Start with your situation.

The position you don't talk about

There's a holding you've stopped mentioning — the stock that made you, or the one held so long that selling feels like a tax event and a betrayal at once. You know roughly what it's worth. What you don't know is what unwinding it costs at the wrong time, in the wrong state, in the wrong order — or what it quietly does to every other decision while it just sits there. It has been the elephant in your portfolio long enough that you've furnished the room around it.

Robert and Carol Fenton asked about moving. The answer was about the stock. Read their case →

The window that's open right now

You could retire. The math said yes a while ago — maybe years ago — and you keep not doing it, for reasons harder to say out loud than "one more year." Here's what nobody tells you about the waiting: the years between your last paycheck and your first required distribution are the most valuable tax years of your life, and every year the salary continues, that window stays sealed. The delay isn't neutral. It compounds.

Michael Greer waited four years past yes. Read his case →

The inheritance

Someone loved you, was careful for decades, and left you something — and now grief and paperwork share the same desk. Everyone says don't make big decisions for a year, and mostly they're right. But somewhere in what you inherited, a clock may already be running: an account with a deadline, distributions cheapest exactly while your life is paused. Doing nothing feels respectful. It isn't always free.

Tyler Novak asked if he could afford college. Read his case →

The equity that keeps arriving

Every vesting date, more of your employer lands in your accounts. Selling feels like a decision — something you'd have to justify. Holding never does. So it accumulates, and the company you work for gradually becomes the company your family is betting on, and you know that, and knowing it hasn't changed anything — because there is never a day when selling feels right. That isn't a discipline problem. It's a missing-system problem.

Sofia Park lived the expensive version. Read the case →

The exit ahead

The business is the largest number on your balance sheet and the least examined — because examining it means asking what it's worth without you, and when, and to whom, and who you'd be once it's sold. So the exit stays a someday. Meanwhile, roughly 80% of the outcome is being decided right now, in ordinary years like this one, by structure, separation, and tax positioning nobody is modeling.

Walt Brozek called about the company's 401(k). Underneath the request was the entire architecture of his exit — and how little of it was actually his. Read his case →

Or see where you stand in two minutes → Exit Readiness Snapshot.

The succession you can't finance

You are the business. Strip away the equipment and the lease and what a buyer is actually paying for is you — your judgment, your relationships, the reason clients stay. That's what made it valuable, and it's what makes it nearly impossible to hand off. The person who most wants to carry it on often can't afford to buy it; the person who could afford it doesn't want what it becomes without you in the chair. So the exit you've assumed was waiting at the end may not exist in the form you pictured — unless someone builds it, deliberately, years ahead.

Alan Reese chose the crisis-free life fifty years ago. The only crisis turned out to be leaving. Read his case →

The partners you built it with

You built it with people you trust — which is exactly why the hardest questions never got asked. What happens to a third of the company if one partner's marriage ends, or their health changes, or their attention drifts to the next thing? Right now the answer lives in goodwill and memory, not in a document. The arrangement works perfectly until the day one of you needs it to do something none of you ever wrote down — and by then it isn't a planning question anymore, it's a dispute.

Keystone's three owners funded everyone's future but their own. Read the case →

The people who outlive the plan

There's an age gap in your marriage, or a diagnosis in the family history, or a child who will still be young when you're not — some asymmetry that means the plan has to work hardest on the day you're not there to run it. You've done the responsible things. What you don't know is whether the documents, the accounts, and the strategy would actually hold together for the people inside them — or whether they're three separate plans that have never met.

David Calhoun brought this to us as a weight, not a question. Read his case →