How To Become Self-Employed Like These 5 Top Bloggers

Self Employed Top BloggersOne of my biggest focuses to build wealth is simply earning more money. For many, that involves creating a side hustle. For some, that side hustle or passion can turn into a full time gig. In some cases, that can turn into something very lucrative.

I’ve always been curious about how to become self employed.  The thought of being dependent on one’s own income is both thrilling and scary.  But even more so, as a financial blogger, how to manage the logistics of self employment seems like a daunting mystery (since I’ve never done it).  If you work full time, many things are just taken care of for you without even thinking: a steady paycheck, health insurance, and retirement planning.  However, if you’re self-employed, you throw all of those givens out the window.

Instead of perpetually wondering about it, I decided to reach out and ask.  And so, I reached out to some of the most well known bloggers that have made the jump to self-employment.  You’re probably familiar with the product or brand they’ve launched to be able to support themselves, but here are their thoughts and stories on the personal finance side of how to become self-employed.

This original article was published in 2012. Over 3 years later, these people are still doing great things being self-employed, which is awesome. Let’s look back at these awesome interviews from:

Pat Flynn from Smart Passive Income

Pat FlynnPay Flynn is the founder of The Smart Passive Income Blog, where he chronicles his journey to build multiple passive income streams.  The interesting thing about Pat is that he started his blog in October 2008 to share his journey towards developing a passive income online, and at blog post #4, ended up getting laid off from his job.  That turning point led him to create his online income streams in depth, and share his insights with his followers.  The result of his hard work is income in excess of $40,000 per month for the past year from his online ventures.

TCI: You started Smart Passive Income to document your journey to creating income streams, with the longer term goal of living off them.  However, you soon found yourself unemployed.  Before making the jump, what financial preparations did you make?

Pat: None.  I was forced out of my 9 to 5 so it came by surprise.

TCI: Since you didn’t exactly plan on being self employed, did you have an emergency fund?

Pat: I definitely had one, and I still do.  At the time of my lay off, I had about 6x my monthly earnings saved up in an emergency fund.  That was about $12,000 at the time.

TCI: Self-employment and budgeting can be tough.  If you have a budget, what strategies do you use for dealing with the irregular income stream of being self-employed?

Pat: It’s tough with an irregular income, but the basic idea is to save it all and only spend money when I have to. We’re lucky because we don’t have very many expenses, so we do get to save quite a bit and it’s nice to know it’s all there just in case.

TCI: What is your biggest money fear about being self-employed?

Pat: My biggest fear was that I wouldn’t be able to successfully manage my business for the long haul. When I first started, I had such great immediate success, I was worried that I wouldn’t be able to keep it going and would eventually tap out. It’s been 4 years and the businesses have been thriving like never before.

TCI: How have you handled dealing with things that an employer typically provides – dealing with taxes, retirement contributions, insurance, etc?

Pat: In the beginning, I did it all on my own – researched it, read about it and just did it all by myself. Now, however, I’ve learned to leave those things to the experts, although I’m quite happy I did research those things beforehand so I have some sort of understanding about what’s going on. I have a CPA who takes care of my taxes and bookkeeping for my businesses, I have a financial planner, an insurance agent, etc.


David Risley from Blog Marketing Academy

David RiselyDavid Risley is the founder of Blog Marketing Academy, as well as  He is all about living the “Internet Lifestyle”, which means having no boss and working at his own schedule.  He is able to do this because he has been highly successful in monetizing his sites and helping his many subscribers do the same.  The result is that he is able to live self-employed very comfortably.  David didn’t exactly make the jump to self employment, as he will admit he hasn’t has a “real job” since college, but he has lived self-employed for over a decade.

TCI: When you started out, what financial preparations did you make (i.e. savings, gifts, etc.), or did you just go for it because you had to?  Were you married then, or still single?  Did your spouse support you?

David:  Well, I sort of had an opportunity to ease into it, but with a few big leaps. I started the business, technically, while I was still in college while I was simultaneously working a job at Sam’s Club. So, I had both things going on.

