I’ve been thinking a lot about retirement planning lately, especially as I work with more legal professionals. There’s something fascinating about how the brightest minds in law approach their own future planning.

And it’s not always what you’d expect.

When I talk with lawyers about retirement planning, I see incredibly smart people making the same mistakes over and over. The good news is that these aren’t character flaws or intelligence gaps. Instead, they’re the natural result of a career that rewards certain mindsets — mindsets that just happen to work against you when planning your next chapter.

Let’s dive into the five biggest retirement planning mistakes I see lawyers make, and more importantly, how to fix them.

1. Tying Your Identity to the Practice of Law

You’ve spent decades building expertise that matters. Clients depend on you. Colleagues respect you. Retirement can feel like stepping off the stage into irrelevance.

But if I’ve learned anything from working with lawyers, it’s that the skills that make you exceptional in law — analytical thinking, problem-solving, advocacy — don’t disappear when you leave the office. They just find new outlets. Lawyers who have successfully bridged this “life-gap” become mediators, teach at universities, serve on nonprofit boards, or mentor young attorneys.

Interestingly enough, many report feeling more fulfilled, not less.

Start your “identity expansion project” now. Pick two non-law activities that intrigue you and dive in while you’re still practicing. You might discover parts of yourself that have been waiting patiently in the wings.

2. Overconfidence in Future Earnings

Your earning power has always been tied to your intellect and skill. Age feels irrelevant because good lawyers just get better with experience, right?

I get why this feels true, and it often is, for a while. But health issues, industry changes, or simple burnout can shift the landscape faster than you expect. That confidence in “always being able to make more money” becomes a trap when it prevents serious planning.

The approach here isn’t to tie yourself into one particular outcome. Instead, create multiple financial independence timelines. Map out what retirement at 60, 65, and 70 would require. Having these scenarios gives you control and choices. You can still work as long as you want, but now you’re doing it from a position of strength rather than necessity.

3. Lifestyle Creep and Keeping Up Appearances

The right car, the private schools, the country club membership. These weren’t just purchases — they were investments in your professional image and family’s future.

I won’t lecture you about lifestyle choices because that’s missing the point. There’s absolutely nothing wrong with these things. Afterall, money is simply a tool to help us connect our capital resources (e.g., income, assets, opportunities) with what’s important to us (e.g., time-freedom, experiences, lifestyle purchases).

The real issue is when these commitments become financial handcuffs as retirement approaches. You end up working longer than you want, not because you love it, but because you need the income to maintain obligations.

Get super clear on what truly matters versus what you’ve been doing on autopilot. Some lawyers I work with discover they can downsize their lifestyle without feeling deprived — they just need permission to stop performing success for others.

4. Avoiding Hard Conversations About Succession

Nobody wants to trigger family drama or disappoint partners who’ve been counting on inheriting your book of business. So you postpone the conversation, hoping it’ll somehow resolve itself.

But avoiding succession planning isn’t protecting anyone. It’s creating a ticking time bomb.

To frame this in a more positive light, you’re building something bigger than yourself. A well-planned succession becomes part of your legacy, ensuring clients are cared for and the practice thrives without you.

Start these conversations early and frame them around growth, not endings. What would need to happen for your practice to run beautifully without you? That’s a strategic challenge worthy of your best thinking.

5. Postponing Joy for “Someday”

The legal career trains you to put clients first and delay personal fulfillment.

“After this case closes.”

“When the firm is stable.”

“Once I make partner.”

Ever find yourself whispering these thoughts to yourself?

The problem with “someday” thinking is that it becomes a habit. You get so good at deferring satisfaction that you forget how to prioritize your own well-being. Come retirement, you might find yourself with financial resources but diminished energy or health to enjoy them.

Try “retirement rehearsals” — extended breaks or sabbaticals while still practicing. Test-drive activities and rhythms you might want in retirement. This removes the all-or-nothing pressure and helps you discover what actually brings you joy.

I recently enjoyed a beach vacation in Cape May, NJ with my family — beautiful weather and even better memories. But after just a week, I realized that sitting in the sand probably won’t be my version of retirement. I need more purpose, and maybe you do too. (Of course, there’s nothing wrong with parking yourself in the sand — you’ve earned it!)

The Bottom Line

The solution here is comprehensive planning that starts now, regardless of when you actually want to retire. There’s nothing wrong with working as long as possible, assuming that’s what brings you fulfillment. But maximizing your plan at any age gives you clarity and peace around your options.

Retirement planning really is about building your ultimate fallback plan — financial independence and life satisfaction insurance. In my Money Meets Law newsletter, I dig deeper into these ideas, offering fresh perspectives on how attorneys can build more flexibility into both their finances and their lives. If you’re curious, it’s written with lawyers like you in mind.

For years, your focus has been on creating winning outcomes for clients. Time to turn that brilliant strategic mind toward your own future.

David Hunter, CFP® is a CERTIFIED FINANCIAL PLANNER™ and owner of First Light Wealth, LLC, a financial planning & wealth management firm with a unique focus on serving attorneys nationwide. David has over a decade of experience helping clients build financial plans and has been featured in publications such as Attorney at Work, ThinkAdvisor, MarketWatch, Financial Planning, and InvestmentNews. David also writes weekly to attorneys in his popular Money Meets Law newsletter. For more about David, visit firstlightwealth.com/lawyers or connect with him on LinkedIn.

The post The 5 Biggest Retirement Planning Mistakes Lawyers Make (And How To Fix Them) appeared first on Above the Law.