What if you Could Take a Do-Over on your Career?

Do you ever wonder “what if” when it comes to your career choices and how fate has played out?




Looking back over my career, I would not say it has been an ideal fit to my personality and interests. But for comparative purposes, I think I’ve had it pretty darn good in my career and with this here little blog.

Still, I occasionally wonder, “what if I had chosen differently or fate had dealt me a slightly different hand?”

What if I hadn’t pursued the marketing degree, and instead chose one of the dozens of other degrees I considered in my confused college years?

What if I had decided not to get a degree at all?

What if I hadn’t accepted my first job offer? Or 2nd or 3rd jobs after graduating? Or took different jobs? Or had never been offered at all?

I don’t obsess over it, but it does grab my imagination at times.




career change

In a casual friend/co-worker setting, I think most would say they would do something similar to what they are doing right now, if put on the spot. Confirmation bias (who wants to admit they jacked things up?). However, if asked the same question on their deathbed?

I’m a bit of a realist when it comes to career change. I have seen people do it with success (including my wife, who left landscape architecture behind for a nursing career) and I’ve seen others with less successful results. Whether we want to acknowledge it or not, age, previous career, financial obligations and goals, family, and other circumstances definitely do play a factor.

But what if they didn’t? What if you could start over?




It’s fun to imagine the possibilities, with a little reason sprinkled in. So let’s do just that. Here are the rules:

  • You are 18 again, having just graduated high school at the top of your class and can go anywhere.
  • You can go directly to work or get in to any school, apprenticeship, vocational training you would like. No scholarships – you have to pay 100% of the cost if you choose school or training.
  • You have no kids, no significant other, and you are in great health.
  • You have no debt.
  • You can’t rely on someone else (parents, spouse) for money for the foreseeable future.

You basically get a mulligan, clean slate do-over. Knowing what you now know about your value set, careers, money, status, the pursuit of happiness, and life in general – what career path would you choose, and more importantly, why? And is this scenario still in your future?

Maybe you’d do everything exactly the same, but come on… that’s no fun. No judgments here – so be honest.

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