Early Retirement Is Exactly Like Being An Entrepreneur: Awesome!

Everybody fantasizes about being their own boss. Yet very few people take the leap of faith because they either don't have an idea, don't have the financial means, or don't have the confidence to execute. But I tell yah, early retirement is exactly like being an entrepreneur: so awesome!

It took me almost three years of moonlighting on Financial Samurai as a personal finance journal before realizing I might be able to make enough money to survive off this site.

And here's the thing. You don't have to go all-in with your business! It's not like in the past where you had to set up a brick and mortar shop, borrow money from the bank, buy lots of inventory and equipment, sign a one year rental lease agreement, and hire people in hopes of just making it. Now you can simply start your own business for under a hundred bucks a year on the side.

I left my multiple-six-figure day job in banking at the age of 34 due to three main reasons:

  1. Saved and invested aggressively for 13 years
  2. Negotiated a severance package that paid for 5-6 years of normal living expenses after 11 years at my job
  3. Started Financial Samurai when I was 31

My savings and investments gave me the confidence to dream of a different life. The severance was the catalyst to take the leap of faith and become an entrepreneur. Finally, running Financial Samurai was something I loved to do. Make sure you retire to something, not from something.

Early Retirement And Being Your Own Boss

Despite making much less than my day job my first two years of going solo, I was much happier. How is it possible to make 80% less, but feel at least 50% happier? The simple reason is because I controlled my destiny.

All I've ever wanted was a correlation with effort and reward. I'm sure many of you wish the same thing as well. Very few day jobs provide an absolute meritocracy.

Can you imagine working harder than your peers only to get a 3% raise? How demoralizing! No wonder it's so easy to lose your motivation after several years on the job. How about seeing loyal soldiers work for years only to get laid off? Not good.

But imagine a scenario where the sky is the limit. I'm sure many of you would work much harder and be much happier if you knew there was a stronger correlation between good work and reward. 100% of the spoils go to you, instead of only 3% to you and 97% to your company and its overpaid management team.

Being your own boss is like a short cut to early retirement. As someone who went through an identity crisis an an early retiree and then as a online entrepreneur for the first two years, I can say with absolute certainty the feelings of retiring early and being your own boss are EXACTLY THE SAME.

So for those of you who aren't able to retire before 65, or those who still have a ways to go before retiring early, starting your own business may give you a whiff of what a free life smells like.

And for those who retired early, but don't have the energy to be an entrepreneur, you're living a similar reality!

Killing Two Birds With One Stone With Entrepreneurship

I now believe starting a website while in retirement is the perfect combination for all retirees.

The biggest problem with retiring early isn't the lack of money, because you wouldn't be able to retire early in the first place if you didn't have money. The biggest problem with retiring early is BOREDOM. With so many more hours of free time a day, you will easily get bored if you don't have something meaningful to do.

what percentage of people hate their jobs
Are you one of the 68.5% who are not engaged at work?

For the first year and a half after leaving my day job, I constantly found myself bored by 10am. My writing was done by then and everybody I knew was at work.  

There were many days when I'd just chill in Golden Gate Park twiddling my thumbs waiting for somebody to show up to play a pickup game of tennis. It didn't matter if they were terrible, I just needed something to do.

My wife was a night owl, which mean should would often sleep in until 9am or 10am. I woke up regularly by 5:30am while it was still dark. I was conditioned for 11 years to get into the office by 6:30am PST before the stock market opened.

Having a family would instantly cure my boredom, but a family takes time to create. The next best thing is having Financial Samurai, where I can instantly connect with readers every day.

Boredom is not the worst feeling in the world. But if you've been used to constant stimulation for years thanks to work, boredom can really change your attitude for the worse. It's important to keep your mind stimulated during retirement. Everybody needs a purpose, no matter how small.

You Don't Have To Register As An LLC Or S-Corp

Another stumbling block people have is feeling like they need to register as an LLC or S-Corp to start a legitimate business. This isn't true. You can simply be a sole proprietor without a business ID number, just your social security number.

All you do as a sole proprietor is earn income as a freelancer. You report the income on your Schedule C tax document, where you can deduct all your business expenses. You can contribute some of your profits to a retirement plan, like a Solo-401k. Then you pay taxes on your operating income, which is your profit before tax.

The main reasons for starting an LLC or S-Corp are liability protection purposes, dividing ownership, and having an asset to sell sometime down the line. You can't sell yourself. Well you could, but that would mean you'd be an employee again.

I didn't create my S-Corp until after I left my job because before then, I was just writing purely as a hobby. My severance negotiation book wasn't published yet and I wasn't selling anything.

If you plan to moonlight on the side, it actually might be best to not incorporate your company. Many companies have outside interest limitations because they want their employees to focus on their jobs. There're also business taxes you must pay. 

But if your business starts gaining traction, you might as well incorporate and take it more seriously. Besides, there's no limitation to free speech if you were to start a blog.

Finally, if you remain a sole proprietor, make sure you have some type of protection in terms of an umbrella policy so that in the unfortunate case when someone wants to go after you, your assets are protected.

Comparing Work, Early Retirement, And Entrepreneurship

Now onto some more concrete numbers to prove my point that early retirement and entrepreneurship are eerily similar!

Based on my experience as a day job worker, early retiree, and entrepreneur, I've created this chart comparing the three in the most objective way possible.

I rate each of the five variables on a scale of 1 – 10, 10 being the best/easiest and total the scores. The numbers have been crossed checked by a number of other people who've experienced all three stages like me.

Go through each and give your own rating. Let me know where you strongly disagree. It's pretty amazing Early Retirement and Being Your Own Boss both scored the same.

Day Job vs. Early Retirement vs. Being Your Own Boss - Early Retirement Is Exactly Like Being An Entrepreneur: Awesome!


Autonomy can be defined as freedom. Thus, early retirement wins hands down. Entrepreneurship, however, isn't far behind. When you're your own boss, you still have obligations to clients. You don't have to look at your calendar in early retirement to see what's on deck. Work is pretty horrible for autonomy unless you are the boss in a satellite office.

Fulfillment / Purpose: 

Being your own boss is the clear winner because you're actively doing what you love. Hopefully, people who are in their early retirement phase can also gravitate towards doing what they love due to having more spare time. 

Volunteer work is extremely fulfilling. So is connecting with people online and sharing your experiences. Fulfillment is why those who are able to retiree early should start their own business. It's an incredible joy to do something you love when there's no pressure to make any money.

I can see my score of 5 for the Day Job category as being debatable. But even if you raised the score to a 8-10, the total score for Day Job still wouldn't match Entrepreneurship and Early Retirement's scores.


