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What Would You Do If You Were Self-Employed?

To many of you, I’m living the dream. I recently quit my job, moved to sunny Los Angeles to be with my fiancee, and started my new self-employment lifestyle.

It’s really great to be able to sit by the pool whenever I want, lunch breaks are mandatory, and there’s never traffic during my commute. My life sounds amazing, but it’s still not quite what I imagined. It’s possible that I’m a huge complainer and will never be happy, but maybe there’s something I can do about it.

Don’t get me wrong, in the grand scheme of things, it’s great. Business is great. I’ve been able to spent more time writing and pursuing opportunities as a result have made more in the past month through advertising and writing than ever before, but there are too many hours in the day when I’m not doing anything constructive. I need to be busy, so I’m applying for jobs, because what better way to get ahead and save for life’s big goals than to have two incomes?

I’m not content living the dream of college kids: making money but working few hours. No, I always want more, even if I don’t know what that is.

What Would You Do If You Were Self-Employed?

While I’m in the process of getting a job, I’m going to have lots of time on my hands. So I’m taking suggestions from you guys about what I should do with my time. I don’t want suggestions about what I should do. Rather, I want to know what you would do. Would you learn a language? What skills would you improve?

Would you just enjoy it and play video games and watch tv all day? Maybe I just need to appreciate what I have and relax more instead of trying to work more!

Please send me your feedback, if I hear something inspiring, I’ll be motivated to take action and be the self-employed worker I want to be!



  1. If I were you, I’d get a 9-5 job and consider the website venture as additional income. From what I’ve read, managing the websites only takes 1-2 hours a day, so this would leave you with plenty of time for a regular job. I’d do this for the following reasons:

    1. Wasting most of the day on something useless, like video games or even something fun, like learning a language, has no economic benefit in the long run.
    2. If something were to happen with your website revenue (ie: changes in advertising, economic downturn, etc.), you would have to explain to an employer what you did with all that free time. Saying “I spent 1 hour working and then the rest of the day by the pool” won’t look very ambitious.
    3. Doubling your income will help you retire that much sooner or accomplish some other major economic goal, like purchasing a house
    4. You have to replenish your savings after dropping over $10K for an engagement ring
    5. I imagine you’ll have to pay for a large wedding in the next year or so

    I’m the same way in that I don’t like to sit idle for very long. I would have a very hard time only working 1 hour a day. Good luck with your endeavors! :)

    • @Noah, All good points, and I definitely will be getting a job in the future (hopefully soon, but I hear the job market isn’t the best right now). In the meantime, I’m going to spend 30 minutes doing language a day, and hopefully a few other small projects that will make me feel like less of a bum

      • @Daniel, Another option (unless you are already in shape) is to use some extra time to exercise and get back in shape. The sun is great and SoCal hasn’t been that hot this summer. Lots of great hikes and mountain bike trails all relatively close.

  2. Wouldn’t the better question be, what would I do to pass the time if I was unemployed? Haha. If I was self-employed, I’d work!

  3. I would catch up on sleep and raise our baby. :)
    Other than that, I would enjoy the summer while it’s here. Once the long warm days are gone, then I would search for different ways to make money online and offline. Enjoy your time off.
    If you’re in LA, you should get an agent and see if you can be extras in movies and TV show. :D

  4. If I was self employed, I’d for sure read quite a bit more. I think the first day or 2 I’d mess around and waste time, but then I’d really get down to business. I’d read more about business and possibly law, and learn more about my local market to see what sort of business would thrive where I live.
    I’d also learn more about money making ventures that interest me, such as raising livestock.

    • @Jeff @ Sustainable life blog, It’s funny, when I was working, I was reading about 50 blogs a day, every day. Now that I’m home, I need to set reminders to do that. All that extra time and it somehow got pushed to the back of the list!

  5. If I was self-employed, I would just try and find away to work more efficiently and with as minimal anchors as possible. As you’ve seen around the sphere, people are making $50-$500,000 a year just from their sites now.

    If I was unemployed, I would just collect unemployment benefits for 99 weeks and go travel the world, while checking in online to find work every 2 weeks as the gov’t mandates.

    What kind of jobs are you looking for?


    • @Financial Samurai, I’d love to work for one of our ‘advertisers,’ I’d be able to keep up on the latest trends, and I’m a technology junkie, simply can’t get enough!

  6. The only thing that bothers me is getting insurance when you’re self-employed. It can lead to some pretty steep premiums.

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