Work Harder Now for a Comfortable Retirement Later
Last spring my wife looked up from her coffee and said the ten words every DOE lifer dreams of hearing: "You know, honey, you could actually retire whenever you want."
I nearly dropped my bagel.
Thirty-plus years in the New York City Department of Education, and it all came down to this- a quiet kitchen moment and years of thoughtful family financial planning. I didn't win the lottery. I didn't inherit a brownstone in Park Slope from a long-lost aunt. I just did a handful of unsexy, unglamorous things that my future self is now thanking me for.
If you're reading this on your lunch break, half a sandwich in one hand and your phone in the other, I want you to walk back into your job this afternoon a little richer in strategy- and eventually, in the bank.
The Myth of the Victory Lap
Let's get this out of the way: everyone- and I mean everyone- wants to coast during their final year. You've earned it, right? Thirty years of fire drills, chancellor's regs, contract negotiations, and that one copier that's been "getting serviced" since the Giuliani administration. Of course you want to glide into the sunset with a travel mug and a countdown calendar taped to your desk.
Here's the plot twist nobody tells you at your retirement seminar: your final years shouldn't be your slowest. They should be your busiest.
I know. I hate it too. But hear me out.
The Per Session Play (Or: Why I Missed the First Ten Minutes of Jeopardy for Five Years Straight)
In the DOE, overtime is called per session, and it is pensionable income. Most pensions are calculated on the final average salary (typically the last three to five years), which means every extra dollar you earn in those years quietly multiplies itself for the rest of your life.
Let that sink in. A per session gig you pick up at 52 doesn't just pay you once- it pays you every month until the day you die.
So for the last five years of my career, I said yes. Yes to Saturday Academy. Yes to extra parent outreach. Yes to the after-school chess club I couldn't spell "en passant" for. I walked in the door most nights during Final Jeopardy when my kids had already eaten. But I kept reminding myself: I'm not working for present me. I'm working for future me and the future of my family.
Here's the part nobody says out loud, though:
You don't land per session in your final years by asking in your final years.
You land it because for twenty years before that, you were the person who:
Showed up on time. Every time. Reputation compounds faster than a Roth IRA.
Said yes to the small stuff early. The book fair. The graduation committee. The parent workshop nobody wanted to run. Administrators remember.
Followed through. If you said you'd do it, you did it- and you did it well. "Dependable" is the most underrated word in a supervisor's vocabulary.
Built real relationships, not transactional ones. Ask about the assistant principal's kid. Remember the custodian's birthday. Bring the good coffee to the office manager who runs the per session sign-up sheet. (Especially her.)
Kept your integrity clean. One shortcut, one weird timesheet, one email you shouldn't have sent — and doors quietly close. You'll never even hear them click.
By the time I needed those hours, I didn't have to hustle for them. They found me. That's not luck. That's twenty years of deposits into an account nobody can see but everybody feels.
Back in the 1900s, My Mom Gave Me Some Advice
I started teaching in the early '90s when my "starting salary" felt more like "structured poverty with a pension attached." I ate rice and wore ties from a discount bin on Delancey.
And my mom, a teacher who taught for 30 years, said: "Put something in your TDA. Today. Right now. Even if it's small."
The TDA (Tax-Deferred Annuity) is one of the best-kept secrets in public education. Pre-tax dollars, compounding quietly in the background, with a guaranteed fixed-return option that has, historically, made Wall Street envious.
I told her I couldn't afford it. She looked at me the way only a mother and a veteran teacher can- a look that said, "You can't afford not to."
So I started small and gradually increased contributions up before I ever saw the money hit my paycheck. And here's the mysterious, almost mystical truth of it: you don't miss what never lands in your checking account to begin with.
By the time I was in my forties, I was maxing out. And I promise you- I didn't feel poor along the way. I just felt normal. Because normal, calibrated correctly, is a superpower.
Strategies for the New Kids (You Know Who You Are)
If you're in your twenties or thirties- this section is for you. The cost of a MetroCard, a lease, a coffee, and a life in this city has gone vertical. I get it. But here's the truth: the earlier you start, the less you have to sacrifice later.
Some pragmatic moves:
Start your TDA (or whatever investment opportunities your organization offers) this pay period. Not next month. This one. Even 2% is a beginning. Momentum matters more than magnitude at the start.
Automate every raise. Every step, every differential, every longevity bump- send half of it to your TDA before it ever touches your budget. Lifestyle creep is the quiet thief of retirements.
Do the coffee math. That $5 iced oat milk situation? Invested and compounded over 30 years, it becomes roughly $50 in your future account. So the real question isn't "Do I want a $5 coffee?" It's "Do I want to pay $50 for this iced coffee?" Sometimes the answer is genuinely yes. But now you're deciding, not defaulting.
Pick up a strategic side hustle. I have a friend (a sharp assistant principal) who tutors SAT prep on Saturdays for the sole purpose of maxing her retirement contributions. Leveraging your skills for a temporary side job that funds a permanent retirement contribution is one of the best trades you'll ever make.
Know your company's retirement guidelines. Even if it was formatted in WordPerfect in 1996, understanding your requirements, your vesting, and your final average salary formula is worth an afternoon of your life.
Meet with a financial specialist (many companies offer retirement or pension consultations for free). It's confidential. They will not judge you for not knowing what a QPP is. Book the appointment. Bring questions. Leave with a plan.
The Mindset Shifts That Made All the Difference
A few reframes I stole, borrowed, or invented along the way- pass them on:
"Future me is a real person." Every financial decision is a small conversation with a version of you who is older, tired-er, and hoping you were kind to him.
"Boring is beautiful." People don't get rich chasing hot stock tips at a barbecue. They get rich by doing the same modest thing, every paycheck, for thirty years.
"Yes now, freedom later." Every extra shift, every skipped splurge, every automated contribution is a small ransom you pay to buy back your time in your sixties.
"Reputation is a retirement asset." Nowhere on your pension statement will it list "trustworthy," but every dollar of per session you earn late in your career is priced in your reputation early in your career.
"The best time to plant a tree was 20 years ago. The second-best time is this pay period."
Your 30-Minute Move
When my wife told me I could retire, I didn't feel triumphant. I felt grateful. Grateful to my mom, who nudged me into a TDA when I was eating ramen. Grateful to the twenty-something me who said yes to working Saturdays. Grateful to the fifty-something me who missed a lot of Jeopardy so that sixty-something me could sleep in.
The ball in your hands. You don't need thirty years to start. You need thirty minutes.
Thirty minutes to log into your retirement portal and bump your contribution by 1%. Thirty minutes to email your boss and volunteer for something small. Thirty minutes to book that retirement appointment you've been avoiding since the Obama administration.
Your future self is already writing the thank-you note. All you have to do is give them something to thank you for.
References
Board of Education Retirement System of the City of New York. 2024. Member Handbook. New York: BERS. https://www.bers.nyc.gov/.
New York City Department of Education. 2023. Per Session Guidelines and Procedures. New York: NYC DOE. https://www.schools.nyc.gov/.
New York City Office of Labor Relations. 2024. Deferred Compensation Plan: 457 and 401(k) Guide. New York: OLR. https://www.nyc.gov/site/olr/deferred/dcphome.page.
Teachers' Retirement System of the City of New York. 2024. Tax-Deferred Annuity Program Summary. New York: TRS. https://www.trsnyc.org/.
United Federation of Teachers. 2024. Understanding Your Pension: A Guide for Members. New York: UFT. https://www.uft.org/your-benefits/pension.
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