The Comfortable Lifestyle Business Or The Big Payout?

Contemplating the Lifestyle Business In Hawaii - The Comfortable Lifestyle Business Or The Big Payout?

Back in late 2010, I had a dilemma. I was wondering whether to have a comfortable lifestyle business or the big payout. I'm pleased to say that 13 years later, I'm still happily running Financial Samurai as a comfortable lifestyle business.

Sure, I'm not crazy rich. But I feel rich. More importantly, my wife and I have the freedom to do what we want.

One Night At The Poker Table

Over poker one night, we got to talking about what we always talk about: entrepreneurship.  

Out of a table of 10, four work at start-ups, three are at Google, one is a high-tech lawyer, one works as a medical correspondent for CNN, and then there's me, a hybrid. I had just got done working on for three hours after working an 11 hour day. Needless to say, I was a little bit tired.

I love going to Friday night poker mainly because I get to bounce ideas off of really smart and incredibly hard working people. 

When I hear stories of one start-up player working from 7am to 3am every night for two weeks straight to launch a product offering, I get pumped. When the Venture Capitalist player recounts his firm rejecting a pitch by Tim Westergren, Pandora's founder in 2008, I wince, but daydream in amazement.

The Comfortable Lifestyle Business Or The Big Payout

Down about $185 for the evening, I started lamenting what the money will cost in side hustling. A couple hours of work at least, I thought. How depressing, thanks to my opponent's King on the river against my pocket Queens! 

I quickly shifted to more pleasant thoughts about the future of start-ups. Then I posed this question in between hands to my fellow sharks:

Would you rather make $15-000-$30,000 a month and “work” only 2-4 hours a day?  Or, would you rather make minimum wage working 12-18 hours a day for two years with a 25% chance of selling your business for $100 million dollars and netting yourself a cool $25 million?  If you don't, all you are left with are your experiences.

I purposefully left the question open-ended to see what the various responses would be. Already, one was doing math equations of what the capitalized value of $15,000-$30,000 a month would be based on an expected life expectancy compared to the expected value of the big payout. 

After all, we calculate expected value all the time in poker. Instead, I encouraged my fellow players to stop calculating and go with their gut.

What Did They Choose?

Surprisingly, or perhaps not to be unexpected, every single one of them chose option 2: the big potential payout. 

A couple of the entrepreneurs have a $100 million dollar buyout goal in mind, which I find somewhat delusional, but maybe not with Zynga, Youtube, and a host of other companies getting valued in the billions!

As the night wore on, I finally heard someone take the other side after losing $690 in a $2,600 4-way pot when his straight got flushed out.

“Well, $30,000 a month for working only a couple hours a day isn't so bad.  I think I'll go with that.”

Being An Entrepreneur Is Hard But Rewarding

A day job is much easier than being an entrepreneur. But the pride you feel about creating something from nothing is incredible. I highly recommend taking a leap of faith with some proper planning.

Even if you take a leap of faith and your business doesn't work, you can always go back to getting a regular job. If you return to your previous job within three years, you'll likely be able to earn a similar salary.

As you get older, you will regret more of the things you don't try than the things you do try. That feeling of regret will eat you up inside if you don't go for what excites you. The fear in your head is almost greater than reality.

Start Your Own Comfortable Lifestyle Business Today

If you feel you're not getting paid what you're worth and want to boost your income, start your own business online on the side! It used to cost a fortune and a lot of employees to start your business.

Now you can start it for next to nothing with a hosting company like Bluehost for under $4/month. They'll give you a free domain for a year to boot. You can learn how to set up your site with my step-by-step tutorial.

Brand yourself online, connect with like-minded people, find new consulting gigs, and potentially make a good amount of income online one day by selling your product or recommending other great products.

The easiest way to make money from home is with a blog. Not a day goes by where I'm not thankful for starting Financial Samurai in 2009.

Blogging For A Living Income Example: $300,000+
CLICK the graph to learn how to start your own site in under 15 minutes today.

Lifestyle Business Updates

Update 2016: I penned a new post called, Blogging For A Living: How Much Can You Really Make? This is a 3,000 word post that goes into detail on who is suitable to build an online business, and how much you can actually make after so many years. I've included four detailed charts from bloggers with different traffic levels and experience years. You will be surprised at how much one can make online if one sticks to things long enough. This post is a culmination of seven years working online!

