Corbett Barr
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27 Reasons Why Working For Yourself Is Better

I’ve had the pleasure of working for both myself and working for “the man” over the years. Small businesses, Fortune 500s, government, you name it, I’ve been there.

It’s true, working for yourself can be frustrating, scary, difficult and a constant struggle. On the whole though, to me, working for yourself is the ultimate in personal freedom and fulfillment.

For every aspect of being self-employed that is a struggle, there are so many other things that are WAY better than working a job. I’m going to share 27 of them below. These are from my direct experience. Your experience may differ, depending on your situation and how you set up your business.

Here are 27 reasons why working for yourself is better:

  1. You have no one to blame but yourself. Yes, this is a good thing. Looking for other people to blame is a waste of time.

  2. You measure your progress in terms that matter, like audiences built, products created, and profits earned instead of *corporate world* terms like face time, busywork and being a “team player.”

  3. You don’t have to worry about getting a new boss who’s an asshole. That is, unless you turn into an asshole yourself 😉

  4. Vacation time is nearly unlimited. I just spent three weeks in the Pacific Northwest visiting with friends and family and sailing up in British Columbia. Sure, I worked a little, but mostly I just relaxed and enjoyed myself. How many corporate jobs let you take three weeks or more off in a row?

  5. You decide when you work and when you don’t.

  6. You choose which projects to work on. You don’t have to pursue things you aren’t interested in because you know that following your passions is a better way to succeed.

  7. Drinking during work isn’t frowned upon. Although if you work for an ad agency in the 1960s, evidently it isn’t there either.

  8. You can live where you want to. This applies to location flexible situations like working online. There’s no reason I couldn’t be writing this from Berlin or Buenos Aires or Bangkok.

  9. Casual Friday is any day, to the extreme. Ever feel like wearing a robe around the office? Maybe that’s just me.

  10. You can actually be yourself. Like, your real self, not your “business” self.

  11. Every ounce of effort you put into your business benefits you directly. Having pay related to output is a key factor in job satisfaction.

  12. There’s no commute required. You could rent an office far from your home I suppose, but you’re not gonna do that, right?

  13. Getting laid off isn’t possible. Running out of business or clients is possible, but at least you won’t be kept in the dark until a security guard comes to escort you out one day.

  14. You don’t have to sit through endless, pointless, actionless meetings. It’s a wonder anyone gets anything done in companies where you spend 4+ hours a day in meetings. Imagine what you can do with all that extra time.

  15. There are no goddamn cubicles. I hope in 20 years we look back on the cubicle and realize how sad an existence it is for people who spend 8+ hours a day in them. It’s downright cruel. Like you’re part of the Matrix or something.

  16. The office coffee is much better. For that matter, all the food is better when you work for yourself. No crappy cafeteria, no watered-down office coffee, no lunches at Subway or whatever because you can’t take more than 10 minutes away from your desk. And if you quit coffee, you can ask your “boss” to start buying tea.

  17. If you get tired of your office surroundings, you can change your scenery anytime. I love being able to work from a coffee shop, or my wife’s art studio, or my parents’ house or wherever there’s an Internet connection really. A change in scenery can do wonders for your creativity.

  18. You don’t have to feel guilty about doing personal things. Want to leave early to see your kid’s soccer game? How about taking that cooking class you’ve always wanted to that starts at 5pm? What about working out during the day when the gyms are empty? Your schedule is your own when you work for yourself, and there’s none of that worthless office guilt from your boss to worry about.

  19. Who you work with is up to you. You’re in charge of hiring; you get to select the clients; you get to choose the freelancers and consultants. You can choose people who inspire and motivate you and leave out the jerks or boring people.

  20. If you don’t want to do something, in most cases you don’t have to do it. Well, except for paying taxes, that is.

  21. Your income is limited only by your creativity and willingness to work.

  22. No aspect of working for a big company can touch the deep satisfaction and fulfillment you experience from being completely self-sufficient. Knowing that you are completely and solely responsible for contributing enough value to the world to earn your keep is one of life’s great rewards. It’s something you have to experience to fully understand.

Twitter Responses

I asked on Twitter “What’s your favorite benefit of working for yourself?” Here are some of my favorite responses:

  1. Freedom to dictate my day’s schedule and who I interact with. And working till 3am when the creativity is flowing.” – @cstreet10

  2. Flexibility. The ability to work as much or little as I like, when and where I please.” – @kchrist

  3. The flexibility and control over my time and freedom.” – @stanigator

  4. No corporate BS. – >@cosminsky

  5. Fulfillment.” – @massbehavior

Working for yourself can feel like the ultimate in personal freedom and fulfillment.

Working for yourself can feel like the ultimate in personal freedom and fulfillment. That doesn’t mean it’s always perfect, but after being both employed and working for myself, I wouldn’t have it any other way.

Published September, 2010

About the author

Hi, I’m Corbett Barr. I write about the creator economy 🧑‍🎨 digital minimalism 🧘 and tech for social good 🙌.

I’ve been self employed online since 2005, earning a living from blogging, podcasting, online courses, memberships, SaaS and more. I’ve bootstrapped, freelanced, consulted and raised venture capital.

Recently, I started over to refocus on writing, and to reevaluate my digital self.

I’m a big fan of digital media and techology, but I believe we should all be using it more mindfully and that technology itself should be a force for social good.

I write a monthly-ish newsletter for people who make things on the Internet. I hope you’ll subscribe:

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