Afterword
The story is finished. What is left is shorter, and it is about you.
There is a morning coming that nobody warns you about. The firm finally runs without you holding it up. The data room stays ready, the quarterly report goes out without your edits, someone else takes the call you used to take, and you wake up and the morning is yours. Most founders meet that morning alone, and later than they would like. I want you to meet it ready.
A question shows up in the quiet, and you may already know which one. Maybe you have been carrying it for years, or outrunning it. Maybe it is arriving for the first time.
Who am I now, when the firm no longer needs me to hold it up?
I will keep this plain. It is the same honest look you learned to take at the firm, pointed at yourself and held to the same standard. You got good at seeing the firm as it actually was, even on the days you wished otherwise. This is that look, turned inward.
The hardest underwriting any operator does is the underwriting of his own need. I have carried that line for years, because I have watched a lot of good CEOs put off that underwriting for a decade, and I have put it off myself, more than once.
Most founders have already done a partial version of it. It usually comes attached to a partner: the conversation that should have happened years earlier, the relationship the firm outgrew and kept on the books because underwriting your own need to hold on to it was harder than letting it go.
The version waiting at the end is harder. Mine took close to two decades to run. I spent them climbing, through about $3 billion of principal-side transactions and experience as a CIO, and every rung was supposed to be the one that finally felt like enough. None of them did, because what I needed from the climb had nothing to do with titles. I was outrunning the imposter, and no accomplishment ever settled that account. The underwriting finally ran at forty, when I stepped off the ladder to invest and advise on my own and found no next rung to put the question off with. Clayton Christensen’s question, how will you measure your life, stopped being the title of a book and became a question for an ordinary Tuesday.28
What do you need from the next twenty years? The firm’s needs, the platform now handles. The investors’ needs, the reporting handles. Your family’s needs are their own conversation, and a good one to have. The question that is left is yours alone, and for once nobody is waiting on the answer but you.
There is a test I trust for any deal memo: a stranger reading it should be unable to tell whether the firm needed the deal. Run the same test on your own calendar. Could a stranger look at how you spend your weeks and tell that you need the work, the motion and the adrenaline, for its own sake? If so, it is the same contamination, closer to home, and it takes the same kind of structural fix.
One caution first. You have spent decades getting good at performing the right answer to other people’s questions. This is the first question nobody is asking you, so the reflex is to answer it the way you answer everything, by moving fast and closing it out. This one you have to sit with.
Here is the fix. Take ten minutes at the end of the day. Start the Monday after you put this book down, and keep going for as long as you run anything. Do it in the evening, because mornings drift into planning.
Ask three questions, the same ones I ask myself: Where did my attention actually go today? What was in the day that did not belong? What would I correct tomorrow? There is nothing to write down and nothing to show anyone.
You already do this for the firm. You read the variance report, you ask why a margin moved, and you know what it costs when you skip a quarter. I am asking you to point the same instrument at the one system you have never audited.
I know how this can sound. The years after success come crowded with things that look like it: journals, gratitude lists, meditation apps, routines with a brand name on them. This is simpler than any of those, and you do not have to believe in anything to run it. It is a diagnostic, run with the standards you would never let slip at work.
It will feel small the first Monday and small the first month, the way the first written page of a firm’s process feels small. Do not grade it as you go, either; that impatience is the same one that wrecks a deal. Keep the practice and let the result arrive on its own schedule. Six months in, the person running your firm will be steadier than the one who started.
I teach Principles of Real Estate and Real Estate Asset Management at Huston-Tillotson University and serve on the advisory board of its School of Business and Technology, where I support the school’s campaign for a new building and finance program. My students ask me about the entry-level jobs that agents are taking. I tell them that agents take repetitive tasks, and tasks that do not require human judgment or human relationships. There is a lot to be said for judgment and relationships, and I believe that part of business is unlikely ever to be taken by AI, because as human beings we want to relate to each other and to do business with people we like and trust. So I tell them to focus on developing their judgment and to learn to use AI as a tool, because it is a tool like anything else. Today AI is a big buzzword. Ten years from now it will simply be part of standard business, and we will no longer separate the two. None of that is an excuse to skip learning it.
A platform build runs in cycles, and you have just watched one close. What you carry out of it, the practice you have started and the honesty you have earned about your own need, is the ground the next one stands on.
You may be waiting for halftime, the name Bob Buford gave to the turn in the middle of a career,29 or for some third act, or for the conditions to get easier first. They will not get easier, and you do not need them to.
Start tonight, before you close the laptop: ten minutes and the three questions, and then the same again tomorrow night and the night after.