10 Sept 2025 · 6 min
Bill Gallagher argues that business owners who put off exit planning until later face unnecessary complications. He uses stories and examples to show why waiting until "someday" leaves you scrambling when the time comes. Start planning your transition now, not when you're forced to.
Hmm.
Someday is a bad exit plan for you and your business. I've met an awful lot of leaders over the years who want to not think about that right now. They'll think about exiting the business, about selling it, about whatever, someday. And it turns out someday is a really, really bad target date. So I'm going to tell you all about that and personal story, client story. I've got some stories, some examples for you, some, some experience to share and I'll give you some things to think about that hopefully will change your mind. So for most people, someday, if your plan is to SoMeday exit, there's two things that are going to bring that up. One is you're going to realize you've gotten too old and it's time. Problem is that then you may not have the energy, the health, the like, whatever to do that.
Right.
We never know what our path in life is like how our health is going to be. And if you wait until that moment arrives that pushes you to do some action, it could be a real problem. The other one is like, there's a crisis and like you're just long enough, you don't want to tackle that crisis again. Running a business is always filled with crises and then one day it's one crisis too many, which happened to somebody very close to me. So here's the deal. I was to coach this guy, I'll just call him Thomas, so that he doesn't like have to deal with the scrutiny of that. But Thomas got referred to me by another friend who thought he could use our help and great and like, help stand up his team and set up his exit and transition the business, sell it, turn it over to the employees, some kind of plan. But it became clear because Thomas was now turning 70 and he was feeling tired. He was feeling like he wanted more time to do other things in life. But now all of a sudden, right. It became really urgent. So as Thomas is turning 70, he reaches out to someone who connects me and then we go to work on it. Now we go to work on the kinds of things to get the company running smoothly, to detangle a very hands on founder who'd been around there for decades.
Right.
So that's a problem though, because we haven't groomed all those people for some day. They're not thinking about, I'm going to do this role, I'm going to do that role when Thomas moves on, how am I going to run? How do we get Thomas's specific roles taken out of the business? So we're pushing on and implementing things, you know, good practices around execution, clarity around the vision. Distilling out processes from organic, like sort of known within, tribally known kinds of things to things that are actually codified that we could transition, that we could hand over to another person so that the process continue. Not only the processes that Thomas is directly involved, the. The ones that he's indirectly involved, where the people aren't really leading fully, strongly, because he's always been there.
Right.
And it's a small enough company, so the company's definitely worth something and has something really unique in their field. West coast company, really great product, fun, great, loved in the world. Decades of history, good outlook for things. Doesn't look like it's going to get knocked out by some new technology or whatever. So lots of good opportunity. Except Thomas hadn't been building this for decades. He'd just been thinking about it, about it someday. Well, the challenge then became that as much as we tried to do things, there was resistance both by the team, but also by Thomas, because now they're creatures of decades of habit. And we're trying to interrupt those habits to detangle the founder from the company so that it could either be passed on, sold to the employees, or sold to a third party or some combination of those things. That is very difficult. That process that could have taken a year or two ended up taking more than six years and not for the same. Now think about that like you want to do this. You're approaching 70 now. You're 76. You're finally selling the business. Right. That's a lot of lost years at a time in life where you really, you know, you're starting to treat those years as really precious. Right. There's real impacts on a company in running something in that way. So I don't know, like, if you have a young family now or if you're just telling or if you feel like you're just building it or whatever, but thinking right now about what are you going to do and when are you going to get out of the business? And laying from day one or today, right from when you found it or from right now declaring, I'm going to sell the business at this point.
Right.
And don't set it far out in the future, set it sooner, and then consider, and then start working on the exit even now, at the early stage, lead it up someday this company will be yours. Someday you could be like that creates a whole different environment in the business. Thinking about your exit from the business and then creating something that lives beyond you. So After I've left, after I've sold this company, after I've turned it over to you, like whatever it is I imagine this for, and I'm creating that future that's beyond my own role in it, that's a powerful thing to be doing. So thinking about the exit now, here's one other thing. If you create a future for the business that you're working towards, you start to have evidence for it and you start to trend up. You now have a good story and you have evidence. So a good story about the future, like a vision inspires people to work with you, buy from you, invest in you, like all that kind of thing. If you give evidence to it by starting to trend on that future vision, start to move towards it in, like, what looks like a line to it, your company's actually really valuable in that moment. It's valuable far beyond the fundamentals, the. The simple multiple of profit that you might have now. The value is based more on where people think you're going and how credible that is. So a big future with that will make a huge difference. I encourage you today to think about what are the conditions, what do you really want? And start to get out of it. Untangle yourself from the business as quickly as possible. I hope that's helpful. I hope it makes a difference for you. I hope you take these words and get onto it. Now, the companies that I worked with that do this, it makes an enormous difference.
