Earlier in my career, before founding RWT, I was the president of a company and the man I reported to at the time was in his late sixties. This man sold his company to a new owner but was retained to keep working, and he evidently valued his time with his family, his kids and his grandkids, to such a low regard that he preferred to travel on Sunday mornings and early afternoons for the frequent Monday morning meetings he would book with clients and manufacturers across North America. His stated rationale was that flying out on a Sunday ensured he arrived on time, even though the vast majority of the places he travelled were easily reachable on a short early morning flight on a Monday that would have had him in front of his clients by mid morning at the latest. His logic never held up. I still think of this man sometimes and it makes me sad…sad that he preferred to sit on a plane, stay in mid level hotels, eat mid level food and drink even more mid level wine, over being intentional with the life he had left.

In a way, I understand it. There is a level of excitement that comes from the grind of being a founder…the early starts, the long days, the late flights, the business trips you tell yourself you don't want to go on but have secretly become very accustomed to, the constant solving of problems. There are reasons to drink unhealthy amounts of coffee (or worse such as red bulls), and reasons to eat poorly because eating well is simply harder when the demands of the role are high and when you eat out all the time. And maybe, even more secretly, there is the perfectly legitimate excuse to miss the event you didn't want to attend or to skip seeing the people you didn't want to see. The bigger the business gets, generally the more the excitement grows and the more excuses one has. One of our long-term clients is a textbook example of someone who loves the excitement. He finds reasons to work weekend after weekend, keeps a ruthless schedule and is constantly pushing to the max, and he has built a business worth many hundreds of millions of dollars. Why does that last detail matter? Because he does not need to push that hard anymore and he does it anyway.

Yet with that excitement comes a quiet detachment from others, because it is very hard to be a great partner, friend and family member when you are always on the grind. The grind is a frame of mind only a founder can really relate to. The detachment breeds isolation, and the isolation is only ever soothed by going back into the grind and filling the space with work friends and contacts. The spiral becomes one of quiet discontent, masked by the very thing that caused it.

More intoxicating still is the comfort that comes with feeling as though you have made it. The feeling of success, of control, of relevance, of being the team captain (or even having a team at all), of having status (both real and perceived), and maybe even the feeling of power itself, are all things a person gets used to far too easily. Sometimes they stop being feelings and quietly become your identity. For example, I recently had a conversation with a very wealthy client of ours who, at the end of every year, often books flight(s) to nowhere and back on the same day simply to preserve his Air Canada Super Elite status…a seemingly illogical act for someone whose business makes many millions of dollars annually.

In this fog of excitement and comfort it is easy to press on, year after year, without ever seeing the time go by. But strip the comfort and excitement away and a hard question bleeds through. What on earth will make you feel as needed, as secure and as alive once you sell your business? The question only gets more complex when you consider founders earning significant annual incomes. What could selling possibly provide that you do not already have?

For many, the notion of selling is less appealing than simply continuing on, right up until the very things that make the role exciting catch up with you, and at that point you are forced to sell or be buried with the company…an option that is not entirely unappealing to some.

But what is it all for?

The honest answer is that the ability to sell your company for many millions of dollars, to positively impact your family while you are still around to watch it happen, and to leave behind something that outlasts you, is the very thing most of us set out to build in the first place. It is just easily lost in the fog. You start forgetting what actually matters because you have become so focused on the comfort and excitement you have come to know.

So when the fog finally lifts and you begin to think about life on the other side of the deal, it is naturally a frightening thing to consider. Strip away the comfort and excitement and you are left with the image of a life slowly fading into the night, and that is a scary thought. It is easier, much easier, to avoid the thought entirely. There is always another year to sell. Next year will be the year…except next year is never quite right, and so the decision gets punted, again and again. I have had clients who have been waiting for the right time for more than thirty years, which tells you everything. The worst example I have of this is a client who had waited many years and finally decided to sell so he could spend time with his wife, the very person he realised he had so often chosen the business over, only for her to pass away two weeks before close. My point is that the option to sell later will always exist…but the fundamentals of your life can, and will, change.

But it does not have to be like that.

What most founders get wrong is the belief that selling is a step backwards. It is not. It is one of the largest steps forward you will ever take in your life. It trades the comfort and excitement of being a founder for freedom, and for the chance to live a life entirely by design with resources that very few people will ever experience. It is the ability to live on your own terms, to keep your influence, to string together a plethora of perfect days, to choose quality over the endless push, and most of all to build a legacy.

And here is where I want to return to the question I asked earlier…What will actually make you feel as needed, as secure and as alive once the business is gone?

Start with being needed. The grind tells you that you are needed. Every call routes to you. Every decision waits on you. Nothing of consequence closes without you in the room, and after enough years that feels like importance…like proof that you matter. But I sell companies for a living, and I will tell you what indispensability actually is. It is a liability you built with your own hands. A business that cannot run without its founder is not a tribute to the founder. It is key person risk, and it is one of the first things a sophisticated buyer prices out of the deal. The very thing that makes you feel needed is the thing that quietly discounts your multiple in diligence. So it is not just emotionally hollow…it is eroding the value of the asset you have spent your life building, year after year, while you mistake the erosion for proof of your own importance.

