Why Do We Make Life So Hard? — The Entrepreneur Dilemma

One night over some drinks, a good friend asked me why I am making life so hard.

  • Why not take a job and work 9 to 5?
  • Wouldn’t it be nice to come home and not think about the job until the next day?
  • Why travel with the family internationally for so long?
  • Why put all of this on yourself?

He wasn’t the only one to ask some version of that ‘why’. I think that question is on most people’s minds.

Let’s talk about The Entrepreneur Dilemma.

I have historically been a bad employee. Not one that acts up or does a bad job. Just one that gets incredibly restlesss to the point that I can’t be there any longer and I quit. I’ve done it several times.

Why not just suck it up and do my job?

Because I am not wired that way I guess. I have always assumed there is more out there for me, for everyone really. And I feel like I am wasting my time after awhile. The feeling is overwhelming.

I’d rather feel like I took my shots, even when that means Bankruptcy, being semi-homeless with my family for a few months and seeing everyone with ‘I told you so’ on their lips.

I think others feel the same way, but maybe they have buried that piece of them down deep. If you feel like you aren’t happy at work, maybe you should get restless and look for something more. Even if it means turning off the TV at night and researching an idea.

And if you are telling yourself excuses, consider that we lost everything, have 3 kids under 7, didn’t have any internet marketing experience blah blah blah. There are thousands of stories of people more impressive than us that have shattered excuses to try something new.

I doubt you would regret the journey.

After a very public and embarrassing personal failure, I don’t regret the journey. Because I am still taking my shots.

14 Responses to Why Do We Make Life So Hard? — The Entrepreneur Dilemma

  1. Wendi says:

    You never cease to amaze! 🙂

  2. Albin says:

    Amen Jeff. I plan to print this article off and read it at the next meeting I have of a group of potential business partners. Most think you can keep one foot on first base AND try to steal second base too. All you end up with is a pulled groin. The good news is that if you get thrown out stealing 2nd, you get another ‘at bat’ next inning.
    Inspiring article Jeff, best of luck to you although I belive that luck has nothing to do with it.

  3. Keith says:

    I couldn’t agree more. Next year will be 15 years since I started my business and the ups and downs have been extreme but I wouldn’t trade it for the world. I couldn’t imagine punching a clock even thought I usually work 60-70 hours a week.

  4. Whitney says:

    Hi Wilsons!!! I love this website! So excited to see you in a few weeks before you leave on the big adventure….

    • Jeff Wilson says:

      Sorry for the delay…this got lost in wordpress land. We have now seen you, it was awesome and we are away.

  5. Taren says:

    I feel this way all the time. I constantly wonder in the back of my head if I will ever be able to work at one job for more than 2 years (which has yet to happen). I guess I keep listening to what people say, “find a stable job that you can bear to be at and be happy with that.” But it doesn’t seem like enough- I want passion, excitement and freedom…. wow- I guess it is time for me to start taking some shots! Thanks for the inspiration!

    • Jeff Wilson says:

      Take shots Taren. You are young (insert Taren sigh) and have very little to lose on taking shots. Take em now in furious bursts 🙂

  6. World B. says:

    Nice! I look forward to reading about—and maybe somehow participating in—your WWT adventures.

  7. Melanie Ulle says:

    I can’t stay at a job for more than three years. Call it ADD, call it grass is greener syndrome but I know there is something bigger and better which is why I start a new company like every other day….

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