I recently finished my 22nd year at Glidewell.
Twenty-two years.
Which is wild, because I’m 44 years old…that’s half my life.
When I started in insurance, I had absolutely no idea what I was doing. And if we’re being honest, there are still days when I’m not entirely sure. I didn’t grow up dreaming about insurance. Nobody does. There was no third-grade career day where little Brandon stood up and said, “Someday I want to explain deductibles and out-of-pocket maximums to people.”
But somewhere along the way, this became more than a job. It became a career. Then a calling. And eventually, a huge part of my life.
I’ve watched this industry change. I’ve watched Glidewell change. I’ve watched myself change. I’ve gotten things right. I’ve gotten plenty wrong. And after 22 years, I’ve learned a few things.
Actually, I came up with 22.
Convenient.
Here we go.
1. People don’t buy insurance. They buy peace of mind.
Nobody really wants an insurance policy. They want to know their family is going to be okay, their business can survive something terrible, and when life punches them in the face, somebody is going to answer the phone. The policy is important, but it’s ultimately just the tool. What people are really buying is some confidence that when the unexpected happens, they won’t have to face it alone.
2. The policy matters. The relationship matters more.
You can know every product, every carrier and every line of coverage, and you should. But after 22 years, I’m convinced that people still do business with people. When I think back over my career, I don’t immediately think about policies I’ve sold or accounts we’ve written. I think about people, conversations, friendships and relationships. Those are the things that have made this career special.
3. Price gets attention. Trust keeps clients.
Someone will always be cheaper. Always. If your entire value proposition is price, you’re building a relationship that lasts exactly until somebody finds a lower number. Trust is different. When people believe you know them, care about them and will tell them the truth even when the truth isn’t necessarily good for you, that relationship becomes a whole lot harder for a competitor to replace.
4. Cheap insurance can get really expensive.
Everybody loves saving money. I do too. But saving $12 a month feels a lot less exciting when you discover what you gave up to get it. Price absolutely matters, but it can’t be the only thing that matters. Sometimes the cheapest option is cheap for a reason, and unfortunately, you often don’t discover that reason until you need the coverage.
5. Nobody cares about insurance until they REALLY care about insurance.
Most days, nobody wants to talk about insurance. Then there’s a fire, an accident, a diagnosis, a death or a lawsuit, and suddenly the thing nobody wanted to talk about is the only thing they want to talk about. Those moments have reminded me over and over again that what we do matters, even when it doesn’t always feel exciting on a random Tuesday afternoon.
6. Ask better questions.
Early in my career, I thought my job was to have answers. Twenty-two years later, I think a huge part of my job is asking better questions. What are you worried about? What are we missing? What matters most to you? What happens if this goes wrong? I’ve learned that the quality of the solution usually depends on the quality of the questions we were willing to ask first.
7. If your client doesn’t understand it, you haven’t explained it.
Insurance people are good at speaking insurance. The problem is nobody else speaks insurance. We have acronyms for our acronyms, and sometimes we wear complexity like a badge of honor. But our job isn’t to impress people with how much we know. Our job is to take something complicated and make it understandable. If a client walks away more confused than when the conversation started, that’s on us.
8. Sometimes the best sale is the one you don’t make.
This one took me a while. Not everyone needs what you’re selling, not every prospect needs to become a client, and not every dollar of revenue is good revenue. Sometimes the most valuable thing you can tell someone is, “You don’t need this.” You might lose a commission today, but you’ll gain something far more valuable over the long run: trust.
9. Claims are where the promises get tested.
Selling insurance when everything is going great is easy. The real test comes when someone needs it. That’s when all those conversations, recommendations, exclusions, deductibles and decisions suddenly become very real. A claim has a way of revealing whether we did our job well on the front end, and it’s also where we have one of our greatest opportunities to show clients exactly why they chose us.
10. Bad news does not improve with age.
Rates are going up. A carrier is leaving. Coverage is changing. We made a mistake. Whatever it is, pick up the phone. Waiting three weeks and hoping the conversation magically gets easier is not a strategy. I’ve learned that people can handle a lot of difficult news when you’re honest, proactive and willing to help them figure out what comes next. Avoiding the conversation almost always makes it worse. Ask me how I know.
11. People remember who showed up.
I doubt many clients remember the brilliant insurance explanation I gave them in 2011. But people remember who answered the phone when their world fell apart. They remember who called them back, who sat with them through the mess, who followed up when they didn’t have to and who cared about what happened next. Showing up isn’t complicated, but it matters more than we sometimes realize.
