A Day Job Is So Much Easier Than Entrepreneurship

Old Man Carrying A Heavy Load

Old Man In Istanbul Might Not Agree

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 35 is 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’ve just been a hobbyist, 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.


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.

I’m beginning to think 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 and 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 passive income for 20 months in a row before I engineered my layoff. I didn’t want to live at home with mom.


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.” 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.

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.


I’m going to give my entrepreneurial endeavors 100% attention until June, 2013 (it’s now 2015 and things are going well). 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. By June 2013, 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 been around six years since I started Financial Samurai and I’m actually earning a good passive and active income stream online now. The top 1% of all posts on Financial Samurai generates 31% of all traffic. The average age of the top 1% posts is 2.3 years old. In other words, after putting in the hours to write some very meaty content over two years ago, 10 posts consistently generate a monthly recurring income stream that’s completely passive.

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 in 15 minutes with BluehostYou never know where the journey will take you!

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.

Finally, if you’re looking to make some extra money immediately, I’d consider driving for Uber if you have a car. They are currently giving up to a $300 bonus after you make your 20th ride. After 225 hours, my gross pay is $35/hour, which is not too bad! I can see how people can easily make an extra $2,000 a month after commission and expenses with Uber or any ridesourcing company. I’d definitely sign up and drive until at least the bonus. Why not make extra money on your time?

Updated for 2016 and beyond.



Sam started Financial Samurai in 2009 during the depths of the financial crisis as a way to make sense of chaos. After 13 years working on Wall Street, Sam decided to retire in 2012 to utilize everything he learned in business school to focus on online entrepreneurship. Sam focuses on helping readers build more income in real estate, investing, entrepreneurship, and alternative investments in order to achieve financial independence sooner, rather than later.

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  1. says

    I started doing my own thing in 2008 and absolutely love it. I work a lot more hours than I ever did before but wouldn’t give it up for anything. I have the ability to do things that I enjoy during the week if I want to. There is a lot of stress involved, you just have to find ways to relax and rejuvenate yourself.

      • says

        I have bought and sold a few websites, but currently my main website is a coupon/deals website, Freesnatcher.com. I have run it since the beginning in 2006. My situation was almost forced. I was working as an analyst with Bank of America until I was laid off in 2008. I put all my effort into my online marketing efforts and things started to click. Now I am just trying to diversify my online portfolio.

        • says

          Very cool! Six years later, are you making enough from the site to just do that full time? Three years from now will be where you are now for me so I’m curious to hear your perspective on things (the dips, break throughs, ups, and downs). What would you do more of from years 3 to 6?


          Note: Need to start a new thread to respond.

  2. says

    $200,000 a year working only 20 hrs per week? Good luck.

    Of course, anything is possible. What exactly IS your product, though? It isn’t very clear to me if you’re trying to reach this goal using this blog, or doing something differently.

    I do know that you have the get on the map service. If 200 people pay you $1000 each you’ll be well on your way. You have to find a way to sale and guarantee the ROI for you consumers if you use this model.

    Advertisers should be treating you well, right?

    How is the book going? Have you asked all your Yakezie friends to post a banner on their site? Again, I’m sure they will do it free. What’s a simple 125 x 125 banner to someone who learned so much from a network you created? Hell, I’m going to put one up on my site for you.

    You can write a post on Yakezie that asks people to put up your banner. It may be spammy, but you’re an entrepreneur now. Anything and everything within ethical and legal bounds is free game to try. I’m rooting for you!

    • says

      Hi Romeo,

      To make $200,000 a year you need to make about $16,700 a month. That figure can be obtained through selling 438 copies of my book a month. After all, there are millions of working people all over the world, all of whom plan to one day leave their jobs whether by choice or otherwise.

      I have not begun the affiliate marketing campaign for my book yet as I write pertinent content on my site for the first six months first. I’ll open things up in 2013. There’s really no rush as I’d like to gather feedback and be involved in the conversation.

      My product is simply to provide the most helpful, and most entertaining personal finance content on the web from a person who has spent his entire career in finance, went to business school, and made his nut.

      Thanks for your support Romeo! I appreciate it. And for other ways to get to $200,000 I detail the plan in this post: http://www.financialsamurai.com/2012/08/20/life-after-an-engineered-layoff-the-quest-to-work-20-hours-a-week-and-make-200000-a-year/

  3. says

    …and W-2 income is worth so much more than the same amount of schedule C income.

    I’m going to guess that you wouldn’t have been able to finance as much real estate as you had on leverage without W-2 income. And if you had, you would probably need to cut back in other places – say, the 401k – to invest in your rentals.

