long it takes for shares to vest at most startups. I'm sure I also would have gotten bored after four years.

Four years of startup life would have taught me everything I needed to know about online marketing, public relations, customer acquisition, growth, and more. Then I'd implement what I learned on growing Financial Samurai, my X Factor.

4) Find work-from-home jobs in Hawaii.

If I still had a day job when the pandemic began in March 2020, it would have meant Financial Samurai was a complete failure. At age 43 in 2020, I would have been a disgruntled employee three years past my original ideal retirement age of 40.

I'm confident that by 2021, I would have negotiated a severance and retired completely or found a new job I could do from home in Hawaii. Like for millions of people, the pandemic would have been the ultimate catalyst to change my life for the better!

Ideally, I would have spent my time writing Buy This, Not That on a lanai overlooking the ocean in Hawaii. But in order to get the book deal, Financial Samurai would need to have been around! Ah, the mind games we play, always imagining ideal scenarios.

Given I would have worked for five more years after I originally fake retired in 2012 and failed by 2015, I might have been richer by 2020. Therefore, I probably would have permanently left work for good by 2021.

Finding Constant Themes In Taking Entrepreneurial Risk

Going through this thought exercise of what to do if I failed at entrepreneurship, I realize I would still publish on Financial Samurai no matter how well the site did. I've always used this site as a creative outlet. It's the perfect thing to do for a retiree who loves to travel or someone who gets easily bored with their day job.

Money is a byproduct of doing what I enjoy. Every day I'm still amazed we can make money from the internet.

Would Have Taken A Leap Regardless After Age 40

Another theme I discovered from writing this post is that I anchor to age 40. Instead of retiring after achieving a certain amount of money, I was focused on doing something new by age 40 regardless of how much money I had. You can always make more money, but you can never make more time.

Trading time for money in your 20s and 30s is easy. But after age 40, unless you truly enjoy what you do, work starts feeling like a suboptimal use of time. Sure you might still need the money, but the feeling of dread about going to work starts becoming more common.

You also start knowing people who pass away in their 40s and 50s. Steve Jobs died at 56 for goodness sake. He was the healthiest eater with the best healthcare money could buy. Kobe Bryant died at 41 in a helicopter crash. The list goes on and on.

Maybe this whole exercise is pointless because I've always had confidence Financial Samurai would not fail. There are too few storytellers with finance backgrounds who also have the grit to keep going for decades.

I knew if I could speak forever, I could write forever. One of the greatest things about running an online business is that the harder you try, the better you do. Besides, it only costs about $6,000 a year to keep this site up.

If You Plan To Take A Leap Of Faith

There is no doubt that being an entrepreneur is stressful, especially if you have a family to raise. Here are some suggestions I have before you take a leap of faith and go out on your own.

1) Work on your business after hours while you still have a job.

Unless you have a major amount of funding, please don't leave your job to work on your business full-time without testing it out for at least a year. We all know that most businesses fail. Working from 5 am – 7 am or 9 pm – midnight is plenty of time to see if your business can gain traction.

I hired a guy from Craigslist to come over to my house and create a website after work in 2009. Nowadays, you can launch one on your own in thirty minutes with my step-by-step instructions.

2) Refinance or get a mortgage before you leave your day job.

Once you lose your W2 income, you are deemed too risky for banks. Only after you have at least two years worth of 1099 (freelance) income will banks consider you a creditworthy candidate. Despite having a significant amount of assets, one of my refinance attempts got rejected in my early years post-work.

You may also consider taking out a line of credit, such as a HELOC. The rates are much higher than a conventional mortgage. However, it's nice to have a line of credit in case of emergencies.

Having at least two banking relationships so you've always got access to credit and cash. The bank runs that have been happening in 2023 is a good reminder to diversify and manage your cash.

3) Leave your day job after you see hockey stick growth or steady operating profits.

If you plan to become a lifestyle entrepreneur, then it's best your lifestyle business generates at least a minimum livable income stream before leaving. If you plan to grow a non-lifestyle business, then you either need to wait for a visible path to profitability or raise enough funding to last at least 18 months before quitting your job.

4) Negotiate a severance before you take a leap of faith.

A severance will buy you months, if not years of runway to grow your business without overly worrying about profits. If a business focuses too much on profits in the beginning, the product or user experience may not be the best.

If you can't negotiate a severance, then have at least one year's worth of living expenses in the bank, preferably two. The longer your cash runway, the better before starting a business.