In the initial stages, it's much easier to make money from a day job than it is as an entrepreneur. A paycheck is steady, and hopefully you'll get raises and promotions.

It's harder to make money in early retirement because you're not motivated by money. Freedom and fulfillment are your priorities. However, when nobody is pushing you, it's easy to get lazy.

Initially, it's difficult to make money as an entrepreneur. You need to survive long enough to build a brand and create a loyal following. But once you get over the initial hump, the money is far, far greater than any day job. The richest people in the world are all entrepreneurs, not folks with day jobs.

Here's a detailed post about how much bloggers make for a living. I think you'll be surprised by the income potential compared to the median household income of ~$65,000 in America in 2020.

Below is a real example of how much one of my blogger friends makes with 300,000 pageviews a month. $151,200 a year from his website alone ain't too shabby!

Blogging For A Living Income Example: $300,000+
Blogging income statement


A day job is a walk in the park compared to being your own boss (9 = easy). Go to work, do some work, do as you're told, and leave it all behind once you go home.

As an entrepreneur, you're always on call. You've got to be the CEO, CFO, COO, and CMO of your business. But that's the fun part of it! When you're thinking and working 100% for yourself, it doesn't feel so much like work. It feels like fulfillment!

To make things less difficult, you can hire freelancers to help you with areas you don't like e.g. taxes.

Thankfully, it's never been easier to start your own website than it is today. Back in 2009, I paid a guy from Craigslist $300 to come over to my house to launch a website. It was called RichBy30RetireBy40. The site stunk, so I scrapped it and hired another guy for $1,000 to launch Financial Samurai. Then I had to pay another $500 for some graphics and customization work.

Today, anybody can start a website for less than $3/month in 30-60 minutes with Bluehost. It's so cheap and easy to start from the comfort of your own home.


The initial euphoria of getting a job wears off after a year or two. Sooner or later, a job becomes mundane due to: office politics, a poor correlation between reward and performance, repetitive work, envy for those who make much more, and exogenous variables outside of your control.

Early retirement life is filled with more happiness due to having 100% autonomy. You're spending time doing whatever makes you most happy because you can. As an entrepreneur, you're happy because you have a lot more autonomy to do what you want. If you start feeling your business is losing purpose, you can always pivot.

The best combination really is to moonlight while having a day job. Second best is to do something entrepreneurial once you are able to retire. And if you can have a spouse earning a steady income while you go after your idea, well, all the more power to you!

I will say that after 13+-years of running Financial Samurai, I'm very happy because I have a purpose. In 2022, I'm publishing my first traditionally published book called, Buy This, Not That: How To Spend Your Way To Wealth And Freedom, which I think will be a big hit. And if it's not, I'm thrilled to have created something of value to society and made my children proud.

Freedom Is Much Greater Than Money

I'm glad I spent 13 years in Corporate America. If I didn't, I wouldn't be able to truly appreciate how awesome it is to be my own boss. The difference is night and day. And that's coming from someone who enjoyed his job ~70% of the time and made a very handsome salary.

Progress is my one word definition of happiness. When you own your own business, there's an endless amount of progress to be made!

I really can't believe it's been over 11 years since I started Financial Samurai. This site has enabled my wife and I do be stay-at-home parents to our two young children. Every day there's something interesting to read from a user comment.

Finally, given we're in a global pandemic, it's a blessing to be able to operate an online business that cannot be shut down. Everybody should be figuring out a way to make money from home, even if you don't retire early.

Starting an online business, no matter how small, could be the best thing you ever do.

Interested in starting your own website?

Check out my step-by-step tutorial guide on how you can launch a site like mine in under 30 minutes for just $2.95/month. A website legitimizes your business and becomes your online portal.

Not a day goes by where I'm not thankful for starting Financial Samurai in 2009. In just 2.7 years, I was able to quit my job and be free. Everyone should leverage the internet to build a brand, build a business, and become untethered from an office to live a life of purpose!


Invest In Entrepreneurs As Well

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

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

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

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

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

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

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107 thoughts on “Early Retirement Is Exactly Like Being An Entrepreneur: Awesome!”

  1. Hi Sam – love the consistent thought-provoking content you provide. I’m going to comment from the perspective of someone who knows a lot of people (ex-tech) who are financially independent, and for whom it doesn’t work out so well.

    I think there’s a lot of people now working towards financial independence/early retirement that write prolifically about it, and earn money on their writings. Not slamming you, Sam – I love your writing and your positivity. And I don’t think that NOT being financially independent is so great. But anyway – the best way to promote these writings is to consistently project a positive image of fi/re. So a lot of the more negative aspects are ignored.

    Another reason why the downsides of fi/re are ignored is that you’ll consistently get one of 2 responses to people who comment on them (on forums, blog comments, etc):
    1. “I’d like to have those first-world problems”/”I’m playing the world’s tiniest violin for you”
    2. “If you’re bored in fi/re, you must be boring. I have a list of projects as long as my arm that I’d love to work on if I ever had the opportunity.”

    One negative thing is that what people are not compelled to do, they frequently don’t do, even if over the long term it would be better for them. For instance, most people are better off getting out of the house every morning (work, school, gym, whatever) and interacting with people, rather than staying at home. But a LOT of people who aren’t forced to get out because of a job or school will actually tend towards staying home, and being hermits. Sure, there’s plenty of counter-examples, but from what I’ve seen of life, this is the tendency.

    Related to the above – it’s tough finding the structure that’s not a job or school, and that gets you regularly out of the house, and seeing people every day. Most people would say – do some volunteering. That might work for some people. Don’t just assume that it will, though, without having spent significant time at some non-profits. In my experience, they’re not necessarily better than regular jobs. Lots less efficiency, lots of little fiefdoms. I do know two fi/re people who work one day a week at a hospital gift store, they enjoy it. I also know one lady who started out volunteering at a very well-run senior center, and is now a part-time bookkeeper there, and absolutely loves it. So, it can work. It’s just lots harder than you might think.

    Also, once you’re financially independent and don’t *need* to work, every potential new job is evaluated against the impossible standard of complete freedom. This makes it much harder to accept the inevitable negatives that any job will have. It’s much easier to quit the job, or not even start, because it doesn’t give you time to do (insert here something you probably wouldn’t do anyway – working at the homeless shelter, become an artist, etc.)

    People that are fi/re are kind of like trust fund babies. Trust fund babies also don’t need to work, and many proceed to mess up their lives. And the main thing that messes up their lives is that they are not compelled to do something – i.e. work. You can say – and I think it’s partially true – that trust fund babies and people who retired early after working hard in a career or business are completely different. I’d say – yes, they’re different, and the early-retirees that I know aren’t ruining their lives with drugs. It’s more that they have empty lives, without interacting with many people, without contributing to the world.