But, then it came time for graduation. The “normal” thing to do would be to blast the world with resumes and try to land a job. I probably would have ended up being a code jockey in some cubicle somewhere. But, I simply did NOT want to do that. This little side business I had created online was making some money, so I figured if I’d go full-time at it, perhaps I could make it work. And that’s what I did.

So, the first leap was the decision not to try to get a “real job”. The second one was the birth of my daughter several years later and the realization that now I had a real family DEPENDING on this business I had started as a hobby.  When I first started, I was single. I got married several years later and we quickly went into parenthood.

TCI: Do you have an emergency fund?

David: I do. Some in a separate bank account, and some of it in non-cash assets (such as gold). I think it is important for anybody to have a reserve fund available, especially when you’re an entrepreneur. All businesses have ebbs and flows in them, and you need to not be so stressed out about those ebbs that you start to fear it.

TCI:  If you have a budget, what budgeting strategies do you use for dealing with the irregular income stream of being self employed?

David:  Well, I keep cash reserves and I try to put a percentage of gross into reserves. I also keep a keen eye on expenses, including those expenses needed to keep the business not only operating, but expanding. And, I plan the income needed to meet those demands.

TCI: What is your biggest money fear about being self-employed?

David: Not making enough, which I assume would be the fear of most anybody in this position. I have awesome months, but I also have slow ones. And my family’s expenses are rather high, with 2 young children.

TCI: How have you handled dealing with things that an employer typically provides – dealing with taxes, retirement contributions, insurance, etc?

David: Taxes simply must be planned for, and I try to withdraw a certain amount each month into an account for taxes purposes later.  As for retirement, I tend to look at it differently.  I don’t really plan to retire in the traditional sense, as I truly love what I do and don’t look at it as work.  For me, the greatest security for “retirement” would be large reserves, along with a business which is self-sustaining and doesn’t require me there unless I want to be.  That’s what I’m working on.  And, as for insurance, it is currently taken care of via my wife’s employer (she went back to work a year or so ago because she simply got tired of being home with the kids all the time).


Leo Babauta from Zen Habits

leo babauta self employmentLeo Babauta is the founder of Zen Habits, a site about finding simplicity in the daily chaos of life.  He is a family man, and writes a lot about how to achieve goals and get things done.  He also is supported by his blog and books he has published.  He has noted in the past he was in debt before starting to write, and so I was especially fascinated by how he made the jump to self-employment.

TCI: Before making the jump to self-employment, what financial preparations did you make?

Leo: I had been deeply in debt before I became a blogger, so for more than two years my financial goals included 1) save and grow an emergency fund; 2) eliminate my debts one by one; and 3) grow my income. I did all of that before quitting my day job, and grew my income until it exceeded my regular job’s income.

TCI: I know you didn’t exactly plan on being self employed when you did, so where was your emergency fund at?

Leo: I had an emergency fund because it’s a key component in eliminating debt, and kept it because it’s so important for being self-employed. I started an emergency fund about 2 years before I took the leap, and it was only $100 when I started. It was about 2 months’ worth of expenses when I took the leap.

TCI: If you have a budget, what budgeting strategies do you use for dealing with the possibly irregular income stream of being self employed?

Leo: I pay as many bills as possible in advance, when I have the money, so that when the income stream gets smaller I don’t have to worry about the bills. These days I’m lucky enough to pay my rent 6 months in advance, and have very few bills to pay. I also stay debt-free so I don’t have to worry about debt payments or waste my money on paying interest.

TCI: What has/was your biggest money fear about being self-employed?

Leo: That I would fail and not be able to feed my family. That’s why the emergency fund was so crucial. I don’t worry about that stuff anymore though — I’m now confident that even if what I’m doing fails, I could build something else and succeed.

TCI: How have you handled dealing with things that an employer typically provides – dealing with taxes, retirement contributions, insurance, etc?

Leo: I hired a tax guy for the taxes. We are self insured. And I am still in the process of setting up an individual 401(k) account, though I do have savings and investments.