Update 2023: I'm now on my 14th year blogging on Financial Samurai and couldn't be more pleased with the decision. FS attracts over 1 million visitors a month and generates a very healthy revenue stream. I feel like I have the best of both worlds.

But most of all, I still enjoying what I'm doing! I get to spend time raising my two kids under three and do what I love. In addition, Financial Samurai gave me the opportunity to land a book deal, something I've had on my bucket list since 2011. Buy This, Not That ended up becoming an instant Wall Street Journal bestseller.

That said, the global pandemic has also worn me out. I'm back to retire mode again. It's nice to relax more and spend more time with family. Even a lifestyle business entrepreneur needs a break.

Join 60,000+ others and subscribe to the Financial Samurai free weekly newsletter by clicking here. You can also subscribe to my weekly podcast as well on Apple.

About The Author

65 thoughts on “The Comfortable Lifestyle Business Or The Big Payout?”

  1. first off when you say make 180k-360k a year is that total annual revenue for the business, or net income? Also, if it is net income, is that actually what you pay yourself or is that just the net income for the business, im assuming if it is just a one man operation the profit will all go to you. Also if it is indeed the profit your talking about, im assuming its before taxes?

    why dont you say that its gunna most likely take years of work and long days to build this lifestyle business until u get to maybe the point where u can work 4 hours a day because of all the years of work u put in, in the past. There is no such thing as passive income, yes you can eventually have passive income, but thats only after putting tons of hours trying to build a client base which obviously is totally non passive, thats completely hands on. Im sorry its just you make like its so easy to build a lifestyle business and just make 200k a year for yourself. its hard to build and business and make any money at all, obviously as u know most of em fail, to me its already gunna be hard to just build any business, small, medium or big and since im really only interested in making an absolute minimum of 5-10 mil in a lump sum after tax, i want to go for the homerun, id rather fail then settle for less, and building a lifestyle business for me personally is settling for less, not just settling for less money, but settling for less mentally, not dreaming big, not doing everything i can to get ahead and outwork the competition and take the road less traveled.

    this was not meant to hate on you, if you think im wrong on anything please respond i would appreciate ur opinion, this was not meant to talk down upon lifestyle business, its great alternative for many but not for me personally, it was just a critique thats its just not as easy as you put it and also please give your comments on anything you would like feel free to be brutally honest no hard feelings thank you.

    1. Revenue or operating profit, since operating profits are so high in the online business.

      Things DO take YEARS. In fact, it will likely take at least 1 year to make $1,000/month in operating profit online, and 2 years to make enough to survive sparingly. This post was for me to think about what route to take, and perhaps others in the same situation. I wrote this post in 2H2010, 1.5 years BEFORE leaving a day job in early 2012 to pursue online entrepreneurship full time. How did you find this post?

      Check out:

      Blogging For A Living: How Much Can You REALLY Make

      This new post was written after 7 years of blogging/online business experience.

      Also read:

      Adopt An Abundance Mentality Already To Grow Your Wealth

      Stop Self-Sabotaging: You Are Your Own Worst Enemy

  2. Pingback: Can Financial Samurai Be The Next Billion Dollar Financial Technology Company? | Financial Samurai

  3. Curt Worrell

    It’s all about lifestyle for me, Sam! I would definitely choose option #1, but not for the security of knowing that the money would be there as opposed to hitting the jackpot later on, but for the lifestyle aspect. I’d much rather work only a few hours and enjoy this life, my family and friends than work my butt off and miss out on life, just for additional money.
    Great post by the way.

  4. Briana Ford

    I would choose the first option. I would love to spend time with my family and enjoy that money as opposed to slaving for a POSSIBILITY of hitting it big.

  5. Option 1 for me as well. I went in early in a startup once 10 years ago but not early enough to cash in big. I than said no to 3 startups since then (none of them have cashed in yet). The economics have a very thin line of working out and require constant soul pouring into the business. It also take on average 4 years to build up the business and than you are on the hook for 3 or 4 years to really cash in.

    I have to admit that I am always thinking of a business plan to start my own in the background. If someone comes along and it clicks … I may take the leap of faith :) So far, the offers I get for startup are from very good pitches and you have to look through that to see what’s really behind and how much it’s really worth.

  6. Khaleef @ KNS Financial

    I definitely would take the $3,000/hour job! There are so man other things that I can do with the other 20-22 hours each day.

