Exit Planning Before Retirement | Seek & Find Financial

Picture a 58-year-old owner of a $13 million commercial landscaping company in Porter County. His crews roll out before sunrise. He's got snow contracts all winter and a waiting list for spring installs. When his CPA brings up exit planning before retirement, he laughs. 'I'm not retiring. Ask me again in ten years.' Fair enough. He loves the work, and the business is humming. But that answer hides an assumption I want to pull apart in this post.

I'm Dan Delaney, Founder & CEO of Seek & Find Financial, and I hear some version of that line all the time. It almost always comes from owners who genuinely like what they do. That's a gift. But 'I'm not ready to retire' and 'I don't need an exit plan' are two completely different statements. Most of the risk lives in the space between them.

Investing involves risk, including possible loss of principal. No investment strategy can ensure financial success or guarantee against losses. Past performance may not be used to predict future results. Provided content is for overview and informational purposes only, reflect the opinions of the author, and is not intended and should not be relied upon as individualized tax, legal, fiduciary, or investment advice.

This information is being provided only as a general source of information. These views may change as market or other conditions change. This information is not intended and should not be used to provide financial advice and does not address or account for an individual’s circumstances. Past performance does not guarantee future results and no forecast should be considered a guarantee. Please seek the guidance of a financial professional regarding your particular financial concerns.

Investment advisory services offered by duly registered individuals through Seek & Find Financial LLC, a Registered Investment Adviser. Licensed Insurance Professional.

Why exit planning before retirement isn't a retirement announcement

Let's stay with our landscaping owner for a minute. When he hears the word exit, he hears 'you're finished.' He pictures handing over the keys, a cake in the break room and a lot of empty Tuesdays. So he tunes out. Who wants to plan their own goodbye party when they're still having fun?

Here's the thing. An exit plan isn't a date on the calendar. It's a description of how strong you are on the day something changes, whether you chose that day or not.

Christopher Snider's book Walking to Destiny has a chapter called 'Changing Your Paradigm' that I come back to often. One idea from it fits this situation perfectly. Snider describes owner readiness as a stool with three legs. Pull one out and the whole thing tips, no matter how sturdy the other two are.

The three legs, with no retirement date attached

Leg one: the value of the business

Not what it earns for you each year. What it would be worth to someone else, and how much of that value walks out the door if you do.

Leg two: whether you're personally and financially prepared

Could your household keep its life intact if the business sold for less than you hoped, sold later than you planned, or didn't sell at all? That depends on what you've built outside the company.

Leg three: a real plan for life after you stop running things

Not a vague 'I'll travel more.' A picture of what you'd actually do with your days, your identity and your energy once the company doesn't need you every morning.

Notice that none of the three legs asks when. They're conditions, not deadlines. That's why they matter just as much at 50 or 58 as they do at 68.

What the stool looks like inside the landscaping company

Back to our owner. If we checked his three legs honestly, here's what we'd likely find. It's a pattern I see a lot in owner-led trades businesses.

On leg one, the value is real but fragile. He prices every commercial bid himself. The property managers and HOA boards call his cell, not the office. His operations lead is great with crews but has never sat across from a client.

On leg two, most of his net worth sits in the company and the equipment yard. Every good year, the profit went back into trucks, mowers and a new salt barn. His personal savings are thinner than anyone would guess from the outside.

On leg three, there's nothing. When his wife asks what he'd do if he stepped back, he says he'd 'probably still come in.'

Now imagine one of two things happens next spring. A back injury keeps him off job sites for six months. Or a regional consolidator that's been buying up landscaping firms calls with a real offer. In the first case, revenue wobbles because the bids stop. In the second, he can't really evaluate the offer, because he has no idea what number he needs or what he'd do the morning after closing. Either way, he's reacting. He's not choosing.

Why not ready to retire is the best time to start

I'd argue the owner who says 'not for ten years' is in the strongest possible spot. Time is the one ingredient you can't buy later. With a decade of runway, you can make changes slowly, test them, and fix what doesn't work.

Here's what ten years can do for each leg:

Develop a second person who can price, sell and keep the big accounts happy, so value doesn't depend on one phone number.
Move part of each year's profit into savings and investments you own personally, instead of sending all of it back into equipment.
Separate the real estate question from the operating business, so you know what each piece is worth and who might want it.
Run small experiments with your own time. Take a full week off in peak season. Notice what breaks and what you actually miss.
Write a one-page sketch of a normal Wednesday at 66. It sounds silly. It's surprisingly clarifying.

If you want the mechanics of the money side, our retirement planning guide for business owners walks through how owners can fund life after the company. For a broader view of the transition itself, the Exit Planning Institute's research on owner readiness is worth a skim.

How your family reads 'I'm not going anywhere'

When you say you're not retiring, you probably mean it as reassurance. Your family may hear something different. A spouse who has kept the books for twenty years may hear 'there's still no plan.' An adult son running a crew may wonder whether he's expected to take over, or whether he's allowed to say he doesn't want to.

Working on the three legs gives everyone something concrete to talk about. You're not announcing an ending. You're agreeing on what 'ready' would look like, so nobody has to guess. In my experience, that conversation usually lowers the temperature at the kitchen table rather than raising it.

Eighteen months later

Let's picture our landscaping owner a year and a half after that CPA conversation. He's still not retiring. He still shows up before the crews. But a few things have quietly changed.

His operations lead now prices the mid-size commercial bids, and two of the largest property managers have met her in person. He's putting a set amount into a retirement account and a personal investment account every year before he looks at equipment purchases. He and his wife have a single page describing what life might look like at 66, including the lake place and the grandkids' baseball games.

So when the consolidator calls again, he can take the meeting from a position of strength. He knows his number. He knows what he'd do next. And he can just as comfortably say no and keep running the company he loves. That's what exit planning for business owners is supposed to do. It doesn't push you out. It gives you the freedom to stay or go on your own terms.

Frequently asked questions

If I plan to work another ten years, what should I do first?

Start with the leg that would hurt most if it broke tomorrow. For many owners, that's leg two. Get a clear picture of what you own outside the business and what your household actually spends. Everything else gets easier once you know that number.

Won't my team panic if they hear I'm working on an exit plan?

They don't need to hear the word exit. They need to hear that you're building leaders, documenting how things work and giving people more responsibility. Most strong employees welcome that. It looks like growth to them, because it is.

Does planning now lock me into a sale date or a type of buyer?

No. Good planning keeps doors open. You might sell to a competitor, a key employee, a family member or no one at all. Strengthening all three legs supports every one of those outcomes. Talk with your CPA and attorney before you commit to any specific structure.

Check your stool before you need to sit on it

You don't have to be ready to retire to find out how steady you are. I offer a private one-on-one Three-Legs Check that looks at what your business would be worth to someone else, how prepared you are personally and financially, and whether you have a real picture of life after running the company. Just send the word STOOL through our contact page. If you get The Long View newsletter, you can simply reply STOOL. Seek & Find works with owners in roughly the $10 million to $20 million range, usually between 45 and 70 years old, from Valparaiso and Chesterton across Northwest Indiana and into the Chicago area.