My severance package in 2012 provided me with full living expenses through 2017 when my last deferred cash payment was paid. This 5-year runway allowed me not to stress about money and build Financial Samurai without worrying about making a profit online.

5) Learn the pitfalls and build a network.

Speak to as many people in your field of business as possible and learn how they got off the ground and thrived. Learn about their mistakes and figure out ways to help them so that they might one day help you. Listen to as many podcasts and read as many articles as possible about existing entrepreneurs.

6) If you have a spouse, talk things out thoroughly before you take a leap of faith. 

Discuss your entire entrepreneurial plan with your partner. Having a spouse work a stable job with benefits while you go off and do your crazy thing is an excellent combination. Just make sure you have some revenue and time guidelines in order to not burn each other out.

The leap will be scary, but the regret of never leaping will eat you up inside if you have a good business idea. Limit your entrepreneurial endeavors to three years and you'll likely be fine. After three years, all bets are off.

Enjoy Your Wonderful Journey!

Taking a leap of faith is scary. I get it. But the fear in your head is often greater than reality. The worst that will likely happen is that your business fails, you lose time and money, and have to go back to work.

The best that could happen is you do something you love and get incredibly rich in the process! If you want more control of your time, then you can always start a lifestyle business that focuses on cash flow instead of a huge exit instead.

Having to go back to work if your business fails isn't the worst thing in the world. But can you live with the regret of not trying? I couldn't so I took the leap.


Every business needs its own website. Here's a step-by-step tutorial that shows you how. Not a day goes by where I'm not thankful for starting Financial Samurai in 2009.

Back when I started, I had to hire someone for $1,500 to launch FS. Now you can launch in under 30 minutes for less than $50. It's nuts how easy it is to start our own business online nowadays.

Learn how to negotiate a severance by reading How To Engineer Your Layoff. Use the promo code ‘saveten‘ to save $10. Negotiating a severance was my #1 catalyst to live my banking job behind in 2012 because it provided for five plus years of normal living expenses.

How To Engineer Your Layoff Ebook 6th edition

Invest In Entrepreneurs As Well

Taking a leap of faith to become an entrepreneur is hard. Instead, you may want to keep your day job and invest in private growth businesses. This way, you get to have brilliant entrepreneurs work for you. Or you can do both! I certainly am.

Companies are staying private for longer, as a result, more gains are accruing to private company investors. Finding the next Google or Apple before going public can be a life-changing investment. 

Check out the Innovation Fund, which invests in the following five sectors:

  • Artificial Intelligence & Machine Learning
  • Modern Data Infrastructure
  • Development Operations (DevOps)
  • Financial Technology (FinTech)
  • Real Estate & Property Technology (PropTech)

Roughly 35% of the Innovation Fund is invested in artificial intelligence, which I'm extremely bullish about. In 20 years, I don't want my kids wondering why I didn't invest in AI or work in AI!

The investment minimum is also only $10 while most venture capital funds have a $250,000+ minimum. You can see what the Innovation Fund is holding before deciding to invest and how much.

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51 thoughts on “What If You Take A Leap Of Faith And Your Dreams Don’t Come True”

  1. Mr. Optimistic

    I work for a company that probably frowns on side hustles. I obviously need to get the word out about any product I create and sell on the side. However, I worry if I do that my company will find out when I start creating content to market it. Do you have any advice on how to side hustle discreetly for someone in my situation?

  2. Ms. Conviviality

    I’ve heard so many times the advice to not quit your job until the side hustle brings in enough income to cover expenses but it’s so difficult to move with the momentum of starting a business while having a full time job. The message that I got out of this article is that the FS blog would have been successful no matter what. I believe that will be the case for my own business. It’s clear to me that Sam has a gift for writing and research. I’ve been told enough times that I’m good at making beautiful things, which in the past I shrugged off as “no big deal, it was easy to do.” The more that I got those compliments, the more I began to see that maybe this was my gift.

    It’s not a matter of knowing with certainty that my business plan will be successful but rather the certainty that I can pivot and tweak until I am successful. I know this because there are so many examples of successful people doing similar things to what I want to do. If there’s one thing I know about myself, it’s that I’ll put in the hard work and I’m not a quitter. If there are others who are successful, why not me?

    It has been over 15 years of learning and planning and obtaining the right tools/skills to be successful in what I want to do but I don’t have enough time to execute as quickly as I want.

