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The Best Career Advice I Ever Received

Think about leaving your job, before you've even started

I know it's hard to believe, but I wasn't always a middle-aged engineering manager [1]. At one point in the distant past, I was a fresh-faced college graduate with ambition, and a new Computer Science degree, and a no clue about how the real world worked.

I've had many good bosses and managers in my career; far more than the average (as far as I can tell from my discussions with others) and far more than I deserve. During the second year of my career, as I was beginning to understand how professional opportunities developed and presented themselves, I received a little nugget of advice from an excellent project leader named Rupert. What Rupert told me was this:

When starting a new job, enter with an exit strategy.

At the time, I didn't realize it was a unique riff on "Begin with the End in Mind"; one of the habits from Stephen R. Covey's popular book, The 7 Habits of Highly Effective People. Rupert was well-respected in the company, several levels above me in the organization, and a generally nice guy. I began to follow his example, and his advice.

So what does it mean to enter a new job with an exit strategy?

When beginning your new job, don't enter with a mindset of "This job is forever", instead think "This role is one step on a path I'm walking. Today, I don't know the ultimate destination, but I do know it's going to be great!".

This mindset takes several forms:

  • Ask yourself, what does success look like in this new job? What would it take to leave and feel satisfied that I've accomplished my mission?
  • Early on, identify your replacement (preferably two potential candidates) so when another opportunity arises, you can jump on it and leave without creating a disruptive vacuum.
  • Finally, after approximately 3 years in a role, your “effectiveness per hour” typically starts to diminish. You can still be effective, but you will be less so. Personally, I think this is a side-effect of growing comfortable in your role, losing your fresh perspective, and becoming a defender of the status quo (since actually, you've become the status quo).
“Remember, inertia is a powerful force working against you”

Some of the hunger and passion begins to fade. And as Steve Jobs famously spoke to the 2005 graduating class of Stanford : "Stay hungry. Stay Foolish."

Remember, inertia is a powerful force working against you.

Artificially force yourself to move on from a comfortable job after you've achieved your success criteria. It may feel a little unconformable in the beginning, but that's actually a good thing. It will rekindle the hunger.

Take care, and I'll talk to you next time.


  • [1]: Technically, according to the Oxford English Dictionary, I'm actually not middle-aged, despite the fact that my back often tries to convince me otherwise.

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PostedJanuary 23, 2018
AuthorMitch Cooper
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