Sam from The Financial Samurai

Sam DogenSam is the founder of The Financial Samurai, and is the only anonymous blogger among the group.  Blogging anonymously can make your self-employment story hard to share, but it is actually something that Sam has been focused on for a long time: leaving his job and making the leap to self-employment.  And he just did it as of 7/9/12, so the most recent of the group.  Since Sam just recently “retired” and made the jump to self-employment, and he is a personal finance blogger, I thought his perspective would be interesting to know and share!

TCI: Before making the decision to leave your job, what financial preparations did you make?

Sam: I saved 50-75% of my after-tax income for 13 consecutive years.  The savings was then divided almost equally into CDs, stocks, and real estate.  As a result of my investments, the principal has compounded at a rate of around 15% on average, with a resulting monthly gross cash production of around $7,000.  I wanted to shoot for $10,000+ a month originally by working another 3-5 years, however, I did not anticipate my foray online would make me enough money to pay some bills and put ramen noodles on the table!

TCI: You did a lot of planning prior, so where was your emergency fund at?

Sam: When I retired, my “emergency fund” stood at roughly 15-18 years, or 180-216 months if I did not change my living standards at all.   I give myself a three year range to be conservative, but I’m sure I could make my EF last for 18-20 years if I didn’t make another cent of income in this period.  If I sold my house in San Francisco  and moved to Hawaii, the EF would be enough to last indefinitely.

My emergency fund already provides a ~$3,000 gross a month “emergency” cash return.  Furthermore, I can happily live off $7,000 a month in gross income from all my passive investments, especially without a mortgage.  Hence, without having to sell anything, one could say my existing EF can last forever thanks to other income producing assets.  Generating cash flow is what it’s all about.  It all depends on what type of lifestyle I want to lead and what’s included in an EF.  I’m pretty frugal, but I probably do spend a little too much on vacations and have more house than I need. But, I’m hoping to just grow into the house and own it forever like my grandparents did.

I encourage everyone to look past the use of the words “emergency fund” because it becomes a crutch.  If one is still thinking in emergency fund terms, it’s hard to build real wealth.  I write about this subject in a post entitled, “The Emergency Fund Fallacy And Your Brain.”

TCI: If you have a budget, what budgeting strategies do you use for dealing with the irregular income stream of being self employed?

Sam: One of my goals is to “reset to zero” and rely only on my online income to survive.  The passive income generated from CDs, rent, and dividends shall be left untouched so they can continue to compound. This way, I keep the hunger inside to go out and build new income streams.  For the last 20 months before I retired, I made sure my entrepreneurial income alone could support my operating expenses without dipping into savings.  With the passive income buffer + entrepreneurial income, I figure I’ll survive.  Besides, who doesn’t love ramen noodles and tasty water every day?

TCI: What is your biggest money fear about being self-employed?

Sam: One of the concerns about self-employment is feeling isolated.  As a result, I’ve made it a habit to either play tennis with my USTA league team, play golf, go on a hike or meet up with friends for a drink or a meal after my morning work is done.  My favorite is exercising with friends.  It slices two birds with one sword.  Due to self-employment, I have more energy to go out at night since I can nap in the afternoon.

Another fear I have is enjoying life a little too much and getting lazy.  I’ve always enjoyed the struggle and the potential triumph.  When things come too easy, as a lot of things do living in America, we start taking things for granted.  It’s important I don’t lose perspective after growing up in many poor countries as a kid.

TCI: How are you dealing with things that an employer typically provides – dealing with taxes, retirement contributions, insurance, etc?

Sam: Like everybody else.  Just got to stay on the ball and do it.  Taxes are quarterly, retirement contributions are automatic with my passive income and savings, and insurance is provided for thanks to my negotiated separation package.   I’ve got certain revenue targets and operating profit margins to hit.  It is somewhat thrilling to not know whether I can pay my bills at the end of each month!

Corbett Barr from

corbett barrCorbett Barr is the founder of (previously Think Traffic), where he seeks to help people build things online and teach them how to create their online business.  On his blogs, he has helped thousands of people learn different aspects of blogging and marketing.  Corbett is also one of the few individuals who actually made the jump from a decade of corporate life to being self-sufficient online, instead of just falling into blogging while unemployed.  Read what Corbett has to say about making the jump:

TCI: Before making the jump to self employment, what preparations did you make?

