After more than 40 years of practicing law, Mark, a senior litigator at a mid-sized law firm in the Pacific Northwest, began thinking more seriously about retirement.

At 68, Mark still enjoys his work. He is sharp, engaged, and sees legal practice as a meaningful part of his identity. He is not rushing toward retirement, but he knows it is getting closer. Many of his peers have already stepped back. Some are consulting. Others are traveling. And while he is not quite ready to follow them, he is starting to ask himself a quiet but important question:

“Could I retire if I wanted to? And what would that actually look like?”

It is a surprisingly difficult question. Especially for lawyers who have spent decades immersed in their practice, but only minimal time thinking through the financial realities of life after it.

If Mark’s situation sounds familiar, you are not alone. Many attorneys in their 60s feel a similar mix of confidence and uncertainty. On paper, they appear prepared. But under the surface, they are wrestling with lingering doubts.

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The Hidden Tax Trap of Traditional Retirement Savings

Over the years, Mark saved diligently through his firm’s retirement plan. Most of it sits in tax-deferred accounts. His provider estimates that he could withdraw $300,000 to $350,000 per year starting at age 71.

That number sounds impressive. But here’s the issue. It is pre-tax.

Mark understands that every dollar he takes out will be taxed. That includes his retirement distributions, Social Security benefits, and possibly capital gains from outside investments.

And that’s where the anxiety kicks in.

The real fear?
– “What if I’m walking into a massive tax bill I wasn’t prepared for?”
– “What if I leave tens of thousands on the table just because I didn’t know better?”
– “What if I’m penalized for saving the ‘right’ way all these years?”

Many lawyers share this fear. The problem is not the size of the account. It is the lack of a plan to use it wisely once the paycheck stops.

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Lifestyle Assumptions That Have Not Been Stress-Tested

Mark is not chasing an extravagant retirement. What he wants is peace of mind and the freedom to enjoy life on his terms. He recalled how his spending dropped during the COVID lockdowns, but he admitted that version of life is not what he envisions for retirement.

Here’s what he is really thinking:

“I don’t want to downgrade my lifestyle just because I didn’t run the numbers.”

That hesitation is common. Many high earners assume they will “figure it out” when the time comes. But without stress-testing their projected income against real-world expenses, inflation, and market fluctuations, they remain stuck.

Not because they can’t afford to retire.

But because they don’t know for sure.

This is where uncertainty creeps in:
– “What if the income projection is wrong?”
– “What if I spend too much too early?”
– “What if I regret stepping away?”

It is not just about numbers. It is about trust. And when that trust is missing, people delay making any move at all.

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Feeling Underserved by Generic Advice

Mark’s retirement plan is managed by a national provider. While they offered basic projections, he felt the advice was thin. No meaningful tax strategy. No guidance on timing withdrawals. No conversation about how his spouse fits into the plan.

He was not looking for a product. He wanted clarity.

What he really needed was someone to ask:
– “What matters most to you in this next phase?”
– “Where are the blind spots?”
– “What will it take to give you real confidence?”

This is where many professionals feel let down. They have built significant wealth. But no one has slowed down to help them connect the dots.

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What You Can Do Without Hiring Anyone

If you are in a similar position—still working, still sharp, but starting to wonder what’s next—here are a few practical steps you can take on your own:

1. Estimate Your Real After-Tax Retirement Income

Start with your projected income from pensions, retirement accounts, and Social Security. Then run a basic tax scenario. Do not assume the gross number is your spending power. Focus on what you will actually keep, especially if you live in a high-tax state or have mostly tax-deferred savings.

2. Map Out Your Lifestyle Baseline

Build your retirement budget based on the life you want to live. Include travel, hobbies, health care, and generosity. Don’t use your lowest-spending year as the model. Be honest about what a meaningful life in retirement looks like for you.

3. Explore Tax Diversification

Look into strategies such as Roth conversions, backdoor Roth IRAs, or changing the order of account withdrawals. A little planning now can dramatically reduce your future tax bill.

4. Get a Second Set of Eyes

Talk with a CPA or fiduciary financial advisor. Not to be sold something, but to pressure-test your plan. A second opinion can help you catch mistakes, identify opportunities, and feel more confident about your next move.

You do not have to be ready to retire.

But you should be ready to act when the time feels right.

Financial confidence does not come from guessing. It comes from understanding your numbers, your values, and your options. Even if you love your work, it is powerful to know that retirement is a choice, not a question mark.

Next week, I’ll walk through practical strategies for drawing down from a mostly pre-tax retirement portfolio with a focus on optimizing your tax exposure throughout retirement.