    Why has it taken me so long? I’ve been busy doing other side hustles like renovations for Airbnbs, driving for Uber, creating products for an Etsy shop, doing wedding flowers and cakes, and helping my husband with his business. Not to mention the 40+ hours I put into my job as an audit manager.

    1. And indomitable believe that you will succeed definitely helps. Perhaps what helps the most is having no other option but to succeed.

      If I didn’t have any passive investment income or severance, I would have tried extremely hard to make Financial Samurai a success. But given I had these economic buffers, I took my time to do things my way without the need for monetization. I’m still like that today, as friends say, I should start a YouTube channel, hire, freelance writers, be more aggressive in marketing, and so forth. But what’s the point if I have mostly everything I want?

      You really need to have the need and the hunger to want to make it as an entrepreneur. It’s worth trying once I say!

      1. Ms. Conviviality

        Thanks, Sam. I’m going to take your comment as permission to quit my six-figure job. J/K! I’m too risk averse to do that. I think that’s why so much of my life has been to save and buy properties that would generate some income. Once we have two years of expenses saved up or non-W2 income is enough to cover expenses then that’s when I can devote as much time as I want into my business.

  3. My advice would be to find a business that generates residual income. My personal expertise is in the traditional energy space ( oil and gas). Put in the upfront work then enjoy long term cash flows. I also run an investment company which I self fund with rental properties, biotech holdings, breweries, restaurants and even a yoga studio which I finance 100% from my residual income. Also it’s gotta be ROI driven and it todays market hard assets that generate tax preferred income in at least the mid teens even low 20% would ne needed as the risk free rate is going up and will continue to rise at least until 2024. So what you love and love what you do.

  4. Susan from LA

    This is a great post for people thinking of starting their own company. I just wanted to share my experiences.

    I started a family company in 2001. We grew from no employees to over 10 in a few years. It was an import company so I had to work 16 hours days, eight hours here and again when China office started in the afternoon. I didn’t mind the hours when I can see progress being made. What I didn’t think through carefully is hiring and managing employees.

    I was a manager in my previous career. That is not the same thing as being an owner – manager. Every wasteful and careless mistakes employees made comes out of your bottom line. Being an owner, my first concern is never about making a lot of money for myself. It is always about making enough to cover all the costs, especially salaries for all my employees.

    My experiment ended after 2008’s financial crash. Our industry was especially hard hit by the crisis. One part of me was almost relieved by the end. I went back to my old employer and continued to climbed the corporate ladder and did well financially anyway.

    I agree with a lot of your points about being prepared and start small. I am not trying to discourage people from starting their own business. I just want them to understand that, starting is just one stage, growing and managing is a completely different game.

    If you are not into managing a lot of people, consider something like online business where you can work on it yourself (like FS) might be the way to go.

    1. Thanks for sharing your story and great points about the pain of managing people. I don’t like managing people, which is one of the reasons why I left the finance industry, and why I haven’t hired freelance writers and more to help grow the site. I just want to keep things easy and simple you know? the last thing I wanna do is create a work environment that I had left.

      You make a great point on appreciating work more after becoming your own boss. Entrepreneurship is harder than having a day job.

  5. I have a good friend who couldn’t hack it working for someone else, so she started a business. Went ok for a number of years, then it started falling apart. She violated many of the points you made in your article, being somewhat tone-deaf to her situation. She struggled for 10 years until she was totally broke and ended up homeless. Not exactly homeless, but house-challenged, staying with friends. She eventually married a guy who had some money, but now works a bit while retired to boost her income. Ironically, he was her competition in her business space, so in some bizarre, roundabout way, she was successful!

    This stuff happens. To a lot of people. And some never get back on their feet, especially if Plan B doesn’t work or there is no Plan B, as in my friend’s case. We could be very judgy with those who spectacularly fail, seeing flaws in their ideas and business models where they don’t. Hate to see people suffer when that happens – and sometimes it is not their fault, as happens in any recent or distant recession. One can only feel empathy and hope they find a way back to some solvency.

    1. Glad she landed on her feet with her competitor!

      It’s worth going beyond empathy and speaking hard truths to those we care about. Set up time limits for your entrepreneurial endeavor. When you have a deadline to succeed, the chances of success are greater. But if you don’t succeed, go back to work. There is no shame in failure. In fact, I look upon all people who are willing to pursue their dreams with admiration.

