The Mentorist

Take a Walk on the Wild Side: Finding a Career You Love

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The longer you stay in a career, the harder it becomes to switch to another.

Some of the causes of career inertia are practical ones:  You’re earning too much money to consider leaving; or you have your kids’ orthodontist bills to pay; or you spent hundreds of thousands of dollars getting the degrees required to practice your profession; or….

But another reason some people stay in careers that no longer make them happy is lack of imagination:  They’d like to “run from” what they’re doing now, but have no idea what to “run to.”

Figuring out what alternative careers are likely to increase your happiness level requires some creative thinking.  Oh, sure, you can always go to an industrial psychologist to take Myers-Briggs and a battery of other aptitude tests.  And those tests can add value.

But, first, try this simple exercise:

 Step 1 For the moment, assume that all jobs pay exactly the same.  Now, take out a blank sheet of paper and ask yourself this question:



“If I didn’t need to be good at my job, but I did have to choose one that would give me immense pleasure, what job would that be?”

Leave your inhibitions at the door when answering.  Write down anything — and everything — that comes to mind, as fast as you can scrawl. The point here is to expose your impulses.  No “super-ego” filtering allowed.  Stop writing after 60 seconds.

Step 2 Now, take out a second sheet of paper and (again, assuming that all jobs pay exactly the same) answer this question:

“If I had to be really good at my job, but (with that as my only constraint) could choose any job that would give me immense pleasure, what job would that be?”

Again, write down whatever pops into your mind — absolutely no censoring.  And, again, stop after 60 seconds.

Step 3 Now look at your answers.  They might surprise you.

[A buttoned-up lawyer I know took this “no-holds-barred” brainstorming approach to heart:  His list of answers to the first question included “gigolo.”  (Ultimately, he became a venture capitalist.  You may draw your own conclusions….)]

Some of your answers will be pure flights of fancy.  Others will be impractical.  But take a moment to analyze them:  See if you can spot any common themes running through the mix.  Ask yourself:  What traits and beliefs are associated with the jobs I wrote down?  Might there be a “realistic” new career I should consider that would tap into those traits and beliefs?

I’ll use myself as an example here:  Without a moment’s pause, I scrawled out “Teri Gross,” in answer to the second question.  (She’s host of public radio’s “Fresh Air.”)  I’d make a terrific Teri!

Of course, the only person who can be Teri Gross is Teri Gross.  But, analyzing my answer, I realized that my choice was grounded in three things:  (1)  my intense curiosity about the lives of other people, (2) my belief that everyone has got something interesting to say (you just have to ask the right questions) and (3) my talent for “connecting” in a way that frees them up to say it.

Once I’d figured out the reasons for my “Teri Gross” answer, I looked at “real world” careers I might choose that would draw upon these same talents (i.e., I’d be good at them) and make me happy (i.e., the whole point, isn’t it?).

Two jobs immediately came to mind:  journalist and therapist.  And, indeed, elements of both these professions thread through my current mentoring practice –- something I both am good at and get pleasure from….

Even staying within my chosen professional field of law, a look at my reasons for answering “Teri Gross” confirms that I’m best suited to a legal specialty involving lots of “face time” with others and exchanges of ideas.  Negotiating deals?  Bring it on!  Becoming the resident expert on arcane tax rulings?  Are you kidding…?

So, give these questions a try.  If you find that the results are nonsense, you’ve wasted 10 minutes and two good sheets of paper.  Then again, your answers might surprise you….

changing careers

Author: Jane E. Owens

Jane E. Owens, The Mentorist’s chief blogger, has spent her career immersed in the business and culture of corporations and law firms. A former general counsel and corporate lawyer, Jane is fascinated by those who thrive (as well as those who don't) in the professional world – and, through her mentoring practice, hopes to increase the ranks of the former. To learn more about Jane or suggest topics you'd like The Mentorist to discuss, go to: www.mentorist.co

One thought on “Take a Walk on the Wild Side: Finding a Career You Love

  1. I can already tell that’s gonna be super helpufl.

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