MML #067: What a Real Attorney Transition Plan Looks Like

You've been "almost ready” for a while now.

Maybe you've said it out loud — to your spouse, to a colleague, to yourself at the end of a long week. One more year. Let me just get through this case. Let me hit one more number.

Staying stuck in "almost" usually means the path forward isn't clear enough to actually walk.

Most attorneys I talk to have done some planning. They have a financial advisor, maybe a decent portfolio, a vague sense of when they'd like to stop. What they don't have is a real transition plan — one that connects the financial decisions to the timing decisions, accounts for the tax consequences, and gives them an honest answer to the question they're actually asking: am I ready?

Here's what that kind of plan should look like.

Phase 1: Clarity — before anything else, you need an honest baseline.

This sounds obvious, but most planning skips it. Real clarity means more than knowing your account balances. It means understanding your full income picture, your balance sheet, how your firm structure affects your financial position, and — critically — your initial tax situation.

For most attorneys, taxes are the biggest variable in retirement. The difference between a well-timed and a poorly-timed exit can be six figures. You can't make good decisions without first understanding where you actually stand.

If you don't have a clear answer to "am I on track, and what's missing?" — you don't have a plan yet. You have a portfolio.

Phase 2: Design — a real plan models the transition, not just the destination.

Once you have the baseline, the planning work begins. This means running actual retirement timing scenarios — what changes if you leave at 62 versus 65 versus 68 — not just picking a target date and hoping the math works out. 

It means building an income replacement strategy, thinking through multi-year tax planning, and if you're a partner or equity owner, modeling your buyout or transition terms as a financial variable, not an afterthought.

Most attorneys have never seen these pieces laid out together in a way that shows how each one affects the others. That's the point of this phase. A coordinated, tax-aware strategy looks very different from a collection of accounts with a target withdrawal rate.

Phase 3: Decision — the timing question deserves a real answer.

At some point, the planning has to produce a decision. Not a perpetual "almost" — an actual go/no-go. That means looking honestly at your timeline, considering whether a phased or part-time transition makes sense for your situation, and sequencing the key financial moves in the right order.

It also means stress-testing. What happens to the plan if markets drop 30% in year two of retirement? What if you live to 95? What if your health changes? A plan that can't answer those questions isn't finished. Confidence in your decision comes from having looked at the hard scenarios, not from avoiding them.

Phase 4: Transition — retirement is a 30-year chapter, not a single event.

The day you stop practicing is the beginning of a long, dynamic phase of life that requires its own financial approach — income distribution that's tax-efficient, investment management that adapts as you age, and a spending strategy flexible enough to handle the unexpected.

The attorneys who struggle in retirement are often the ones whose planning stopped at the exit. The ones who navigate it well have an ongoing framework that adjusts with them.

A simple question worth asking your advisor

If you're working with a financial professional and haven't seen your transition modeled this way — timing scenarios, tax implications, income sequencing, stress tests — it's worth asking why.

A good transition plan for an attorney isn't complicated. But it does require someone who understands what's actually at stake in the move from practicing law to retirement, and who knows how to address it in the right order.

Over the coming weeks, I'll be going deeper on each phase — the questions worth asking, the mistakes worth avoiding, and what good planning actually looks like at each step. If any part of this resonated, stick around.

If this resonates, I'd love to hear where you are in the process. Reply and tell me — I read every one.

— David