How to decide when everything feels unfigureoutable

Deer, meet headlights. Here's your way out.

Author

Jen Phillips
October 14, 2025

Hi it's Jen,

You're staring at your career crossroads. Again.

You know how I know that?

BECAUSE WE ALL ARE. What even is work in a year, anyway?

So while we’re all in the middle of inner monologues like, “Should I stay and try to push through? Leave and risk the job market? Pivot my skills? Get a side hustle as a YouTuber?”

And AI is rewriting job descriptions faster than we can update our resumes.

So our brains do that thing - simultaneously shouting into the mental abyss: "I NEED A PLAN" and "EVERYTHING IS TOO UNCERTAIN TO PLAN."

What happens next? Deer, meet headlights. Today I’m talking about clarity when it all seems … unfigureoutable.

Today's issue:

Read time: 6 minutes

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You've probably done the research. You've made the pro/con lists. You've talked to friends, mentors, maybe even a therapist. You know the facts of your situation.

But you still can't see your next move.

That's because, as therapist Lori Gottlieb points out in her TED talk (7.6M views, so you know we all need help with clarity), we're unreliable narrators of our own lives.

We tell ourselves stories about our situations. And they feel completely true. Why we're stuck, why we can't move, why nothing will work. And those stories determine what’s clear. And what isn’t.

We feel stuck, trapped in emotional jail cells. So many of us are shaking the bars - desperate to be free - and the way forward is right next to us.

We can't see it because we're the ones writing the story, and we've written ourselves into a corner.

That's the clarity problem.

We've decided what's possible and what isn't. What we're capable of and what we're not. What's "realistic" and what's "crazy." And those decisions become the bars of the cell we build for ourselves.

Luckily, it gets worse. (Oh, you thought we were done?)

We won't walk around those bars to freedom because we know there's a catch.

Freedom comes with responsibility.

If we admit that maybe we're not seeing the full picture, we might have to change the story. Which means we might have to change ourselves. Which means admitting we had the power to do something different all along.

And that? That's terrifying.

We say we want to change. But what we really mean is: "I want my circumstances to change." I want the market to stabilize. I want my company to figure itself out. I want the tech industry to stop being chaos incarnate. I want [insert external wantable thing] to be different so I don't have to be.

So chronic stress and uncertainty do make thinking harder. Decision fatigue plus uncertainty equals cognitive overload. That's real. (American Psychological Association )

But adding to that problem is that we’re looking at our situations through stories that keep us stuck.

And until we edit the story, no amount of added info will get us clear.

Ambition

Here's what I learned the hard way: editing for clarity doesn't come before action.

It’s built through action. Put another way, it’s super unlikely we’ll let go of the bars just because we keep ruminating over new information. We’ll need to take a step. And we’ll be happier when we do.

Psychologist Barry Schwartz’s research found that "maximizers" - people who need perfect information before deciding - are less happy than "satisficers" - people who make good-enough decisions and move forward.

The goal isn't to see the whole staircase before you take a step. The goal is to identify the “rightest” next step and take it.

In a world where women in tech are leaving at every stage of the pipeline, and AI is transforming work faster than anyone can predict, perfect clarity is too high a bar.

The instability is real. The layoffs are real. The “do more with less-ness”, it’s real, too.

But you know what else is real? Your ability to move through uncertainty instead of being paralyzed by it.

If we wait for perfect clarity, we risk staying locked up in our stories too long.

The new ambition is having the courage to act without it, iterating as we learn by doing.

What helps? Having a framework that makes getting out of jail slightly less terrifying.

GO | DO

Estimated time: 10 - 15 minutes | Estimated energy: minimal

This week: The 3-Question Clarity Framework

When you're locked up in your own story, try this:

The Energy Test (5 minutes)

"When I imagine doing X in 3 months, does my body relax or tense up?"

Your body knows things your brain hasn't figured out yet. Neuroscientist Antonio Damasio's research on "somatic markers" finds that our physical responses guide good decisions before our conscious mind catches up.

So, if your shoulders tighten every time you imagine taking that promotion, your body is telling you something. If you feel a sense of relief when you picture leaving your current role, that's data.

Take the test

Close your eyes. Picture yourself 3 months from now, having made Choice A. Notice what happens in your body. Tension? Relief? Excitement? Dread? Then do the same with Choice B.

Your body votes before your brain does. Listen to it.

The Regret Filter (5 minutes)

"If I DON'T do this, will I regret it in 12 months?"

Cornell University research shows we regret inaction far more than action. The job you didn't apply for haunts you longer than the one that didn't work out. The conversation you didn't have eats at you more than the one that went badly.

This question cuts through fear and gets to: What matters enough to risk being uncomfortable?

Apply the Filter

Write down: "In 12 months, I'll regret not [ thing under consideration ]" Fill in the blanks for each option you're considering. The one that makes your chest hurt? That's probably your answer.

Not necessarily because it's the "right" choice. But it is the one you need to test.

The Next “Rightest” Thing (5 minutes)

"What's the smallest step I can take THIS WEEK to test this direction?"

Researchers call this "lowering activation energy" - the smaller the first action, the more likely you'll actually do it.

You don't need to quit your job. You don't need to commit to a new career. You need to take one action that gives you more data so you get clearer about what you actually want.

Some Actions to Consider:

  • Considering a pivot? Schedule 3 informational conversations this week.

  • Thinking about leaving? Update your resume and send it to one trusted contact for feedback.

  • Wondering if you have a skill gap? Take one free course module tonight.

  • Curious about fractional work? Research 2 companies that hire fractional roles in your domain.

Small action → New data → Next decision becomes clearer.

The goal isn't to have all the answers. It’s to get one action-informed data point that makes the next step more clear.

What’s In It For All Of Us

When we give ourselves permission to move without perfect clarity, we model courage for other women while proving to ourselves that "figuring it out as you go" isn't failure - it's strategy in an uncertain world.

We stop hoping for someone else to fix the system, the market, or the circumstances.

We edit our own story. We write a flipping fantastic next chapter.

🆓 And that is our get out of jail card.

Quick favor: forward this email to someone who needs some support to get unstuck. Clarity is a team sport.

Get In There

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What's unclear for you right now?

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Well, you got all the way down here. I hope you got some clarity on how to get clarity. And why action > rumination. Look, it’s hard out here in the world. But taking action is a surefire way to begin to build the tiniest bit of momentum. And that momentum? It comes with a side of clarity.

P.S. If you're a leader who's spent the last 6 months saying, "I'll figure this out once things stabilize," I have news: things might not be stabilizing. But you can.

I'm opening 3 spots for Success Options Planning (SOP) Sprints in November. It’s a 4-week advisory engagement where we map your options, evaluate fit against what actually matters to you, and design your next 90 days with clarity.

This isn't coaching. This isn't therapy. It's strategic decision-making for leaders who are ready to get unstuck, leveraging my strategy and operations expertise.

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