  7. Sunil from The Extra Money Blog

    without even reading the comments i guessed most readers of this blog would opt for #1, as would i. such is the group that gravitates to blogging type activities (and the internet).

    CNN published a recent study where the BE number to happiness was not 200k, it was actually 75k believe it or not. this number varies for every individual IMO.

    for me, using money to live the life i want is the name of the game. there is no value i can place to my time spent on activities i enjoy with the people that are near and dear to me the most. building several streams of passive income over the years has helped me live the life i want, and i wouldn’t trade it for anything…

    1. Yep, we all know about the widely quoted 75K figure for happiness, which is why I wrote this post, b/c I am here to say it is untrue and selling yourself too short. $200,000 is that magic number!

  8. Option 1 without even thinking about it, even at the lower range ($15k/month, 4 hrs/day). I could use the rest of the time towards other productive ends.

  9. I would definitely go with option 1. $250k – $360k per year or $100 million over my lifetime, both will give me everything I need in life, Sam.

    All the best,

    Len Penzo dot Com

    1. But, how long do you know how long you will have to live? If you are say, 40 right now, are you sure $250-360K = $100 million over your lifetime?? The $25 million in 2 years could be sweet!

  10. I find it interesting that you mentioned the range to be $15-30K a month working for 2-4 hours. Most responders took the high end of both ranges (working 2 hours and making $30k a month). Says something about people selectively hearing what they would like…

    With regard to option 2, what is the certainty that the start up will better humanity? There are plenty of businesses that make big bucks (high frequency trading bots) that don’t necessarily do much to help people. I would consider putting Farmville into that category as well.


    1. It is interesting how nobody wrote 4 hours a day and $15K a month huh? Option 2 doesn’t necessarily have to save humanity, it just has to provide some type of value, but it world peace stage or simple entertainment.

  11. It’s true, after $200,000, you really aren’t much happier. You save more, but other than that, it’s all about the same.

    Beyond $200,000… or $360,000 for this matter…. it’s about creation and a challenge b/c you’ve discovered that making money is pretty easy.

  12. One more thing…

    In the big hand you mentioned there were four players. The flush took it down, the straight was in second… what were the other two players holding as they went into showdown? My guess would be pocket aces and someone else made a set with a pocket pair…?


  13. I’m old now and no longer have the energy to work consecutive 14+ hour days for so long. But, if I was in my 20s, I’d go option #2 all day long. However, come to think of it, I think I already work 16 hours a day Mon-Fri, so maybe I will just go with option #2 because I’m less worried about money anymore, and happy to create something!

  14. My first inclination was to go for the “security” of Option 1. It seemed comfortable, easy, and a nice way to make a living while having time for so many other family-related things I would want to do.

    Then, my brain took over. Looking at a 25% chance of $25 million profit with the other 75% chance being I would have toilled at minimum wage for 2 years – that’s a pretty good expected value.

    I just might take Option 2, with that much on the line. Work like heck for 2 years, and if it fails, you capture all the learnings you can from the experience. If it succeeds, it’s a game changer for your life and your family’s security, and some real aspirational lifestyle dreams.

    All hypothetical, and I would have to have the guts to pull the trigger on doing it, but I like the EV and upside of Option 2.

    1. It REALLY is a game changer. Two years is NOT a lot of time to work hard. It perplexes me why so many blogs fade after 1 year for example. Why do anything, if one doesn’t spend AT LEAST two years? I don’t go into anything without expectations of working on it for less than 5 years. Maybe as a result, I don’t feel like I’m ever really in a rush. That’s good and bad.

      Option #2 baby!

  15. I would’ve picked option #1 because that’s most likely the happiest choice, but only if it’s 100% guaranteed, which in reality is impossible.

    However, when you are making $10,000, you will want $15,000 and when you hit $20,000, you will want $30,000. When you get there, then either out of fear of losing $30,000 in the long run or the greed of more, you work more hours. Pretty soon, you are working towards a $100 million goal anyway.

    So really, option one has money in the meantime while you work towards the 25% $100 million goal, while option number two means bleeding money all the way and have the same chances. Which one would you pick then?

    But btw Sam, in reality, do the owners typically still have 25% of the company by the time they sell it for $100+ million? I’d think that unless it’s those instant successes like admob, if the start up is not making money (as most big ideas seem to be for a while), it’s hard to not sell shares to investors continuously to keep the thing afloat for the years that it’s propping up the economy.