    There’s more to it than just the work and income. The way things are, $100,000 in W-2 income is worth far more than $100,000 on a schedule C. In some sense, it is entirely irrational to start a new business.

    • says

      Indeed. The benefits of having a job are often overlooked. From health insurance, to retirement savings, to paid vacations, to being able to get a mortgage to buy property.

      I do think it is best for someone to get work experience and build a financial foundation while working on the side for a while. Although many entrepreneurs have done well with no experience.

  4. says

    If you do have the dedication you say you’ll have until mid 2013, you are indeed going to achieve great things. Compared to the few bloggers who display income, I think what you are reaching for is perfectly reasonable and attainable. Good luck!

  5. says

    Great article, Sam! Success is relative. It’s all in your mind because you set the gauge. Having said that, I agree that it’s much harder being an entrepreneur. I have been on both side of the aisle for a long time now.

    I like the steady income that job brings, but I like excitement and sense of purpose with being an entrepreneur.

    I think everyone should take a plunge at least once in lifetime. Life is too boring otherwise.

    • says

      Thanks Shilpan. Everybody really should take the plunge, see if they succeed or fail, and then just get a job again and appreciate everything about it and then some!

      Life does get a little too predictable sometimes. It’s fun to shake things up, and thank goodness for the internet!

  6. says

    So true! It is so much easier for me to make money going to work than the amount of effort is has taken me to earn the .10 cents I’ve made since I started my own online business a month ago. Although, knowing that one day the amount I’ll make passively from my online business will be more than my salary makes all the sweat equity I’ve built worth it.

    Regardless, I’m grateful that I even have a job that will hold me over until I make enough to no longer be a wage slave, I know a lot of friends and family who have been unemployed for a long time and are on the hunt for a job.

  7. says

    I definitely have been thinking about keeping my job a few more years to build up that nut, partially thanks to our conversation. But, there still is a part of me that knows how much more I could do without working. It would take a while to make up the difference of my dayjob income, but probably not too long.

    All that to say that I can understand how tempting it would be to just return back to a dayjob and keep working the side business. Financial independence is nice, but making something out of nothing seems more valuable.

    • says

      You can do much more, but it won’t necessarily translate into that much more revenue. It could be a 1revenue/10work ratio for all you know. The thing is, you never know until you try.

      Just give your job 10 more years Corey! With what you’ve got and what you know, you’ll definitely be set for life!

  8. says

    My situation is different but similar to yours. I am about to sell and walk away from a small business I have owned for ten years. I did not invent anything or turn it into a fortune 500 company, but it has provided well for my family. As much as I have grown to hate the management, taxes, and regulation of the whole thing, it has never, ever been boring. While, I think I will enjoy not having that monkey on my back, I am very concerned that I might get bored or lazy. I also feel that I am supposed to still be working full time at my age. My hope is to find enough contract work to replace my income while working less hours per month. I hope to invest the money I will make from the business sale (I am carrying the balance on the loan for 10 years). After those ten years, I hope I can retire from optometry if it’s not fun anymore and/or find that business that I will be motivated to run. We have a few ideas that are drastically different than what we do now. Or I could just take a corporate job and work on autopilot, collecting my salary. It does seam appealing sometimes.

    • says

      Congrats on selling the small business! When you say “carrying the balance on the loan for 10 years), do you mean the business sale is not enough to pay off the loan, or do you have a loan from something else?

      I think a lot of people get the idea that mega millions come after selling a business. I know I do. Please help clarify!

      Thx, Sam

  9. says

    I’m really close to the one-year mark and I can honestly say I haven’t been tempted to go back to my former career. A few times I’ve missed the money (especially during the slow weeks!) but I have never missed the work I used to do.

    I still REALLY need to work on separating work and personal time – forget 20 hours a week; I’m doing more like 20 a day! But overall I’m thrilled with my decision to become self-employed and doing everything I can to ensure that I get to stay that way.

    I have a great deal of confidence that you’ll be just fine, Sam! The first few months were the hardest for me, but now I’m in a groove and nothing has ever felt as natural as what I’m doing now. Looking forward to watching as it becomes easier for you – I know great things are in the works!

    • says

      Andrea, your encouragement means a lot! That is wonderful you haven’t been tempted at all to go back. And in that way, you are lucky that you disliked your job. I was just getting a little bored. When you are at one place, doing the same thing for over 10 years, it does that!

      20 hours a day is a lot! Maybe I need to work more, but that would definite my goal of a more balanced lifestyle :) But, perhaps I’ll take some inspiration and work a double digit work day once a week and do some supercharging.

