A Day Job Is So Much Easier Than Entrepreneurship

You know what's easier than entrepreneurship? A day job. I say this with emphasis after not having a day job since 2012! I've been running a lifestyle business, this site, since I started it in 2009.

But let's go back to September 2012, three months after I left banking for good. Here are my words from way back when. I'll then share how I feel about entrepreneurship now.

The Desire To Be An Entrepreneur

No sooner had I announced my retirement did e-mails and phone calls start flooding in from competitors who wanted to meet. Some were curious why I had retired, while the majority of them were basically trying to see if I would be a good fit to work with them.

Fortunately, or unfortunately, the carrots that used to be delicious are not as orange anymore. Still, getting offered big bucks to work in a new environment, with a growing product is an exciting proposition!

The main reason why I retired from corporate America at the age of 34 was so that I can see what I can do entirely on my own. With all the work experience, education, and moonlighting, I'm curious to know if I can create a sustainable and fun business that can grow long after I'm gone. What I lacked was enough of my own time to make it happen.

Up until now, I had just been a hobbyist blogging, writing online and not focusing much on the business aspect of things. I enjoy doing things for fun because I get impatient with boring activities the older I get. However, what I'm quickly discovering is how enjoyable it is to learn about business online no matter how slow the progress is! I just need more patience.

A Day Job Is So Much Easier Than Entrepreneurship

Old Man Carrying A Heavy Load - A Day Job Is So Much Easier Than Entrepreneurship
Old Man In Istanbul Might Not Agree

With a job, all you've got to do is be a nice person and do your work no matter how mindless it is. You can put in 60% effort or 110% effort, you will get paid an expected salary. Maybe you'll get a nice bonus at the end of the year as a sweetener if you are extra special.

With entrepreneurship, you've got to not only come up with an idea, you've got to market and execute your vision. Even if you execute your vision, there's no guarantee you'll be profitable. Think about all those small business owners who borrow startup capital only to close down and lose all their investor's money a couple years later.

Everybody who is disgruntled with their job should try their hand at entrepreneurship for six months to appreciate what they have. Starting a small business will also make you realize how much government bureacracy there is that seems to want to keep you from succeeding. You'll also never want to pay taxes again.

Your job may be soul-sucking, but at least you'll be able to put food on the table and insure yourself from any unfortunate disasters. With entrepreneurship, you might be ecstatic every single day, but you might also end up living in your mother's basement. You might sacrifice your entire social life for the sake of a dream that might not come true.

This is why I made sure I could live off my existing passive income for 20 months in a row before I engineered my layoff. I didn't want to go back and live with my parents. That would be too embarrassing for a 34-35-year-old man.

The Regret Minimization Framework

I don't want to short change myself before I even get started with my entrepreneurial endeavors. As a result, I'm trying to go off the grid and not keep in touch with old colleagues and clients for the first three months.

I know there will undoubtedly be job opportunities which I will be tempted to take before giving my new journey a go. I don't want to have to choose, because if a great person gives me a great offer, it's going to be next to impossible to turn down!

When I look back on life, I want to know I at least gave entrepreneurship a full year before calling it quits. That way, I won't be asking myself “what if?” I don't want to be an old man, filled with regret, waiting to die alone.” 

The older you get, the more you will regret the things you didn't try versus the things you did try. Go through a regret minimization exercise to see what you might regret in the future.

Real entrepreneurs are successful, otherwise we're just hobbyists. We can't go on and on, spinning our wheels and not make enough to live a comfortable life. At some point, we have to face the music and realize we are failures. I will know in 12 months whether I am a failure based on my goals or not.

The Original Goal Of Work

Originally, I planned to work for another five years until the age of 40 and really kick back after. The problem is, it's not in my nature to kick back, and I never anticipated five years ago there would be such opportunity online. Funny how opportunities randomly appear. It's the X Factor I tell ya. You've got to be in the game to win.

So often we want things, and we want things now. We aren't willing to wait for when we can afford something, which is why we get into consumer debt. We aren't willing to accept we are “C” students foolishly trying to live “A” lifestyles. I am no different.

I want my online success to be immediate rather than put in my dues over the next three years. As a result, I get frustrated with myself when things aren't going the way I want. I've got to remind myself that I've only just begun and need to give it some time.

After all, it took 13 years to generate ~$80,000 a year in passive income, what makes me think I can replicate that amount in just several months? Patience is indeed a virtue. Besides, what the hell is the damn rush?

