Stop Trying to Think Your Way Into the Perfect Career Decision

When people are trying to figure out what to do next in their careers, they usually start in the same place.

They take personality assessments.

They clarify their values.

They make a list of must-haves and deal breakers.

They reflect on what they've enjoyed in past roles, what they're good at, and what gives them energy.

They research different career paths.

None of these are bad ideas.

In fact, I use many of these exercises with my coaching clients because they're incredibly helpful.

But they're only half of the equation.

The biggest mistake I see people make during career transitions is assuming they can think their way to clarity.

The missing piece is experimentation.

Discernment Requires More Than Thinking

One of the words I use often in my coaching is discernment.

To me, discernment is the practice of making decisions using multiple ways of knowing.

Your analytical mind is one source of wisdom.

Your emotions are another.

Your intuition.

Your lived experience.

The trusted people in your life.

Your body.

Most of us naturally rely on one or two of these more than the others.

The goal isn't to stop using your preferred way of making decisions.

It's to strengthen the parts of your decision-making process that you've been overlooking.

Over the years, I've noticed that many people fall into one of two patterns.

The Fast Mover (confession: this is me 🙋🏻‍♀️)

The Fast Mover knows when something feels wrong.

They're quick to recognize when they've outgrown a job, a manager, or an organization.

When they feel the pull toward something new, they trust their instincts and want to act.

This is a strength.

But it also comes with a blind spot.

Sometimes they're moving away from discomfort faster than they're moving toward something they're genuinely excited about.

The antidote isn't to become someone who overthinks every decision.

It's to slow down just enough to gather better information.

Let's say you think you might want to work with animals.

Instead of immediately updating your résumé and applying for jobs at animal shelters, design an experiment.

Volunteer one Saturday.

Shadow someone in the field.

Invite someone to coffee and ask them what a typical day actually looks like.

Notice what happens in your body before, during, and after the experience.

Were you energized?

Curious?

Drained?

Bored?

Did you leave wanting more?

Those are data points your brain could never have generated on its own.

The Analyzer

The Analyzer has the opposite challenge.

They don't make impulsive decisions.

They research thoroughly.

They reflect deeply.

They compare options from every angle.

They're thoughtful and intentional.

Until they become stuck.

The more they try to find certainty before taking action, the harder it becomes to move at all.

Eventually the decision feels so important that their nervous system interprets it as a threat.

Overwhelm sets in.

Action stops.

The antidote isn't more research.

It's making the decision smaller.

Instead of trying to figure out your entire next career, ask yourself:

"What's one tiny experiment I could run over the next two weeks?"

Maybe you attend one networking event.

Maybe you spend two hours volunteering.

Maybe you interview someone whose career intrigues you.

Maybe you take one class.

The goal isn't to discover your forever career.

The goal is to collect one new piece of information that you didn't have before.

Then repeat.

Why Experiments Work

Experiments are different from research.

Research tells you about something.

Experiments tell you what it's like for you.

You can read everything there is to know about nonprofit fundraising.

You won't know whether you enjoy asking people for donations until you've helped with a fundraising campaign.

You can spend months researching what it takes to become a coach.

You won't know whether coaching fits you until you've actually sat across from another human being and experienced what it feels like to help them.

Some forms of wisdom can only be accessed through lived experience.

You Don't Need More Certainty. You Need Better Data.

Whether you're a Fast Mover or an Analyzer, the solution is surprisingly similar.

Neither needs to become someone else.

The Fast Mover doesn't need to stop trusting their intuition.

The Analyzer doesn't need to stop thinking carefully.

Both simply need to broaden the way they gather information.

That's what discernment is.

It's not choosing between logic and intuition.

It's learning to use both.

Career transitions rarely unfold because we finally have enough information to make one enormous leap.

More often, they unfold through a series of small experiments, thoughtful reflections, and increasingly informed decisions.

If you're waiting until you feel 100% certain before taking action, you may be waiting for information that only action itself can provide.

A Reflection for You

What's one question you're trying to answer about your career right now?

Instead of asking, "How can I decide?"

Try asking, "What's the smallest experiment I could run that would teach me something I can't learn by thinking alone?"