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Retirees

I’ve saved for decades — how do I start spending it?

The hardest transition in personal finance is going from earning to spending. It requires three things the accumulation years never asked of you: an order to withdraw in, a claiming decision for Social Security, and a tax plan for the years between retiring and required minimum distributions — which is usually the cheapest window you will ever have.

You’ve worked hard in your career, and are ready for relaxation and celebration.

Switching from a paycheck to a portfolio is the hardest transition in personal finance. We build the withdrawal order, manage the tax consequences, and keep the plan current as rules change.

A retired couple sharing coffee on a sunlit balcony, unhurried

The decisions that actually matter now

  1. Which account you draw from, and in what order

    Withdrawal sequencing changes lifetime tax, not just this year’s. The conventional taxable-then-deferred-then-Roth order is a starting reference; the better sequence depends on your bracket each year and on whether drawing deliberately now shrinks the required distributions later.

  2. When to claim Social Security

    Benefits can start at 62 and grow for each year deferred up to 70. The right age depends on longevity, whether you are still working, and — for married couples — the survivor benefit, because the claiming decision outlives the person who made it.

  3. The gap years

    Between the last paycheck and the first required distribution, earned income has stopped but mandatory withdrawals have not started. That is often the lowest-bracket stretch of your life, and the clearest window for Roth conversions done at a deliberate size.

  4. Medicare and IRMAA

    Premiums for Parts B and D are set by modified adjusted gross income on a two-year lookback, so income recognized today can raise premiums two years out. This is why conversions and large withdrawals get sized rather than taken in one lump.

What working together looks like at this stage

We build the income plan first: what comes in, from where, in what order, and what it costs in tax each year. Then we stress-test it against the two things that actually break retirements — living longer than the plan assumed, and a poor first decade of returns arriving while you are withdrawing.

That second risk is why sequencing matters more than average return. A portfolio that averages a fine number over thirty years can still fail if the bad years land first and withdrawals lock the losses in. The structure of the portfolio has to reflect that you are now a seller, not just a holder.

We build your tax picture in Holistiplan from your actual return rather than a generic assumption, and the whole thing is revisited every year — because brackets, thresholds, and the rules themselves keep moving, and a plan set once at 65 is not the same plan at 72.

What we see go wrong

  • Claiming at 62 by default

    Sometimes claiming early is right — health, cash flow, or the chance to leave a portfolio untouched can all justify it. What we see far more often is that it was never actually compared against waiting.

  • The conversion window spent doing nothing

    The gap years pass quietly. Nothing forces a decision, no form arrives, and then required distributions begin and the cheapest years to have acted are gone.

  • Forgetting the survivor’s tax bracket

    When one spouse dies, the survivor typically files single on roughly the same income. The same money, taxed in narrower brackets, with a smaller standard deduction — a foreseeable change that very few plans account for in advance.

  • Cash held as a reflex

    Some cash reserve protects against having to sell in a downturn, and that is sound. A decade of spending held in cash is a different decision, and over a thirty-year retirement inflation makes it an expensive one.

Retirees

Questions we get asked

  • By deciding which account each dollar comes from and in what order, then managing the tax consequence year by year. Withdrawal sequencing changes lifetime tax rather than just this year’s, and it is the piece the accumulation years never required you to think about.

Not quite you?