    Sam, if you’re interested in article ideas, I’d love to hear more about people who no longer need to work, but still do. Or even if they don’t work, they manage to stay engaged, and productive, and specifically how they do that. How they find an in-person social network, etc.

    1. Hi S,

      You will enjoy these posts:

      The Dark Side To Early Retirement
      It’s Impossible To Stay Retired Once You’ve Retired Early
      Life After Financial Independence

      I’ve got so much content reflecting on my FIRE journey that’s real and real-time. I’m a little different in that I aggressively built my passive income portfolio and then negotiated a severance that is still paying out until 2017. A lot of folks write about FIRE and make a lot of their income writing about FIRE. That’s fine with me as that income often makes up the “gap” of existing income and needed retirement income.

      But now that I’m almost 5 years into FIRE, I’ve somehow created a lot of online income writing about my journey. Very surprising, but just goes to show you never know if you stick with things long enough and build a brand online! So much fun writing and connecting. I think blogging is the perfect activity in retirement!


  2. Middle Class Millionaire

    I am a big supporter of starting a side business while still working full time. Sure in a perfect world we could quit our jobs right away, start our business and see instant success. But the reality is that it often takes a few years for a business to become profitable… let alone enough to completely support you.

    A website is a great idea. Another one is a Youtube or Instagram account. My brother has an Instagram page that just recently broke 1 million followers. He started the page about 3 years ago, and so far this year he has made over $70,000 from selling tee shirts (through a drop ship style company) and selling advertising on his page… All of this he does from his iPhone. All in all he probably spends about 2 hours per day working on his business. There is no reason someone could not do this while still working a full time job… at least until the business reaches your income goal.

    1. Wow, 1M followers on Instagram? Amazing. What does your brother do?

      You remind me I need to put a cool widget button on the site for people to buy a newly redesigned Financial Samurai shirt. It is so cool, you’ll have to see it!

  3. Paul Andrews

    You hear over and over again that it’s retirement is really what kills the elderly generation. I definitely think that as a society we need to revamp what really is considered “retirement.” I’ve never seen the point in working your ass off for 40-ish years to finally earn some free time when your body and your mind starts to go. I’d rather fewer hours a week and more years so I can spend some of the best years of my life running around Europe (personal dream).

    In other words, if/when I grow up, I’d love to have what you’ve got going on here: multiple income streams that allow for early retirement. Frees up time for sailing (not as good for the heart as tennis, but fun all the same). Great post!

  4. If I spend $50,000 on bills etc. for the year, how much would I need to retire on by 40 years old?

    1. 25x your yearly living expenses is the general rule. at that point the amount of money you earn in interest every year is greater than you’d be taking out for living expenses. so in your case, 1,250,000 (approximately)

  5. Mark Eichenlaub

    Hi Sam,
    This post and your entire site is freaking gold. You probably hear it all the time but THANK YOU! Not only are you telling people to build a blog, how to do it but YOUR BLOG is a supreme example of good writing.

    I am an English teacher and while the writing is sound in that regard it is more importantly relatable and full of what we lack a lot of today…common sense.


  6. valuetradeblog

    How in the hell could a man enjoy being awakened at 6:30 a.m. by an alarm clock, leap out of bed, dress, force-feed, shit, piss, brush teeth and hair, and fight traffic to get to a place where essentially you made lots of money for somebody else and were asked to be grateful for the opportunity to do so?”
    ― Charles Bukowski,

    I hope I will be sometime in the same situation as you.

    kind regards

  7. Self employed for 7 years. Never took it really serious until the last three years. Have been building my business slowly and steadily. Working on establishing a great reputation and “brand.” The business provides a living but money is still – at times – very, very tight. However I do see a breakthrough in the near future. All the pieces are in place. A year ago I started another company for buying and selling land. It segues great with my branded business and has the greatest potential to be a major wealth building mechanism. I didn’t get serious until I was in my late 30’s. Wish it had been earlier. However, to anyone who is middle aged – its not too late. You just have to be disciplined and have vision.

    1. YES! Build your brand. I will be working on a post on brand building this weekend. So, so important.

      Nothing is too late. Technological as made doing things so much faster than before.

  8. When I first started my blog I too found it to be such an incredible learning experience because you learn so many new things about business, taxes, your ability to manage time and self-motivate all while knowing the potential really is unlimited. My blog did well for awhile but became too dependent on facebook once facebook went public it really hurt my traffic and its just now starting to come back some.

  9. Good post, Sam. One other big related benefit of being your own boss…. PEOPLE! Specifically, being able to be more selective about the people you work with. Don’t like a certain customer / client / vendor? Poof! You can choose not to do business with them. Don’t like working with that certain attorney in the Legal department because he’s annoying and just tries to make himself look smart? Well, as your own boss, that guy would have never been hired in the first place. :)

    The freedom of being able to surround myself with people I like is one of the biggest benefits I’ve noticed of being an entrepreneur / being my own boss. It all became quite apparent after starting my own company, then selling said company and operating it as a subsidiary of a larger company (losing freedom in the process).

    Now I am an exec at a startup (not founded by me). I have fairly good autonomy in my day to day activity, I feel reasonably fulfilled, and I have reasonable financial upside potential… but I still don’t have as much autonomy as I’d like when it comes to people. Yes, I can pick and choose the people I personally hire, but there are still plenty of customers and other colleagues I can’t.

    I’m looking forward to my next thing, where I’ll be starting my own thing again, and where I can surround myself with people who I honestly enjoy spending time with. That will make me happy. (although I’m sure I’ll still run into the occasional customer that I don’t like… that’s part of business!)

  10. When I was 38 I made a choice to quit my strategy consulting job, however I was not going to retire – I like to do things, I just did not want to have a boss any more.

    I was trying to figure out what business to start, but could not come up with an idea that I thought would be both interesting and would make good money.

    I ended up buying an existing business, where the owner was retiring.

    In retrospect, this was the best decision I could ever make.

    1) I make more money then I ever did, and it’s tax-efficient
    2) I have more control
    3) I have more freedom

    There is only one downside – taxes and regulations that I have to deal with.. but i guess it’s a price to pay.

      1. It took me a while ..
        I started out with Bizbuysell.com.. that site has a bunch of trash, but also a bunch of real/good listings. I also asked a few local accountants.. Ended up looking at around 30-40 businesses, evaluated 4 businesses seriously, wrote 2 LOEs, 1 was accepted.

        Overall the whole process from figuring out I wanted to buy, to closing took about a year.

