I’ve published a lot of victories in this newsletter. Today I owe you an honest read from the other column of the ledger.
Not every deal we make in our career is an enthusiastic yes. Sometimes a job is just the thing that pays the mortgage. Yes, even VP roles in the F500.
I’ve sat on the phone with countless clients the day they said yes to a job they didn’t want.
To the untrained ear, they sound excited. But we all know the faux passion voice.
It’s the tone that whispers, “Sure, I got a job. Having a job is good. Don’t press me on it and I won’t have to perform for you.”
You know what I’m talking about. It’s a close sibling to the networking voice.
The faux passion voice is not excitement.
It’s relief.
One of those calls came from a client I’ll call Sam.
His comp package was fine. Below what he wanted, below what the scope deserved, but fine.
The market was cold that quarter and his search had dragged on long enough that savings were becoming a real conversation at home.
“I think I have to take it,” he said.
Notice the construction.
Not I want this. Not this is the move. I have to.
I asked him one question:
If you believed another offer was coming in ninety days, would you sign this one?
The pause answered before he did.
He signed anyway. And I understood why.
But what does that yes cost five years later?
Almost nobody finds out. The Docusign is where the story goes dark—the recruiter moves on, the congratulations fade, and the person who signed stops talking about it.
But I stay in their corner and I see the ongoing decisions and their impact for years after.
The Other Decision
Same season, same cold market, I was working with someone else staring at nearly the same decision.
Let’s call her Jane.
An unenthusiastic VP role at an F500.
Right title. Wrong company. An offer that solved her next twelve months and mortgaged the five years after. And we all knew it.
We treated it as an at-bat anyway—full swings, real prep, every round taken seriously. You don’t sharpen your eye standing outside the batter’s box.
Then the pitch came in low.
She walked.
Not recklessly—we had a read that Sam didn’t have.
Her strongest advocate, a leader she’d built real trust with over years, had just landed at a new company and was still navigating the politics. Feeling around in the dark for the walls, as I call it.
So we waited.
We let her advocate spend two quarters winning ground—earning the standing to make an internal case for a hire like Jane. My job during the wait was simple.
Keep her ready, keep her patient, keep the eye sharp.
Then she joined—six months later than the original plan, into a role shaped specifically with her in mind before she ever interviewed. We earned a sign-on bonus that more than made up for the downtime.
She didn’t walk into a job. She walked into earned air cover.
Nearly five years on and she’s still in the seat.
Her incentive plan runs well into seven figures as she clears her marks. I’ve seen the plan—I helped build the case for it, alongside the same advocate we’d backed through the transition.
And when the company reorged last year and her function landed on the chopping block, Jane wasn’t in the room where her career got decided.
But our advocate was.
That’s not luck. That’s construction.
Where The First Decision Is Now
The deal Sam made in fear only lasted ten months.
The equity that justified the below-scope package—the upside that made “fine” feel survivable—had a twelve-month cliff. He burned out two months short of it.
Wrong company, wrong opportunity, and no amount of gratitude makes a wrong opportunity right. He walked away from the discount deal without ever collecting the discount.
Then came the search he’d signed to avoid.
Eleven months. Not the ninety days he’d feared—eleven months, this time with a ten-month tenure to explain and none of the momentum he’d had the first time around.
The wait he took the deal to escape happened anyway. It just happened later, at a worse price, without leverage.
The next yes came from further underneath.
A VP title at a company a fraction of the previous scale, a step taken to stop the bleeding rather than build anything. Seventeen months, then another exit.
He’s been out of work ever since.
Run the math on the full arc and the number is ugly—the time out of work alone cost millions more than waiting with momentum on his side ever would have.
Every move made his story harder to explain. At some point he stopped shaping it and started running from it.
Today he’s consulting fractionally—not as a strategy, as a landing—and talking about retirement even though the math doesn’t work yet.
And here’s the tell that matters more than the résumé.
Listen to Sam talk about his career now and you’ll hear the market described the way people describe weather. Something that happens to him—fast, indifferent, liable to turn again.