Corbett: I focused on reducing expenses to the bare minimum (no car payment, reasonable rent, etc.) and cut out unnecessary luxuries. I reviewed all expenses and tried to eliminate or reduce each where possible.

TCI: When you made the jump, where was your emergency fund at, if you had one?

Corbett: Before becoming an entrepreneur, I had worked in the corporate world for close to a decade. I had saved enough to be able to live on savings for a couple of years.

TCI: If you have a budget, what budgeting strategies do you use for dealing with the possibly irregular income stream of being self employed?

Corbett: I don’t work from a budget. Instead, I simply review income and expenses at the end of each month and consider what is necessary and what can be reduced during the next month.

TCI: What was/is your biggest money fear about being self-employed?

Corbett: Living without a salary was a huge fear. It ended up taking the better part of a year before I earned a salary again with my first company.

TCI: How have you handled dealing with things that an employer typically provides – dealing with taxes, retirement contributions, insurance, etc?

Corbett: I found a good accountant to help with taxes.  Retirement contributions have been suspended for the most part for now.  Insurance is purchased on the open market out of pocket.


What I Learned

I’m so grateful that each of these individuals took the time to answer my basic questions!  It says a lot about who they are online.  I’ve actually been compiling these interviews over about 2 months, so I’ve had a lot of time to digest what they’ve said…a yet it still seems overwhelming.

On Making The Jump… The first thing I learned is that all of them had basic savings or an emergency fund ready to go when they made the jump.  They weren’t living paycheck to paycheck beforehand, and they had plans in place to live should the income not come in as planned.  The other interesting thing is that, I think unlike most people, they focused on building income rather than cutting expenses.  Maybe it is because they wanted to be self-employed, but I think it applies to people in many situations – if you lose your job, look to make money instead of looking to just cut back,

On Budgeting… It was interesting to see that most don’t work from a specific budget.  Instead, they plan on saving as much as possible, and paying expenses when they come.  I really liked both Leo and Sam’s strategy of wiping out expenses as much as possible.  Leo prepays his when the cash is in hand, and Sam is seeking to eliminate his debt or keep it to a minimum.  Either way, it seems that most avoid the depressing cycle of budgeting.

On Financial Logistics… This area has fascinated me because it seems like it could be a hassle to try and plan out the logistics of how to become self employed.  I appreciate how Pat shared how it was a hassle when he was trying to do it himself, and he has since started paying professionals.  I also found it interesting how Sam found it “thrilling” to see if the bills could be paid each month…I guess each person has a different idea of thrilling.  It seems like, once you reach this point of income, it makes sense to get some good advisers in your corner to help you navigate the finances: a financial planner, an accountant, and probably a good lawyer.  Hopefully I will need to consider these things soon.  I’m also looking into the different types of self employed retirement plans.


Once again, I want to thank each of these individuals: Pat, David, Leo, Sam, and Corbett, for taking the time to answer my questions and allow me to share their answers with the world.

Your Turn:

What are your thoughts on making the leap to self-employment?  How would you handle it?

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  1. says

    Great profiles, thanks for providing this! It’s always interesting to see how and why people make the jump. One of the toughest things for me is health insurance. My wife’s job covers this right now but it would be great if we could have her stay home.

      • Sam says

        Don’t think online insurance quotes are that expensive thankfully. Worst I’ve seen for a family of four is roughly $1,500/month. Often times you can get cheaper.

        • Brecht says

          I’ve been paying for my own insurance for 7 years 6 of which were in the most expensive state for insurance in the country (MA, look it up) and it is about $1100 for a family of 4 if you set up a business. ‘Group insurance’ is better than individual but requires you to have a ‘group’ which, for me, is my corporation and my group is my wife and me. I put her on the payroll to qualify.

  2. says

    I like how every single one of them had what many people would consider large emergency funds. (And of course Sam had focused hugely on investing.) I think that goes to show that preparation is key.

