42 Questions to Ask When You Hit a Career Roadblock

As you pursue your career goals, you will inevitably come face to face with big, gnarly obstacles.


As you pursue your career goals, you will inevitably come face to face with big, gnarly obstacles along the way. How you deal with them will do a lot to determine where your career takes you. If you bump up against those obstacles, feel the resistance, and decide that it’s impossible, then it will be. But if you hit a roadblock and view it as a signal to go into problem-solving mode, your potential is infinitely greater.

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If there is one habit you develop in your career, make it the fine art of asking questions. Part of how I make my living is asking questions (as a career coach), and every day I have a front-row seat to their power to overcome and even dissolve obstacles. It’s amazing to watch.

As I started writing this post, I did a brain dump of questions to ask when you hit an obstacle and feel stuck. Scanning back through them, it struck me that they all boiled down to two main things: clarity about the problem, and clarity about the solution. Next time you find yourself bumping up against a barrier to your goals, spend some time with the questions below and see if anything breaks loose.

[See 12 ways to sabotage your career goals.]

Clarity about the problem

Why am I stuck?

What are the steps to get from here to where I want to go? Which steps am I getting stuck on? Why?

What pieces of the puzzle need to be in place for me to reach my goal? (Map it out.) Which ones am I getting tangled on? Which ones are missing?

What information am I missing?

What skills am I missing?

What assumptions am I making? Are those assumptions valid? Am I 100 percent sure? Could there be a different perspective?

What makes this seem unmanageable?

What am I trying to do myself that I should be getting help on?

What do I need to do differently?

Do I want to do this?

What/who is blocking me?

Is the problem external, or is it internal (i.e. between my ears)?

What external barriers am I encountering?

What internal barriers am I encountering?

What behavior have I been repeating that leads to this problem?

What limiting stories am I telling myself?

What habits are contributing to the problem?

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Clarity about the solution

If I had to make this happen, how could I?

How many ways past this obstacle can I imagine? (Use this to brainstorm solutions--they don’t all have to be good.)

What one step can I take?

What one change could I make that would have an impact?

What if I ____?

What could a bridge from here to there look like?

If I can’t make this happen now, then when could I?

Where can I find the information the information I need (books, classes, etc.)?

Who has the information I’m missing? (Think of individual people.)

How can I develop the skills I need?

Who can I brainstorm solutions with?

Who can help me? How?

How could I shift my perspective?

Could my limiting stories be replaced with more enabling stories? What would they be?

What could I try that I have been resisting?

What habits could I develop that would help me overcome the challenges?

This is far from an exhaustive list, but it’s a great place to start. Any time you bump into an obstacle, make it a habit to stop and first get clarity about the problem (including whether it is real or manufactured in your own mind), and then get clarity about the potential solutions. Above all, ask questions!

After years as a professional malcontent, Curt Rosengren discovered the power of passion. As speaker, author, and coach, Rosengren helps people create careers that energize and inspire them. His book, 101 Ways to Get Wild About Work, and his E-book, The Occupational Adventure Guide, offer people tools for turning dreams into reality. Rosengren's blog,The M.A.P. Maker, explores how to craft a life of meaning, abundance, and passion.


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