Career Wayfinding: Building Your Way Forward

So many people begin their conversation with me with “I just don’t know what I want to be when I grow up. “ These are folks in their 20s, at the outset of their careers; in their 40s, at mid-career; and in their 50s and 60s, in the twilight of their careers. They’re all searching for the perfect career.

They’re Asking The Wrong Question

People start with the wrong question: How do I figure out the best career for me?

That question assumes that there is a singular career for us that’s better than all the  alternatives; one that we’ll have forever. That approach just doesn’t work in our lives.

Dave Evans, the co-creator of Stanford University’s most popular class, “Designing Your Life,” notes that “before you do problem solving, you have to do some problem finding. You have to decide what’s the right thing to be working on.”

Engineers and designers have similar problems in new product design. How do you build something when you don’t know what to build? They use an approach called Design Thinking.

Design Thinking is about recognizing constraints, realizing that there’s no one answer, and then trying something. It’s about building a prototype, getting information from it, and trying something else.


Design thinking distinguishes between tame problems–those you know how to solve, and wicked problems–unstable problems with changing criteria that require inconsistent solutions.

It examines navigating–following a clear path to resolution and wayfinding–getting comfortable with the idea of multiple destinations, where there may be more than one right answer.

When you can’t know what you’re doing, you can’t navigate. You have to wayfind–take one step at a time, try a few things, tune it up, and do it again.

Wayfinding isn’t about where you need to go, it’s about getting comfortable with the idea that you may not have just one destination.

For most of us, planning–or designing–a career is wayfinding through wicked problems.

Design thinking is one way to work in these circumstances. Looking hard at your circumstances for room to maneuver. Always taking action on the problems you’re confronted with; adjusting and moving forward. No one can know the future, we design it as we go along. It’s life and careers in beta. And we keep doing it indefinitely.

And we do this throughout our careers.

There’s no one ideal job for us. The best we can do is to find out what we need to consider for the next 2 to 5 years. We should develop alternative scenarios and prototypes that address the actual problem we’re trying to solve at the time.

Are you asking the right questions about your career?

What are the career challenges you need to consider for the next 5 years?

Are they tame problems or wicked problems?

Can you get comfortable with multiple solutions to your career challenges?

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