        1. I have looked on bizbuysell for about 2 years and haven’t been able to find anything interesting. Although, I don’t exactly know what I’m looking for. I’m also particular as I want something close to home. I also put an ad in a local paper and got no response.

    1. That’s great to hear Mike! Can you reveal what exactly the business is? Or at least whether it is an online or offline business? I love hearing different business ideas and stories.

  11. I want to retire early BECAUSE of a small business. Does that count for anything? I’m in talks right now to join a bakery business a friend started because she has no idea how the “business” stuff works. You want to talk about a start-up? 5k in revenue and no investment capital.

    Having the time and money to do what I want, when I want, just sounds so alluring. I already volunteer with juveniles in the court system and I would love to help fund that with more than just time. The freedom to be *ME* and not some corporate politic sounds amazing.

    1. Wait… you want to retire early b/c a small business is driving you nuts? Or because you want to join the bakery business?

      The bakery business is HARD! Make sure every product tastes great, has a unique name, and a great social media strategy!

  12. Same,
    Great analogy…
    How will Social Security be effected if so many people retire in their 30 and 40’s?

  13. Mrs Smelling Freedom

    Hi Sam, your title practically jumped out of the screen at me :)

    You see I lived the life of an entrepreneur, running my own business for 18 years, and it felt nothing like early retirement :) I agree that it is great to build something based on your passion and that nothing beats working for yourself because you are not funding someone else and you get to keep the results of your hard work. So I understand where you are coming from, but I think that the parallels between being an entrepreneur and being an early retiree depend very much on the type of business you are building (and at what stage in the entrepreneurial life cycle you are). In my case the business totally took over my life for many years and there was a point when I felt totally drained.

    I sold my business just over 6 weeks ago and I recently started a blog to chronicle my experience post-sale. Two of the posts deal with the harder side of being an entrepreneur – the loneliness that you feel at times (www.smellingfreedom.com/2016/04/the-lonely-life-of-an-entrepreneur/) and entrepreneurial burnout(www.smellingfreedom.com/2016/04/entrepreneurial-burnout/)

    I absolutely do not want to imply that setting up a business is not a great thing. I have been there and done that and for a long, long time, I loved it. However there does come a point when it does not remain fun any more, and that is when it becomes time to move on.

    So seen from my perspective being an early retiree beats being an entrepreneur hands down ;) Well done for finding a way to combine the best of both worlds!

    1. Good point! Being an entrepreneur is HARD, and amazing you did it for 18 years!

      Check it out: https://www.financialsamurai.com/a-day-job-is-so-much-easier-than-entrepreneurship/

      Most folks get a job, work for a while, and then become an entrepreneur relative to people jumping straight into entrepreneurship. I’m just hear to provide the prospective that early retirement is pretty amazing, and as amazing as being your own boss.

      Of course, if your business is sucking wind, then being your own boss may be super stressful. But the freedom to choose is all one has ever wanted!

  14. Well, a few years back I would have felt this is a mystical article which would never realise. Reading all the experiences from different freedom fighters has given me the confidence to take the plunge.
    I happened to meet a friend last week who started off as an entrepreneur after college, but had to shift to a corporate job later. After 15 years of corporate work, he dumped his job last year to relaunch his venture again. This time his corporate experience helped him make a successful restart and is doing good. Moreover as you have mentioned he loves being his own boss doing what he likes.

  15. hi Samurai — I am semi-retired. I left a similar finance job to yours in NYC and moved with my wife to a lower cost location (Colorado). We now have a 5 month old. I took a significantly lower paying job primarily for health insurance and 401k with matching but the income is only a modest part of our retirement income. My wife has her own business which she works part time and makes a good income. One thing i’m grappling with is health insurance. It’d be great if you could write a post about what early retirees are doing for health insurance (families and individuals). thanks

  16. TiredTechie

    Hi Sam,
    the frustrating part of my tech job is trying to navigate others’ agendas. Seems like 25% of my work is working 24-7 to finish my designs, and 75% is a combination of meetings and emails protecting, positioning and selling in order to make my team’s deliverables happen smoothly. Also, it’s super cut-throat to get awarded more from the fixed pool of stock options. Maybe other techies think its swimmingly wunderbar…. I don’t.

    I’ve been working in the Valley for about 16 years now, different roles and some startups, and find that the tone is always there. I love “what I do” and met some great colleagues, but I do not love the intensely selfish competitive atmosphere – its not positive or healthy imo. And, maybe silly, but lately the commute here has become Re-Diculous!

    1. Oh man, I hear you about the ridic commute and the 75% of time doing meetings and busy work for meetings sake! Painful. Once you are your own boss, you become much more efficient.

      With your experience at startups, what did you think versus non startup tech? Any big hits? How did the financials payout? I’ve read lots of angst about employees getting screwed out of their options for whatever reason.

      1. TiredTechie

        I did my own startup (spectacular bust) and was first-in to one (ipo’d flat). Funny thing the money I have made in tech has been mainly:
        1. Owning a simple san jose house and trading up (nearly paid off)
        2. Managing and saving in my 401k and IRA – getting there slo but sure.
        I got some options lift from big tech corporate gigs but i used it to pay for kids university.

  17. I love posts like this. They encourage me to keep hustling, keep moving even when things don’t work out. I don’t think I have anything to offer the blogging world but I do know I have a very old dream which I’m ashamed to tell you at my age, I haven’t really tried to make happen.

    I’ve always wanted to be a novelist and thanks to the motivation on this site, I’ve dusted off one of my old manuscripts and I’m reworking/editing it for self-publishing this year. The fear of “not good enough” is gone. I’m going to be published come hell or high water.

    1. That is a wonderful dream. Let’s turn it into a reality! I didn’t ask permission to publish my book on severance negotiations. I just went out and self-published. The internet and all the tools around the internet serve as a GREAT EQUALIZER to allow anybody with enough desire to get things done.

  18. TiredTechie

    Hi Sam,
    I really like this article a lot. Thanks! In 2 years I plan that my finances will allow me to do my own thing. I can hardly wait.

    But, I have been thinking, one thing about my frustrating high tech job is that I do get some pretty cool design work to do – sometimes – using expensive tools. The company provides s/w and h/w + tools and a team which (in my case) are necessary to build a network or cloud driven product.

    Do you think it would make sense to add “Funding Creative Design Effort” into your table? I mean, that would maybe swing the score towards employment for many.

    1. Howdy,

      I don’t think that category would be broad enough. But it should fall under the DIFFICULTY category as I do say it is harder to be an entrepreneur than a day jobber.

      That said, I absolutely think you should moonlight before or after work, and on the weekends while you have a stable job. It makes the side-hustle that much more enjoyable!

