The Safety Trap [Field Notes #7]
The hidden dangers of following the 'safe' path
Stop me if you’ve heard this story before.
Four years ago, I was promoted to VP of Talent Acquisition. This was the culmination of the career path I had been chasing. I remember the day — the Zoom call with my boss, her telling me she was really proud that I had worked hard and put myself in a position to be here. My face must have been blank, because she even stopped to tell me, “You skipped AVP entirely to get to VP. That doesn’t usually happen.” (I know she was a big part of why that happened, and thanked her in the moment).
If I could have shown twenty-two-year-old Mike that moment, knowing that he was on the Senior Leadership Team and running a department that would soon scale to nearly sixty people, he would have been fucking thrilled.
And for a week, I was fired up. New title. Hearty congratulations, “well deserved,” and “you’re gonna crush it!” from my colleagues and friends. My team was pumped for me. I think my wife let out a sigh of relief, knowing that I had achieved the milestone I had been going after for a while, and maybe now I’d take a breather.
A week later didn’t have the same momentum. Just kind of... the same. New title in the system, new signature in the email. Everything else was static.
The next week, I was in a new meeting I hadn’t been a part of before. But other than an increase in cold outreach from vendors on LinkedIn (“Congratulations on the recent promotion! Here’s my product. Can you connect on Tuesday for a 15-minute call?”), nothing really changed.
It wasn’t until the third week that I really looked at things and went: Oh, shit.
I’ve been on this conveyor belt chasing this thing.
I finally got it. I should be elated.
And I don’t feel anything at all.
The Map We’re All Handed
The progression we all get handed looks like this: get good grades, go to a good school, get a good job, get promoted, add some letters to the end of the name (MBA, PhD, CISSP, LMNOP), get more titles, get a higher salary, add more accolades.
Each one just kind of leads to the next. Nobody really tells you where it ends. So we all just plod on with the same approach: keep climbing until we retire (or die).
And then it happens. The moment when we look up from the race we’ve been running and wonder why we’re still on the track. More importantly, didn’t we want to play basketball? Why the hell are we outside, sweating in short shorts and a pair of Asics?
So we look on the horizon for the next thing. We pick a new target. We move our own goalposts and tell ourselves that happiness is just over the next ridge.
That’s the wrong read on what’s actually happening.
What you’re feeling is real. It’s the diagnosis that’s off.
The problem isn’t the job, it’s the game. And a new job playing the same game won’t fix anything.
The Dead Zone
While you’re in the midst of existential contemplation, there’s something silently happening at this stage of your career that few people talk about. I call it the Dead Zone.
In the early phase of your career, the math works in your favor. Companies are paying you less than you’re worth, and you’re willing to work more than you will later, when you have different obligations and different commitments. High output, lower cost. You’re competitive everywhere. If you have a reputation for being good, you’re in high demand.
Then you hit Director, Senior Director, VP — and the equation inverts in three directions at once.
Your specialization works against you. What makes you successful in one environment disqualifies you for others. Leaders who work for the Oracles and Workdays of the world get killed when they step down to a resource-constrained company of 1,500 employees. Working in a scaling start-up doesn’t prepare you for the bureaucratic drag of working for a company the size of a small city.
You’re not differentiated enough to command a C-suite placement. You’ve been managing systems, not building a track record that reads at that level.
The market won’t let you go backward. And even if you’re willing to step down to survive, the market won’t let you. You’re too expensive to be a doer. Every company that sees your title assumes you’re overqualified and will leave the moment something better shows up. And they’re not entirely wrong — because you’ve also been out of the trenches long enough that the execution skills have atrophied.
So you can’t go up. You can’t go sideways. And going down is harder than it sounds.
I’ve led these layoff conversations half a dozen times, and I’ve been on the receiving end of the news, too. When they happen at this level, the recovery is not what people expect. They have no idea how much the deck is stacked against them:
There are far fewer Director and VP jobs than there are qualified people competing for them.
Nobody is promoted into the C-Suite from the unemployment line; their only shot is to start somewhere new at the VP+ level and start building again.
