Your Job Is a Single Point of Failure [Field Notes #8]
The 'safe' plan can be blown up tomorrow
The employees I lose sleep over aren’t the ones who are upset when the layoff call comes.
They’re the ones who never saw it coming.
Never considered they could be at risk.
And are now being walked through a severance package with HR.
When I’m in these calls (my part over, having delivered the bad news), while the HR Business Partner delivers their script, I watch the eyes of the soon-to-be-former employees. Most are glazed over, thousand-yard stares. They look like fighters who just ate a vicious right hook and don’t remember they’re in the ring.
The disbelief makes it impossible to ground what’s happening in reality. And in that moment, we both share in the knowledge of a terrible truth:
When the severance money runs out, they have nothing else to fall back on.
Savings will be drained. Retirement accounts will be pilfered. If it goes on too long, uncomfortable conversations about loans from banks or family will be the last resort.
I’ve been in the tech sector for most of my 17-year career. I started supporting IT in banking, and saw the mass layoffs during the financial crisis of 2008-2009 (Welcome to recruiting, kid). My boss’s words of encouragement: if you can recruit in this market, you can recruit in any market.
Since 2022, tech company after tech company has been cutting its workforce with a scythe instead of a scalpel. We see the big companies trim 10-20% - tens of thousands of people. Whole functions get wiped out. My field, Recruiting, has been decimated. Since 2023, teams have been systematically reduced by 60-75%. Two in five survive the hit squad, doomed to overwork and told to be grateful they still had a job (and, despite the overwork and exhaustion, they were).
The rest? Severance. Unemployment. Disorientation. Fear.
With nothing of their own to fall back on, it’s like being shoved out of an airplane without a parachute.
And that ground comes up at you fast.
Seniority Feels Like a Shield. It’s a Red Flag (and a Highlighted Cell in a Spreadsheet)
Most senior candidates I work with operate under certain assumptions:
Longevity means security. They’ve been there been there long enough that their knowledge would be difficult to replace.
Performance means protection.
Titles mean leverage. Senior leaders assume they’ll be involved in the RIF (reduction in force) planning calls.
This is wishful thinking. As we’ve seen with regularity in the layoff news on the LinkedIn sidebar, nobody is safe.
While these people may be valuable to our organizations, when hard choices need to be made for the sake of the business, they are made. It leaves surprised leaders looking for something new.
And from the headhunter seat, when these long-tenured Sr. Directors and VPs hit the market, it’s a different picture entirely.
These candidates are expensive, context-specific, and increasingly ineligible outside the environment they’ve built themselves inside.
The longer the tenure, the more the specialization, and specialization in one environment can be disqualification in another.
Working in scaling tech start-ups for the last 8 years, I see it all the time. Leaders come out of large, structured environments (think Oracle, Salesforce, Workday) and come into a place where you hear the word “scrappy” every day. They get killed in resource-constrained environments.
The flip side also applies - people who are used to moving in nimble, fast-paced organizations collapse under the weight of bureaucracy and unfamiliar corporate politics.
This corporate trap isn’t visible from inside the system. That’s what makes it a trap.
And when it snaps closed, the rebound is very different from what these leaders expect.
There Are Two Default Paths. Neither is Ideal.
There are two default paths people take from here. Neither is setting them up for long-term success.
The first path is finding the next version of the same (or similar) job at a different company. Most people take this path. It’s “the thing to do.”
The second path is what I call “the lottery ticket.” It’s the passion project, the side interest, something that carries the emotional weight of a plan (if not the architecture of one).
It’s the bolder approach, but it’s flawed. Building when you’re out of work, when you need this thing to work, is the worst place to build from. While there are benefits from operating under strategic stress, it’s difficult to classify this stress “strategic” when it arrives unplanned and results in doom-checking a dwindling bank account.
I know this from experience. At my last organization, I was the surprised VP.
From late 2022 to the end of 2023, I oversaw 3 rounds of layoffs on my team. The first cut was the deepest, reducing the team by roughly 40%. The next was the most difficult, cutting a good chunk of the people “I couldn’t live without.” The third was pruning: “right-sizing” for our anticipated 2024 hiring plan.
I had more visibility than anyone at the table into how exposed we all were. But I suffered from the high-performer paradox: in my mind, my track record was evidence against the risk. The story of “it happened to others who weren’t as good/valuable/essential as I am” holds water until it doesn’t.
So when I got the “Can you talk? It’s important” text on a Sunday afternoon three weeks before Christmas, I was caught off guard.
Though, in hindsight, I wasn’t actually surprised. The writing had been on the wall. I had just blown past it, the same way you don’t think about your daily commute or don’t register the mural on the building down the street.
After processing the news, I went down both default paths. I started looking for another corporate gig, and I dove head-first into my lottery ticket—a post-apocalyptic fiction novel. I didn’t have enough runway to become a full-time novelist, but my thinking was, if I could finish and sell the book later that year, whatever corporate job I had to take would be temporary.