12. Our job is to make complicated things simple.
Insurance is complicated enough without us making it worse. Knowing all the technical details is important, but dumping all those details on a client doesn’t necessarily help them. The goal isn’t to demonstrate how much we know. The goal is to help someone understand what they need to know so they can make a good decision. There’s a big difference between the two.
13. Automate the process. Never automate the caring.
Technology should make us better at relationships, not give us an excuse to avoid them. AI, automation, texting, client portals and all the tools coming next can make us faster, smarter and more efficient, and I’m all for it. But the goal should be to use that efficiency to create more space for the things technology can’t replace: listening, empathy, trust and real human connection. If technology saves me 20 minutes, I don’t want to use those 20 minutes to become less available to people. I want to use them to be more available. Let technology handle the things that don’t require a human, so we have more time for the conversations that matter.
14. The best salespeople I know listen more than they talk.
Which is unfortunate for me because I really enjoy talking. But the older I get, the more I notice that the most successful people I know are incredibly curious. They listen. They ask the second question, and then they ask the third. They aren’t just waiting for their turn to talk or trying to steer every conversation toward a sale. They want to understand the person sitting across from them.
15. Calling people back is apparently a superpower.
Want to stand out? Return the phone call. Answer the email. Do what you said you were going to do. Follow up when you promised you would. I wish there were a more sophisticated secret I could share after 22 years, but there really isn’t. Reliability has become strangely remarkable, and simply doing what you say you’ll do will take you a long way in this business.
16. Retention starts the day after the sale.
You don’t earn a renewal when the renewal shows up. You earn it all year. Every phone call, email, claim, question and interaction either adds a little bit to the relationship or takes a little bit away. If the first meaningful conversation you’ve had with a client in 12 months is explaining why their premium increased, you’ve probably waited too long.
17. A “book of business” is actually a book of people.
We love numbers in this business: premium, revenue, retention, policies, loss ratios and commissions. Those numbers matter, but there’s a human being behind every row on that spreadsheet. There’s a family, a business, an employee and a story. Growth is important, but I never want us to become so focused on the numbers that we forget the people those numbers represent.
18. You don’t need every client.
There was a time when I thought every opportunity had to become a sale. Nope. Some people aren’t a good fit for us, and sometimes we aren’t a good fit for them. That’s okay. The goal isn’t to work with everyone. It’s to do really good work for the people we can help. Learning to say no to the wrong opportunities gives you a lot more capacity to say yes to the right ones.
19. Reputation compounds.
Your reputation isn’t built in one giant moment. It’s built in thousands of tiny ones. Did you call back? Did you tell the truth? Did you admit when you screwed up? Did you keep the promise? Did you do the right thing when nobody was watching? Make enough of those decisions over 22 years and they start adding up. Your reputation might be one of the most valuable assets you’ll ever build, and unlike an insurance policy, there’s no easy way to replace it when it’s gone.
20. Everything changes. People really don’t.
I’ve watched technology change, carriers change, products change, markets change and regulations change. AI is going to change this industry again, probably in ways we can’t fully imagine yet. But humans still want the same basic things. We want to be heard. We want someone we trust. We want someone who can look at a complicated situation and help us understand what happens next. I don’t think that part of this business is going anywhere.
21. Insurance is the tool. Health is the goal.
This has become a big part of how we think at Glidewell. Yes, we sell insurance, but insurance isn’t the destination. It’s a tool. The bigger question is whether the people, families and businesses we serve are healthier because we’re in their lives. Financially healthier. Physically healthier. Organizationally healthier. Better prepared and more confident about the future. That’s a much bigger mission than simply selling another policy.
22. I still don’t know what I’m doing.
Okay, that’s not entirely true. I know a lot more than I did 22 years ago. But when you’re young, you think experience means eventually reaching a point where you’ve figured everything out. Then you get some experience and realize the opposite is true. The more I learn, the more I realize how much there is left to learn. And I love that. I hope I never reach the point where I think I’ve got all the answers, because curiosity is a whole lot more useful than certainty.
Twenty-two years ago, Glidewell gave me an opportunity. I had no idea where it would lead. I couldn’t have imagined the people I would meet, the friendships that would come from it, the mistakes I would make, the lessons I would learn or the doors that would open because of this little industry called insurance.
And here I am, 22 years later. Still learning. Still screwing things up. Still asking questions. Still trying to get better. And incredibly grateful that I get to do it with people I care about.
Twenty-two years. Thousands of conversations. A lot of mistakes. A lot of lessons.
And I’d still choose this industry. Because at the end of the day, it was never really about insurance.
It was always about people.