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, so I have 13 years of perspective doing both.
But let's go back to September 2012, three months after I left banking for good. I decided to focus full-time on Financial Samurai because I loved to write about personal finance and connect with like-minded people. Heck, I even helped launch the modern-day FIRE movement, which is grown all over the world!
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 pass. 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
With a job, all you've got to do is be a nice person and do your work no matter how mindless it is. Whether you put in 60% effort or 110% effort, you'll earn an expected salary. No wonder the quiet quitting movement took off. Maybe you'll get a nice bonus at the end of the year as a sweetener if you are extra special.
With entrepreneurship, not only do you have to come up with an idea, you've got to market and execute your vision as well. Even if you execute your vision, there's no guarantee you'll be profitable. Think about all of the small business owners who borrow startup capital only to close down and lose all of their investor's money a couple years later.
Appreciate Your Day Job More
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 traditional W2 job may be soul-sucking, but at least you can 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 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 may 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 can get frustrated with myself when things aren't going the way I want. Thus, I've got to remind myself that I've only just begun and need to give it some time.
Generating Enough Passive Income Takes A Long 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!
In 2017, I actually did achieve my goal of generating $200,000 a year in passive income. I attribute the success due to a bull market and regularly saving most of what I earned after I left my day job in 2012.
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!
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!
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!
Always Negotiate A Severance Before Leaving Your Job
Finally, check out my bestselling and one-of-a-kind ebook, How To Engineer Your Layoff, on why you should 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 ebook is newly updated with recent case studies and additional resources. It's already helped educate thousands of people with the knowledge needed to walk away on their own terms with money in their pockets. Negotiating a severance was the catalyst for me to leave banking for good and focus on Financial Samurai.
Use the code “saveten” at checkout to save $10. Leaving a job you no longer like with a financial cushion feels like winning the lottery!
Never quit your job, get laid off instead with a nice severance package. For those millions of federal government employees receiving buyout offers under the Trump administration, I strongly consider taking it.
Being An Entrepreneur 13 Years Later
It's been 13 years since I left my day job in 2012 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. The reason is because you created something from nothing and know that it was all you who made it happen. When you are working to build someone else's dreams, you don't know how much of an impact you are truly making. Most of the time, it's the existing product or company's reputation that matters more.
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. Here's my perspective on making money online since 2009.
Being A Solopreneur Enabled Us To Live The Life We Wanted
We traveled the world for 6 weeks a year for the first five years. Then, with the birth of our son in 2017, we both appreciate the freedom to raise our son every day even more!
And with the birth of our daughter in 2019 and then 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 stays up.
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.
Invest In Entrepreneurship The Easy Way
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Ways To Stay In Touch
For more nuanced personal finance content, join 60,000+ others and sign up for the free Financial Samurai newsletter and posts via e-mail.
In addition, here's a great post on why it's harder to work for yourself than work for someone else. For the longest time, I wondered why one of my best friends in the world wouldn't simply put all her effort in her own business. Now she reveals why.
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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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!
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?
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.
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.
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!
Sam
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!
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!
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.
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.
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.
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!
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!
@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!
Derek, can you discuss bottom line income with $1 million in sales? How much could you keep after taxes and operating expenses?
Here’s a post you might like that talks about it: Quit Your Job And Die Alone
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.
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!
Just a note: the $300,000-$350,000 is not after tax profits. It is before taxes.
Brandon
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!
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!
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
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.
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
Nice Inception quote, I say that all the time! Good luck in your entrepreneurial endeavors, get ready for the greatest year of your life
Entrepreneurship is so, so hard, and that’s why I am not interested in it at all, despite most of my peers longing for it. I don’t want my life to be about work. I don’t want to look back on my life and regret putting in 16 hours a day trying to build my business when I had a tolerable job that I liked that only required 8. But then, I might get sick of working for a company and want to be creative. I just don’t think that’s me right now. I admire those who have the stamina to work for themselves!
I agree. If you are doing well, love your job, and can kick back, then don’t bother with entrepreneurship!
Have you joined free money finance Daisy?
Sam,
I am a first time reader of your blog. I really like the content and especially the honesty. I am in a similar situation as you. I worked my way up the corporate ladder, went on international assignments and was generally successful by the age of 33. I was grossing nearly $200k a year in salary and bonus. Yet I found that money alone wasn’t really motivating me any more. I wanted to see if I could reach beyond my potential.
