Why Planning Is So Hard

The biggest reason lawyers struggle with retirement usually surprises people. Yes, lawyers wonder about having enough money or minimizing taxes. But those questions often mask what they’re really worried about.

Why Do Lawyers Struggle With Retirement? (It’s Not About Money)

I have the privilege of talking with lawyers about retirement all the time. I often hear something to the tune of, “I’m probably five years away from retiring, but honestly, I have no idea what I’d actually do.”

It’s typically not the money. That’s not the issue.

Rather, it’s the lack of a vision for what comes next. And that’s the part that keeps so many attorneys chained to their desks long after they’re ready to leave.

When Work Becomes Who You Are

Here’s what makes retirement planning for lawyers different from almost any other profession: The law is more than just what you do. It’s a part of you. It’s who you’ve been for decades.

Everything you’ve built — reputation, expertise, identity — all revolves around being an attorney. Walking away from that feels like losing yourself.

I get it. The thought of introducing yourself at a dinner party without mentioning you’re a lawyer feels uncomfortable. Maybe even a little scary.

Fighting the ‘Just One More Year’ Mentality

This identity crisis shows up in a predictable way: Procrastination.

Lawyers tell themselves they need to save just a bit more. Hit one more milestone. Take on one more case. But I’ve seen the brokerage statements. Most of the time, the money is already there.

What’s really happening? You’re avoiding the harder question: What does a meaningful life look like when you’re not practicing law? Without an answer to that question, it’s easier to keep working.

The problem is that retirement eventually happens whether you’re ready or not. A health scare. A firm restructure. Pure exhaustion. When someone else decides for you, your choices can disappear fast.

Retirement as a Beginning

Retirement means starting something new, not ending your career.

The attorneys I work with who make the smoothest transitions are those who view retirement as their next phase, not their final one. Some become mediators or teach at law schools. Others focus on pro bono cases they always wanted to take but never had time for. A few finally write that book or travel to places they’ve been reading about for years.

Read “The Second Act: How Successful Lawyers Are Redefining Retirement.”

The point isn’t what you choose. The point is choosing something and building a vision around it.

Try Before You Commit

You wouldn’t buy a house without walking through it first. Don’t treat retirement any differently.

Start testing what your post-law life might look like while you’re still working. Take an extended sabbatical if your firm allows it. Cut back to part-time for six months. Pick up a hobby that’s been sitting on your “someday” list. I know, easier said than done. But aren’t most things that are worth pursuing?

These experiments give you real feedback about what you actually enjoy doing when work isn’t filling your calendar.

And here’s the financial glue that can bond that vision together: Once you know for certain that your savings can support you, the biggest excuse for staying disappears.

The Missing Half of Your Retirement Plan

Most lawyers I meet have done some preliminary math around retirement. They know their nest egg number. They’ve mapped out their expenses (always the most tedious part of this journey).

But these lawyers struggle with retirement because they’ve completely ignored the other half. The part about how they’ll spend their days. What activities will give them purpose. How they’ll stay engaged with the world.

You need both pieces.

A solid financial plan gives you freedom. A solid life plan gives you fulfillment.

Start working on both now. The earlier you begin, the more options you’ll have when it’s time to make the move. That’s all retirement planning is at its bare foundation — building options for yourself.

Your Turn to Decide

A practical way to start is to ask yourself, if your calendar cleared tomorrow, what would you fill it with? Not what you think you’re supposed to say. What would you actually want to do? Answer that honestly. Then build a financial plan that supports it.

Retirement planning for lawyers requires having enough money and creating a life you’re excited to step into.

Interested in how finances connect with retirement purpose? My weekly newsletter, Money Meets Law, dives into it. Sign up and join the conversation.