Recent conversation with a physician who’s nearing retirement.

• ~ $8.5M in taxable brokerage
• ~ $4.5M in retirement accounts
• Big positions in a handful of large tech stocks
• ~ $120k in Roth, ~$200k in HSA
• Home worth ~ $1.2M

His main goals were simple to say, hard to execute:

• Glide comfortably into a retirement strategy
• Simplify an overly complex portfolio he’s been managing himself
• Target $200k–$250k per year of spending, with flexibility for things like renovations on the house

The core questions we talked through:

• Concentration vs. timing risk.

With retirement so close, how much of that tech concentration is he actually comfortable carrying into the next decade, versus systematically diversifying? A 351 exchange can provide a simple, tax-efficient way to diversify and rebalance the stock portfolio.

• What does “enough” look like?

At $14M with a $200k–$250k spend target, the math looks very different from someone at $3M. It changes how aggressive you need (or don’t need) to be with the portfolio.

• Which accounts do dollars come from, and when?

Coordinating withdrawals between taxable, traditional retirement, Roth, and the HSA so taxes are managed over the next 20–30 years instead of one year at a time.

• Estate and legacy without kids.

With no children, it becomes a question of: What causes or people do you actually want this money to impact, and how do we make that easy to execute on without adding more complexity?

He’s done an impressive job building wealth and managing investments on his own.

For a lot of late‑career professionals in this position, the win isn’t “beating the market.”

It’s simplifying the structure, making taxes a plan instead of a surprise, and giving yourself permission to actually enjoy the thing you spent 30–40 years building.

If you’re a few years from retirement with several million saved and a portfolio that feels more complex than your lifestyle goals, it might be time to revisit the plan, not just the positions.