What pushed me over the edge was the same Jeff Bezos video you posted above where he describes his “regret minimization framework.” Another one was a 2011 McKinsey report on big data.
Anyhow, I quit my cushy corporate job earlier in the year to start my own tech venture. I decided to not pursue venture capital funding and do it solo… You’re right – doing a start up is 5x harder than being a regular employee and at least 2x harder than being a high performing manager. There are days when I have a lot of self-doubt about my decision to venture out on my own. But I would be disappointed with myself if I didn’t attempt to create something. I wanted to find out if I had what it takes to be successful on my own.
It is a sobering feeling seeing my checking account being depleted month over month as I race against the clock to finalize the software I am attempting to build (did I mention that I’m not a software developer). It’s scary to say the least.
But when I look back at my life, this is the story I want to tell. Keep fighting Sam and remember that whether you think you can or think you can’t make it, you’ll be right.
Good to have you here! Thanks for sharing your story. As a software developer, you’ve got a great competitive advantage in this day and age!
Good luck on your venture and check back and let me know when it’s launched! One of the things I’m also trying would be entrepreneurs is to really strategize their day job exit. Severance can be a huge safety net for months if not years!
Good luck! I’ll be watching closely to see you how you. I am 35 too, running a blog that I don’t dedicate enough time too (but would like to expand and get into more online busienss’).
Thanks Andy. We’ll see in 9 months time what’s up!
“C” students wanting live “A” lifestyles, that speaks for many of us nowadays. We tend to ignore how much effort it takes to really achieve any of the things we see other people have accomplished. For entrepreneurialship, my personal experience is that it’s much easier if you do it while you have a part-time job or means to support yourself untill when your own thing can support you full time.
Harry, that’s exactly what I did. I began writing online as a hobby in 2009 until sometime end of 2010 I realize there was income potential due to the traffic increases. Two years after that, it’s balls to the wall and let’s see!
As I near Year 2 with my company, I’m seeing that the discipline and commitment that you require in the first 6 months to a year, while brutal are nowhere near as tough when you reach a phase when you are aiming for LEGACY. To get legacy, you start thinking about scaling, and going beyond yourself, and that will mean hiring and training others.
The minute I started to think about employees and hiring, it just became infinitely more complex and required even more personal discipline. It’s been challenging to balance personal reward with business needs as we grow.
For me it’s important to balance out the marathon of discipline with occasional moments of splurges (or somewhat irresponsible purchases). It’s like the balance of order vs. disorder. Both need to exist in some form.
Good to know Pashmina about your experience. I don’t plan to hire any employees in the foreseable future, but I am looking for a partner to help build a platform to harness the collective readership of the Yakezie Network.
I’m taking my time finding a partner. Whoever s/he is, I think they are going to do very well in terms of leaving a legacy!
Yep! And, no, I haven’t been tempted yet. Working as a dev isn’t quite as lucrative as what I imagine your old job was like.
I’m so thankful that you wrote this post and exposed some of the myths about becoming an entrepreneur. I feel like the media has glorified entrepreneurship without talking about the extreme amount of effort and responsibility it takes to run your own business.
I personally am using the one foot in, one foot out approach. I still maintain a full time job, but work VERY HARD after my wife and daughter go to sleep to get my blog and brand going.
If there’s anything you need or any questions you have please don’t hesistate to ask. I wish you luck brother and will be rooting for you.
I employed your footsie approach for at least the last 20 months of my career. I do think it is the spot on right approach for everybody to take as they build towards something new! It’s just that no matter how much you prepare, you have to keep fighting and expecting things to change.
Will have to check out your ventures!
I wish you luck on your venture to entrepreneurship. There is really be a big difference with working on an 8-5 shift in an office and owning a business of your own. When working in an office, you just do the same tasks over and over and get pad, but with having your own business, you have to strive hard everyday and evolve to succeed. I agree with you, but I think 24 months would be a pretty good gauge to see if you will succeed or take another route.
You are truly correct with that, being an ordinary employee is so much easier although you can always complain about your salary. On the other hand, you have the budgeting and the competition as the enemy in being an entrepreneur.