    1. There’s definitely a lot of dilution in startups due to capital raising. However, a 25% ownership for the original founder is quite common, if not conservative.

      If I’m making $15-30,000 online every month working only 2-4 hours Mon-Fri, I’m pretty happy and won’t feel the need to work 4 more hours a day to try and double it to $30-60,000/month. It doesn’t mean much after $200,000/yr if all ones debts are gone.

      1. Thanks for the insight on the start ups. I always wonder about this when I heard of those $200 million paydays! :)

        You say you are happy with $15k – 30k a month, but you opted for #2. It sounds like that when you are actually only working 2 hours a day, you’ll want more, because by then, you already have option #1 and it would tilt your desires towards option #2 even more.

        When your online ventures hit its stride, don’t say I didn’t tell you so :) We can talk more about this then!

        1. Cool. I just think that making money is pretty straight forward. I really enjoy staying under the radar and having little to no one know my business. It is the greatest achievement if after all this time, people think I haven’t hit any stride and am stuck in neutral.

          If you need any non online income advice, let me know!

  16. Man, that’s a tough one. I lean towards option 1 just because it leaves so much free time to work on other projects, possibly start other entrepreneurial ventures, and volunteering my time for causes I find worthwhile. Who says you can’t do both! earn 30k/month on the one venture and then work the other hours on your possible jackpot job!

  17. Option 1 anytime over option 2. Simply because you have “something to do” with all that free time everyday and it really takes up a small portion of your day.

  18. Money Reasons

    With a family to support, I’d have to go with option 1.

    But if I were 18 or 21 again (or younger), I’d go with option 2. In fact, once my son is that age, I would recommend him going that route too if the opportunity were available to him…

    Sounds like a great game of poker, I haven’t played in years now! :(

    1. Go online! It’s fun and free. However, it’s more fun to play with a group of real guys, where you can chat and socialize.

      I hear you on Option #2 during your younger days.

  19. Sam, I’m for a combo of both. Bust your but out of college and then hopefully get to a point where you can make a decent chunk of change working a moderate amount (but not killing yourself) WHILE shooting for the big 100 mil payout. I totally think this is achievable with the right combintation of hustles and side-hustles…but only if you do what you love.

    1. Investor Junkie

      I shoot for $30k I’m not looking at $15k :-) Still for 2-4 hours daily that’s not bad.

      That’s at minimum $125/hour.

      That’s much higher than the approx $20/hour the average person white collar
      worker makes (I always use that
      number as a method to determine if a project is worth taking on)

  20. FB @

    I already do the former, so I’ll stick with that thanks!

    I am not into big payouts, and I don’t mind working for a steady income knowing I can save so much more on the type of lifestyle I live.

    I don’t exactly work only 2-4 hours a day, but if you average out the hours into a year, that sounds about right, although the money average per month goes down.

    This year I worked about 9 months, making $20k/month, working 6 hours a day.

    I got 3 months off to chill out.

  21. Just going on gut feeling it is that 30K/month + the freedom associated with that choice. The other time could be used to pursue another income stream , vacation, or a smaller company (lets say in the range of $20mil lol).

    I wonder what people would say if you made the numbers a little bit less extreme. Make 10K/month for 20 hour/week work vs working for 5K/month for 80hours/week with a chance of pay out of 3 mil….

  22. Without a doubt, I’d take the $30,000 per month. 2-4 hours a day?? This is clearly my dream job. What are you trying to get super rich for? So you can work less than 2 hours a day??

  23. The 25% probability is just too low. If it was 50% then I would do it. Give me the $15,000 to $30,000 for 2 to 4 hours a day. I would use the rest of to build my fortune!

    P.S. How do I get a seat at the poker table with all of you multimillionaires? LOL.

    1. Who says we are all Multi millionaires? The two guys at startups are probably only makig 70-100k/yr and busting their balls to try and make it big! They all are going with option # 2, but are making morethan min wage. One probably makes nothing and is just living off savings or funding and not drawing much.

    2. Who says we are all Multi millionaires? The two guys at startups are probably only making 70-100k/yr and busting their balls to try and make it big! They all are going with option # 2, but are making morethan min wage. One probably makes nothing and is just living off savings or funding and not drawing much.

