Essay•Retirement & Income Planning
The quiet first year of retirement.
The decisions that shape the next thirty years get made in the first twelve months, before the calendar fills up.
Education Archive
Ideas, conversations, and guidance for thoughtful retirees.
A curated library of essays, conversations, and retirement insights designed to help thoughtful people make better long-term decisions.
Essay•Retirement & Income Planning
The raise nobody applauds.
After fifteen years of safe money paying almost nothing, the market finally raised its wage. What that quietly gives a retirement, and what it asked for on the way in.
Essay•Widowhood
The reset you did not ask for.
When your spouse dies, the tax on a lifetime of investment gains is largely forgiven. What resets, what does not, and why it quietly buys you time.
Essay•Widowhood
Choosing a financial advisor after you lose your spouse.
What actually matters when you are ready for help, and how to tell who is on your side from who is only selling.
Essay•Widowhood
The money mistakes that follow a loss.
The financial mistakes widows and widowers actually make are mostly one mistake wearing different clothes. What can wait, what cannot, and how to tell the difference.
Essay•Widowhood
What needs you, and when.
A calm checklist for after a spouse dies: what matters this week, the calls that fill the first month, the paperwork of the season, and the decisions that should wait a year.
Essay•Retirement & Income Planning
You were never your job title.
For forty years, what you did was a complete answer to who you are. Retirement is the morning that answer goes quiet, and you learn how much of you was the title.
Essay•Retirement & Income Planning
The firm I would have wanted for my friend.
The real origin of Considerate Capital, and what a friend taught me about what this work is actually for.
Essay•Retirement & Income Planning
Why I made this show
A note on what A Considerate Retirement is for, and why I made it the opposite of the money media that only wants to sell you a product or scare you into it.
Essay•Retirement & Income Planning
When the blues does not lift.
Most low moods in retirement are the ordinary kind, and they lift on their own. A few are something else, and telling the difference in time is the part worth getting right.
Essay•Retirement & Income Planning
What your bonds are actually for.
After a hard couple of years for bonds, the useful question is not whether to own them, but what job you are asking them to do.
Essay•Retirement & Income Planning
What a CFA charterholder actually is.
Of all the initials in finance, these three are the ones worth understanding. Here is what the CFA charter takes to earn, what it teaches, and what it does not promise.
Essay•Retirement & Income Planning
Two million dollars is not a yes or no.
Whether you can retire at sixty depends far less on the size of your portfolio than on one number you actually control.
Essay•Retirement & Income Planning
Three million at sixty is a two-part retirement.
Whether it carries you depends less on the number than on the seven years your portfolio works alone, before Social Security arrives to share the load.
Essay•Widowhood
The widow's penalty.
Why a surviving spouse can owe more tax on a smaller income, and what the two of you can do about it ahead of time.
Essay•Retirement & Income Planning
The shape of a retired day.
Work handed you a schedule whether you wanted one or not. The morning that stops arriving is a quieter problem than people expect, and the fix is a rhythm you build rather than one you are given.
Essay•Taxes
The order you draw from your accounts.
After a lifetime of saving, no one teaches you how to spend it down. The order you choose is quietly a tax decision.
Essay•Retirement & Income Planning
The loneliness no one plans for.
No one budgets for it, but retirement can quietly shrink the week's human contact down to almost nothing. This is why that thinning matters to your health, and how the connection gets rebuilt.
Essay•Retirement & Income Planning
The dip is a stage, not a verdict.
The first year or two of retirement has a rough emotional arc: a giddy high, often an unexpected low, then a slow settling. Knowing the shape is what keeps the low, when it comes, from feeling like a mistake.
Essay•Taxes
The trust that bets on your marriage.
A SLAT lets a married couple pass more to their heirs and pay less estate tax, while one spouse can still draw on the money. In return, the gift is permanent, with no taking it back.
Essay•Retirement & Income Planning
Retiring into the same house.
Two people can love each other for thirty years and still have no idea how to share a Tuesday. Retirement is the morning you both find that out, with all the hours arriving at once.
Essay•Retirement & Income Planning
The order of your returns matters more than the average.
Two retirees can earn the identical average return over the same years and still end up in completely different places. What separates them is when the bad years land, not how bad they are.
Essay•Retirement & Income Planning
How to choose a financial advisor.
Behind the wall of credentials, a few plain things separate real expertise from good marketing, and one thing no credential can prove.
Essay•Retirement & Income Planning
How I got into the room.
At twenty-three I talked my way into a firm that had never posted a job. What got me in is the same thing worth looking for in anyone who wants your trust.
Essay•Retirement & Income Planning
Five million is rarely the hard part. Fifty-five is.
Whether five million carries you from fifty-five depends far less on the number than on the ten years before the safety nets arrive.
Essay•Taxes
The four-million-dollar line.
Most people think the estate tax is a problem only for the very rich. In Illinois, an ordinary home and retirement savings can cross the line.
Essay•Retirement & Income Planning
A retirement needs somewhere to go.
You spent thirty years planning the money. The part almost no one plans is what the mornings are for once the work that filled them is gone.
Conversation•Retirement & Income Planning
What your bonds are actually for.
After a hard couple of years for bonds, the useful question is not whether to own them, but what job you are asking them to do.
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