The income / work goal is $200,000 a year / 20 hours a week in three years. It sounds like a pipe dream, but if you read the post, you'll see that maybe, just maybe with some focused work, it can be achieved!

Take a couple minutes to watch Jeff Bezos talk about his regret minimization framework and why he left his stable, high paying job to start Amazon.com.

Trying Entrepreneurship For 12 Months Or Bust!

I'm going to give my entrepreneurial endeavors 100% attention for one full year. It's brutally difficult to make a meaningful amount of income on your own, but at least it builds character!

There are plenty of newly listed IPOs with millions of clients who still don't make any money. But hey, the public is willing to buy a piece of a founder's dream and make them wealthy.

The temptations of going back to work are everywhere. I miss the corporate card to spend with clients and friends on steak dinners and SF Giants ball games. I enjoy the occasional international business travel to a new country.

Meanwhile, a healthy paycheck and benefits are also quite a treat. These are all the good things and I won't mention all the bad things.

Alas, in order to realize my dreams, I must forsake these benefits. And if I decide I'm not on track to build something I'm very proud of that can also make enough money, then I'll just have to re-strategize. In one year, at least I'll be able to look back knowing I gave it my best and have no regrets.

For all of you who have taken the leap of faith and gone out on your own, I commend you! I know your struggles and have felt your highs, your lows and your frustrations.

Remember that nothing good comes easy. We must fight for what we want and never fail due to a lack of effort. In the end, the journey is the reward, so let us never forget!

Related: Why Blogging Is The Best Business In The World

It's Worth Starting An Online Business

Although being a successful entrepreneur is much harder than having a day job, it's easier than ever to start your own website or online business now.

I never thought I'd be able to quit my job in 2012 just three years after starting Financial Samurai. But by starting one financial crisis day in 2009, Financial Samurai actually makes more than my entire passive income total that took 15 years to build.

If you enjoy writing, creating, connecting with people online, and enjoying more freedom, see how you can set up a WordPress blog like mine in 15 minutes. It's imperative that everybody brand themselves online and take advantage of the 3 billion+ internet users today. You never know where the journey will take you!

Blogging For A Living Income Example: $300,000+
A real income statement example from a blogger. Look at all the income possibilities!

Always Negotiate A Severance Before Leaving Your Job

Finally, never quit your job, get laid off instead. If you get laid off, you can potentially get a severance, unemployment benefits, and job training. If you quit, you get nothing. You have more rights as an employee than you know.

The book is on its 5th edition and has grown to 200-pages from 100-pages. Negotiating a severance was the catalyst for me to leave banking for good and focus on Financial Samurai.

Never quit your job, get laid off instead with a nice severance package.

Being An Entrepreneur 11 Years Later

It's been 11 years since I left my day job and I've enjoyed the entrepreneurship ride immensely. Yes, the beginning two years were a little dicey, but having my severance package and a working wife let me sleep well at night.

Although being an entrepreneur is hard, you feel so much more proud earning $1 on your own than through a day job. Once you earn your first $100, it becomes easier and easier to earn more. The freedom an online business has provided us since 2012 has been wonderful.

We traveled the world for 6 weeks a year for the first five years. With the birth of our son in 2017, we appreciate even more the freedom to both raise our son every day!

And with the birth of our daughter in 2019 and the global pandemic, entrepreneurship has been a life-saver. The value of online businesses have increased immensely because they have more defensible income streams. Even during a pandemic, an online business can't get shut down.

Here's my 10-year entrepreneurship recap. I plan to run Financial Samurai for as long as I can think and type. I see owning a small business as a productive use of my mind.

Having a small business also serves as career insurance for my children, who are facing an increasingly competitive world. With college acceptance rates dropping to the single digits, it's very hard to get ahead nowadays.

Ways To Stay In Touch

Pick up a copy of Buy This, Not That, my instant Wall Street Journal bestseller. The book helps you make more optimal investment decisions so you can live a better, more fulfilling life.  

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About The Author

81 thoughts on “A Day Job Is So Much Easier Than Entrepreneurship”

  1. Let me tell you my story, having a very high paying job, plus company paid vacation in a year. 4 Years back a itch forced me to call it quits, I quit my job though my company try to persuade hard to stop me. Now Since I don’t have a job so to satisfy that itch started a company, Data analytics. Try to find clients, does pilot projects for free, for 1.5 Years it was hell, infact worse than hell. I don’t even have money to pay my kids fees it was really sad/Hard. Then all of sudden a client gives us a project (they are occupied so they offer us to do it for mere $100), I grab it put my everything. BAAM client stunned, ask if you have capacity do 250 projects per Year. wow. the second client then third. Presently paying double the taxes what I was earning 4 years back. To all entrepreneurs just one thing never ever call it quits till you are breathing…..imagine the confidence if you break it.