  6. Love this very timely post! Reflects my current situation. I was diagnosed with a heart condition over a year ago and required surgery 6 months ago and doing well. Working my full time job, I also did houses on the side and either lived, rented or sold them depending on the market. At first I could only afford cheaper small properties so smaller profit margins. But eventually my profits accumulated enough to buy a rundown house on 900sqm. I had dreams of building multiple townhouses and selling them for a huge profit but alas 3 months later Covid came and than my heart and health issues.

    As I plan more on taking care of my health now and slowing down, the developer dream is no more. I will still double my money when I sell and currently having flatmates paying my mortgage and have returned to part time work. My retirement has been pushed by 3 years as a result. But my forced mini retirement of a few months, showed me that I actually dont spend a lot of money when I am not working. There are cheaper smaller eatries, walking and parks are free, movies are cheaper and malls are empty week days. But my healthcare costs have gone up but still my yearly budget has decreased by 30%. Maybe my health issues were a blessing in disguise to show me to get off the hamster wheel.

  7. Wow. This is a Hall of Fame post to be sure. I’m thumbing on my phone, so plan to comment in full later after digesting these thoughts and find a keyboard.

    For context, I just sold my tech services company after 18 years. It was a bootstrap startup out of a spare bedroom. I was able to roll 25% of proceeds into the new firm which is funded by private equity. Decent shot at doubling my 1st payout in 3 to 5 years. I’m turning 57 next month, so good midterm outlook. I’m set for a comfortable retirement even if I don’t make a dime on the 2nd bite, so it’s basically house money so let’s do this! Should be fun.

    Back to your post. You touched on just about everything possible in my life over 35 years of entrepreneurship and education. Bravo sir! You are wise far beyond your years, and everyone that will listen is better for it!

  8. Sam, I love this post! So timely for me as I am planning on starting my second business in a few months. In fact I just bought your book because of this post! Look forward to reading it and getting additional encouraging advice. Thank you!

  9. Very smart advice. Not everyone is cut out for entrepreneurship, but everyone who has a dream with a great idea should give it a try on the side if they have the opportunity.

    Some people quickly realize that their day job is way easier than entrepreneurship and end up recommitting to the traditional route much happier having at least tried.

    A few grind it out and realize they are actually on to something truly great and are much better suited on their own.

    Overall, I like your guidance on trying to gain traction within three years. That makes a lot of sense!

  10. Well said. You’re in control of your destiny when you’re running your own show (business), and there’s no real ceiling.

  11. This is a great, thoughtful approach to taking that leap toward entrepreneurship. The point about trading your time for money as you get older really resonates with me.

    You also make an interesting point about how long to give yourself for an entrepreneurial endeavor. I think people generally seem to overestimate the risk of trying to start a business. It’s almost like when people imagine the possible outcomes, one outcome involves sitting on an island counting millions of dollars and the other leaves them destitute. Of course, the vast majority of entrepreneurs wind up somewhere in between this wide gap.

    The reality is that even if you try to start a business and it fails after a year or 18 months, you can probably get back into doing something similar to what you were doing before, and your life will be that much richer for the experience. Personally, I think when I look back on my life some day, I would rather look back as someone that took a chance and failed than to be someone that never took the chance at all.

  12. Thanks for this Sam! Just ran into your site via https://www.financialsamurai.com/the-proper-asset-allocation-of-stocks-and-bonds-by-age/

    Have you written about the 4% rule? I feel like you might have strong opinions on it…

    I don’t have your level of knowledge, but it seems to me that a 100% stocks (VTSAX) portfolio while working and a 75%/25% VTSAX/Total Bond Market portfolio once retired is a simple, low-maintenance method that gets good results.

    What do you think?

      1. Thanks FS.

        I like your point about retiring happy and safe (I plan on living to 100+!! :) ). There’s no rush.

        And that plus the overblown fear of running out of money makes me feel pretty confident that when I do manage my early retirement things will be just fine.

        Every time I come here, I end up spending much more time than I meant to…lots of good stuff

  13. I think that you are doing a really great job. I enjoy your blogs with all of their great bits of information. Please keep them coming with or without errors.

