There is a saying that has always resonated with me, that the two most important dates in your life are the day you are born and the day you realise why. The "realise why" part is the piece I am fascinated by. Particularly as it relates to founders and the decision to sell their business. Why exit? And what is your actual why? These are questions I face personally, and ones I watch so many of our clients wrestle with in real time.

What I notice most is that founders struggle with the "what is your why?" because many are under the impression that the business is their why. That part is easy to understand. But I would argue the business being your why is only a first level why, if there is such a term for it. It is imperative to understand the difference between the why that caused you to take such a big risk, to start your company and see it through to the stage you are at now, and the why you carry today. That journey almost always included major challenges, the kind that tested the very nature of who you are, tested your family, and pushed you to the brink.

Nearly every founder I have worked with has been through real trials and tribulations… there is a great saying in business that there are two types of founders, those who have gone broke, or nearly broke, and those who will. One founder I know told me how he could not afford groceries for his family because he had put everything on the line for his company… and this was only a few years before he sold that business for many millions of dollars. The risk founders take is extreme, but so can be the payout. Case in point, the story above. And so the initial why many founders carry is to prove themselves, to build something of real value, and to improve the lives of the people they love… and simply to venture into that equation is scary. Scary because it asks you to trade a good enough existence for the possibility of a great one, with the emphasis firmly on possibility.

Yet as founders find success, it is common for the why that first sent you down this otherwise impossible path to become the why that underpins your identity. Your why shifts from building a business to being the owner, the founder of the business… which is to say it is no longer a growth mindset but a plateau state. And this plateau state is where most founders find comfort. I have seen it cause great deals to fall apart… these founders choose good enough because it felt less scary than choosing to level up. One US founder we worked with, in his early seventies at the time, had built an electrical control and instrumentation business to the point where it was generating $1.25 million in EBITDA a year. He was then presented with a once in a lifetime offer from our client, the buyer, who wanted a presence in Texas, where the business was located. The challenge was that this founder was the business… he had made many of the classic mistakes a founder can make, but he had also built some core capabilities that our client wanted strategically. Our client offered him $7.5 million for the company, all of it in cash, with only a six month requirement that he stay on through the handover, because he had told us he could never work for anyone. Yet a week before close, he collapsed the deal. I spoke with him at length about legacy, about how at his age this amount of money was game changing for his ability to make a difference, to leave something real for his family or for a cause he cared about… but it did not matter. He shrugged at the idea of his family benefiting from everything he had built, and he shrugged off the chance to help others. What was clear was that his identity was bound entirely to the business.

For many founders, the only way to move past the business being your why is to make the intentional decision to choose something greater instead. That something greater is your legacy. To determine the real reason you were born. Which, after working with hundreds of founders through their M&A journeys, I am convinced is about more than simply making money and "being" a founder. Money is a vehicle, it is not the destination. And so the decision to live a life by design, to choose your legacy, is the most important decision a founder can make.

Why is this? Because the legacy you choose, fueled by the millions of dollars made after selling your business, is a blank slate. One that you get to decide. One filled with freedom, with the ability to make a difference in the lives of the people you love, to have adventures, and most of all to create the future for you and your family. That is a gift few people ever receive. The sad part, however, is that most founders fail to see it as a gift at all. They see it as a curse. They see selling the business as a loss of identity, the loss of all the wonderful, ego boosting parts of being a founder, a loss of self.

It is hard for people, generally, to trade a good life for a great one. You see it in people who stay in mediocre marriages because things are "not bad enough to leave." You see it in people who never start the company they dreamed of because it was too frightening to imagine life without a steady paycheque. And you see it in people who fail to take care of themselves physically, because it is harder to be healthy than not.

Founders, though, have already built this muscle, even if they do not always know it. They built it the day they entered the fray and chose to take the leap. To risk something good for something great. This is worth remembering. The life you know as a founder can be fabulous, exciting, status driven… a serious boost to the ego… but life on the other side of the deal offers something far more fulfilling. That is, if you switch your mindset from building a business, from being a founder, to being someone who is building a legacy. And a legacy has power.

What that legacy is differs for everyone… and there is no wrong answer. I have had clients go on to start family offices, generating long term wealth for their children and their children's children. I have had clients buy homes in several cities around the world and simply spend time with the people they love, in beautiful places. And the list goes on, often woven together from several pieces that make up the whole. Building a legacy is not an easy thing to do. It requires intentionality. But when you pair an innate ability to navigate serious complexity and uncertainty with a desire to live an even better life, the freedom to actually do it, and the many millions of dollars that come with an exit, you have an equation that very few people in this world ever get to unlock. Most are limited on one or more of these fronts. The legacy they desire remains, as Bob Marley sang about peace in the song "War," a fleeting illusion to be pursued but never attained… and for the record, I love Bob Marley, particularly on a beach, and even more so with a pina colada in hand!

The point is that founders hold a gift, within themselves, in their innate abilities and hard-earned experience, and in the wealth they have built, that far surpasses what is available to 99.99% of the world's population. They can build their legacy, and they will, if they so choose.

So this raises an important question. How do you choose your legacy? The answer is not as complex as you might think. What I have seen, in the founders I have watched struggle with this, is that it starts with spending real time on what you want your life to look like in five, ten and twenty years… what you want it to mean, and what you want it all to have been for. To make that easier, I suggest founders look at their legacy from a six angle perspective. I ask them to picture the life they want across each of these categories, and what legacy means within each. In some cases a specific angle may mean nothing, or simply not apply… but within each, I ask founders to list one to four outcomes that would make their legacy real and meaningful, both to them and to those they love, or hope to love in the future.

The legacy wheel — six angles on a life by design

1. Family – What does your family legacy look like? What do you want it all to be for?

2. Self – What do you, as a human, want from your legacy? Think health, adventure, fulfilling the passions you never had time for.

3. Business and Wealth – How involved do you want to be in business or wealth management going forward? Do you want to do another venture, or simply invest and advise other founders as they go down the path of building their own dreams?

4. Experiences – What experiences make up your legacy? Is it travel, climbing mountains, sitting in the world's finest restaurants?

5. Community and Others – What will your contribution to your community, or to the causes you care about, look like?

6. Spiritual – If you are spiritual or religious, what does your legacy look like in this regard?

When reading this, you likely notice that these angles are interconnected, and so it is important to prioritize the points that are most poignant, the ones that feel right in your heart. Most legacies are not single-faceted. You can be an amazing parent, build a family cottage that creates years of memories with family and friends, and at the same time get involved in your community or build a family office to fund other ventures. The only caveat is that with age comes less time to action it all, and so for some of our baby boomer clients, the emphasis often falls on the items that carry the most immediate impact.

The next step is to build out a map of what this looks like. Visualize it, write it down, draw pictures. Think about what this future legacy looks like, feels like, even smells like. Using the cottage as a reference, what is it like to sit on the dock with a coffee and listen to your kids play.

When you know what your legacy looks like, moving forward becomes easier, because now you can move towards it with intention. And the way to do that is simple. You make it happen… just like you did with your business. There will be new things to learn, but you will overcome them, and on the other side of the deal is something almost everyone wants and almost no one gets to build. But you can.

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

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