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  5. OMG THANK GOD someone is telling THE TRUTH!

    It’s like some entrepreneurs are like in LA LA LAND.

    Killing myself with my business but its finally where I want it to be.
    But it has been a 10 year Battle, mostly of WTF did I get myself into.

    But I’ve developed alot of great intellectual properties and will be able to sell those for years to come but trust me it was by pure force, and I guess destiny my father was an entrepreneur.

    But trust me, sheesh, if I knew then what I know now…I would have GLADLY BEEN the #2 guy in any company…sigh..

    Thanks for this article, I was wondering if ANYONE realized that a day job is freakin fantastic!

    1. Been running an IT services business for 12 YEARS!!! It was a little struggle in the beginning , then boomed! Making 100k Take Home at peak…

      Then 2009 …. BAM down it went! I had an injury to top it off….
      Bankruptcy in 2012 …. small blip back up i2014 and now down in the red again. Totaly Broke in 2016!!!!
      With Microsoft, Google and the lot … practically giving things a way there are little margins.
      New companies offer commission plans which never payout. Microsoft has lost all my O365 accounts – never got a dime.,Services as an add-on . Now people dont seem to find the value of good people and are simply shopping on price. PS WINDOWS 10 is a DISASTER!
      YELP and Google places have people who are not even customers givig us bad reviews because we are too expense and offer nothing for free …. wtf I got something free for ya alright, and they know where the can stick it!

      Im getting a job, then going into ceramic, painting , etc for hobby side bus.
      IM gettiung out , looking for Full time gig ……
      Broke nowhere to go, no one to go with, and rent isi in the rears….. YIkes.. What to do?

  6. Stefanie @ The Broke and Beautiful Life

    I think people who’ve never tried entrepreneurship don’t have a clue. Even with a low risk/low cost business like a blog, the amount of time and effort I have put in before making a penny has been astronomical. There’s no feeling like seeing something you created gain momentum though.

  7. Great article! I’ve been an entrepreneur for 3 years now. Thinking it’s time to throw in the towel, I really miss benefits and a steady income and yes, the stress just to thrive is constant and never ending. I especially like your benchmarks and the philosophy of “if I make it I make it and if not, I tried.” No regrets! Helps me in the transition. I made it, I did it, but I am burnt out. I’ll always keep my business and have it but those benefits are calling my name. I’m finding it to be a hard switch as I peruse the job market. I learned more in the last 3 years than I would have in 10-15 yrs on the corporate ladder. But the majority have no idea about the work involved, the mental stamina required, the rolling up of sleeves to get the job done and above all, to mindset to “go confidently in the direction of your dreams” as an entrepreneur.

    Has anyone on here gone from entrepreneur back to corporate? Did you feel like your experience was valued in the job search or did you receive numerous confused dog looks? How do I explain that yes, I was a ninja for 3 years? hahahaa :)

    Good luck on your book! Can’t wait to read it.

    1. Hi Angela,

      Three years is an admirable achievement.
      The benefits of work really are great aren’t they? My book is out. Check out the banner to the right or the Store tab above.

      It depends on how well one has kept the connections to get back to a day job.

      Good luck!


  8. Hey Sam! Great post! You are just over 6 months until you June 2013 date. Are you happy with where you are at?

    I sure hope I don’t end up in my parent’s basement, although my mom doesn’t have one now that I think about it.

    I hope you are insanely happy!

    1. Thanks Kris. The progress has been good so far. There is no way I could have done so much if I kept working a full-time job.

      Even if I return to work in 2013, I can imagine an inner giddiness where I will stress much less about performance b/c my 12 months of online endeavors has set me up for a long time. In addition, work income would make me stress less about online as well. Either way, I’m good b/c there is also passive income. I just want to do the most I can and see what happens!

  9. Opportunity Knocks

    Just about ready to dive into a new venture myself and while some would argue that franchising should not be included when talking about entrepreneurship, I disagree. I’ve recently lost my job and instead of looking at this as a negative, I grabbed my severance and ran. I am somewhat older then your average risk taker (43 yr old part-time dad ) but have had this dream for many years now and definitely have the drive and energy to make it happen.
    Although I am entering into a proven, established business model, only I can make this work through the same hard work and dedication that other successful entrepreneurs on this board pride themselves by.

