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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 income: what has to be covered every month no matter what, what's already guaranteed — Social Security, a pension — and how to close the gap with income that can't run out before you do.

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 line up the guaranteed income first: Social Security timing, pension elections, and where a guaranteed-income contract can cover what those don't.

Then we try to break it. A longer life than the averages, a care event late on, a spouse left with one check instead of two. The plan that survives the stress tests is the one you can actually stop working on.

On the table

  • Income modeling — what your essentials cost, and what has to cover them
  • Social Security claiming analysis, including spousal and survivor math
  • Pension and lump-sum elections, and what each leaves a surviving spouse
  • Guaranteed-income options for the gap Social Security and pensions leave
  • Healthcare costs, including the gap before Medicare begins
  • Stress testing against a long life, a care event, and the loss of a spouse

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, which guaranteed sources cover the essentials, and what we'd adjust if life moves. If you're already retired, the same modeling becomes a second opinion on the income 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, whether the essentials were actually covered — 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 how much guaranteed income had to be in place, 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 Josh 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 — is the income floor secure, what happens to it if one of you dies, does a care event break it — but the value of having them answered doesn't.

The decisions inside this one

Social Security Planning

The claiming decision, modeled properly.

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Annuity Review

The guaranteed check you may already own.

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Life Insurance

The right amount, the right type, and a reason for every policy — reviewed…

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Josh Wood

Josh Wood

President - Insurance Professional · Outrider Planning

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 — income, coverage, obligations, timelines, and the goals behind them.
  3. 03 Your plan We walk you through written recommendations together, including the trade-offs behind every one and how we're compensated on it.
  4. 04 Ongoing partnership Regular reviews, coverage and income check-ins when life changes, and a direct line when something comes up.

Talk it through with Josh

What would you like to talk about? (optional)

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

Protect Your Legacy. Preserve the Lifestyle You’ve Worked Hard to Build.

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