Preparing for Retirement

Preparing to decumulate a lifetime of wealth requires standing up structural scaffolding years before the paycheck stops. Let’s look at the primary levers to minimize taxation and maximize your starting balance.

Maximize IRA, 401(k) contributions

Contribute the maximum allowable amount to your 401(k) plan: $24,500 in 2026 (the base employee-deferral limit, indexed). Age 50+ adds an $8,000 catch-up, and SECURE 2.0’s “super catch-up” for ages 60–63 raises that to $11,250 (or 150% of the standard catch-up, whichever is greater). These deferrals reduce your taxable income today; the trade is paying tax on withdrawal, ideally at a bracket you have engineered to be lower (section “Tax-Efficient Decumulation”). Pair with Roth IRAs or Roth 401(k)s during your working years to diversify the tax exposure of your future distributions. If your income exceeds the Roth IRA contribution limits, use a backdoor Roth IRA conversion—contribute to a traditional IRA and convert. You will pay tax on the conversion, but future withdrawals and growth are tax-free, hedging against future rate increases. OBBBA made the TCJA individual brackets permanent, but “permanent” in tax law means “until Congress changes its mind”; converting in low-income years still locks in today’s relatively low rates.

Leverage Health Savings Accounts (HSAs)

Max out contributions to an HSA if you have a high-deductible health plan. Contributions are tax-deductible, grow tax-free, and withdrawals for qualified medical expenses are tax-free. Post-65, you can use HSA funds for non-medical expenses without penalty, though they will be taxed as ordinary income.

Delaying Social Security

Postpone your Social Security claim toward age 70. This increases your monthly payment by a simple, guaranteed 8% per year past your FRA. Build sufficient taxable cash reserves to fund the gap years so you do not have to tap pre-tax retirement accounts early.

Decumulation choreography

Roth conversion timing, withdrawal sequencing across taxable / pre-tax / Roth buckets, QCDs, cliff management (IRMAA, NIIT, the Social Security tax torpedo, 0% LTCG harvest), buy-borrow-die and the C-corporation as a fourth bucket, domicile-change arbitrage—all of it lives in its own chapter (chapter “Tax-Efficient Decumulation”). The retirement chapter sizes the engine; the decumulation chapter runs it in reverse at the lowest lifetime tax cost the law allows. Do not skip that chapter on the assumption that a default “taxable first, then pre-tax, then Roth” ordering is correct—above a meaningful pre-tax balance it is precisely wrong.

Part-time work or consulting

Part-time work or consulting in early retirement keeps you mentally engaged and provides marginal income; billing through a C-corporation rather than as a sole proprietor lets you decouple the timing of earning from the timing of recognizing personal income, an IRMAA and tax-bracket lever discussed in section “The Three Buckets and Their Tax Surface”. Hobbies-into-income work the same way—the entity structure determines whether the cash flow lands on your 1040 or sits inside a wrapper until you call it out.

Charitable Remainder Trust (CRT)

A CRT lets you contribute an appreciated asset, defer the capital-gain recognition, receive an income stream for life (or a term of years), and take a present-value charitable deduction for the remainder. The mechanics, the tax treatment of the income stream, and the choice between CRAT and CRUT variants live in the charitable-giving discussion of chapter “Estate planning”.

Optimize expenses and investments

Maximize itemized deductions and establish tax-efficient asset location. Hold tax-inefficient municipal bonds or dividend stocks where their yield is shielded or taxed favorably, and audit health insurance plans before enrolling in Medicare at age 65.