After 30+ years in public education, most people would have expected me to coast into retirement, maybe consult a little, travel a lot, and finally breathe easy.
And to be fair, that was the plan.
But at 55, I did something that surprised even me.
I left my job as Director of Technology for a New York school district and stepped into the fast-moving, high-stakes world of cybersecurity, as the head of U.S. market development for a small, agile Irish firm.
It was exciting. It still is.
But let me tell you: the shift has been anything but smooth.
No More Biweekly Paychecks and Payroll Comfort
For over three decades, I was part of a system that just worked.
Every two weeks, money arrived.
Taxes? Taken care of.
Medical? Covered.
Dental? Check.
Retirement contributions? Handled.
Social Security? Withheld.
I never had to think about it. The system took care of me.
Then came my “new normal.”
Becoming a Business Owner… Out of Necessity
Since I was now working with a company based in Ireland, I couldn’t just hop on their payroll.
To get paid, I had to form an S Corporation.
So instead of just submitting a W-4, I was suddenly:
Creating a company
Opening business checking accounts
Registering for an EIN
Hiring an accountant
Learning about international wire transfers (and the painful fees that come with them)
Filing quarterly taxes instead of having them automatically withheld
Every dollar I made required me to be the middleman between the company and the IRS.
Taxes and Healthcare Hit Different on the Outside
Here’s something no one really prepares you for:
When you’re self-employed, you pay both sides of payroll taxes.
That’s 15.3% for Social Security and Medicare, all on you.
Previously, my employer covered half of that. Now? It’s just me, myself, and the IRS.
Medical and dental insurance?
Now I pay those every six months, after taxes.
No employer subsidy. No automatic deductions. Just another massive expense I have to plan for.
Household Financial Whiplash
After decades of stable income, we had built a life around predictability.
You don’t realize how comforting that biweekly paycheck is until it stops.
Suddenly, cash flow became real. Planning became critical. And so did compromise.
Our household had to adjust. My pension helps, sure, but it’s modest.
And the earnings from this new role don’t arrive like clockwork. I invoice. I wait. I eat wire fees. I plan for taxes before I ever touch the income.
The Emotional Cost of Reinvention
There’s a kind of safety you feel in the public sector.
And there’s a real sense of vulnerability that comes with leaving it.
It’s not just the systems and routines, it’s the identity shift.
I went from being a known quantity with a clearly defined role and a trusted reputation in a district to being “the new U.S. guy” in a company that runs like a startup, learning the ropes of SaaS sales and B2B marketing.
I’m not just the new guy.
I’m somehow also the old guy.
It’s thrilling. But it’s humbling, too.
Why I Did It Anyway
Because growth doesn’t stop at 55.
Because cybersecurity excites me, and I believe in what we’re building.
Because helping schools and businesses better protect and manage their data, and providing solutions for significant pain points for system admins, is still service, just in a different form.
And because I wasn’t ready to stop learning.
If You’re Thinking of Making the Leap…
Know this: it’s hard.
But it’s also worth it.
Just go in with your eyes wide open.
Set up your S Corp before you land the gig
Find a great accountant
Brace for taxes
Rethink your cash flow
And give yourself grace. Reinvention isn’t linear.
This is just the beginning of Shifting Gears at 55.
I’ll be sharing more about the journey, what’s working, what’s not, and what I wish someone had told me sooner.
If you’re in the middle of your own pivot, or thinking about one, I’d love to hear from you.