  14. A topic dear to my heart! My husband is an entrepreneur and we live in the Bay area. I have a stable job and benefits to support us. We have a 3.5 yr old. We moved here for my husband to pursue his dream of running a startup (she sold startup#1 a month before the 2008 crash). it’s been 3.5 years and though he and his team have taken a modest salary (from angel investor money) it’s been a HUGE risk financially for us to do this. Thankfully he raised a seed round couple of months ago, so the runway has been extended half a year. We rent (and own a house in NC) and I really wish we had bought a place when it was in our range of affordability in 2015 (now we’re certainly out). Long story short, I wish we had done 1 and 3 you listed above. It would have mitigated the risk by a large extent. We do talk about the business (setting deadlines and timelines is something we do every few months after advice from a marriage therapist to mitigate stress!) but overall I think the perspective of a startup spouse is somewhat different from a founder. So yeah, we’ve certainly burned each other out but hopefully the worst is over!

  15. Great post, Sam. I like that you kept the message grounded, and gave adequate exposure to the risks of the dreams not coming true also. As it goes, “it is better to have tried and failed, than not to have tried at all”. That was the basis on which I started my website, and while it’s a tiny fraction of your readership, has its own set of regular readers for whom my content “clicks”.

  16. Very accurate list.
    On your #2 item I would go a little further and suggest getting multiple unsecured Credit Lines and or a Home Equity LOC too. As you said it’s easy to get a loan with an income. It’s a lot harder as a start up.

    That advice is also good for soon to be retirees.

  17. When you started your blog in 2009, did you keep it secret from your employer? Was it easy? Any tips? Asking for a friend

    1. Never, ever, ever tell your employer or anyone at work what you’re doing for yourself. You never know who will throw sand in your food (as my mother says).

      A lady at work was leaving for another company. Long story short, corporate lawyers got involved and the other company rescinded their employment offer. She was then unemployed for several months until she managed to get another job.

      Rule of corporate life, KEEP YOUR TRAP SHUT!

      1. Such great advice! It’s really hard not to brag to your colleagues what you are working on. But it’s best to keep dreams to yourself until you gain some traction and know that you have a way out.

        In my case, I disclosed to them about my plan before the site started and the plan got rejected. But I decided To start my own site anyway because that is my right after work hours. I can do whatever I want at home. Work cannot determine whether you have a Twitter account or a journal, so I forged ahead and never talked about my endeavors.

        1. Hi Sam,

          You are right to mention that it is better not to reveal the plan to others at all. One should continue to execute the plan remotely. If it is successful, it’s good. If it does not come to plan, it is perfectly alright as one will have gained valuable experience and decide on the next course of action.


        2. For as long as I have read your blog?, you keep mentioning negotiating a severance. I have worked in the same industry for longer than I care to remember, but, it has been very financially rewarding, more so than I could have ever expected. Having said that, I doubt very seriously that my employer would do anything but say goodbye if I wanted to leave. I cant conceive of them giving me any type of package, especially one like you received, that allowed you to do as you wished for about five years. They might at best hire me to consult for a period of time, to protect the business I brought in, but only with the idea of keeping me until they could shore up their forces.I also believe that about 95% of the working population would never find themselves in that position, including most of the people who read and respond to your comments. I would, out of a great deal of curiosity, like to know how you did it, and
          why would they pay you not to work, and not bring them any value, thanks, Frank

  18. Well now I’m glad I signed up with Bluhost for a 3 year domain. LOL. I bought that plan because it was the most economically sound one. Now it looks like it lines up perfect with your theory.

    Well looks like 2021 will be when Xrayvsn will be faced with a decision. Actually even if it never becomes a financial juggernaut (odds are it won’t), the costs are very low for a business venture and it can just be stratified into hobbyist endeavors.

    1. That’s the thing. When I first started out, it only cost about $300 a year to keep The site up. Because of the growth, I’ve had to get a private dedicated server and some firewall stuff which boosted the cost. But that’s OK because revenue also increased by a lot more.

      Hi remember think to myself, if I could only make $1000 a month on my site, I’d be set is this income would nicely complement my other passive income.

      You just never know. But with focus and consistency, good things happen. It’s much better than not trying at all.

      1. That would be amazing if I get to the point where I would need a dedicated server.

        Did you determine that point or did your hosting company suggest the transition? If you did, what was the criteria you used to pull the trigger?

