Planning
John Stoj · October 7, 2026
My crystal ball is a lot like the Liberty Bell: cracked.
I’ve had plenty of chances to test it. In 2000, I day-traded the dotcom bubble with real money and a great deal of confidence, and I made just about every wrong move in the book. That was fun. Every time I’ve tried to outsmart the market, I’ve failed, and the market never noticed.
That’s not false modesty. It’s the one thing I’m sure about. Nothing I do will affect the markets. All I can control is how I react to them.
What nobody can tell you
Returns, interest rates, inflation, the next recession, the next rally: none of it can be reliably forecast. Someone will always explain, with great authority, why the market did what it did yesterday. Explaining yesterday is easy. Being, “right,” about tomorrow, repeatedly and early enough to profit, is another job entirely.
So a plan that needs a forecast to work has a problem before it starts.
What you might be able to tell me
Now try a different set of questions. Roughly when does your youngest start college? Is the house you live in the house you’ll retire in? About when would you like to stop working, and what does a typical year of spending look like? Might a parent need help within the decade?
You probably know more about those than about anything the Federal Reserve is going to do.
Is any of it certain? No. Jobs disappear. Health changes. Plans that looked settled at 45 look different at 55. But look at what those uncertainties are made of. They’re about your life, and you can describe them. You can say how likely an obligation is, how much its timing or amount can flex, what inflation will do to its cost, and what happens if the money isn’t there when it’s due.
That’s what I mean by, “knowable.” It doesn’t mean predictable. It means describable. And a describable obligation can be matched to an asset whose characteristics fit the job.
What my father knew
My father started buying stocks in the early 1950s. For most of his investing life he didn’t even have a broker; he purchased shares directly from companies, on a fairly regular basis, until he retired at 70.
Do you want to know how many times he sold stocks because of a market disruption? Zero. No times. None.
Why? Was it the statistics on market timing? Perhaps. He was an engineer, after all, but I never thought to ask him. What I do know is what he understood: it can always get worse, and even after it’s bad, even really bad, life goes on. He’d lived long enough to watch successful companies fade and new ones surprise everybody. He saved, he invested, and he stayed invested.
He didn’t have a forecast. He had a life he understood (a career, a long runway, a retirement at 70), and nothing in his plan asked the market a question. (His biggest, “losses,” by the way, came from the fees he paid the advisor I recommended. Mea culpa.)
What the institutions knew
When I managed money for institutional clients, including a large international insurance company, I didn’t spend my days worrying about the client’s cash flow needs. Other professionals handled those and gave me what I needed to match assets to liabilities. My job was to hit the portfolio’s return targets inside that structure.
In my experience, the work started with the obligations, not with a forecast of the market. A household is no different. The catch is that nobody hands it the schedule.
Happily, you can write one yourself.
What changes when the life leads
Here’s the quiet benefit. When the next few years of spending are matched to stable, liquid assets, and the long-term money really is long term, a bad market stops being a referendum on the whole plan. The money that has to show up soon isn’t waiting on a recovery. The money that has time, has time.
Most of the damage I’ve done to my own portfolio came from doing something. Jack Bogle’s advice was, “don’t do something, just stand there,” and if I’d heeded it, I’d be in a significantly healthier financial position. Standing there is a lot easier when the near-term bills aren’t standing next to you.
It’s also the point of the sequence of returns piece: money matched to a near-term obligation isn’t waiting on the market’s timing.
The short version
The market can’t be known. The life can be described. One of those is a far better place to begin.
This resource is part of the Asset Life Matching library. Start with What Is Asset Life Matching? →
Keep reading
Further reading
Christine Benz, Morningstar, April 2026. Benz treats underspending in retirement as a planning failure.
I chose these links because I think they’re worth reading. I have no financial relationship with the authors or their firms, and I’m not paid for them. Their views are their own.
Receive new resources, examples, and research related to Asset Life Matching.
No spam. Unsubscribe anytime.