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5 Unusual Reasons Why I LOVE Self Employment


It has been over a year now that I left my corporate job and became a stay at home dad/blogger. I LOVE being self employed part time. If I knew what a great fit it was, I would have tried to get here much sooner. Every day is like Christmas combined with Thanksgiving!

For this article, I’m scratching my head trying to come up with a list of entertaining reasons why I like being self employed. Of course, wearing PJ all days and not having to go into the office are great, but I’ll try to list the more personal reasons here. Everyone is different and I know many people like the structure of being an employee, but I’m really loving my life right now.

1. Keep More Money

The first thing that popped into my head is I get to keep more of the money I generate. I always felt like I wasn’t being compensated fairly at my old job. In 2012, Intel paid Paul Otellini (CEO) $19 million. Sure, he deserves more compensation than a regular employee, but I don’t think he should get paid that much more. Intel stock went from around $25 to $21 in 2012 and they didn’t make any progress in the mobile market. As an employee and shareholder, I find it offensive that the executives were getting paid so much. I was paid a little over $100,000 and I knew I generated much more revenue for the company than that since I worked in the core CPU group.

Of course, I have no idea how much I really contributed to the bottom line at Intel. It would be nice if they can compute it somehow and pay people accordingly. Now that I run my own business, I know where every dollar goes. For 2013 so far, I get to keep about 85% of the revenue (after expenses.) I LOVE knowing where the money goes.

While I am making much less money overall, I feel good because I’m keeping a bigger piece of the smaller pie. I guess that’s just psychology, but I don’t really care. It is very gratifying to know that I am being fairly compensated for my time and effort. A self employed business can also grow and hopefully at some point I will make about the same pay rate as my old job. I’d be deliriously happy if I ever hit $50,000/year. That would be great for the half time I put in.

2. Residual Value

I’m building a business and it will have some residual value when I’m ready to walk away (I hope.) I’m having a lot of fun right now and I think I can do this for a long time. However, if I can’t handle it someday, I should be able to sell my online properties. Who knows where Retire By 40 will be in 5 or 10 years?

I’m also building a personal brand. It’s much easier as an entrepreneur to promote yourself. When I was an engineer, everyone always had that glazed over look when I talked about what I did. Now, random strangers have heard of RB40 and it’s pretty cool. Blogging is actually a great stepping stone to building your brand and then branching out to do other stuff.

3. Autonomy

I don’t like being told what to do, but I just didn’t realize it. I hated going to those mind numbing meetings where everyone is banging away on their laptops. I hated deadlines and all the extra unpaid hours I had to do. I hated being nice to people I didn’t like. I guess I wasn’t really cut out for the corporate culture.

Now I am free to set my own agenda and do whatever I want. I can write about anything I want and promote it how I see fit. Every article doesn’t have to be a home run. I can make a mistake and nobody will have a coronary. I will just learn from those mistakes and take my own sweet time dealing with them. It’s great to be accountable only to myself and not my employer and coworkers. I guess I like being a lone wolf. Life is much simpler now and it’s stupendous.

5 unusual reasons why I LOVE being self employed

4. Go At My Own Pace

You know what? Whenever I did an annual review, one of my “strengths” was being a team player. I’m always nice to everyone and can get along with my coworkers. Now I know that’s not really being a team player. It’s just being polite.

This one is actually a bit complicated. I never really liked team sports or rallies. Our family has a form of inherited mitochondria myopathy and I can’t exert myself for an extended period of time. I can do anaerobic activities, but I can’t do much aerobic activities. I’d faint if I overexert myself (ask Mrs. RB40 about our first uphill hiking trip). So team sports that require a lot of running are out for me. I can do some aerobic exercise, but I need to monitor my heart rate to make sure it’s not too high.

So physically, I need to set my own pace and it’s slower than most other people. This must have carried over psychologically. I like going at my slow and steady turtle pace and I dislike being pushed. Self employment enables me to do I what I need in my own time.

