How to stop overthinking and take action at work

A few years ago, my friend Taylor and I went hiking in Montana.

I wasn’t familiar with the area, and I wanted to pick the “perfect” hike.

When we passed a park ranger, I bombarded her with questions:

“How far is the lake? What’s the incline? Is one trail muddier than the other? Which view is nicer at the end? Are they doing active forest work on this trail? Do you recommend the out-and-back or the loop?”

Looking up, I saw that Taylor was already well ahead of me.

“Jenny, it’s all gorgeous,” she shouted without pausing. “Let’s go!”

She was right. And I would’ve missed it if I’d stayed frozen in indecision.

The Problem

You’re doing this at work right now.

You won’t speak up in the meeting until you’ve thought through every objection. You won’t introduce yourself in an icebreaker until you’ve silently rehearsed it 13 times.

You won’t apply for the role until you meet every qualification. You won’t start the project until you’ve researched the perfect approach.

You tell yourself you’re being strategic. But you’re actually avoiding discomfort.

And the moment of certainty you’re looking for will never come.

The Big Small Thing

Your solution? “Move, Then Map.”

(This is what I call being “reckless” in my book Wild Courage. It’s the courage to take calculated risks even when you don’t have perfect information.)

Movement makes the magic. Action provides clarity, not thought.

Here’s what “Move, Then Map” looks like:

Example #1: You want to start a consulting business

DON’T: Build the perfect website, research pricing for 3 months, and create a full business plan.

DO: Text one former colleague today. Say: “I’m exploring freelance consulting. Do you know anyone who might need help with [your expertise]?” Use a free consulting agreement template. Get one client, learn, then map your next move.

Example #2: You want to ask for a promotion

DON’T: Wait until you’ve documented every accomplishment and rehearsed the perfect pitch.

DO: Schedule 15 minutes with your manager this week. Say: “I’d like to discuss my career growth. When can we talk?” Start the conversation and learn what they need to see. Then build your case.

Take one small action. Learn. Adjust. Repeat.

You’re not eliminating uncertainty completely, but moving through it.

My friend Simone Stolzoff just released a book called How to Not Know about navigating uncertainty. (It’s one of my favorite reads this year. Funny, practical, and refreshingly honest about how messy real decision-making is.)

One concept from his book that I loved: “Trust your future self to solve your future problems.”

To take risk, you must cultivate faith in your own ability to course-correct, adapt, and evolve. Trust that you’ll handle whatever comes up. (You always do!)

Want more tips on how to grow in your career? Here’s a FREE guide to saying no!

How This Helps You Get What You Want

When you’re uncertain, you consistently get the balance between preparation and action wrong. Instead, move and map in tandem. Take one small, smart risk after another.

What small step feels scary today but would fill you with pride tomorrow?

Stop waiting for the perfect moment. This is it.