I was driving up Highway 35 in Onalaska early one morning when I saw the electronic sign: Retire on your terms.
I almost laughed out loud. What does that even mean?
Because if you’ve lived long enough, you already know the quiet truth: almost nobody actually retires on their terms. The terms keep changing on them.
Taxes rewrite themselves. Medicare premiums quietly rise when you take too much income in the wrong year. Affordable Care Act credits disappear the moment money moves outside the “right” account. Social Security rules shift depending on when you claim and how long you live. And every once in a while something completely off-script shows up — like a global pandemic — and blows the whole plan sideways.
You can have the perfect spreadsheet. You can have the perfect “number.” You can even DIY the entire thing with absolute confidence.
And still wake up one day realizing you cut the green wire when it should have been the blue one.
I’ve watched this play out for decades. People fall into two predictable camps.
Some are so terrified of running out of money that they never really enjoy the money they spent a lifetime building. They hold back. And hold back. And hold back. Until the only thing left is the fear itself.
Others — especially those without a pension — suddenly receive a large sum they’ve never had to manage in reverse. They know how to put money in. Money in, was automatic. Money out, is a completely different skill. And without the right combination, the spending accelerates faster than they expected. The fear of running out of money before they run out of life becomes very real.
Both groups thought they were retiring on their terms. Both groups discovered the contract had been rewritten, while they weren’t looking.
That’s why the slogan bothers me. It sells the aspiration while ignoring the fine print that actually decides the outcome.
Retirement isn’t a finish line you cross on your own schedule. It’s a series of moving targets that respond to tax law, health policy, market sequence, longevity, and pure randomness. The people who navigate it best aren’t the ones who insist on doing it alone. They’re the ones who finally admit they don’t know what they don’t know.
So, if the sign made you feel hopeful, good. Hope is useful. But hope without a second set of eyes is just a pleasant form of risk.
If you’ve never had a thorough look under the hood — or if the last “plan” you received was more brochure than diagnosis — maybe it’s time.
Schedule your Financialoscopy®. Because the only thing worse than not retiring on your terms… is not realizing it until the terms have already changed.