5. Flexible Schedule

Working part time is really the key for me. I don’t have to put in a full day and as a blogger, my schedule is very flexible. I’m writing this post at midnight while RB40 Jr. and I are visiting my brothers in CA. I can be a stay at home dad and spend time with my son most of the day and snatch a few hours here and there to work. Being a stay at home parent is not for everyone, but I love it. I always wanted a son and I can’t believe I’m able to spend so much time with him. It’s inconceivable!

When I had a full time job, the kid was at daycare for 55 hours/week. That’s way too much time with strangers.

Self employment is a great fit for me

I can’t tell you how much I enjoy being self employed.  While I do feel accountable to myself (and to my readers), I find the hours that I put into my online business to be so much more rewarding than when I was working for a mega corporation.  It’s gratifying to know where every dollar and hour of my time goes. I can go at my own pace and slowly build up my online empire without having to compete with a coworker. The added bonus of being able to spend such an amazing amount of time with RB40 Jr. and my family.  That alone is worth the decision to be self-employed. Of course, I’m making less money, but we can live with that so it’s not a big deal.

Are you self employed? What are some unusual reasons why you like it? 

Photo credit: flickr [email protected]!

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Joe started Retire by 40 in 2010 to figure out how to retire early. He spent 16 years working in computer design and enjoyed the technical work immensely. However, he hated the corporate BS. He left his engineering career behind to become a stay-at-home dad/blogger at 38. At Retire by 40, Joe focuses on financial independence, early retirement, investing, saving, and passive income.

For 2018, Joe plans to diversify his passive income by investing in US heartland real estate through RealtyShares. He has 3 rental units in Portland and he believes the local market is getting overpriced.

Joe highly recommends Personal Capital for DIY investors. He logs on to Personal Capital almost daily to check his cash flow and net worth. They have many useful tools that will help every investor analyze their portfolio and plan for retirement.
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{ 52 comments… add one }
  • C. the Romanian October 28, 2013, 2:56 am

    These are some great reasons and I agree with all of them. I personally make more blogging than what I did when I was employed (but yet again, salaries in Romania are really low) so that makes things even better. I get the feeling that I keep less money than what I’d like to (about 25% goes towards tax and health insurance and mandatory pension payments) but overall, the fact that I still make more makes me feel great.

    As an unusual reason, for me the fact that I can take a day off whenever I want to really matters. I don’t do it often, but every now and then I will feel like not working and I can do it. That feels great!

    • retirebyforty October 28, 2013, 9:11 am

      Oops, I forgot about tax. This year I’m sending most of the income to the solo 401k though so I don’t have to pay much tax at all.
      The flexible timing is huge.

      • Wilson October 28, 2013, 10:12 am

        Curious as to why you chose the solo 401(k) route versus a SEP IRA? Greater amount of contributions? If I’m correct aren’t the tax implications the same, or is the 401(k) more advantageous?

        • retirebyforty October 28, 2013, 3:15 pm

          For my situation, I can contribute more with the solo 401(k). The more you contribute, the less tax you’ll pay.

  • Maverick October 28, 2013, 3:16 am

    Joe, FYI, when I look up Intel stock, I see revenue per employee to be about 500k.

    • retirebyforty October 28, 2013, 9:12 am

      Thanks for that info. I was in the core CPU group so I’m sure my contribution would be like a million! They had a lot of labs and groups that didn’t make any money.

  • [email protected] October 28, 2013, 4:11 am

    Hi Joe,
    Sometimes when I work long hours I always wonder if it’s better to work for myself. i’m probably a few years away from that, but when we have kids that’s something I would consider.

    • retirebyforty October 28, 2013, 9:13 am

      Good luck! By the end, I was pretty much working 40 hours/week. When I was young, I worked 60 hours/week pretty often though.

  • Jon October 28, 2013, 4:41 am

    Number 3 resonates most with me Joe. Having to be at meetings when I’d rather be surfing, mandatory conferences that run late so I can’t make it home in time for dinner. Sometimes I cover other teachers’ classes without being paid extra. Lately, the South American Olympics committee came to town and I was the translator for the Korean President of Tae Kwan Do, but no extra pay was involved even though I showed him around town for a day! Can’t wait to be “retired”…

    • retirebyforty October 28, 2013, 9:13 am

      Extra work should mean extra pay. I didn’t like working extra at all because I never got any overtime. It’s just expected because everyone did.