      Glad you’re back to writing on the blog after the week hiatus. Like water off a duck’s back I say!

  10. says

    When I did you’re interview (and those of the other bloggers), I’ve always had a notion that being self-employed was harder than being an entrepreneur. However, it is always a choice between doing what you want or doing what others want and taking it a little easier. I think you’d rather do what you want, even if it is a little harder. Regardless, I know you’ll be successful.

    • says

      For sure… making $50,000 from a job is a walk in the park compared to making $50,000 from your entrepreneurial endeavors.

      It builds character though, and it all depends on how much you want to work and make. Gotta last for the long run though!

      Thx Rob!

  11. says

    There is a reason the majority of the population have jobs, rather than their own businesses, online or otherwise. Most comments mention the relative income, and that’s all true. But I believe that’s not the main point.

    The main reason most people have (and keep) regular jobs is risk. On your own you have a higher risk of failure, because, let’s face it: most of us know (more or less) how to succeed at a job. It IS a lot easier than succeeding at a business of your own.

    • says

      Risk is a funny thing. I was risk loving from 22-28, and now I’m risk adverse ever since.

      Yet, I guess I’m back to risk loving b/c I no longer work by my choice, but the severance package was a HUGE catalyst. I would say at least 35% of people who are working would quit their job if they could get a severance package worth 6 years of living expenses wouldn’t they?

  12. AJ says

    I and my husband run our retail business. It took 2 years to start generating ok income. In 4 years we double our income of before we started the business. And yet still a lot of potential we are going to make. At the beginning (first year) we both worked very long hours (10-15 hrs / day) in order to build up good and strong business foundation. After you start pick up your clients base, you will start be able to focus on specific marketing and your business will start expand and take off. One rule I really appreciate in business is you are never perfect, always have room to improve and do better. and also open eyes look for opportunity along the way all the time !

    Be patient, have clear vision in your business, plan and do Execution well, always evaluate results compare with energy and effort you put into it, and Adapt !

  13. says

    Working a job is easy because it’s consistent and steady.

    The hard part of being an entrepreneur is managing the ups and downs – especially when it comes to income.

    I’ve been an online entrepreneur since 2004 and until I created products that produced recurring revenue (membership sites, hosted services, SaaS web apps, etc.), the income was very hot and cold – meaning some months I’d do very well ($15K – $25K) and others I wouldn’t ($3K – $5K).

    So it was very hard from a planning perspective.

    My advice Sam is build a residual revenue stream into your product mix because it will quickly help you stabilize the income each month. Plus, it’s far more predictable and consistent than income from your book, consulting gigs, etc.

    I’m not trying to plug our software but we’ve seen it from the customers of WishList Member (our WordPress membership site plugin). Those that dedicated time to really make their sites work are doing very well ($10K – $40K per month). In my opinion, you have a great topic of which I think would be perfect for a membership site.

    Just my two cents.

    All the best.


    • says

      Hi Stu – What exactly is a “residual revenue stream” in your opinion? Love to get some examples of what you recommend. Is it simply a membership site? If so, are we talking a new membership site, or a subdomain from financialsamurai.com?

      Thanks for your thoughts. I hope you are killing it with your WP plugin!

      Best, Sam

  14. baylortutor says

    I agree with you Sam on many points. I can’t wait to be done with residency and start earning a decent income to (hopefully) invest in properties which will allow me to retire one day. No one have been supportive of my plans to invest, especially in property rentals and CDs. Makes me want to succeed even more!

    • says

      Isn’t the great thing about being a doctor is the fact you can work to 70, make good money, and dictate your hours? That’s what I’ve always thought! Late start to making money, but you can make for way longer than most!

  15. Carlos o says

    In my experience being in a high complexity sales position such as Technology Sales is very close to being an entrepreneur. Yes you have a base salary, but if you want to really make money being nice and “doing your job” its not enough.

    In high complexity sales you are responsible for demand generation, delivering proposals, sales orders follow ups, distribution channels recruiting and enablement and bundling/pricing, customer loving etc. Similar as being an entrepreneur, the lack of planning and executing this activities will just cause you to miss you sales, your quota and therefore you will miss your commissions.

    What differs being in a sales position is if you have a couple of bad months you don’t have to worry about paying employees wages, rent and other fixed costs; being in such position as entrepreneur will wake you cold sweating everyday until you are back to breakeven.

    • says

      Good analogy on the “high complexity sales” position. Would you say then that this is one of the best jobs in the world then? What is the burnout rate, and how long have you been doing Tech Sales? Do you ever plan to hang it up?