      Tell me why your tech job is frustrating?


  19. Armen Tanzarian

    Isn’t another reason to register as an LLC or S-corp to protect yourself if someone sues you? As a sole proprietor, if you get sued by someone (say for libel) I believe you (and your assets) are personally liable.

    1. Yes sir. Check out what I wrote under the LLC / S-Corp section:

      The main reasons for starting an LLC or S-Corp are liability protection purposes, dividing ownership, and having an asset to sell sometime down the line. You can’t sell yourself. Well you could, but that would mean you’d be an employee again. I didn’t create my S-Corp until after I left my job because before then, I was just writing purely as a hobby. My book wasn’t published yet and I wasn’t selling anything.

      If you plan to moonlight on the side, it actually might be best to not incorporate your company. Many companies have outside interest limitations because they want their employees to focus on their jobs. There’re also business taxes you must pay. But if your business starts gaining traction, you might as well incorporate and take it more seriously. Besides, there’s no limitation to free speech if you were to start a blog.

      Finally, if you remain a sole proprietor, make sure you have some type of protection in terms of an umbrella policy so that in the unfortunate case when someone wants to go after you, your assets are protected.

  20. I like this post. “The opposite of happiness is boredom.” I run my own business and love it most of the time, but I have a business partner who is not on the same page. It takes away from the love of being an entrepreneur. For that reason, I may sell the business in the next year and run a medical marijuana dispensary startup. I would have stock in the company but it would feel like more of a job than the business I own currently. I think I would enjoy this transition but the truth is… You never know. The other option would be to sit on the couch and collect rent checks. I would much rather have perceived progress.

  21. Sam, what an inspiring post. I have been working in Corporate America/Silicon Valley for the past 9 years and while it has been exciting, my interest is starting to taper off, mostly because the rewards (salary/benefits) do not equal the amount of work I’ve been putting in. I like to think I’m good at what I do and my organization did give me a 5% annual raise but the work just doesn’t provide me with a sense of fulfillment. I have been contemplating over the past year now about starting an online business but seem to be experiencing a mental road block. I have ideas and products scouted out but just need to start establishing an online presence. Thanks for being a continuous inspiration – I’m trying to make 2016 THE year I start diversifying my income and hopefully a few years from now, I can retreat from Corporate America and spend more time on a cheap tropical island somewhere in the world.

  22. I was becoming bored at work and then found FI blogs. Now I am obsessed and engaged with FIRE planning! Pretty soon I won’t have time for my full-time job (and hopefully I won’t need it).

  23. Hey Sam, nice motivating topic.

    I am aiming to achieve what you have done; become your own boss, work from home, be happy!

    One day I will be able to come back here and say “I did it” thanks to you and every other FIRE website out there as encouragement.


  24. Family will definitely keep you from being bored, but worse, in my case, severely constrain my writing time. Looking forward to my sons being a few more months along and being able to reclaim my 5am 90 minutes as my time rather than feeding / sleep recovery time.

    I fondly recall the 3 month hiatus I took between my first job out of college and my first Valley job. While I’ve not been bored in decades, having the freedom to be bored if you so choose is a vastly underrated luxury.

  25. For most people in corporate America and majority of your readers, your article makes sense. However, there are certain percentage of super ambitious people who crave power and influence. No amount of money would be enough for them. I would guess they crave power more than anything. For those types of people, I would probably argue that majority would be better off to stay in corporate america or politics and climb the ladder rather than try their hand at entrepreneurship. As you say, being an entrepreneur is hard, but building a lasting multibillion dollar business from scratch is much more difficult. If you’re good and you know how to build relationships with other people in power, it’s an easier path to reach the upper echelons of society.

      1. As I said, most people including myself would agree with you and value independence and freedom the most. However, people live in a society with other people, and certain segment of a given population will always crave power and influence that matters within that entire society rather than just within a small group of people in their own circle. Just look at the two front runners in our election, people who aspire to be A list world wide celebrities, media tycoons, etc. Some people don’t like to live a stealth wealth life, but rather to be king of in a society.

        1. FinancialFree123

          For the overachievers, it’s about your impact level on the world. If your dream is to be a rocket scientist and send humans to Mars, you kind of have to join a big aerospace company, take on more and more responsibility, unless you are Elon Musk. If you want to be a high impact Oncologist, you have to be part of a reputable organization, hospital to have patients, lab support, graduate students to help you deploy your brilliant ideas.

          There are some people in the “rat race” because they want to make large impact o the society. I do envy them a bit. When I was young I had big dreams of changing the world. Now I realize I do not have the assertiveness, persuasiveness, charisma to reach the top of such large organizations. And unless you are at the top, it is better off to be independent.

          So Sam, I don’t agree that being your own boss is more powerful. It is a better alternative for most people. But for those who have all their ducks in a row, they can achieve more by leading a large organization.

  26. Getting a side hustle that can grow into being your own boss looks to me the best to happen. This way, you can grow into the new setting. It sounds indeed more difficult to be all that roles in one.

    I guess by early retirement you mean doing nothing and drinking cocktails all day long :-) That probably explains why fulfilment is only 8 and not 10.
    In my personal case, I do get more fulfilment out of the job. I am happy for that.

  27. Financial Slacker

    I made probably the worst decision of all – leaving a high paying corporate job to start a company that I wasn’t passionate about. And I did it in 2007 just prior to the Great Recession.

    It wasn’t a completely reckless decision as Ms. Financial Slacker was still employed making good money. Unfortunately, her job was in real estate which obviously didn’t do too well in 2008.

    That said, I learned from the endeavor. It cost us some money, but we have more than made it up.

    And instead of quitting a job again, I actually got myself laid off. As you and your readers know, that’s a much better deal.

    1. Ouch. But, I’m sure you learned about the experience, and since the downturn didn’t kill you guys, you guys are much stronger. I feel much, much stronger post recession too.

  28. I remember being an employee, and the 3% raise. There must be something in every HR department of traditional Fortune 500 companies, that says “talent doesn’t matter, just treat everyone the same”.

    I am always surprised by how few people have side hustles. I have a blog I recently started, along with a real estate business. It really helps putting your day job into perspective, when you get rewarded for your efforts directly in the side hustle. The world is so full of opportunity, and there are so many areas to make money no matter what your skill set, it truly is just apathy that stops most people. Which btw is fantastic, as it leaves far more opportunity for the rest of us.

    1. There must be something in every HR department of traditional Fortune 500 companies, that says “talent doesn’t matter, just treat everyone the same”.

      It’s a little known clause in the the HR Handbook labelled “How to preserve HR jobs by ensuring the best people are always leaving”.