      • [email protected] October 29, 2013, 10:58 pm

        I would say it is better to work for yourself as companies don’t hire you out of the goodness of their hearts. They always pay you less than you are worth, otherwise how do they make a profit?

        I stopped working in 2008 and do not regret the move at all. I hated dressing up and putting on makeup to goto work and make small talk with everyone. It’s so freeing to wear sneakers, jeans, and to stick to my own schedule.

        • retirebyforty October 30, 2013, 7:59 am

          That’s 5 years already. Great! I really hope I feel the same way after 5 years.

  • Jane Savers @ Solving The Money Puzzle October 28, 2013, 5:58 am

    I work with a lot of other people and some of them and a lot of my clients make me crazy. If I got to work at home I would miss the brain challenging rapid fire problem solving that I am required to do on a daily basis.

    Some days, like this weekend, I come home and my brain is fried and I can’t work on my writing because I am no longer capable of thought. Ideally I would love to go to work 3 days each week to keep my brain and skills sharp but with enough down time to be able to build my own business and work on my writing.

    • retirebyforty October 28, 2013, 9:14 am

      Hopefully you can transition to 3 days/week at some point. I have been through those weeks too.

  • moneystepper October 28, 2013, 6:14 am

    Being able to understand your true worth to your employer (or yourself if you are self-employed) is a huge benefit of self-employment that I’ve never really thought about before.

    • retirebyforty October 28, 2013, 9:18 am

      Yeah, it’s great to see how much you’re really worth. If you work hard and are lucky, the business will grow and you’ll get a raise.

  • insourcelife October 28, 2013, 6:50 am

    All of these are good reasons for sure. For me, one of the reasons I like being self employed is that I don’t usually have to participate in or worry about office politics. As a contractor you generally keep a low profile while employees are all involved in power struggles, never-ending performance reviews and other similar BS that seems to permeate every company/business.

    • retirebyforty October 28, 2013, 9:20 am

      The office politic is ridiculous. It’s more important who is your manager than the work you did. I probably should have tried the contractor route when I was younger.

  • Dear Debt October 28, 2013, 7:53 am

    I think autonomy and flexible schedule would be so nice. Sounds like a really good fit for you and your family. I agree that you can really see where your money goes and how you make it!

    • retirebyforty October 28, 2013, 9:20 am

      It’s the ideal situation right now. Maybe it will change in the future, but for now it’s great.

  • SavvyFinancialLatina October 28, 2013, 8:02 am

    So far what I haven’t liked of working for the man is performance evaluations (bosses don’t really evaluate you) and office politics. I hate office politics and they are everywhere in a corporate job. I really want to end up working for myself. Now I have to figure out how to get there.

    • retirebyforty October 28, 2013, 3:03 pm

      Office politic was fine as long as I got along with my boss. When I got a boss who I didn’t like, the office politic got really bad… Good luck to you!

  • The College Investor October 28, 2013, 8:36 am

    Having a flexible schedule makes being self-employed very tempting, it means being able to do some things you probably won’t be able to do if you’re working in an office and being more productive because you can do more when you’re working.

    • retirebyforty October 28, 2013, 3:05 pm

      If I’m in a time crunch, I’m definitely more productive. I can just do the essential stuff and cut out the unnecessary stuff until I have more time.

  • Kurt @ Money Counselor October 28, 2013, 9:03 am

    I’m self-employed, and I concur with all of these Joe. For me, flexibility and autonomy are probably the two biggies. As you point out, I also like that there’s a direct connection between my abilities and motivation and how much money I earn. I’m not working 40-50 hours a week mainly to make someone else wealthy(ier).