Title definitions are inconsistent across companies and industries — a VP at one company is a Senior Manager somewhere else, and the job boards don’t reconcile the gap.
And when a company does hire at your level, they’re hiring for a niche: they want someone who’s done exactly that job in exactly their industry. Coming out of SaaS into construction isn’t a pivot; it’s a disqualification.
When you fall at this level, the landing is harder, and the climb back is longer than at any other point in your career.
The trap isn’t visible from inside the system. That’s what makes it a trap.
Oh, I just got promoted. I got more money. I have more responsibilities. Things are good.
But from my seat as a headhunter, it’s super visible. Your organization’s grip on you is tightening…right up until the moment they drop you for cost savings or the need to “head in a new direction.”
Every year you go through this without building something that’s yours, that window narrows further.
Band-Aid on Cancer
Even if we’re successful at sidestepping the RIFs, layoffs, and fallout from leadership changes, our built-in reaction to uncertainty is a default setting: something feels wrong, so I'd better go find something else. Update the resume, tighten up the LinkedIn, start networking.
It’s a band-aid on cancer.
Sometimes, it helps. Bad boss? Maybe changing jobs will help.
Significantly underpaid? Sure, you could raise your market value elsewhere.
Genuine growth on the other side? There might be. But is it better the devil you know, or the devil you don’t?
And I’ve seen what happens when the knee-jerk reaction doesn’t work. You go through eight, nine, ten interview cycles throughout a year. You get some offers. And you end up turning them down for vague reasons. You can’t even articulate why they’re not right.
That’s when frustration descends into hopelessness.
You tried to leave. You can’t. You’re trapped.
Optionality, Not Escape
Here’s what I want to be really clear about, because this is where most people get it wrong:
When you’re building something of your own—something that can’t be taken by an unexpected 1:1 that HR joins—you’re not building an escape. You’re building a negotiating position.
Across 10,000 interviews with Director-to-VP and C-level candidates, I could always tell when someone had something else going for them.
It wasn’t what they said, but what they didn’t do. They didn’t chase. They didn’t oversell their skills. They turned down offers that weren’t a slam dunk, and they could tell you exactly why. These are the players who had real estate investments generating income, or an app doing real revenue, or a consulting practice on the side. When you’re negotiating with someone with that kind of leverage, the standard levers (more money, more equity, a sign-on bonus) don’t move them.
I’m experiencing it firsthand right now. The idea for my 2nd Act first popped into my head a year ago. I got serious about building it over the last 4-5 months. It became a reality last month.
And now, when I take calls, my negotiating position is entirely different. The bar a company would have to hit to pull me away from what I’m doing is higher than it’s ever been. Never say never, but I honestly think I’m impossible to recruit right now.
The job is still the runway — the paycheck, the health insurance, the stability. When we don’t have options, we see it as a cage. But it’s your fuel. You can spend that time running interview cycles for the next version of the same thing, or you can use that runway to build something nobody can take from you.
I have three kids that are six and under. I have realistically ten to twelve hours a week — and that’s giving up sleep. I’ve got a mortgage. I’ve got a full-time global Senior Director job.
The build is happening anyway.
It’s hard. At times, it’s fucking brutal. But I’ve seen (and experienced) the downside of not building, and I’m not willing to live with that anymore.
That’s what the 2nd Act Launchpad is about. Building something that’s yours, using skills companies are already paying you for, without destroying your first act to fund the second one.
You Can See This Before the Floor Falls Out
The slow drip doesn’t require a layoff to be real. You can see this trap before it closes.
Your first step is both zero risk and mind-expanding.
Get a notebook and start a list: what problems are you already qualified to solve? Where do you have deep expertise? It could be your current job. It could be an element of your current job that you’re particularly good at. What advice do your friends come to you for? What work do your colleagues come to you for help with?
These are starting points. Sit alone, set a timer for 15 minutes, and start writing. Start with your job title if you have nowhere else to begin. You’ll be shocked at how much is on the page by the time the timer goes off.
That list is not a business plan. It’s not a commitment. It’s the raw material that everything else gets built from — and it costs you nothing to make it.