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Retirement Planning

Answering the question that matters most: can I retire, and what does it look like when I do?

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The question changes

Thirty years of "am I saving enough?" ends with a harder question

For thirty years the question had a comfortable answer: more. Then, somewhere in the last stretch of a career, it quietly becomes a different question — "is this enough, and how do I turn it into a paycheck?" — and almost nothing about the saving years prepares you to answer it.

The accumulating stops being the point. What matters now is sequence: when you stop, when you claim, what you spend from first. The order of those decisions can move what your savings are worth by more than another year of contributions ever could.

For thirty years the question was "am I saving enough?" Then it quietly becomes "is this enough?" — and nothing about the first thirty years prepares you to answer it.
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The work itself

The decade gets modeled, decision by decision

We model what your retirement actually costs — your life, not a percentage of final salary — then assign each year of income a source: which account it comes from, in what order, and how the withdrawals, Social Security timing, and taxes interact with each other.

Then we try to break it. Poor early markets, a longer life than the averages, a care event late on. The plan that survives the stress tests is the one you can actually stop working on.

On the table

  • Income modeling — what you can sustainably spend, and when
  • Social Security claiming analysis, including spousal and survivor math
  • Withdrawal sequencing across taxable, tax-deferred, and Roth accounts
  • Healthcare costs, including the gap before Medicare begins
  • Stress testing against poor early returns and longer-than-expected retirements

The decade of decisions

Retirement isn't one date — it's a sequence of deadlines, each with its own rules.

  1. 59½Retirement accounts open up, penalty-free
  2. 62–70The Social Security claiming window
  3. 65Medicare begins — and the coverage gap before it ends
  4. 73Required minimum distributions start

Each date changes what the smart move is. A plan made at 55 has time to use all of them deliberately instead of meeting each one by surprise.

Ages shown reflect current law and common cases; individual rules vary.

What you keep

A retirement date you can defend with numbers

You leave with a picture instead of a hope: the date, the paycheck, where each year's income comes from, and what we'd adjust if life moves. If you're already retired, the same modeling becomes a second opinion on the plan you're living on.

Hypothetical

A couple, 61 and 59, planning to retire "sometime in the next few years." Their savings were solid, but every question — when to stop, when to claim, which account to touch first — was circling with no order to it. Modeling the decade ahead put the decisions in sequence: the retirement date drove the healthcare bridge, the bridge drove the withdrawal plan, and the claiming decision could wait for a year that made it obvious.

Hypothetical scenario for illustration. Not an actual client. Individual circumstances and results differ.

Want a real answer instead of a rule of thumb?

Model my retirement or send us a note below

The two questions everyone asks first

How much do I need to retire?

There's no universal number, and anyone who gives you one without seeing your situation is guessing. It depends on what you plan to spend, when you claim Social Security, what other income you have, and how long the money needs to last. Modeling those together is the work.

What if I'm already retired?

Plenty of our work is with people who are already there. The questions change — withdrawal strategy, tax efficiency, required minimum distributions, whether spending is sustainable — but the value of having them answered doesn't.

The decisions inside this one

Income & Withdrawal Planning

The paycheck side of the same question.

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Social Security Planning

The claiming decision, modeled properly.

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RMD Planning

What the calendar forces, planned for in advance.

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Kingsbury Financial Advisors

True wealth is more than money.

Kingsbury Financial Advisors is a full-service comprehensive financial planning and wealth management firm located in Tampa, Florida. Alongside our strategic partnership with the leading comprehensive financial planning firm Caitlin John Private Wealth management, we have all of the necessary resources to support our clients in conquering their financial goals.

What to expect

  1. 01 Introduction A short conversation about what prompted you to reach out. No preparation needed and nothing to sign.
  2. 02 Discovery We gather the full picture — accounts, obligations, timelines, and the goals behind them.
  3. 03 Your plan We walk you through a written plan together, including the trade-offs behind every recommendation.
  4. 04 Ongoing partnership Regular reviews, proactive tax and planning work, and a direct line when something changes.

Talk through your situation

What would you like to talk about? (optional)

A 20-minute conversation, no cost and no obligation. Please don’t include account numbers.

True wealth is more than money.

Start with a conversation. No cost, no pressure, no obligation to continue.

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