  29. I’m probably biased but I would rate early retirement as a clear winner over day job or being your own boss. :)

    The only downside that I would agree with your ranking on is money. If you are early retired you can’t just work harder or more to secure overtime or a bigger bonus/raise/promotion/new job or more/better clients (for self employed). Your income will be constrained by the 4% rule or whatever income your investments throw off. Of course it’s easy to develop a profitable side hustle in early retirement that could be ramped up or down as your spending wants and needs change.

  30. Awesome chart! I think you nailed the ratings on the head with the similarities and differences. I’m consulting for a former employer now and I am so much happier than when I was a full-time employee. Even though I have clients that I have to please, I have so much more autonomy and flexibility now that I am self employed fulltime. It takes a lot of discipline, organization and drive but it’s worth it for me and I also love having my own website. My life would be so different without it!

  31. Hey Sam,

    Doing just what you said. Working my day job as a pharmacist and moonlighting with my website I started a month ago, having been influenced from reading you.

    I’m also long real estate since I bought my first rental property this year. My hope is to retire early and increase my happiness and autonomy in the process.

    Never commented before, but have been reading for years. Glad you decided to continue writing. Such a great site.

  32. Ryan Goosen

    After running a company for the last 8 years, it may be time to finally follow through and start that blog that I have thought about for the last 3 years. If for nothing else than something to do when I decide to quit this daily grind. Thanks Sam for all the wonderful content.

  33. When I created my own blog, there was a feeling of fulfillment, something that I don’t usually feel with work even though I love my work. I know I am way too far from earning money through my blog but I love what I am doing right now. My blog is my outlet when it comes to sharing my thoughts and experiences on just about anything related to finance.

    I still keep my day job for now just because I love what I do and the benefits that comes along with the job. Maybe down the road.

  34. I think you have launched many on us into developing our own brand. It is pretty cool seeing the content grow with each article.
    I was laughing when you mentioned 3% raise because that is exactly what I got and felt. I think it may be time for fire some negotiation for a new plan.

  35. Hi Sam:

    I agree with your chart. I really liked your point about working harder than your peers and only getting a 3% raise. My company likes me and thinks I do a great job, but by policy, employees are limited to raises of 5% annually. I have realized I can’t meet my early retirement goals by relying on my full-time job only.

    Therefore, I took your advice and recently started my own website. It is very humbling and exciting at the same time. While very few people have visited my site, that fact that I have created original content and put it out there is very satisfying. Hopefully, my site turns into something.

    Thanks for the inspiration!

    1. Yes! And I think a lot of people are in your situation and feel your way. How the hell can one achieve early retirement or financial freedom by only getting 3% raises (1% above inflation)?! One would have to save like a maniac and take some bigger investment risks.

      Good job starting your own site!

  36. Aliyyah @RichAndHappyBlog

    Having a day job that I am not too passionate about has definitely motivated me to be my own boss. I am in the process of creating my online business, and I agree that it is a lot harder than a working a traditional 9-5. I am up for the challenge though, because I am naturally an autonomous person.

  37. I’m so glad that I started a site. Not only does it give me an outlet for what’s on my mind, but in the long run, I should be able to start making some advertising/affiliate money from it. While still working a day job, it takes a lot of my free time, but I think it’s worth it and will be a great (partial) cure for boredom once I’m done with the 9-5.

    Having the day job, my site, and helping raise our daughter doesn’t leave me a ton a free time to moonlight. However, I’m filling any gaps I have with focusing on learning/buying real estate which should pay off in the long run.

    That’s awesome that you have that freedom right now – I can’t wait to be there as well!

    — Jim

  38. Mark Eichenlaub

    Fantastic. Your site is amazing. I love the chart you made today. Really liked your interview on NichePursuits.com as well.

    Keep it up Sam!

  39. Right on! Intel is going through another big layoff process and I am so glad I got out 4 years ago. They are purging left and right. I think you got the table about right for a single guy. I wonder what it would look like when you have a family.

    I didn’t have problem with boredom because my crazy little guy kept me extremely busy and blogging took up the rest of my time. It’s ridiculous how much energy the little kids have.

    Do you think you would work less if you have a little one to deal with? I bet the fulfillment would creep up a bit in the early retirement column.

      1. Too bad kids don’t sleep if they don’t want to. :-) My little nugget (she’s 17 months now) only sleeps one hour during the day. Arrrrgh! Yeah, try and get stuff done … I care barely manage to open the oven door without her jumping in it.

        I don’t see how I could manage a business unless she still went to daycare. (I work, and she’s in daycare, but I would love to run a biz one day.)

  40. Did you consider adding security (predictability) as a category in your assessment? Many people like the predictability of a salary over the potential swings associated with being your own boss.

    1. Sure. The variable I use is DIFFICULTY. It is more difficult being your own boss, but much more rewarding.

      Difficulty: A day job is a walk in the park compared to being your own boss (9 = easy). Go to work, do some work, do as you’re told, and leave it all behind once you go home. As an entrepreneur, you’re always on call. You’ve got to be the CEO, CFO, COO, and CMO of your business. But that’s the fun part of it! When you’re thinking and working 100% for yourself, it doesn’t feel so much like work. It feels like fulfillment! To make things less difficult, you can hire freelancers to help you with areas you don’t like e.g. taxes.

      1. I would dispute this. I think the difficulty depends more on your field. As a fellow banker, Sam, even though we did two very different types of banking, wouldn’t you say that a banker’s job is way more difficult, stressful, and complicated than someone who owns, say, an ice cream parlor?

        I guess, though, that within one field, it’s more difficult to be the owner than the employee. The owner of my hypothetical ice cream parlor has it harder than the kid hired to tend the register. The protagonists of the Clerks films will find that owning and running that convenience store will be harder (or at least less simple) than working there as employees. Then again, being the owner does away with office politics, meaningless metrics, and subservience to nasty customers, so perhaps being the owner is LESS difficult than being the employee.

        Also, don’t conflate difficulty with security. I don’t think an employment paycheck is as safe and secure as society makes it out to be, but I do see where people are coming from. The guaranteed (for the work you’ve done) paycheck vs the risk of creating a business whose profits never come. Some people want the comfort that comes with being contractually guaranteed to be paid every week or biweekly for their time and effort.

        ARB–Angry Retail Banker

  41. Excellent and motivating post Sam!
    I had the same experience with a previous part time job that paid considerably well. While I wasn’t earning enough to save long term working 2 days a week, what I was provided with was a stress free job that allowed me to concentrate my energy into the other 5 days and my own projects.

    Now as I focus towards my own self employment I want to recreate that experience – with better planning and saving for the future.

