Most people think of a move as one transaction. But in reality, it’s usually two: selling the home you have and buying the one you want. The hard part is that those two events rarely line up as neatly as you might like.
For most of our adult lives, our financial arrangement is simple. We go to work, and somebody pays us. Every few weeks, a paycheck appears. Then one day, if we are fortunate and have planned well, something remarkable happens. We retire. But the bills? They don’t get the memo.
Imagine you own a productive farm. You’ve owned it for years, cared for the land, invested in equipment and watched its productivity rise. Every year, your farm yields a crop. The harvest varies each year, but over time, the crop and its income have grown.
Now imagine that every morning, a stranger pulls into your driveway and offers to buy your farm.
When I started my career in Colorado in 1978, I wasn’t thinking about how different prices would be almost 50 years later.
Imagine playing Monopoly but never buying a property. Instead, you simply advance your token, collect $200 when you pass GO, pay rent and try to evade jail. It sounds ridiculous, yet that is how many people approach their financial lives. I think a useful investing lesson is hidden inside that cardboard box.
One of the great ironies of personal finance is that most people spend their working lives pursuing raises, promotions and bonuses, yet devote far less thought to creating an income stream that can continue growing after they retire.
I believe in the value of home ownership and regularly encourage it. But beyond a primary home, the financial picture muddies. Put simply: Some assets help fund your life. Others require that your life funds them.
As I write this column, the S&P500 is again hitting an all-time high. This isn’t unusual, all-time highs are much more common than they feel. But it leaves many near retirees with a nagging question: “What happens if I retire just before a bear market?”
There is an old saying on Wall Street that stocks climb a wall of worry. It persists for one simple reason: Investors constantly forget that markets do not require a peaceful world in order to advance. They require businesses capable of adapting, earning, innovating and growing … despite the worries.
Most people spend decades learning how to build wealth, only to discover in retirement that they must learn an entirely different skill: how to live from it.
Most investors don’t abandon a sound plan because it stopped working. More often, they get distracted by someone else’s results that seem better, faster or more exciting.
We often measure history by wars, presidents, elections and crises. While those events are relevant and notable, another story runs parallel: that of free people asking a simple question on repeat.
What is possible?
The greatest enemy of successful investing is not always inflation, recessions, elections, interest rates or even market declines. Often, it’s distraction: the shiny object promising an easier path; the belief in “something better” than patiently following a well-designed plan.
AI raises an important question, especially for any business that offers advice: What can technology do, and what can it never truly replace? I believe technology can provide information, but a good advisor provides understanding.
I’ve held many versions of this same conversation over the years. Sometimes they genuinely seek perspective. Other times they want reassurance that everything will be all right. Sometimes they’ve already decided what they want to do and hope an advisor will simply reinforce that choice. Those are three very different conversations.
Most people think of a move as one transaction. But in reality, it’s usually two: selling the home you have and buying the one you want. The hard part is that those two events rarely line up as neatly as you might like.