He’s not wrong about the facts—the market is fast and it is indifferent. But he’s wrong about his role in the story.
Somewhere across five years he stopped driving his career and became a passenger. And if you asked, he’d tell you the keys were taken. They weren’t. They were handed over—one fearful yes at a time.
He complains, and the complaints are accurate—but they change nothing.
Accurate and useless is a brutal combination. I’d rather he were wrong.
That’s the real price. Not the delta on the package he signed that day. Rather what the yes trained. And not just in him—the market was taking notes too.
Playing Small, A Rehearsal
Here’s the pattern I keep seeing.
When you accept an offer out of fear, the fear stops. Immediately.
The dread that’s been sitting on your chest for months lifts the moment you sign, and your body files the lesson away. The shrinking worked.
Taking less made the pain stop.
So the next time you reach a decision point, the reflex is already installed. You don’t deliberate your way to the smaller ask. You arrive there.
The retreat happens before the thinking starts, and it feels like prudence, because that’s what a well-rehearsed retreat always feels like.
And you’re not the only one learning.
Every fearful yes teaches the market something too—what you’ll accept, how fast you’ll fold, what your signature costs under pressure. The recruiters compare notes.
You rehearsed. They watched. You fed the zombie.
Sam rehearsed retreat three times in five years. Jane rehearsed patience once and has been collecting on it ever since.
This Is Not A Verdict
Now the part I need you to hear. Truthfully, I need to hear it again and again myself.
I’m not judging Sam. I’ve made his exact call at least ten times in my own career—signed the thing, felt the relief, told myself it was the smart move.
And even now, with all the deals behind me, I catch the hedge running in my own head. Who am I to have this much confidence that better will come along?
Because I’m not aiming small.
I want the seat across from Bartlett and Rogan. I want Predetermined on the NYT list, the movie, the foundation.
I want a movement—not a newsletter.
And the hedge has an answer for every one of them. Who are you to want that?
The audacity of it all.
The hedge doesn’t check your résumé. It ran when I had nothing, and it runs louder the bigger the ask. The only thing that changed is that I stopped letting it draft my answers.
I see the reflex in others because I live with it myself.
Everything I write lives under one question—was the outcome predetermined before you walked in?
Theirs wasn’t. Neither is yours.
The spiral doesn’t need to be permanent.
It’s a script—and a script only runs when you choose to read the next line.
Every offer is a fresh decision point, which means every offer is a chance to break rehearsal. The pattern has momentum, not authority.
The interruption is available at exactly one moment—the next time you hear yourself say—
I have to.
That sentence is the alarm.
When it goes off, stop and ask the question I asked Sam. If you believed another offer was coming in ninety days, would you sign this one?
If the answer is I’d sign it anyway—sign it and go build. The deal is sound and the fear is just noise.
If the answer is I’d wait—then you’re not evaluating an offer. You’re medicating a feeling.
And there are cheaper medications than five years of your career.
The Correction
If you found your own story between these lines, the fix doesn’t start with a better résumé or a sharper script.
It starts earlier than that—with an honest look at who is narrating your career.
Is it you—or them?
Start with the people around you and build what Jane had.
Not just “go network more”—the short list of your people.
Five or six specific people who have watched you deliver and would put their own reputation behind you.
Know where each of them works, where they’re headed next, and which of them wants to pull you into a role rather than just forward your résumé. When one of them changes companies, pay attention. And stay useful to them too—this only works if it runs both ways.
And one honest consideration. Sometimes the bridge job is the right call.
If the yes buys oxygen for your family, take the oxygen, and don’t let anyone shame you for breathing.
Just know your numbers and know your exit before you sign.
Do that and the fearful yes becomes a tactical one. The difference isn’t the signature. It’s whether you’re still the author.
The Invoice
Two people. Same market, same season, nearly the same decision.
One bought relief and has been paying for it ever since.
The other waited six months and earned a seat she still holds—next to someone who protects it.
The offer you take out of fear is never priced in dollars. It’s priced in who you have to become to keep taking offers like it.
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Stay fearless, friends.