  42. Apathy Ends

    Hey Sam,

    I am still a ways off from being able to try the retirement thing – but I can relate to the joy in starting your own blog, even if it turns out to be a complete failure – I have learned a lot and it broke down a barrier – the fear of trying something new. It has changed my goals completely, I no longer want to continue down the corporate path and even if I cant “retire” early I want to be working for myself.

  43. “Despite making much less than my day job my first two years of going solo, I was much happier. How is it possible to make 80% less, but feel at least 50% happier? The simple reason is because I controlled my destiny. All I’ve ever wanted was a correlation with effort and reward. I’m sure many of you wish the same thing as well. Very few day jobs provide an absolute meritocracy.”

    This is exactly what I am aiming to achieve! My current role is very limited with regard to the effort/reward correlation, and with my personality type, I find it demoralizing. Sure, pay day is fun, but the other 28/29 days per month are a drag.

    I appreciate that are real in your description of your journey with Financial Samurai. It gives me, and surely countless others, great insight and also solace.

    You state that the euphoria of a new job wears off in time, which I agree with 100%. Has any of the thrill of Financial Samurai’s success dissipated yet? I think I know the answer, but I still feel compelled to ask.

    1. I have had times of burnout with Financial Samurai. So many comments, e-mails, and things to deal with can get overwhelming. Hence the post, Shutting Down For Now.

      But if I were to rate euphoria levels running FS, I would get it a range of 8-10. 8 is when I feel I need new topics and random comments say unkind things. 10 is when I’m writing new posts, inspired by new things, folks are sharing new insights, I’m learning new things, and I’m seeing revenue and traffic grow.

      For a job, my euphoria level is around a 2.

  44. Hi Sam, I agree that early retirement, and being your boss is great, I took a year off to try out early retirement and started a couple of businesses. I love it, it combines joy, flow and money.

    As for your table, I’d say that the concept is true but the details will range for each person, two that call out is the money and business part. It depends at what income you started with and what business you choose to venture in.

    Another one: some people might say they are very fulfilled and happy in their job, maybe surgeons, physicians, scientists, just a stab in the dark

    I think I chose the more conservative path, building a real estate portfolio and venturing into project management consulting (which is leveraging my past skill set). My favourite thing about being my own boss is that I’m choosing the work I want to work on (not based on money)…

    Initially it was hard to start in a new path (moonlighting buying and managing real estate) then starting a couple of businesses but I can say that I have no regrets and now money is better than before.

    Thanks for writing this article and stimulating deeper thinking.

    By the way, what books do you recommend readers who are looking into finding their way?

    1. True. What ranks would you give Money and for each of the three choices? I want some concrete numbers!

      On physicians and surgeons… actually there’s a lot of unhappiness due to compressed earnings due to Obamacare. I’ve spoken to many, and many are not happy. “I went through all these years of school and spent all this tuition to see my earnings get compressed by 50%?! What the hell!”

      On a book to find one’s way….. I’ve read too many. The Secret, The Dhamapada, The I-Ching, Who Moved My Cheese?, The Alchemist, How To Engineer Your Layoff come to mind.

      1. As a physician, I can assure you that time and income pressures significantly predated Obamacare. Nonetheless, at its best, practicing medicine is a combination of service to others, intellectual stimulation, and a reasonable and secure income. After 25 years, I am still glad to go to work each day.

      2. Here is my guestimate:
        working at a job for money (1 easy, 10 hard): 4 because money keeps coming as long as you are a good employee, but this number can easily drop if you are at a high income

        early retirement: 6 –> early retirement doesn’t mean you don’t want to work at all??!

        Entrepreneur: 8 –> depends what you are leveraging (if its a completely new path then of course it will be hard!)

        As for physicians/doctors, I know a lot of them have their own professional corporations which means less taxes for them, at least in Canada—> so more money for them.

  45. I ran my first blog for three years before quitting my job. There’s no reason a leap has to even happen and I think people put that in their minds because it puts a real life barrier to something that is mostly a psychological one. When I quit, my blog was making 5x my salary. FIVE TIMES! Me quitting wasn’t about $, it was about psychology.

    Also, a lot of the “other things” are procedural. The whole “should I be an LLC or an S Corp” blah blah — pick one, file the right paper work, get on with the work. The work is what’s important.

    Lastly, being your own boss rocks but does come with its own pressures. You’re responsible for bringing in business and getting paid, no one else, and sometimes that can lead to a failure in work life balance… but man, that freedom is fantastic.

    1. Ten Bucks a Week

      I see your face in every comment section, if I may ask, what is the main source of your site’s income?

      1. EVERY comment section? Or just on FS? I don’t think I’m everywhere :) but I like Sam’s blog and comment when I have a comment to leave. :)

        My revenue streams are probably not unlike Financial Samurai’s, a mixture of affiliate income and display advertising.

        1. Ten Bucks a Week

          Every FS article near the top. Thanks for the info, that seems to be the way to go with PF blogs. Hope to grow into one of you guys someday.

  46. “All I’ve ever wanted was a correlation with effort and reward.”

    Oh, me too. And yes, I can totally relate to getting a 3% raise no matter how hard I worked. That’s exactly how my old job was. I hated it.

    I think that’s why I like self-employment so much in general. When I put in effort, I get a larger reward. If I want more rewards, I put in more effort.

    At my old job, it didn’t really make a difference as long as I did the minimum to get by like everyone else.

    1. So logical right? Nothing feels better than putting more effort and getting more reward! And nothing feels worse than putting more effort and not even getting a thank you e-mail from your boss. Screw that.

  47. Believe Fire

    I like the comparison between early retirement and entrepreneurship. We left our jobs to test out early retirement on a budget by living abroad. We’re currently traveling the world to see if we can find an affordable destination that we’ll fall in love with. We started a blog as our first entrepreneurial effort to inspire others to do something similar. I think your chart is good for the masses, but so far, being my own boss is a lot easier than my prior job. I was on call 24/7 with the responsibility of not just answering the phone, but physically being somewhere while performing physically and mentally demanding tasks. There was no cap on hours worked consecutively, or cumulatively.

    1. True. I guess it’s much easier to be in charge of one, than in charge of more than one. I’m talking about the taxes, government registration, and all that crap that comes once you incorporate. Luckily there are people to pay to do that stuff if you don’t want to.

      1. Believe Fire

        You’re definitely right. Everything will become a lot more complicated due to growth. We’ve just started so it hasn’t become complex yet. When it does become more difficult, at least it will be fulfilling.

