I helped build the office that laid me off. Here's what I learned.

I got laid off for the first time early in my career.

Not because of my performance. Not because of anything I did wrong.

A private equity firm had acquired the company, decided engineering was the biggest line item on the cost sheet, and cut two thirds of the team in a single day. Just like that. Gone.

It was a gut punch. My first real job in the industry, my first time back out in the market, and a crash course in something nobody teaches you: the decision to keep your job is not always yours to make.

Four months later, my old Engineering VP called. He wanted me back. By then I had landed at iHeart Media, was one the last engineer standing on a massive new initiative tied to a $70M contract.

Most of the original team had already moved on (TLDR - toxic people, toxic work environment - luckily the toxic people also moved on). I used the offer from my previous employer to negotiate a 15% salary increase and stayed at iHeart to help them build their HD Radio system.

The second layoff hit differently. And the reason it hit differently has a detail I don't think I've fully told before.

I joined a small cybersecurity startup. Good role, good team, felt like real momentum. One month in, they announced a remote engineering office in Cluj-Napoca, Romania. Two months in, a colleague and I were on a plane to Bucharest.

Two weeks. Evaluated the office, met the engineers, assessed how the operation was being built. Filed our reports. The office looked capable. The engineers were solid. We said so. Then went back to work.

For the next sixteen months, I kept building. Nobody said anything that made me think the trajectory was pointing in any particular direction. No slow-burn dread, no reading between the lines of all-hands meetings. We were just working.

And then the calendar invite showed up.

They laid off the entire local team. I was the one exception — not because I was safe, but because my product line hadn't transferred to Romania yet. They needed me for two more months to hand it off. I had a guaranteed runway, a specific end date, and an engineer in Cluj-Napoca waiting to receive everything I'd built.

Going out on my own felt like the fix. And in one way it was: I doubled my income almost immediately. The gross numbers looked like I had finally figured something out.

Then I took a vacation.

Every day off was a direct financial loss. Not just not earning. Actively falling behind on the math I had built the whole thing around. The mental tax never stopped — client work, pipeline, business development, invoicing, the constant background hum of is the next engagement lined up, is this client happy enough, what happens if this contract doesn't renew.

Evenings. Weekends. Every hour I was supposed to be off.

I eventually made a decision that confused everyone who heard it: I went back to a full-time W2 role at a 20% pay cut. My effective hourly rate actually went up, because the hours I wasn't working were now actually mine again.

Vacations felt like vacation again, because the hours were already factored into my salary. I went from the thought of losing hours to vacations, to now making sure I took all my vacation days so I didn’t lose them at the end of the year. The mental calculus had flipped in my favor.

I have dabbled in real-estate here and there with some success and a lot of lessons learned. I won't go deep on this today — that's the full story for next issue, because the decisions I made then are directly connected to the path I'm on now and why I'm not going back.

The short version: I owned 2 rental properties, remotely managed. Multiple tenants moved out at the same time. Unfortunately, mortgages don't pause when your tenant moves out. Financial pressure hit all at once and I made an emotional decision to sell everything. Then came the surprising tax bill.

While I had figured in capital gains taxes on the properties, I didn’t realize that most of the gains would be taxed as recaptured depreciation. This meant a $15k jump in my tax bill, which wiped out a huge chunk of the proceeds from the sales.

At the time of sale, I walked away from what would have been $500 a month cashflow, from raising rents to market rates (both properties had long-term tenants and I had not been raising rents fast enough to keep up with the market). With where rents have gone in the 8 years since, those same rentals would be throwing off close to $1,500 a month today. I'm kicking myself for selling them.

More on all of this next week — including why I'm making a conscious decision not to go back to REI right now, and what I'm pursuing instead.

I have spent 25+ years designing systems with redundancy, failover, and disaster recovery plans built in. It took 2 layoffs, a consulting stint, and a painful real estate exit to notice I had never built any of that for my own income.

That's what Career DR Plan is. The newsletter I wish had existed when I was sitting with a calendar invite and a 2-month runway.

A 25-year engineer working the problem in public, sharing what he finds.

I built a Career Insurance Calculator to answer the question that started all of this: if your W2 disappeared tomorrow, how long could you actually survive — and what would you need to replace it?

4 minutes. It'll give you your real runway, your actual Freedom Number, and a first read on which path — buy, build, or hybrid — fits your capital and timeline. Free. No pitch at the end.

Run the numbers. If you want to talk through what you find, reply here.

More next week — including the full REI story and where I'm actually putting my energy instead.

Thanks for following the journey

Charles