I’m Thinking About Retirement… Not Retiring

For the past 38 years, my conversations with many of you have circled around one big question: “Do I have enough to retire… and will it last?” That’s been my bread and butter – helping you figure out how much you need, how long it might need to last, and how to make it stretch while still enjoying life along the way.

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When I first started working with many of you, you were in your forties. Today, you’re in your late seventies or early eighties. And here’s something I’m proud to point out: in a lot of cases, your retirement savings are still very close to where they were when you retired – even though we’ve been taking out income every single year. You’ve essentially been living your retirement dream without draining the tank.

Now, I’d love to take all the credit for that… but let’s be honest – it’s been a team effort.

You’ve held up your side of the bargain by:

• Sticking to our investment plan
• Staying calm when the markets acted like a roller coaster
• Living within your means (and resisting the urge to buy that private island—most of the time)

On my side, I’ve been focused on:

• Managing your cash flow
• Raising cash when markets were strong so your yearly expenses were covered without selling in a downturn
• Designing portfolios with less volatility

Here’s why that last point matters: during your working years, volatility is like a sale sign – it gives you a chance to buy when prices are low, which often boosts long-term returns. But in retirement, sharp market drops can really sting. If you’re taking out 5% a year for living expenses and your portfolio falls 18%, you’d need a whopping 30% return just to get back to where you started. If the drop is only 10%, you’d “only” need 18% to recover. That’s why we work hard to smooth out the ride.

Holding Your Hand Through the Storms

We’ve been through our share of market shakeups together:  1987, 2000, 2001, 2008, 2020, 2022… each one felt dramatic at the time, but we got through them with patience, discipline, and perspective. Sometimes my role has been as much “financial advisor” as “calm voice on the phone,” reminding you not to jump ship when the waves get rough.

Planning for the Long Haul

A client once asked me if he had enough money to last the rest of his life. At 86, I confidently told him yes, thinking he might make it to 95. Then he reminded me his mother was still alive – at 106. (I quietly went back to my spreadsheets.)

These days, someone retiring at 65 could easily have another 30 or 40 years ahead of them. That’s a lot of birthday candles – and a long time for your money to keep working.

People often ask, “Is $1.2 million (you pick a number) enough to retire?” My answer is always: It depends. It depends on how much you plan to spend, when you plan to retire, and how long you might live. That’s why we create personalized wealth plans – to turn all those moving parts into a clear picture, so you can feel confident about your future.

And that’s why, even after nearly four decades in this business, I’m still thinking about retirement – not for me, but for you.