  3. says

    These guys wisely made it happen through careful preparation and reasonable ‘fall back’ plans, to compensate for unforeseen events. They realized success wouldn’t happen overnight and sensibly planned around it. And then blazed ahead courageously.

    Loved this comprehensive interview series and these inspirational stories.

  4. says

    Absolutely great interviews and fun stories to share! It’s quite impressive to think what all of these guys have built and for most of them it didn’t happen overnight. I think that’s a big part most new bloggers fail to realize.

  5. Sam says

    Good to speak with your Rob and read about other people’s stories.

    It’s pretty crazy how much the Internet has ables to change our lives in the past decade. I never would have expected such a difference so quickly.

    Everything just takes some time, planning, and consistency. Then you hope for the best.


    • says

      Thanks for stopping by and answering my questions! I agree with you – who would have thought 10 years ago that the internet would play such a fundamental role in our lives. It is crazy how times change! What will be around in another 10 years or 20 years?

  6. says

    Loved this article because it seemed liked each one was a little different. I’m looking to keep debt out of the picture and my expenses low while I create passive income.

  7. says

    Wow, this is a great resource Robert, thank you for putting this together. I have always had these exact same questions! It’s awesome to know how they did it, and how it really is an attitude and planning ahead that makes it happen. So, when are you going to write your story of how you made the leap? 😉

  8. says

    That is an impressive collection of bloggers. I consider myself a self-employed blogger since I do get the majority of my income from blogging. I’m just much less successful at it then these guys.

  9. says

    Robert, thanks for putting this together. Appears there is a common theme. Reduce your expenses to the minimum and have a nice emergency (living) fund before you start.

    It also doesn’t hurt that all 5 are exceptional at what they do and would probably be successful in any situation.

    • says

      Interesting thought about whether they would be successful in any situation? Maybe what they were doing before wasn’t the right fit, and that jumping to self employment helped them become more successful?

    • Sam says

      Hi Jason,

      Thx for the comment. Not sure whether I’d be successful in any situation as I’ve had plenty of failures. But, what I won’t do is fail do a lack of effort. I don’t want to look back telling myself I wish I could have tried harder.

      Best, Sam

  10. says

    What a collection of blogging heavyweights, nice job Robert! I’m sure you’ll be join them soon. Great takeaways and love your new site design. Are you planning to make the leap one day?

    • says

      It is a long term plan – maybe when I’m 35 or so. I’ve set a personal goal for my side businesses, and if I hit it, I may take the leap. However, it requires the totality of the business to earn substantially more than it is now, and do it for a consistent period of time.

      • Sam says


        I’m sure you will get there at your pace!

        I didn’t start writing online until I was 32, so you are way ahead of the game!

        Just save and invest like a mad man!



  11. says

    Seriously great job putting this together man. I don’t think I’ll ever earn enough from my blogs to make the jump, but I have entertained the notion of putting a few books out there and using my blog (and my blogging network friends) as a platform. Combined those two sources might eventually generate a reliable income.

  12. says

    This was a great idea. I appreciate the notion of actually having money saved and a clear plan. I’m not impressed with the whole message of just “following your passions.” That doesn’t describe anything. This is the sort of post that should be bookmarked by all future full-time entrepreneurs.

  13. says

    Found your post through Len Penzo’s recommendation. This was an excellent read. I’m married to a wanna-be full-time blogger( and it was nice to read what others have done before him. We currently have 6-7 years or savings but it sounds like some of these guys had more. I personally like the idea of waiting until the online income exceeds our expenses($600/wk) but time will tell if Derek is up for waiting that long. Thanks again!

    • says

      I agree with you that online income has to be sustained for a long time and be enough to replace full time working (including insurance costs and retirement). But people do get antsy sometimes!

  14. says

    Excellent post! So many times we get the idea that entrepreneurship takes a huge risk and requires a “leap into the unknown”. As these five bloggers proved and you captured, it is possible to minimize your risk by saving beforehand and starting your side job while you’re still working full time.

