Experimenting in the Messy Middle
Ask my mom, and she will tell you: one of my toxic traits is staying way too long in relationships and situations that no longer serve me.
And I know I’m not alone in that.
Sometimes, when we’re in a relationship, a work environment, or even a volunteer role, it feels impossible to budge. We’ve made a commitment. We’re not the type to go back on our word.
So we stay.
We try to rationalize things as they are. We tell ourselves clarity will come if we just put in a little more time, a little more effort, a little more patience.
But what if the thing keeping you stuck… is where you’re starting?
Because I see this same pattern show up all the time in career transitions.
Most of my clients are in some kind of transition. Some have been laid off and are trying to find their footing again. Others are still employed, but know they’re ready for something bigger—and aren’t quite sure what that is yet.
And some aren’t actively trying to leave at all—they just know they’re not exactly happy where they are.
Different situations, same pattern.
When they’re looking for clarity, they try to figure out the right path upfront.
They think it through. Map it out. Try to make the smart move.
And that instinct—to keep analyzing, to keep adding options to the roster—is exactly what keeps them stuck.
People start by looking outward—job boards, résumés, applications.
More effort. More scrolling. More tweaking.
And when that doesn’t work, they assume they need to try harder.
When in reality, the shift usually needs to happen in the opposite direction.
Inward.
That’s where these questions come in—the ones I come back to with clients in that “in between” space:
What do I actually want? (Not what I should want. Not what looks good on paper.)
Who do I find myself envying—and what is that really telling me?
How much of my identity is tied to my work?
What habits, stories, or mindsets am I carrying that no longer serve me?
What does work/life integration look like for me—not just in theory?
These aren’t questions you sit down and solve in one go.
Some will hit right away. Others take time.
The point isn’t to force clarity—it’s to notice what comes up without judgment.
Because that’s where the signal is.
And this is usually where people slip back into overthinking.
But clarity doesn’t come from thinking harder. It comes from testing, trying, experiencing.
So instead of asking, “What’s the right next move?” try this:
What’s one small experiment I could run to learn more about this?
Not a full life overhaul. Not a perfectly mapped plan.
Just something that gives you data.
Because that messy, unclear middle phase?
It’s not a failure. It’s part of the process.
You’re not supposed to have it all figured out yet!
And one more thing—because this part matters more than people realize: Transitions are emotional. They’re ambiguous. Which means your decision-making gets a little… distorted.
So if things feel unclear right now, don’t rush to fix it.
Get curious instead.
Try something. Have a conversation with someone who intrigues you. Notice what you learn. Get uncomfortable. Adjust from there.
That’s how you move forward.
And if you’re in that in-between and want help making sense of it—this is exactly the work we can tackle together.
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Productive procrastination? I think not.
Spring is here, hiring is about to shift, and here’s what you need to know as we move into April.
Want more meaningful connections? With LinkedIn, you go broad. IRL, you go deeper. One place to try? A focused local community.
As a résumé writer, the question I'm most often asked by friends is, “Will you take a quick peek at my résumé and give me some feedback?”
Why yes, I'd love to! And I've done you one better...
As hiring shifts, it may be time to refresh that stale résumé. I’ve got you covered (and you don’t have to spend a dime!).
Beyond the Office
You know that friend who makes you love something just because they love it so much? Well, I’m not usually a movie gal, but this year I saw most of the Academy Award nominees because of one such buddy and was thrilled with One Battle After Another’s Best Picture win (though I was quietly rooting for Sinners). Both can be streamed now on HBO Max.
It was sweltering in San Francisco the past couple of weeks, and this burrito bowl got me in and out of the kitchen and fed in 5 minutes flat. I added some chili lime chicken from Trader Joe’s and a little shredded cheddar on top—perfect, easy dish to share with my book club.
Speaking of books, need your next read? I was completely captivated by Charlotte McConaghy’s newest novel, Wild Dark Shore. I listened to the audiobook—narrated by a full cast—which made it feel more like an experience than just a story. It quickly became my favorite companion on long walks this past week.
If you’ve been waiting to feel 100% certain before making a move, consider this your permission slip to start investigating now.
Clarity doesn’t come first. It follows action.
Try one small thing this week. See what you learn.
Work with me 1:1 → Step into a focused alignment experience to clarify your direction and intentionally reposition your leadership. I’m currently scheduling for April and have 1 spot left!
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