  16. says

    I just left a few months ago so I haven’t been tempted to go back yet.
    We planned for a sustainable lifestyle after I quit my job so the finance hasn’t been a problem yet either. I’m completely done with a corporate job. Even if I go back to work, I’ll work for myself. Being an entrepreneur isn’t easy, but I’m more suited to that. I hated working for corporate for some reason.

  17. says

    I completely agree that being an entreprenueur is way harder and more time-consuming and soul-sucking thana rgular job. My regular job is soul-sucking, but at least I know I get my paycheck every 2 weeks and I don’t have to manage stuff or market or come up with crazy ideas. Absolutely. It takes real balls to quit and be an entrepreneur!

  18. says

    The tough thing about being an entrepreneur is there is less separation between work and life. They become much more blended and that can make it a big challenge to sit back and relax. And getting adjusted to irregular income is tough. I know a guy in Silicon Valley who keeps getting tempted to go back to mainstream corporate work for this very reason. He’s held out for about four years now because even though he keeps getting job offers he just doesn’t want to part with his freedom and flexibility.

  19. says

    Sam, I am just watching how things go with you as I contemplate my future as well. My wife and I have been chatting about this a lot, as of right now I have three jobs: I am a audio/visual systems engineer at a fortune 50 company. I help design and build conference rooms and other meeting spaces to integrate audio and video into those spaces. I am also an Enrolled Agent working for a small (high-end) CPA firm during tax season. My third “job” has become my blog.

    I am trying to figure out how to transition from my 50-hour a week A/V job to just taxes and online endevours. Honestly, I’ve got a 5-year plan roughed out, and I need to dive into details and reverse engineer the steps to get there.

    But having done taxes for a bunch of self-employed individuals, I can easliy say that it is EXTREMELY hard to succeed on your own. No 401k, supplemented health insurance, etc… Most people are netting like $25-$30k, and need their spouses to work to keep up with the bills.

    But man, every book I’ve read, or advice I’ve gotten from successful people starts with owning their own business, bootstrapping it for a decade, and then enjoying the fruits of their labor. Sam, you’ve got the drive and the passion for this, and you’ve obviously planned out some short-term/long-term goals to set this thing in motion, so you’ll probably succeed. Unless the universe suddenly stops revolving around money….then you’re screwed ;-)

    • says

      Thanks Jacob. That’s very interesting how you say most people are netting only $25-30K from their small business. Could be bad, or could be good!

      I know a lot of small business that are providing fantastic lifestyles for their owners. Think if you are a travel writer. ALL your travel expenses are expensible b/c you have to travel to write about your travel! You have to live in the Four Seasons if you write about the top hotels in the South of France!

  20. says

    I went back to work on my terms which is considerably different than the tail between your legs return to work. My return gives me opportunities that I never thought of. I never would have started blogging if I had a regular job that required 50-60 hours a week. I am easing back into retirement through teaching. I only actually work 4.5 hours per day. I am starting volunteering and I am preparing for retirement again. Things could change in the next few years, but that is the plan.

  21. says

    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.

  22. says

    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.

  23. says

    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.

    • says

      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!

  24. says

    This post is really an eye opener to me and of course to your avid readers. I can relate this article because like you I am already 34 years old and then after few months I will be at your age now. I don’t feel like working for another 5 years for someone, I really want to try my own. I am looking forward for one of my plan to set up business back home after 2-3 years from now. I am still in the saving and building passive income mode.

    I have 3 to 5 business ideas as per my plan, I want to set up this while keep blogging. Thanks for the information you share to us, its inspire me to refocus my plan.

    • says

      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!

  25. says

    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.

    • says

      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!

  26. says

    “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.

    • says

      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!

  27. says

    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’).

  28. Fortune Favors the Bold says


    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.

    • says

      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!

  29. says

    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!

  30. CW says

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

  31. Newbie says

    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.

    • says

      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

  32. says

    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!

    • says

      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!

      • says

        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

  33. says

    @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!

      • says

        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.

        • says

          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!

  34. says

    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.

    • says

      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!

  35. says

    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.

  36. Opportunity Knocks says

    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.

  37. says

    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!

    • says

      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!

  38. says

    I would give it longer than a year. Throw yourself into it and dont look back. Our adventure began in 2003 and I have never brought home more than 45K. However I love what I do and am learning. Through the guidance of great mentors I am now concentrating on growth and will be “Up Up and Away” soon enough. Stay the course and never give up.

  39. Angela says

    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.

    • says

      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!


  40. says

    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.

  41. says

    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!


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