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Transitioning to Retirement

Transitioning to retirement? Turn your portfolio into retirement income.

When the salary stops, the portfolio has to cover the bills. We help you think through spending, taxes, and health coverage together, and reduce concentrated positions along the way.

Talk to an Advisor

Rubric Advisors, a fee-only fiduciary in San Francisco, helps professionals, executives, and business owners turn their portfolio into retirement income. We work on a sustainable spending range, withdrawal order, Roth conversions and Medicare IRMAA thresholds over several years, health coverage before Medicare, and reducing concentrated company stock, coordinated with your CPA.

The problem

What changes when the paycheck stops?

For years, your paycheck covered spending and your savings built wealth. In retirement that reverses: the portfolio has to fund your life, for decades, through whatever markets do.

Many professionals who retire in their fifties or early sixties also have an unusual mix to manage: a large taxable account, a 401(k), deferred compensation, company stock or a business interest with a low cost basis, and several years before Medicare or Social Security begin.

The cost of waiting

The years between leaving work and claiming Social Security or taking required distributions are often the lowest-income years you will have. Without a plan, that window for Roth conversions and capital-gain harvesting can pass unused.

Spending decisions made without a plan tend to be either too cautious, leaving you living below your means, or too aggressive, drawing savings down faster than the portfolio can sustain.

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Avoid these

What mistakes do people make when transitioning to retirement?

Relying on one withdrawal rule

A fixed rule of thumb ignores taxes, market conditions, and the order in which you draw from different accounts.

Skipping the early-retirement tax window

Letting low-income years pass without considering Roth conversions or gain harvesting can mean higher taxes later, including higher Medicare premiums.

Keeping a concentrated position by default

A large block of your former employer's stock, or any single holding, adds concentrated risk just when you depend on the portfolio for income.

How we help

Questions we often hear, and how we help

Retirement income is one of the areas we help individuals and families with as part of managing their overall wealth. We coordinate the tax side with your CPA. For clients whose assets we manage, this is part of our ongoing work.

Spending in retirement

How much can I actually spend without running out?

We work with you on a sustainable spending range, stress-tested against weaker markets, and revisit it as conditions change.

Tax bracket planning

Do Roth conversions make sense before Social Security?

We look at conversions, capital-gain harvesting, and Medicare IRMAA thresholds over several years, and coordinate the numbers with your CPA.

Health coverage before Medicare

I'm 55. What do I do until Medicare?

If you buy coverage through the ACA marketplace, your reported income affects your subsidy. We factor that into withdrawal and conversion decisions.

Concentrated positions

Half my taxable account is still one stock.

We plan to reduce the position over time, often timing sales for lower-income years, using the same approach we use for concentrated stock.

Sequence risk

What if the market drops 30% the year I retire?

A reserve of cash and bonds for early spending, plus rules-based rebalancing, can help reduce the chance of having to sell stocks at a low point to fund spending.

FAQ

Common questions

It's my last day at work. What comes first?

Confirm what happens to unvested equity, deferred compensation, and your 401(k); decide on health coverage (COBRA or the marketplace); and map out the next 12 months of spending and taxes before making large investment changes.

How much can I withdraw each year in retirement?

It depends on your spending, other income, taxes, time horizon, and markets. Rules of thumb such as 4% are a starting point, not a plan. Our Withdrawal Simulator lets you explore different rates using hypothetical assumptions.

When do Roth conversions make sense?

Often in years when your taxable income is lower than it will be later, such as between retirement and Social Security or required minimum distributions. Conversions are taxable in the year you make them, so the decision depends on your current and expected future brackets. Review it with your CPA.

What is IRMAA?

The Income-Related Monthly Adjustment Amount is a surcharge on Medicare Part B and Part D premiums for higher-income beneficiaries, based on your income from two years earlier. Large conversions or realized gains can trigger it.

How do I get health insurance before Medicare?

Common options are COBRA coverage from your former employer, typically for up to 18 months, or an ACA marketplace plan. Marketplace subsidies depend on your income, which is why withdrawal and conversion decisions matter.

When is the right time to claim Social Security?

Claiming anywhere from age 62 to 70 permanently changes your monthly benefit. The choice depends on your health, other income, a spouse's benefits, and taxes. Our Social Security Optimizer lets you compare claiming ages.

Is retirement a good time to revisit company stock I still hold?

It is a natural time to revisit it. Once you have left, blackout periods often no longer apply (confirm with your former employer), though you still cannot trade while aware of material nonpublic information and former officers may remain subject to Section 16 for a period. Many people spread sales across lower-income years to manage the tax cost.

Plan your first years of retirement income

Book a complimentary 30-minute call to talk through spending, taxes, and what to do with any concentrated positions you still hold.

Talk to an Advisor

Not sure this is your situation? Find where to start or see our fees.

Guides for this situation

Safe Withdrawal Rates

A safe withdrawal rate is the share of a portfolio you can draw each year with a low historical chance of running out; 4% is a start, not a rule.

Sequence-of-Returns Risk in Retirement

Sequence-of-returns risk is the danger that poor markets early in retirement, plus withdrawals, shrink a portfolio more than the same losses later.

Roth Conversions: When They Can Make Sense and What They Cost

A Roth conversion moves pre-tax retirement money into a Roth IRA. You pay income tax now in exchange for tax-free qualified withdrawals later.

ACA Health Insurance for Early Retirees

Early retirees under 65 can buy ACA marketplace coverage; for 2026, premium tax credits end above 400% of the poverty line, so income timing matters.

Early Retirement Account Access: Rule of 55, 72(t), and Roth Options

Before 59½, the Rule of 55, 72(t) payments, and Roth contributions can avoid the 10% early-withdrawal tax. Ordinary income tax may still apply.

Managing Taxes on Retirement Withdrawals

Which accounts you draw from each year, and how much, affects lifetime taxes and Medicare premiums; the aim is often steadier taxable income.

Medicare Planning: Enrollment, Costs, and Income Surcharges

Medicare starts at 65; signing up on time avoids lifelong penalties, and higher incomes pay surcharges (IRMAA) based on tax returns from two years earlier.

Social Security Claiming Decisions

Social Security can start anywhere from 62 to 70; each year of delay raises the monthly check, and the higher earner's timing shapes survivor income.

Sources

This page is educational and is not personalized investment, tax, or legal advice. Rubric Advisors does not prepare tax returns or provide legal advice; tax and legal decisions are made with your CPA and attorney. Because our fee is based on the assets we manage, we have an incentive to recommend that you place more assets with us; see our Form CRS. Strategies described here are not suitable for every investor, involve risk, including possible loss of principal, and outcomes depend on your individual circumstances and market conditions.