        1. I never understood why people at startups didn’t sell their shares after a few years when the valuations were so high. How many years was the holding period at each startup?

  24. Chris Parsons

    I’d take the lifestyle business all day, every day. I’m not willing to work 15 hour days for any amount of money – much less minimum wage with a chance at a lot of money.

  25. I’d roll with option #1… The idea of $30,000 a month and only working 2-4 hours a day would leave me a lot of free time to start other ventures.

    With that $30,000 a month I might even be lucky enough to start a business where I work long hours but after a few years I’ll be able to sell my side business for $100 million dollars and net myself a cool $25 million.

    Just an idea though ;)

  26. My gut say option 2 while I’m young.
    If you are young, there is no contest. I know people who choose option 1 and some who choose option 2 when they got out of college, not to the extreme in your example of course. People with option 2 grew a lot more. Those option 2 people can always go back to option 1 or more often they go on to another option 2.

  27. Nick Sweeney

    It’s an interesting dilemma, if you think that choosing between a Maybach and a BMW is a “dilemma.”

    I gotta say, Sam, I don’t play many poker games with my friends with a $2400 pot, nor do I hang out with any high-tech lawyers. If anything, your article is a beautiful illustration of the perspective of money and wealth. Personally, I wouldn’t know how to spend $15,000 a month, let alone $25 million.

    How much money does a person really need, anyway? After all, anyone who washes their car with drinking water is already “rich” when it comes to the global standard of living. Even if the car you’re washing isn’t a BMW.

    1. Yep, but we are not all rich as some may expect. Some prob are worth several mil, but others like he startup guys are just everyday guys who love to play poker.

      This blog really is about providing perspective. Hopefully a different one from others. At some point, it’s not about the money, but about the challenge of creationand competition. Cheers

      1. Nick Sweeney

        Your post started a lively conversation here in the CoupSmart office, Sam, so thanks! :)

        Just to be clear, the question is a fascinating one and I think the answers you received shows the true entrepreneurial spirit of your friends. There certainly is a lot of merit with toughing it out for the big pay, but as you probably know, the best (and most successful) entrepreneurs are the ones who put their sweat, tears and passion into their business regardless of that “transparent, dangling carrot.”

        Of course, the payoff always helps, too. ;)

        Keep up the great posts!

        1. It’s great that you are working at a startup as well. I’ve always wanted to see what it was like ever since the dotcom boom days in 1999. Alas, it l took the traditional route but with this site and things we have planned for, I’m goig your route and t sure is a lot of fun!

          You guys having fun or what?

  28. Option 1 popped into my head immediately. I don’t even know what I would do with $100,000,000, and working 2-4 hours a day for decent cash isn’t bad at all. I could save so much of it and guarantee (pretty much) a nice retirement. Maybe I would get a ‘second job’ and double my monthly income to 60k!

  29. I would definitely take option #1 and then build a business with all the extra money and free time I have. And if that’s “against the rules” then that’s fine. I would be making over $300k a year and could invest that money wisely and essentially afford everything I would ever want, including funding a business for personal reasons (even if I’m not “allowed” to make money off selling it).

  30. Invest It Wisely

    I’d go with option 1, simply because it would make such a huge and immediate difference to my life and allow me to get out of the rat race, irregardless if the second option has a mathematically higher numerical value. People’s subjective value scales aren’t linear; I know that mine isn’t. I would be very happy already with just $30k a month for 2 hours of work a day, if I knew that it was fairly sustainable. In that sense, my life EV would be higher by going with option 1.

  31. Interesting. Because of your sample set though, they were probably already making close to that so the prospect of making $360K per year isn’t that appealling. I think most of your readers would take option 1. Here’s why. Option 1 is guaranteed and you could always turn some of that money into a big biz sale anyway. Option 2 is a “chance” and we all have that chance now, but those chances are 1 in a million even if you call it 1/4 here. You’re talking about a disruptive new biz like Digg or something. Not many of us will create anything like that realistically.

    But I’ll take either one :>

    1. I would say half make over 360k and half make much less like 125k or less.

      25% is 25% chance for $100 mil sale as like u said, it’s probably closer to a 0.1% chance for any entrepreneur to get to that level of success!

  32. I’d go with option 1 for sure. I’m going to be working on *something* anyway, just because I always have a zillion ideas to try out. I may as well make $30K per month while I’m at it, and have a life in the process!

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