MML #033: Why Lawyers Struggle to Retire (And How to Overcome It)

My family and I recently spent a week in Cape May, NJ — a charming little beach town with just the right mix of “Beachy” and “Victorian.” We had a blast: sun, sand, and family memories I’ll never forget.

But toward the end of the trip, my wife noticed something. While the rest of the family dreaded going home, I was already looking forward to getting back to work.

I love what I do, and while a vacation is refreshing, I know sitting on a beach isn’t going to be the thing that pulls me into retirement one day. It’s fun for a week or two, but what I’ll need is something deeper — purpose and meaning.

That’s the same challenge many lawyers face as it relates to an impending retirement.

Being an attorney isn’t just a career. For many, it’s their identity. That makes retirement feel less like a financial decision and more like a loss of who they are.

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Why Many Lawyers Delay Retirement

This identity struggle leads to another challenge. Avoidance.

Work itself becomes the way to dodge uncomfortable questions about what life might look like outside of the law. The refrain is familiar: “I just need to save a little more.”

But often, the money is not the real reason. It’s uncertainty. Without clarity — both financially and personally — lawyers end up staying longer than they truly want to.

And here’s the danger: retirement then happens on someone else’s terms. Health issues. Firm changes. Burnout. When retirement is forced instead of chosen, options shrink and stress multiplies.

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A New Chapter, Not the End

I have some good news for you today. Retirement doesn’t have to feel like falling off a cliff.

The lawyers who transition best are the ones who start preparing early — not only with their savings, but with their mindset.

Here’s another way to reframe this: Retirement doesn’t have to be the end of the book. Conversely, it’s the start of the next chapter.

Some lawyers step into consulting, teaching, or mentoring. Others dive into pro bono work or finally give time to the passions they’ve been pushing off for years.

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Test-Drive Retirement Before You Take It

Just like you wouldn’t drive your new car off the lot without taking it for a spin, the idea of retirement wasn’t meant to be a quick purchase either.

You don’t have to figure everything out at once.

Experiment. Try a sabbatical. Scale back your caseload. Start a new hobby while you’re still working.

These small steps give you a glimpse of what life could look like after the office, making the full transition less intimidating.

And on the financial side? Clarity is everything. Once you know you can answer with confidence, “Do I have enough?” one of the biggest excuses to keep delaying disappears.

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Plan for Both Money and Meaning

Here’s where many attorneys miss the mark: they over-plan financially and under-plan emotionally.

You need both.

The numbers will give you security, but the narrative — how you spend your time, where you find meaning, and the legacy you leave — is what makes retirement fulfilling.

Start early. The sooner you address both, the more control you’ll have when it’s time to step away.

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Take Back Control of the Transition

So here’s the question: If you weren’t billing hours tomorrow, how would you spend your time?

What purpose would you want to pursue?

Facing those questions now — and pairing the answers with a financial plan — gives you the power to retire on your own terms.

Retirement doesn’t have to be an identity crisis. With preparation, it can be the most intentional chapter of your life.