        I agree 100% that it better than not trying at all. I had created so many self imposed mental obstacles that delayed the start of my blog. People suggested I write a blog almost 2 yrs ago. Some self doubt included the fact that I felt there were already some physician fire/financial blogs out there that dominated the niche and that I knew nothing of starting a blog or creating a website. I also am afraid of the well running dry for ideas (luckily so far it hasn’t)

        Glad I took the plunge. This is a great community to be a apart of and on a different level if you are a blogger then my past role as just reader/commentator

  19. And on a side note. How in the heck do you write three articles a week? To get one with good content seems to take forever after my 10 million rewrites

    1. I think it gets easier over time frankly. But then again, the first year was so exciting and fun I found it to be a pretty easy as well. So after about the third year, you’re writing quicker and you know stuff that clicks. A lot of times you just have to let imperfection go and press publish and correct it later.

      1. I’ll give it to you. Your ability to crank out so many quality articles is a genuine talent. I see why starting FS was a non-negotiable for you.

  20. Every time I changed jobs was a higher risk for me than most. I have a neurological disorder that I always tried to hide. It causes loss of control, dizziness etc. Interviews were difficult too because stress always brought on the attacks. But I did it anyway. I pushed myself forward. A new job meant I had to prove myself all over again, and work twice as hard because of the disability. Every change in job was a huge leap of faith for me.

  21. It’s so intriguing to think about different scenarios like this. Some things could be so different and others would likely have turned out similar or the same. Of your three alternate scenarios I could picture number 2 or 3. I’m glad things have worked out so well for you that have your current experience though. Really good list of six tips! I can vouch for the benefits of negotiating a severance! Your book and advice changed my life!!

  22. Kristina Clark

    Nice list!! And the answer is yes, I do plan on going out on my own! I started in January this year and going to give it 2 years part time, then quit my day job in 2020! My husband is on board. Of course, now I am working extremely hard, both at my day job and on my part time business.

    1. Best of luck on your journey! Since you have a two-year plan and a spouse, I think things are gonna work out fine. You will naturally just work harder and find ways to earn a living once you’re on your own.

  23. I think it is such a personal decision that your list of things to consider could go on and on. Build a Financial safety net, assess ability to reduce expenses dramatically if things turn sour, build a return to workforce plan, assess ability of your family, friends, others to support you if things go down, make sure your mariage is strong enough to support downside stress, etc, etc. These are the négatives, but you also have to understand the scalability and positive side. All very complicated but I think you have laid out a good start.

  24. Brian McMan

    Fascinating, so if Financial Samurai didn’t work out then Financial Samurai would have worked out.

    Such amazing confidence, I know you recommend starting your own blog but it’d probably be best to pivot into something that doesn’t compete with that. At least that’s my take away.

    Best wishes.

  25. I think having the safety net of passive income helps a ton. Even if FS didn’t take off, you’d still be fine. You have enough passive income to enjoy life in Hawaii even without the online income.
    Out of all the steps you list below, working with your partner as a team is the most important one if you’re married. You need to have the same goals and work on it as a team.
    If Retire by 40 didn’t work out as well as it did, I’d probably focus on keeping our cost of living low first and perhaps work part-time after our son started school. It’s a bit too late to go back to engineering now. My knowledge is outdated already.

  26. “The greatest thing about running an online business is that the harder you try, the better you’ll do. I’m not sure if that’s the case with other businesses.”
    I find this to be very true too. There are some bloggers that are amazingly smart but they don’t have content to reflect it. The only reason is because they don’t try hard enough. That’s it! Dedication goes so far online.

    “If you have a spouse, discuss your entire entrepreneurial plan with him or her.”
    For us…it was more like a fight but still important to discuss it :) My plans included 3 years and then another 5 years for other online projects. I like the work because I like what I do but my husband is unhappy with the decreased amount of attention and quality time we spend together. Talk about burning each other out…

  27. Trading time for money in your 20s and 30s is easy. But after 40, it starts feeling like a waste since you realize there are plenty of people who pass away in their 40s and 50s.

    Well said! That’s why when I realized I was financially independent in my mid-40’s I started thinking “what am I doing with my life, here in this office?” I think your 40’s are the decade when the time/money equation starts to get scrutinized more. To quote a song, when you realize there are “less days in front of the horse than ridin’ in the back of the cart”, it triggers your mind to explore all kinds of things you never considered. That’s what happened to me at least.

    And I never thought I see you mention the possibility of minimalism. That one took me by surprise ;)

  28. I feel number 8 before you start a business could be to have enough in passive income to cover expenses – that way you can grow a business the way it is meant to grow without worrying about short term goals such as a paycheck.

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