  15. says

    Great collection of profiles! I just wish there were some ladies on here too 😉 I’m hoping to make the leap in 2 years but boy do I have a long way to go, including getting out of debt and building an emergency fund from scratch. Can somebody say all nighters?

  16. says

    I think a great point they all make is that they focused on making money and not cutting expenses. I think if you truly want to be wealthy, you have to focus on making more money. The opportunity to make more money is arguably infinite, while cutting expenses is finite – you can only cut so much and still live. That’s not to say you shouldn’t keep your spending in check, but you are more likely to reach financial freedom by seeking out more income streams as opposed to using coupons at the grocery store.

    • says

      I think it’s all about balance. My hubby would like to make a shift to self employment, so we’re working to cut our expenses so the pressure to earn won’t be so heavy when he starts. Saving our pennies won’t make us rich, but will allow us to work for ourselves and increase those streams of income.

  17. says

    I think it is very important to put our expectations in line with what we have. Each of these bloggers have been around for years and have dedicated a great portion of their lives to these projects. Making the jump to self-employment IMO takes a lot of time and patience. It also requires a lot of work. There are hardly shortcuts. These guys spend the majority of their days writing content, providing support to their readers and outreach to new readers. I highly doubt they are searching for tips, tricks and secrets like many bloggers waste time on.

    Another consideration is what you offer to your readers being a metric for success. Each of these bloggers is very transparent and it shows. By refusing to rehash other content and taking the time to thoroughly discuss matters related to their niche and subject is what has led to their success.

    Finally, in order to make enough money over the long term these bloggers have had to diversify their earnings and it is certainly not appropriate to suggest that they only use a common technique such as Adsense. They use their leverage as industry leaders within their respective niches to provide premium content for their users or for other bloggers. Even consulting and freelance writing can lead to income. I would suspect these guys are all very diverse in how their blogs make money and that is something a lot of us need to improve on.

    • Financial Samurai says

      Well said Scott. It’s certainly not easy, but I have to admit it’s been exhilarating to see progress and grow. The Yakezie Network has been both supportive and motivating to keep on going.

      I’m pretty confident the cast majority of bloggers can make a handsome income online if they post 3 or more, 1,000 word+ posts a week for 150 consecutive weeks. It depends on focused and how badly you want to be your own boss and have more freedom.

      Diversity is key and we’ve all got to hope for the best and roll with the punches. Hope to see you on FS or more often.



  18. Yassin Hives says

    I know all of them, comment regularly on their blogs, i love how everyone of them has this commitment to write, update and discover new opportunities, Personally i do my best with what i got, I only learn from the best and i am looking up for my chance to shine.

    Thank You Robert, I’ll Visit More Often

  19. says

    I think it is so incredible that you the chance to interview all of these incredibly brave folk! Very cool, indeed! I would be interested to see how you were able to grab them all for an interview?? They must be so ridiculously busy to say the least. Bravo for your efforts, and what an inspiring post!

  20. says

    I’m a big follower of Pat and Sam and it’s pretty great you got interviews with them. Even though they are their own bosses, I don’t doubt that they are both very busy guys so kudos on getting them to share a few words with us!

    While I have the greatest respect for Pat, I can’t help but feel that he got in real early and benefited from nearly wide open niches with little to no competition. Now that he’s build power and momentum it’s very easy for him to draw traffic from new areas.

  21. says

    I know this was posted last year, but wow what a fantastic set of interviews from some great people. I was just reading SPI, and it’s just incredible that Pat makes $40,000+ per month. That’s unreal! What an awesome story. Thanks so much for sharing.

  22. says

    Often, I look at what I need to pay instead of what I should be paying. Each seems to have realized, “Hey, how much can I eliminate to get to the basic wants/needs.” From there, they freed themselves to save more for doing what they wanted.

    Great interviews. Thanks to all who shared.

    The Warrior

  23. says

    A lot has happened in the past several years when this article was first published, mostly bullish!

    It’s crazy awesome how much easier it is to grow, once you’ve gained traction. The stock market, private equity market, real estate market is all strong now.

    Time to make lots of hay until the inevitable decline!



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