Experience Is a Wonderful Teacher.
By Brian Wheeler, Director of Wealth Management & Business Brokerage
The Problem Is That Life’s Biggest Financial Decisions Rarely Give Us the Opportunity to Practice First.
The Reality of Once-in-a-Lifetime Moments
A colleague and I were talking this week about a friend who’s preparing to become more involved in her mother’s business. Her mother is in her eighties, still active in the company, and like many successful business owners, has spent a lifetime building something that’s much more than a source of income. It’s part of her identity.
Naturally, the conversation has begun to shift toward the future. At some point they’ll need to decide how ownership should transition, what roles each of them wants to play, and what the next chapter of the business should look like.
As we talked, one thought kept coming back to me: why would anyone expect themselves to know all of their options the first time they face one of life’s biggest financial decisions?
They’ve probably never been here before.
The more I thought about it, the more I realized this isn’t really a story about business succession. It’s a story about life. Most of us only retire once. We sell one business. We become an executor for the first time. We help aging parents navigate difficult financial decisions. We settle an estate. We transition a family business. These aren’t decisions we make every year. They’re once-in-a-lifetime moments.
Yet we often expect ourselves to know exactly what to do. Over the years, I’ve come to appreciate something that’s both simple and easy to overlook.
Experience is a wonderful teacher. The problem is that life’s biggest financial decisions rarely give us the opportunity to practice first.
Discovering the Questions We Need to Ask
That’s why I find it interesting when people hesitate to ask for another perspective because they think they should already know the answers. In reality, the greatest value often isn’t someone giving you the answer. It’s someone helping you discover questions you didn’t know needed to be asked. I’ve found that clarity doesn’t usually come from having all the answers. It comes from asking better questions before important decisions become permanent.
I’ve watched business owners learn there were succession strategies they never knew existed. I’ve seen families discover tax opportunities after decisions had already been made. I’ve watched people realize there were more flexible ways to transfer wealth, protect a business, or care for the next generation than they ever imagined.
None of those people made mistakes because they weren’t intelligent. They simply hadn’t been there before. The longer I’ve been doing this, the less surprised I am by what people don’t know. I’m much more surprised by how often they assume they’ve already seen all of their options.
The True Value of Experienced Advice
That’s one of the reasons I believe experienced advice has value. Not because someone else should make your decisions, but because they’ve helped many other families through similar moments. Experience doesn’t replace your goals or your values. It simply helps you make important decisions with a broader understanding of the possibilities in front of you.
Here’s something I’d encourage you to think about this week: is there an important financial decision on your horizon that you’ve never faced before?
Maybe it’s retirement. Maybe it’s selling a business. Maybe it’s helping aging parents.
Maybe it’s updating your estate plan or preparing the next generation to carry on something you’ve spent a lifetime building.
If this is the first time you’ve faced that decision, don’t let it also be the first time you’ve explored all of your options.
Ask questions. Seek perspective. Have conversations with people who’ve walked this road many times before.
One of the most rewarding moments in my profession is watching someone realize they have more options than they thought they did.
Sometimes that realization changes everything. And sometimes, it begins with a conversation they almost never had.