  10. Amen. The real advantage of being an employee as I see it is that it’s a very low-stress lifestyle. You may think you’re stressed out at work, but try running your own business where you are responsible for EVERYTHING when something goes wrong. That’s stress.

  11. I meet a lot of entrepreneurs in my line of work, and I quickly deduced this early on!

    It’s much harder graft, with a high chance of failure, but the rewards are also potentially higher. A big name local investor/entrepreneur once said you’ll never build wealth as a salaryman, which I don’t think is a definitive statement, but there is some grain of truth to that philosophy.

    1. The rewards are actually infinite! You can build normal wealth as a salaryman as I have done. But I’m not sure if a salaryman can get to the point where s/he is really proud of what they’ve created. Both ways are not easy, so I think it’s best we appreciate what we have regardless!

  12. Hi Walt – Sure thing man. Life speed accelerates the older we get.

    My suggestion is to just START one of your ideas now, and work full time and tinker as you go. If you start seeing traction, start working a little harder on your idea. Only when you have some good milestones would I just go for it 100%!

    Good luck!

  13. @Sean @ One Smart Dollar
    Sean Ive been self employed since 2007! I got into eCommerce sites and ran 3 for a few years that were really successful (pushing past $1M/year in sales).. until some circumstances with the product, supplier and fake products being sold.. killed a lot of the market. There’s so much competition that it wasn’t worth putting so much time into it.

    Being self employed has its fair share of stresses! My gosh, no one really knows until they are in that position.. sure you get a lot of free time, but if you aren’t successful you can’t just fall back onto a ‘job’, or ‘unemployment’.

    I then got into doing a few coupons sites, affiliate marketing. Your site seems to be rockin it.

    I love hearing others who have been successful.. gives me drive and motivation. Building a business is hard work!

      1. Hey Sam! What I didn’t say was $1M is sales.. profit margins where around 30-35% max during those years. Since 2009 profits have fallen dramatically and since April of this year its almost not worth running those sites. Which is the reason why I’ve got a better ‘business’ plan in the works.

        The good – very low operating expenses compared to other businesses.

        The bad – I am stuck with a sinking ship since I’m not allowed to ‘advertise’ or do other forms of advertising to drum up new business.. main reason why I’m getting out now.

        Its turning into a time suck and Ive realized that.. which is the first step towards a new direction.

        Great article by the way.. really opens your eyes to the ‘true’ numbers of running a business.

        1. Hi Derek,

          Gotcha. Nothing good comes easy, but unfortunately, nothing good lasts forever either!

          $300,000-$350,000 in after tax profits sounds pretty good!

          I just gotta say thank goodness for the internet. It’s given us all more opportunity, and a chance to lead different lifestyles more than ever before!

  14. I feel your pain. While I finally have a fantastic, well paying job in my field, I started an online shop back in 2004, which has been a ton of work, for little reward. I attribute this to the amount of time I spent on the wrong things, in my time away from work.

    At 37 now, I ‘m starting to use my hard won knowledge for consulting, and eventually go solo. However, there is no way to get the years back!

    I agree, a day job can be easier in many respects. However, if you get to the point of having zero debt, a couple years money saved and at least some offline/online skills to make money, enjoy the freedom while you can!

    1. The good thing is, you learned a great deal from your 2004 experience! With that, I’m sure your new ventures will be that much more successful!

      I originally planned to just kick back after engineering my layoff and writing this blog. But, I realized it’s just not in my nature to kick back. Every morning feels like Christmas to me. It’s odd, but extremely energizing. I can’t even take afternoon siestas anymore b/c I’m working on something!

      Good luck to you!

      1. This is true, all the suffering and learning DID pay off. Just in a different way than
        initially anticipated. Such is life.

        That’s good you keep busy. It’s difficult to really “do nothing” lol

  15. Encouraging article thanks. I started my own international consultancy a few weeks ago and this blog will be helpful for me. My only difference is that I am contacting friends and recent clients as that network I built will be essential to the kind of consulting I am in.

    Walt – keep at it my friend. I’m sure you have those good business ideas and if you stay focused only good will result from it.

    1. Smart go contacting your old clients. I have been thinking of doing the same for my own consultancy business. Good luck!

      My blog is not an entrepreneurial blog but more on the various topics of personal finance, lifestyle, and a little bit of entrepreneurship.

      Best, Sam

  16. Nice Inception quote, I say that all the time! Good luck in your entrepreneurial endeavors, get ready for the greatest year of your life

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