    • retirebyforty October 28, 2013, 3:05 pm

      Working to make someone else wealthy is the pit…

  • dojo October 28, 2013, 9:08 am

    Successfully self-employed for more than 4 years. What I love:
    1. flexible schedule and free time – when I want it, how I want it. If I want to work on Christmas day, I’ll work, if I want to take 3 weeks off, I’ll take them
    2. a lot of savings – am working in a t-shirt and some pants, eat at home, don’t drive the car too much. I’m saving A LOT of money this way
    3. work for myself and my clients
    4. happy and relaxed – I know how to handle my deadlines, so it’s all nice
    5. time with the family – am expecting a baby, she’ll grow with both of us, not the nanny

    • retirebyforty October 28, 2013, 3:06 pm

      Thanks for sharing!
      Enjoy your baby. It will be a big adjustment, but it’s great.
      I haven’t been able to take 3 weeks off yet. 🙂

      • [email protected] October 29, 2013, 11:04 pm

        #5 time with family. I heartily agree with that. Back when I was working I was so tired from the long hours that all I wanted to do was sleep on the weekends. Having dinner with my parents and in-laws was a huge chore because I felt that they were cutting into my precious personal time.

        Nowadays, I have so much more time and I make sure to have dinners with family every week. They no longer are a chore and actually happy times.

  • [email protected] October 28, 2013, 9:36 am

    I am not self-employed but the reasons you mentioned are things that I crave for my work life. I definitely think being self employed is a lot more motivating when you’re earning for yourself, not someone else. Well I work in government so it’s not really a “business” but there are also a lack of incentive for a job well done. Now with a family, I do crave more flexibility.

    • retirebyforty October 28, 2013, 3:08 pm

      Flexibility is huge when you have a family. Money is less important as long as you can make ends meet. Time is a lot more important.

  • Michelle October 28, 2013, 10:13 am

    As you know, I just recently became self-employed (around 2-3 weeks ago). It has been great, and I honestly don’t think I could ever go back to my day job. I love not having a commute, I love building my brand and my business, and my self-employment has changed my life for the better in so many other areas.

    • retirebyforty October 28, 2013, 3:16 pm

      Congratulation again! Self employment just fits some people better than others.

  • This Life On Purpose October 28, 2013, 10:36 am

    Glad to hear you are enjoying self-employment! Those are all good things to look forward to, if I ever get there.

    • retirebyforty October 28, 2013, 3:16 pm

      Good luck!

  • Kali @ CommonSenseMillennial October 28, 2013, 11:03 am

    I cannot wait to reach self-employment, for all these reasons and more! I’m definitely like you in that I don’t like being told what to do – I’d rather do things my own way (and definitely at my own pace). The flexibility of being able to set your own schedule and be able to work how and where you want to is another huge advantage. Hopefully I’ll be joining you in the ranks of the self-employed sooner rather than later! I certainly can’t wait to get there.

    • retirebyforty October 28, 2013, 3:17 pm

      Good luck to you as well. For those of us who don’t like being told what to do, it’s the way to go.

  • Done by Forty October 28, 2013, 12:30 pm

    I love the autonomy point. There’s nothing quite like being at the wheel, you know? Pink’s book “Drive” mentioned autonomy as one of the three big motivators, and I find it to be true. Whether you’re self employed or not, a job requires a degree of autonomy if it is to satisfy over the long haul.

  • chitownmom October 28, 2013, 5:31 pm

    congratulations, Joe! looks like your plan is working out splendidly for you! do you find that needing to balance the blogger and stay-at-home-Dad roles stressful at all? after all, I could see both being a full time job (hours and the thinking/ emotion , etc)

    • retirebyforty October 28, 2013, 11:34 pm

      Thanks! It’s getting more stressful because my mom is not here anymore. We are looking for a babysitter to help out during the day though. I just need a couple of hours in the afternoon to blog. It’s definitely less stressful for me than working a corporate job.

  • Anne October 28, 2013, 9:18 pm

    I also love being self employed because I can spend more time with my siblings. I now do have a flexible time schedule. I can blog at anytime I want 🙂 You can now earn money while you enjoy!

