A friend of mine sponsors a hole at a golf outing every year. This past summer he was parked at his tee, watching foursomes roll through, when one guy stepped up and crushed a drive straight down the middle. The guy turned around, grinned, and said, “There you go. We’re good to go.” Grip it and rip it.
It was a scramble. Best ball. That one drive meant the other three could swing free, because the team already had a shot sitting in the fairway.
He told me the moment stuck with him for days. Play golf by yourself and every shot is yours. You miss, you own the miss, and the next swing carries it all. In a scramble, one good swing lifts the whole group. The weight on any single shot drops, because someone already covered you.
Room for error is built, not summoned
That same friend found a Morgan Housel line that I think fits this topic. Room for error, he wrote, is what lets you endure a range of outcomes. For a long time I read that as a portfolio idea. Keep some cash on hand. Do not stretch to the edge of what you can afford. It is bigger than that. Room for error is mostly what a good partner gives you. When someone can cover a miss, a bad day stops being a disaster and turns back into just a bad day.
People assume I run my firm alone. My name is the only one on the door, and that's true. But I do not work alone, and the firm would fall over if I tried.
I came to this work after twenty years in corporate finance, the last stretch as a CFO. That job drilled one lesson into me that carried straight over. A small operation lives or dies on two things: the systems you build and the people you can call. I run portfolios and planning for far more families than most people assume one advisor could manage, and I do it solo.
The only reason that is even possible is the bench standing behind me. The software firm that runs my back office. The custodian that holds the accounts. A short list of specialists who pick up when I call. Take that bench away, and I am not a leaner version of the same firm. I am a worse one, swinging at every shot myself, missing balls I would never have missed with a partner already in the fairway.
There is a quieter piece of this too. The families I work with know that if I get hit by the proverbial truck tomorrow, they are not stranded. The state requires a succession plan, but I had one anyway. That is room for error built into the one place most people never think to look: what happens when the person they rely on is suddenly gone?
The household version is four solos, not one bench
Here is where it turns toward the families I sit with, because most of them are running their financial life the way you play stroke play. Alone. Every shot is theirs.
The families I work with are usually two careers, kids still at home, and real money moving in several directions at once. They are not short on professionals. There is a CPA. Someone handles the 401(k)s. Maybe an attorney who drew up documents a while back. An insurance person somewhere in the mix. On paper, a full roster.
The trouble is that the roster is four solos, not one bench. The CPA has never spoken to the advisor. The attorney has no idea what the insurance actually covers. Each one takes a clean swing in their own lane, and nobody watches the balls that land between the lanes.
That is exactly where the misses live. A job change sets off a benefits decision the advisor never hears about until the window has already closed. Equity comp vests into a tax bill nobody saw coming, because the person who does the taxes and the person who runs the investments were never once in the same conversation. Two retirement accounts get pointed in some direction during onboarding and then sit untouched for a decade, because each spouse quietly assumed the other one, or somebody, was keeping an eye on it.
And usually one person carries it all. In most of these families, one spouse has quietly become the one who owns the money, not because they wanted the job, but because someone had to and the other one had even less room to spare. So the entire financial life now runs through a single overloaded person, taking every swing, covering every lane, with nobody behind them in the fairway. That is stroke play. Every shot theirs, every miss theirs, and the exhaustion is the tell.
None of those decisions is hard on its own. That is the part people get backwards. They assume the answer is a smarter professional. It is almost always a connected one. And the reason these families don't fix it themselves isn't ability. It is hours. They already run teams and budgets all day at work. They are perfectly capable of being the project manager of their own financial life. They just don't have a single free evening to do it, so the coordinating never happens and the balls keep dropping in the gaps.
You feel the gap on the worst day
You do not notice any of this on a normal Tuesday. You notice it on the worst day.
This year I walked more than one family through a death for the first time in the firm’s history. The ones who had their estate plan already in place, the will, the trust, the beneficiaries named, and the accounts actually funded, still faced a hard road. Settling an estate is a grind no matter how ready you are. But they got to grieve. The family whose documents were never finished is sitting in probate right now, carrying the loss and the scramble at the same time, and the scramble is the part that did not have to be there.
That room for error is something you can see with your own eyes. Nobody feels the value of a finished plan on the afternoon they sign it. They feel it two years later, on a day they did not choose, when the work that was quietly done in advance is the only reason they are still on their feet. Room for error is never something you reach for once the bad day lands. It gets built long before, by a set of people and documents that were already talking to each other.
So here is the small thing worth doing this week, and it hands you something you can actually look at. Write down every financial professional you pay. The CPA, the advisor, the attorney, the insurance agent, whoever belongs on the list. Then next to each name, write the last time any two of them spoke to each other about your situation.
Most of that second column will be blank. Those blanks don't prove you hired the wrong people. They are the shots landing between the lanes, waiting on a day you did not plan for. You have a roster. The work in front of you is turning it into a bench, so the next time life knocks a ball into the rough, someone is already standing there to hit it.