  48. I’ll quibble with the happiness column of your comparison table for no other reason than because I can.

    I have a day job. I get paid a steady salary with the absolute greatest job security available in the US (tenure), while also receiving government-job-like benefits. In this day job, I basically act as an entrepreneur, since roughly 80% of my actions are self-directed. If I want to make more than my colleagues, I can work harder, secure grants, build partnerships with industry, consult, etc. and double my income. Or, I can choose to do the bare minimum and still make a base salary significantly higher than the average household income. At this point in my career, the bare minimum I could get away with is like 15 hours of actual work per week. Every 3-5 years, I have the option of taking 6 months to a year off to do whatever the hell I want (sabbatical). Early retirement doesn’t seem so appealing when my job is looked at in this way.

    This is why being an egg-head, good-for-nothing, ivory-tower university professor is probably one of the best jobs on the planet. Hell Sam, with your background in finance, you could get a Masters degree and command close to $200k as a finance instructor at most universities in the country. I know our business school would trip over themselves trying to make you an offer. Anyone that could stomach the absolute crushing boredom to complete a PhD in accounting would be looking at Haseeb-level offers for significantly less expectations.

    I just have to write that down every now and then, because everyone around me spends 28 hours per day bitching about their job (including me from time to time), which baffles me since as a tenured professor you basically control your own workload. But … we are all pretty driven people, that find more and more work for ourselves because we want to make more and more of an impact. I know I do. Most all of the entrepreneurs I know bitch even more, because they’re pretty much always working. They “take their work home” with them everyday.

    Some of the happiest people I know operate a back hoe digging ditches throughout the day, make just enough money to support themselves, and go home tired but without the slightest thought about what they have to do the next day or the next week for their jobs.

    Probably the happiest I’ve been in past jobs (I’m only just realizing the level of pure awesome freedom I really have in my current job) was when I worked as an electrician’s apprentice. I got to solve challenging problems on the job site, which kept me intellectually stimulated, I got to do some manual labor outside, which strangely feels good, and I got to go home and not give a single f about anything work related. The money sucked, but since I didn’t need much money back then, it didn’t really effect my happiness.

    Basically, I think happiness can vary significantly across all categories, depending on what you do and how you approach life. Work can make you happy whether you’re a basic laborer, a corporate drone, or a business owner. It can also crush your soul even in a cushy job such as tenured professor, and definitely when you are your own boss.

    1. Are you offering me a job doc? If so, sign me up! I already have my master’s degree, so I’m good to go. Are you public about which university? I also accept the best that charges tuition of $48,000 or more.

      Also, happiness is subjective for sure. As the Gallup poll shows, almost 70% of people are not engaged at work. Unhappy people are disengaged.

      But if you bumped happiness to a 9, the total score still doesn’t come close to Early Retirement or Entrepreneurship!

      1. Offering you a job? If I had the power. Not quite as “self-employed” as that, and if I was I’m pretty sure I wouldn’t be throwing that kind of money around. But then again, with the way we’re legally allowed to fleece teenagers … maybe I would.

        Seriously, though. No one should read my comment and rush out to start a PhD program with hopes of being a professor. The opportunity costs are huge, and there are basically no jobs. That goes for science, engineering, as well as the hippie-dippie liberal arts. At least with the sci/eng fields, you can get a real job in industry, but English? Ha.

        The only recommendation for someone that wants to be a university professor that has decades of demand and low supply is accounting. PhD in accounting = high six figures. Choose your university. But who could actually stomach the life-sucking agony that would result from years and years of doing research and teaching accounting? AND forgo the even higher salary working for MegaCorp or hanging a shingle?

          1. Hadn’t read that one. You write so much about so many topics. Geez! Pretty spot on for someone who hasn’t been in the academy, too.

            It’s a high entry fee, with a loooong wait to get in the door IF you ever do, but if you ever do get in, it’s pretty cushy.

  49. The Green Swan

    Being a fairly new to the blogging world (and still in corporate America, working to achieve FIRE) I decided a website and blog community would not only help to connect with others like me, but could also bring me through retirement.

    I agree with the boredom comment, that’s one thing I want to avoid after leaving my day job. I also decided not to moonlight with my blog and jump right in. Luckily the blogging community and world on the web has helped me make the plunge.

    I’d hate to come up with my own numbers to chart the difference until I do actually retire. Might be something I reflect on once that plunge is made.

  50. Matt @ Distilled Dollar

    Thanks for writing this post! I hope more of your audience decides to moonlight while working their day jobs. Spoiler alert: it’s awesome!

    I started a blog at the beginning of this year and not only has it created a future source of revenue, but as you mentioned, I’ve become happier. I’m learning more about what interests me by connecting with people who share the same passion. I’m not sure if there’s anything more fun than that!

    “Progress is my one word definition of happiness.” I’m glad you wrote this because this is also my definition. I would say ‘growth’ but ‘progress’ sounds like the same thing to me.

    1. Yes indeed. The internet has made it easy to “find our people.” Connecting with folks who share common interests and goals is fun. That’s the unquantifiable value in doing what you love, online or offline.

    2. I’ve owned and operated a popular blog for more than 8 years. It’s been a good source of revenue, but I found that I enjoy it much less now that I actually *rely* on it for the revenue (and have found it hard to keep growing it while keeping my job). so, there are pros and cons, but overall I’d agree it’s a great thing

  51. I started moonlighting as a virtual assistant about six months ago and you are bang on about the happiness factor. I am in control of my business compared to my day job where I’m just a pawn in a giant, corporate chess game.

    1. Hi Tam,

      Are you using a go between site to get your VA jobs? Are you seeing good opportunities for people with skills that they can leverage for $?

  52. PhysicianOnFIRE

    What else have you done to cure The Boredom? You mention the obvious (this blog) and I know there’s been some travel and tennis. Anything else exciting to occupy your time?

    1. This is something I really cannot understand: why would anyone who’s the master of his/her own time get bored or lonely? I’ve been freelancing for 12 years now (the last 7 years it’s been full-time) and I’ve never been happier before.

      I’ve done some really serious traveling, I’m raising my daughter and spend all day with her, while working for 2 hours in the evening on my network, my freelancing course and doing web design work. I earn way more than I ever did before, have no stress or worries.

      And I spend a lot of time outside, I met many people etc. Being able to schedule my work around my life (as I like to call it), has really made it all possible.

      1. Some people are used to routine decided by structure decided by someone else.

        If all you are used to is your work routine for decades, it can be hard to self motivate.

        You’ll just have to trust me on this. Because you have been freelancing for so long you know your own routine. If it stops things might be a little bit different.

        1. Hi Sam, I congratulate you on all of your success, you have worked intelligently and done well. I wish that I would have worked intelligently like you, I did not however, and now I am just an old (much older than you) loser.

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