  • Paul N October 28, 2013, 9:33 pm

    Hi joe
    I’m going to agree with most of your comments. For you personally it’s obvious you have a great dislike of the 9-5 world, office structure and being someone’s employee. It’s great you have found a way to work at things you like and make money as you do. It’s also great your wife can support you and cover your family under her health plan while you ramp up your alternative income streams. Your very lucky. I really think you have managed to make a good outcome for yourself.

    The one point I will disagree with you on is your comments about not getting fairly compensated vs. your former CEO’s compensation. You were paid $100k. That for some people is a dream pay. I also feel as a salaried employee you assume zero risk other then just showing up every day and doing your job. The CEO of Intel and it’s owners built the company and assume all it’s risks and liabilities. It’s their company they should decide what fair pay is. I feel some bitterness in your words. I feel more amazed that a small group of people could put a company together like Intel and employ quite a lot of people that will have decent life and never be without want of anything being paid that much. Not everyone deserves $100 k and no company can pay everyone what they think they deserve and stay in business. You stated how much you hated doing your job every day. I manage about 15 employees myself. I would find it hard to have a conversation with an employee that hated his job and at the same time felt he was worth much more then he was paid and asked for a raise.
    I see my boss do 12 hour days and he usually works weekends. I’m sure he makes 3 x as much as I do although my dept which I recreated from nothing (actually it was losing money) creates the most profit. Maybe I should be paid more then our CEO ? I honestly never feel that way. I would however consider starting my own competitive company then later pay myself as much as my boss gets now or whatever I wanted to pay myself when the company could afford it. I just look at that differently.

    • retirebyforty October 29, 2013, 8:35 am

      I just think they should be held accountable for their recent performances. Why should Paul get paid so much when the company isn’t doing that well. I admire the founders too, but that’s ancient history. As a shareholder, what have they done for me lately? 15 years ago, I liked my job and worked 12 hours/day too. That’s how I got raises in the past. I didn’t start out hating the job.
      Anyway, many people are happy working 12 hours/day to enrich the executives. It’s just not for me. Good luck with your business.

  • [email protected] October 29, 2013, 6:43 am

    I am self-employed and like it for all of the reasons you’ve mentioned! I’ve always been a solo worker, even when I worked for someone else. I don’t think I would work well in a group or on projects with other people anyways. I like doing my own thing.

    • retirebyforty October 29, 2013, 8:38 am

      It’s tough to work with other people sometime. I like doing my own thing too. I’m self driven enough to do it.

  • Mike October 29, 2013, 3:13 pm

    I definitely agree with the majority of your points that you listed-which is why I am getting ready to return to it after my adventures in teaching in China. There are a lot of things that you feel a lot more free to do when you are the boss! That’s what I like-I can choose my own projects rather than the projects that someone else wants to pursue.

    • retirebyforty October 30, 2013, 7:57 am

      Good luck with self employment. It’s a better fit for some people than others.

  • Justin @ Root of Good October 29, 2013, 5:12 pm

    I hear you on the benefits of self employment. You are doing what you want, for yourself, at your pace and keeping the fruit of your labor.

    If you’re like me, some days you get too busy to do much “work”. And that’s ok. One of the fringe benefits I guess.

    • retirebyforty October 30, 2013, 7:57 am

      I usually can get in an hour or two at night, but it does get too busy with life sometime.

  • Lauri October 31, 2013, 7:10 pm

    People seem to mostly agree with you, Joe, but I am so thankful to work 4days a week. I really need to get out of the house and be around other people. I did not do well the year I was home with Baby. But full time would not be ideal because I dont want strangers with my kids so much. My kids are my first priority. I just think I am a better mother working part time. Also, I am more productive because I’m not trapped there 40+hours a week.

    • retirebyforty October 31, 2013, 11:11 pm

      Mrs. RB40 would agree with you. There is no way she can stay home with the kid. It just depends on the personality. 🙂
      It’s great that you were able to figure out the right solution for your family.

  • CentSai May 19, 2016, 12:43 pm

    Very true! Being your own boss can be really nice. We have a similar story on our website that discusses why freelancing was a better choice for the author than her 9 to 5 job for similar reasons. If you don’t mind me sharing, here’s the link: http://bit.ly/1siIhWI.

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