What drives you as an entrepreneur?

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After a long time of being on my “must-read” book list, I finally started reading The Art of Non-Conformity by Chris Guillebeau. The book is all about “Setting Your Own Rules, Living the Life You Want, and Changing the World.”

And I gotta say, I can’t put it down.

Seriously, this is the only book that has ever caused me to miss my train stop because I was so into it I wasn’t paying any attention to anything else.

But all train-missing aside, here’s why I love The Art of Non-Conformity.

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It helped me realize the real reason I love being an entrepreneur.

Don’t just escape from something, escape to something

One key principle Chris talks about is making sure you don’t just aspire to escape from the common work-related plagues we often hear about.

Many times, when I talk to aspiring entrepreneurs, I hear reasoning like:

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  • “I can’t wait to get away from my boss.”
  • “I can’t wait to get out of a cubicle.”
  • or “I can’t wait for all the red tape to come down.”

What I don’t hear very often is what entrepreneurs will be escaping to.

And no, you can’t escape to “life without a boss.” You’re really just escaping your boss.

Get it?

Here’s what Chris says on the subject in his book:

“…’escape’ is a common theme of many self-employment resources, and I can understand why. […]But be careful. When you focus on escaping the humdrum of the cubicle (or wherever you spend your workdays), you also need to have something to escape to. Otherwise you may end up no happier than you were prior to the escape. Like the bride and groom who spend dozens of hours planning a wedding but little time actively planning the life they’ll share after the big day, the other side of escape may be abrupt and unfulfilling instead of the exciting adventure it should be.”
-page 102, The Art of Non-Conformity, Chris Gillebeau

What I really want as an entrepreneur

So it got me thinking…what do I escape to as an entrepreneur?

As many of you know, I have a full-time office job.

But I’m also an entrepreneur with a bunch of side projects that bring a pretty paycheck each month too.

So why do I do both?

Because one of the biggest reasons I’m an entrepreneur is to provide stability and security for my family.

The medical benefits and steady income I get from my day job and the extra cash I pull in from the rest (what I’ve decided to start affectionately calling my “train job”) give me exactly the lifestyle I want for me and my family.

What I don’t want as an entrepreneur

I know it may sound a little ridiculous to the rest of you that I don’t mind having a boss. Or that I get paid the same amount from my day job whether I put in 40 hours a week or 80.

But I like it.

Because I don’t use entrepreneurship to escape to a boss-less life. I use it to escape to added income and family security.

I’m not an entrepreneur set out to make millions. (Thank goodness.)

I’m not in it to be able to travel the world and work from the beach.

I’m not in it for the fame or recognition.

I’m an entrepreneur for the added financial security and to make my family’s lifestyle more confortable.

That’s it.

For now.

I have a terrible memory

Do I forget it sometimes?


Do I aspire to be famous, well-respected, travel the world, buy all the latest electronics and gadgets?


But that’s not what drives me.

What drives me? Three things: My wife, my son, and my (we’re don’t know yet) on the way. (PS: I should have told you…my wife and I are expecting our second child next March!!)

What drives you?

So what drives you as an entrepreneur? Why do you put in the (sometimes) long hours, deal with (sometimes) exhausting clients, and juggle all the small details of your business?

What makes it worth it for you?

What are you escaping to?

Leave a comment on this post and let me know what you escape to and what motivates you to be an entrepreneur!

(PS: All the links in this post for The Art of Non-Conformity are Amazon Affiliate links. If you click through and buy the book, I will get a small kick-back. But I never, ever recommend any book I haven’t personally read (or am in the process of reading). I genuinely think you’ll love this book. In fact, it’s changing the way I look at business and life. If you click through and buy, please let me know so I can thank you personally and we can chat about the book!)

Image by pixelmama

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About Preston D Lee

Preston is an entrepreneur, writer, podcaster, and the founder of this blog. You can contact him via twitter at @prestondlee.

Leave a Comment



  1. Preston,

    Wow. Unbelievably great post. And congratulations on the new little one!!!!

    What drives me as an entrepreneur is schedule freedom. I love being able to go to the dog park with my dogs on a beautiful Wednesday afternoon at 1pm. I love being able to travel when I want (usually to visit family), and being able to stay an extra few days, even if I have to work one of those days. I love being able to volunteer to walk dogs on Friday mornings so my weekends are free.

    And I love having afternoons and evenings free so I can do my second job: officiating youth sports. Often games start at 3:30-4pm, and I’m able to be there for those games, even when I have to travel an hour to get there.

    PS – I do miss cheaper health insurance, but with US heath care reform, we’ll see how that shakes out. I’d love to find a part-time job – 10-20 hrs per week – where I could opt-in to health insurance or just have steady income without having to find it.

    • prestondlee says:

      Thanks, April! Glad you liked the post! Freedom in schedule is a huge one for a lot of people (including myself). Glad to hear you’re doing a lot with your extra time. Best of luck with the health insurance, we’ll see how it all pans out, right.

  2. Evan Cormier says:

    Great insight, Preston!

    I know it’s not for everyone but, personally, I work better with a boss or someone to help keep me on track. Not all of us are Steve Jobs and with a family to care for it’s not a bad idea to keep at least a part-time day (or night) job.

    I’m really glad that you wrote this because I think a lot of people new to the field have this over-glorified perception of what goes on. Not that I don’t love it, I really can’t get enough of what I do but it is a REAL job with REAL pitfalls to look out for. Careful preparation and awareness will ensure not only profitability but also a continued passion.

    Thanks again!

    • prestondlee says:

      Great added points. Thanks for sharing! I know a lot of designers that prefer to simply work for someone else. There’s nothing wrong with wanting to design 24/7 and never have to deal with taxes and legal work, etc. Let’s not get confused: freelancing is a REAL job too. Thanks for the great comment.

  3. Congratulations on your new baby! I read Chris’s book a while ago and loved it. I think I am going to read it again, thanks!

    • prestondlee says:

      Thanks, Maria. I am cruising through the book and I’m almost done. Let me know how it goes on round 2. 🙂

  4. What motivates me? The experience you get from running your own business, as well as the direct contact with clients – there’s no better way to understand who you’re working for than to work with them. Having said that – I’m constantly having to weigh this up with my other goals as I also work full time, and its hard to squeeze everything in!

    • prestondlee says:

      I totally know what you mean. I also work at a desk full-time and run small businesses on the side. But I find it very fulfilling. Best of luck in all!

  5. Entrepreneurship gives me the freedom to think new.

    As an entrepreneur, what drives me is the desire to change situations in my home, community and country. How successful I will be, depend on how many people I assist around me.

    All the best for the incoming one.

  6. prestondlee says:

    Yeah! Awesome, Jude. That’s what Chris’s book is all about: building the life you want and making a difference in the world. Thanks for the comment!


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