How To Think About Career Paths



“Risk something or forever sit with your dreams.” — Herb Brooks.

I’d like to share some of the insights that others have shared with me over the years about choosing career paths.

My favorite insights have always been guiding questions that help me choose my own adventure.

In this post, I share the same questions that some of my mentors have given me that have helped me analyze potential jobs, think through career decisions, and pick my paths.

What’s interesting about the questions is that not only can you use them to analyze potential opportunities, you can use them to analyze a job you already have.  Sometimes the best job, is the one you already have, but you may need to reinvent yourself or your job.

Mentor #1 – Questions for Choosing Career Paths

Here’s suggestions from mentor #1:

  • Do you want more fame, fortune, time, or love?
  • Do you want to be a thought leader or a people leader?

Mentor #2 – Questions for Choosing Career Paths

Here’s suggestions from mentor #2:

  • What are you doing that you currently enjoy?
  • What do you want to do more of each day?
  • What do you want to do less of each day?

Mentor #3 – Questions for Choosing Career Paths

Here’s suggestions from mentor #3:

  • What problems are you working on?
  • Who are you working with?
  • What impact are you making?
  • As more folks ask me about their careers, I’ve found myself talking about three things

Build a Network to Balance Your Strengths

Your network helps you.  It’s a small world.  Don’t burn bridges.

The best networkers I know, balance their weaknesses through strengths in others.

Build your network before you need it.

Your Career is a Portfolio of Experience

Your career is a portfolio of experiences.  What do you want under your belt?

A twist on this is, what are the unique experiences you can have, where you are right now?

For example, what sort of things can I do at Microsoft that I wouldn’t do anywhere else and how do I make the most of it?

Have a Sustainable Approach

Your approach sustains you.  Live your values.  Living your values keeps your energy strong.

Choose experiences that grow your skills.  Knowledge is very transient.

It’s how you learn and how you adapt that carries you forward.  One of the approaches that has always helped me grow is to try to work myself out of a job.

It helps me grow myself, grow the job, and grow others versus stagnate.

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  1. JD,

    This provides good perspective. I like the fact that you gave three different approaches to thinking about a career path, as opposed to preaching just one. This can accommodate different people who think differently. I like mentor 2’s questions best but can benefit from trying to answer the other 2 sets as well. Thanks!

  2. I’ll take one from each mentor.

    As to the first, I don’t want to be famous, I just want everybody to know me.

    We certainly do get ot choose our own path, don’t we?

  3. It’s a great post. It should be very helpful for those who are still seeking to find the right career path or those who have just joined the employment market.

    End of the day, it still boils down to what we truly want to achieve in our life. We need to have clarity of our purpose in life and the rest of the questions raised by all your mentors will be easily tackled.

  4. @ Daphne

    #2 actually helped me decide one of my biggest career moves. The rest are great supplements and health checks.

    @ Jannie

    I’m a fan of the synergy. I don’t think we always get to choose what’s on our plate, just how we eat it. That said, I try to fill my plate with stuff I want when I can.

    @ Wenny

    Thank you. That’s right, without your own map, the advice doesn’t really matter. Then again, the advice helps you figure out your map.

    @ Louisa

    It’s amazing how simple the questions are, yet how profound they can be. I remember the day she gave me the advice point blank and it was such a set of cutting questions. It gave me a new outlook and got me back to the basics.

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