There are two kinds of being needed, and the grind only ever gives you one. There is need by design, where you have engineered an organization to depend on you, and there is need by choice, where someone needs you because it is you and no one else will do. The business needs you by design, and it will replace you the moment that becomes economical. That is not affection. That is dependency, and you are the one who arranged it. The grandchild waiting at the school pickup needs you by choice. One of those is a compliment. The other is a confession. The whole quiet work of a good exit is trading need by design for need by choice…before the business does it to you on its own terms.

Then there is the feeling of being secure. The grind says that security is the income. The cash flow, the control of the machine, the fact that your hand never leaves the wheel. I am holding the controls, therefore I am safe. But look closely at what that security is actually made of, because it is made of one thing only…you, never stopping. The moment your hand comes off the wheel, it ends. That is not security. That is a treadmill you have mistaken for solid ground, and the cruelty of a treadmill is that it feels like progress right up until you try to step off…trust me, my clumsy self fell off a treadmill and the impact was not pretty on my skin!

But here is the part most founders never let themselves truly consider. A founder earning two million dollars a year out of a single business he personally has to run is, by every measure an M&A advisor would actually use, in one of the most fragile financial positions imaginable. Total concentration in one asset. No liquidity. Complete dependence on one person staying healthy, motivated and present, forever. If a client brought me a personal balance sheet built that way, I would tell them plainly that it was reckless and highly risky. He calls it security only because he controls it, and somewhere along the way he confused control with safety. They were never the same thing. The income rich founder cannot afford to get sick. The capital secure founder can get sick, can step back, can disappear for a season or for a decade, and the floor holds. That is the entire difference, and it is the entire point of the event. Selling does not take your security away. It converts a security that is conditional on your permanent exertion into one that does not care whether you ever work again.

And alive? The grind hands you adrenaline and you mistake it for aliveness, but the two were never the same thing. Adrenaline is the body's emergency system left running as a daily setting. Real aliveness is presence…being fully inside a thing rather than half inside it while the phone buzzes on the table. It's being able to sit in a moment without distraction. The deal does not end the aliveness. It finally gives it somewhere honest to go.

That somewhere is what I refer to as legacy, and the beauty of it is that it can be nearly anything. For one founder it is being able to finally put family first. For another, it is half the year spent surfing, or it is finally getting fit, or the cottage where the family gathers every summer and builds a lifetime of memories, or the standing appointment to pick the grandchildren up from school. For others it is a family office built to back companies and founders they believe in, or a foundation built around a cause they cannot stop thinking about or one that has hit very close to home. Whatever it is, whatever you actually care about, the founders who exit well make that the centre of the life that follows. And it works. It delivers a sense of purpose that far surpasses anything the grind was ever able to offer.

Yet for many, the notion of a legacy draws as much concern as it does optimism. Why? Because beneath it sits a harder question than it first appears…will any of those so-called legacy items actually make me feel fulfilled, and will I be as good at chasing a legacy as I was at building a company? The answer is that founders are, by their very nature, exceptionally versatile. Think back to everything you did not know how to do when you started. You likely did not know how to read a financial statement, or hire a senior executive, or let a friend go when the business outgrew them, or sell…and you taught yourself every one of those things cold, with the stakes live, the clock running and no margin for error. That is the core founder skill, learning a foreign domain under pressure, and you did it again and again. A legacy is simply the next domain. And here is the part that should steady you…you get to learn this one under the opposite conditions. You learned the business the hard way, with everything on the line. You get to learn your legacy with resources, with time, and with the floor already holding beneath you. It may feel foreign at first, but you have done far harder things, under far worse conditions, and come through just fine.

So what happens to the comfort and the excitement? They are still there. If anything there is more of both. Founders who exit well are revered. They get asked to tell their story and explain how they made it, so the sense of accomplishment does not fade…it compounds. And they rarely leave the game entirely. They invest, they co-found, they advise, and through all of it they stay close to the action as the person CEOs and boards turn to. The status they once knew simply gets amplified. The excitement of the grind gets replaced by exciting personal pursuits that are more fulfilling and more honestly their own. After all, telling someone you are leaving for an epic fishing trip and telling them you are off on another whirlwind business trip draw two very different responses.

Which brings me back to the man who flew on Sundays. He had done the hard part. He had built the company and he had sold it…something that is very hard to do. And upon doing so, he was handed the rarest thing a founder can ever be given, time, which he did not know what to do with, so he quietly gave it back. He filled it with airports and mid level wine because the grind was the only language he had ever learned to speak. He is not a cautionary tale because he failed. He is a cautionary tale because he succeeded and never once decided what the success was for or what it actually looked like. He reminds me of the lion kept in a cage all its life that, finally given the chance to be free, simply stays in the cage because that is all it has ever known.

The work of a good exit is to refuse that cage…to recognize, while you still have the years and the health to live it, that the life after the deal is not the slow fade you fear but the widest and freest ground you will ever stand on. The deal is not the end of the life you built. It is the beginning of the one you finally get to choose.

Most founders only ever think about the life they already know. The ones who exit well learn to imagine the one that comes after.

Reece Tomlinson is the Founder and CEO of RWT Capital Corp. and the Author of Uncommon Capital

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