Beyond the income plan
The return you keep is the only one that matters.
What tax-smart investing means here
Tax-smart investing means managing the tax cost of a portfolio, not just its returns. In practice that is three things: harvesting losses to offset gains, holding each asset in the account type that taxes it least, and withdrawing in an order that keeps you out of higher brackets.
Tax-loss harvesting
When a holding in a taxable account falls below what you paid, selling it creates a realized loss that can offset gains elsewhere — and, up to a limit, ordinary income. You immediately buy something similar but not substantially identical, so you stay invested and your allocation does not change.
Done consistently across a long retirement, this builds a reserve of losses you can use later, including in the years you are unwinding a concentrated position.
Asset location
The same portfolio can produce different after-tax results depending on which account holds what. Assets that throw off ordinary income are usually better inside a tax-deferred account. Assets with favorable long-term treatment often belong in the taxable account.
Withdrawal sequencing and Roth conversions
The years between retiring and starting required minimum distributions are often the lowest-tax years of someone's life. Filling up a low bracket with Roth conversions in those years can reduce the tax on decades of future withdrawals.
It can also backfire if it pushes you into a higher Medicare premium tier, so we run the numbers before any conversion.
Questions
Common questions
Selling an investment that has fallen in value to realize a loss, then immediately buying something similar so you stay invested. The realized loss offsets capital gains and, up to an annual limit, ordinary income. Your allocation does not change — only your tax bill does.
If you buy a substantially identical security within 30 days before or after selling at a loss, the loss is disallowed. This is why harvesting requires care about what you buy as a replacement, and why it must be coordinated across every account you hold, including a spouse's.
Often yes, in the window between retiring and starting Social Security and required distributions, when your taxable income may be unusually low. How much depends on your bracket, your Medicare premium tier, and what your future distributions will look like.
Also
The rest of what we do
Retirement Income Planning
Concentrated Stock Strategies
If a large share of your net worth sits in a single stock, you may have a difficult time getting out of the stock without an unplanned tax bill.
Private Markets & Alternatives
Private markets can add something a public portfolio cannot.
Let us find out what your portfolio can actually pay you.
Thirty minutes to see where your income will come from. If we are not the right fit, we will tell you.