I stay ready so I don't have to get ready
Four patterns I see in the startup leaders that are most successful
A Director of Growth Marketing said something on a call last month that I keep repeating to other people.
“Andrew, I stay ready so I won’t have to get ready.”
She’d just told me she’d taken three interviews in the past month. But she isn’t looking for a new job. She actually likes her current gig. Her CEO likes her. The team’s hitting its numbers. By every measure, things are working.
But she’d been burned once before.
Stayed at a previous company too long, watched the fit slowly disappear, and didn’t see it coming until it had cost her months of momentum and a real chunk of her confidence. Now she stays in motion. Always ready.
If you’ve been a Director, Head of Growth, or VP for more than 18 months, this is probably you. Or it’s about to be.
Most growth leaders think about their career as a ladder. You get promotions and work your way up, one rung at a time. And if you take a step down (say from VP to Director or from managing a big team back to IC), that’s a sign of failure.
The most successful startup leaders view their careers as a sequence of windows.
Periods of time where their specific skill set is a near-perfect match for what a company needs right now. Windows open. They step in. Execute like hell, hit some level of success, and at some point the window starts to close. When it does, they recognize it, and go find the next one.
That frame shift, from ladder to windows, changes how you think about loyalty, timing, and risk. It’s the thing I keep coming back to with every senior growth leader I coach.
I filmed an entire YouTube video going deep on this (it’s embedded below if you want to watch). But here’s the short summary of what the top leaders do better than their peers.
1. Constantly audit the fit.
Fit isn’t whether you like your team or product. It’s a specific question: is my skill set what this company needs right now?
Four components of fit:
Skill-strategy fit. Do they need what you actually have experience doing?
Scope fit. Do they need an IC, a player-coach, or someone to run a big team?
Stage fit. Are they looking for a 0-to-1 builder, someone to optimize an existing growth model, or an innovator to layer in new loops (shoutout to Adam Fishman for this growth profiles framework).
Cultural fit. Do they make decisions by debate, by seniority, by data, or by storytelling, and is that how you operate?
Most leaders evaluate fit when they join. The best ones re-evaluate it on an ongoing basis.
I learned this myself.
I joined a company that needed a player-coach to help them use data to optimize their current growth model. Someone to question how things had always been done and help them break through plateaus. For a while, the fit was nearly perfect for me.
Then a few years later, the executive team changed.
Then the company strategy shifted. The culture moved away from testing and data - toward brand and polish. It was the right call for them but not the right fit for me.
By the time I ran the audit on myself, it was clear my window had already closed.
Things move fast right now. Companies are pivoting quickly. Executive teams are turning over. And markets are changing lightning quick. Those four fits are constantly in flight.
If you’re not paying attention, you’ll miss the moment your window starts closing.
2. Leave the party early.
I never hear really successful growth leaders regret leaving a job/company too soon.
But I hear many regret staying at a company for too long when it’s clearly no longer the right fit.
A client (I’ll call Katie) is a great example of this. She had been extremely successful in the past. Multiple promotions, raises, President’s Club. By every measure, an A-player at her last job.
Then the four fits started to shift.
There was major leadership turnover. Then a new strategy. And new cultural values. But she didn’t know the signs to look out for.
She told herself, “I’ve been an A-player here. I can get back to it.”
It didn’t get better. And it started to affect her confidence. The environment had shifted, and her skill set was suddenly wrong for it. The fit was gone, and she could feel it before she could name it.
That experience is why she now says, “I stay ready so I don’t have to get ready.” She interviews even when she’s not looking. She doesn’t want to be caught flat-footed again.
The leaders who advance fastest move when the early signals show up: a strategy change, a culture drift, a scope reduction. They don’t wait for the breakdown to be obvious to everyone in the building.
3. Never stop being in market.
You’ve heard the surface version of this advice: keep your resume updated, stay active on LinkedIn, network even when you’re happy.
It’s not wrong, but it misses the point.
Another client, “James”, is always in market. He networks constantly, does client work on the side of his full-time gig, and hosts a conference in his space. He had a great job at a well-known tech company. He wasn’t one foot out the door.
He’d already learned what most growth leaders learn the hard way: no fit lasts forever. So he was constantly laying the groundwork for when the window closed.
Recently it did. The company went through major changes. James decided it was no longer the right fit for him and stepped almost seamlessly into scaling a consulting practice. No frantic LinkedIn update. No reaching out to people he hadn’t talked to in two years. The groundwork was already there.
Staying in market is your career 401(k). Small deposits over time, compounding into a real asset. By the time you need it, it’s already there waiting.
4. Don’t figure it out alone.
The question of “am I still in the right place” is almost impossible to answer accurately when you’re in the thick of it.
Is it the company? Is it me? Is this a hard stretch everyone goes through, or a real signal that something has changed?
I had another client recently working under a technical founder who was meddling and micromanaging. I could see it impacting them on our calls. The spark, the energy, the thing that made him really good, had dimmed. He wasn’t pushing as hard. He wasn’t initiating the tough conversations he needed to be having. I don’t think he fully realized it was happening.
A lot of our early work together was just detangling one question: is this a fit problem, or a hard season? Those two things feel identical from the inside.
The leaders who navigate these moments fastest have someone in their corner who can help them see clearly.
That’s the model
Audit the fit constantly. Skill, scope, stage, and culture. All four shift.
Leave the party early. Move on the early signals, not the obvious breakdown.
Stay in market always. Treat it like your career 401(k). Small deposits, compounding.
Don’t figure it out alone. You can’t see clearly from inside the situation.
The full version is in the video below. The four-layer fit audit, the early warning signs Katie missed, the way James thinks about staying in market. It’s the most honest thing I’ve made about how careers actually work at this level.