It was the equivalent of sitting on the edge of my couch, waiting for the Powerball numbers.
The second path is too unstable to build a future on. The first path sets you up to be in a similar situation in the next 18-48 months.
Even combined, there’s not enough there to guarantee future security.
What the Market Actually Looks Like When a VP Hits It
What’s worse: when the inevitable happens, these leaders don’t have the cushion they thought they had.
A VP from the last generation bought a house for a reasonable amount, had semi-affordable daycare and education costs (or could survive on one parent’s salary), and pensions. Nowadays, VPs in their 30s and 40s graduated in recessions and lived through multiple catastrophic market downturns, a global pandemic, housing costs that made equity harder to build, and daycare costs that now rival mortgage payments.
The result? Less padding.
Now, these people find themselves on the market with a shorter runway for a search that can take 6-12 months. At such great corporate heights, there are fewer roles available.
And what’s worse, the jobs they’re looking for are invisible.
Key senior leadership jobs don’t get posted to LinkedIn (or if they do, they get 1200 applicants in 36 hours - good luck standing out).
In reality, Sr. Director, VP, and SVP roles usually get filled one of two ways:
An internal promotion for a subordinate leader. (This is how I ended up in my current position).
A confidential search to replace someone who hasn’t even vacated the seat yet. They fill the job before it’s even officially open. (This is how I’ve secured my last two external offers).
The advice that everyone hates to hear is true: it’s all about who you know.
But if you’re an entrenched VP with a track-record of success, how aggressively have you been networking? The honest answer is usually, “Not enough.” And now that you need your network, it’s gone cold.
So you’re burning cash, looking for jobs that you can’t see, begging people you haven’t talked to in years for a 15-minute “catch-up call.”
It’s not pretty.
Priming The Pump: 3 Steps You Can Take Today
1. Networking Before You Need It
Start a daily practice of adding a few people to your network. This is easier than it sounds. Here’s a simple protocol to follow:
Go on LinkedIn and search for people at your level, one level above, and one level below. For example, if you’re a VP, you look for VPs, SVPs, and Sr. Directors.
Find 3-5 people who have interesting backgrounds, similar experiences, or just look like the kind of person you’d want to have coffee with.
Send a connection request with a simple, straightforward note. Here’s one I’ve used for years that has a 60-70% acceptance rate: “Hey NAME, I’m a fellow TA leader. Thought it’d be good to connect in case we can help each other down the road. - Mike.”
Once connected, DO NOT ASK FOR ANYTHING. Nobody likes to be pitch slapped by a new connection (no, I don’t have 15 minutes to connect and no, I don’t give a shit about the product you’re trying to demo). Just say thanks for connecting and leave it at that (unless they start a conversation).
Do the low-cost / high-ROI stuff from there. If they post interesting content, like and comment. That way they see your name more frequently than other random connections. Share articles, posts, or podcasts that you found valuable - chances are, they will, too.
TL;DR: connect with peers, don’t ask for anything, add value. If you haven’t done the typical cringe stuff, people are more receptive to a genuine note when you actually need something.
2. Calculate the Runway Number
This takes 20 minutes and will give you instant clarity. Tally monthly expenses. Look at liquid savings (not retirement, not equity). Know your monthly run rate and where you would be pulling your money from.
Worst case, with no severance: how long until you’re pulling from accounts you don’t want to touch, or making decisions under real financial pressure?
Get to the real number. If you don’t like the result, the answer is boring: increase the savings rate.
The runway number tells you how much time you actually have to build before pressure starts distorting every decision you make.
The world isn’t getting any less volatile. Knowing your number is critical.
3. What Could You Build For Yourself Right Now?
Lottery tickets aside, what’s the side business you could start building right now? The most risk-averse people are missing their greatest opportunity (and the proof that they can do it): if you’ve made it to this level of your career, you have value independent from an employer.
What are people already coming to you for? Not your function, your specific judgment. The situation reads, the calls nobody else on the team makes, the takes nobody else on the team has, the things you’re getting texts about while sitting on the all-hands meeting. If you’re already doing something for free, that’s usually a decent signal.
I wrote about a simple exercise to start thinking like this in Field Notes #7: The Safety Trap - you can check it out here.
It changes the whole dynamic of the layoff conversation when you have something on the side. You’re thinking more clearly. There’s less panic. You aren’t questioning your value - because you’ve already built something valuable in your off-hours.
You need to start today. Because every year you’re not building something that can’t be taken from you by your employer, your window narrows. Opportunities evaporate. Potential partners start working with someone else.
In upcoming newsletters, we’ll go deeper into the mechanics of building something while you’re still employed. But for now, these are a few ways to prepare yourself for the thing that takes many great leaders by surprise.