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Dr. Pat Pachciarz® · Answers for women in life transition

Pre-retirement planning at 55: trust planning first, then income, health care and taxes

Women around 55 often tell us the same thing: retirement is close enough to plan for, but the pieces live in different places. Our order of operations starts with trust planning, because a plan for who decides, and who inherits, protects everything else you build.

Home base: Aurora, Illinois · Serving clients in person in Aurora and virtually · 815-486-0722

Written and reviewed by Dr. Pat Pachciarz® · Updated October 3, 2026 · Educational, not individual advice.

From there, the work is income, health coverage until Medicare, and taxes. See the full Pre-Retirement Planning guide on drpat.co for a 5-to-10-year checklist.

What should I know first?

  • Put your trust, powers of attorney and beneficiaries in order first.
  • Know your Social Security options at 62, full retirement age and 70.
  • Plan health coverage from your last day of work until Medicare at 65.
  • Use catch-up contributions while you're still earning.

Common questions

Why start with trust planning before retirement?

Because it decides who acts for you and who inherits if something happens before or during retirement. A trust, powers of attorney and current beneficiary forms protect the savings you're building. It's also easier to set up while life is stable than during a health crisis or family change.

Sources: CFPB: Managing someone else's money · IRS: Retirement topics, beneficiary

What is the rule of 55?

If you leave your job in or after the year you turn 55, withdrawals from that employer's retirement plan generally avoid the 10% additional tax on early distributions. Income tax still applies. The exception doesn't cover IRAs, so rolling the money to an IRA first can lose it.

Sources: IRS Topic 558: Additional tax on early distributions

How do I get health insurance before Medicare at 65?

Common options are retiree coverage from your employer, COBRA continuation of your group plan for a limited time, or a Marketplace plan through HealthCare.gov. COBRA can cost up to 102% of the plan's cost, so compare it with Marketplace prices.

Sources: U.S. Department of Labor: COBRA continuation coverage · HealthCare.gov: Coverage options for retirees

Can I still make catch-up contributions after 50?

Yes. If you're 50 or older, you can generally make extra catch-up contributions to 401(k), 403(b) and governmental 457(b) plans and to IRAs, above the regular limits. The IRS updates the limits each year.

Sources: IRS: Retirement topics, catch-up contributions · IRS Publication 590-A: Contributions to IRAs

How does DAITT® help with this?

Every engagement moves through the five DAITT® disciplines in order, so the tax, legal and investment pieces are decided together.

  1. Trust Planning

    Sign or update your trust, powers of attorney and beneficiaries.

  2. Advanced Planning

    Map income from work, pensions, Social Security and savings.

  3. Tax Strategy and Tax Filing

    Plan Roth conversions and withdrawals around your tax brackets.

  4. Debt Optimization

    Aim to retire the mortgage and other debts on purpose.

  5. Private Wealth Investments

    Shift investments to match when you'll need each dollar.

How do we show our value?

We explicitly show you our value, in writing, before you hire us. If we can't find it or explicitly show you, you don't pay.

Book a Clarity Call or see your Leak Score

Sources

More answers

Also see drpat.co and the Pinnacle FAQ.