The Wide Line: What Cross Country Taught Me About Coaching Operations

Thirty-five years ago I was running cross country in New England.

We'd spent weeks practicing what our coach called breakthroughs. Two runners running side by side, and you'd learn to fit between them, arm forward, chest turned, the other arm falling behind you, the gap opening just wide enough that you don't trip them and they don't trip you. The motion has to be confident. Hesitate and you stumble.

This was preparation for the moment in a race when a pack of runners forms and the only way through is between bodies.

I remember one specific race. The weather was freezing cold with rain coming down sideways. The course was muddier than anything we usually ran, with rocks I wasn't expecting. There was even a tiny river crossing, something I'd never seen in a high school race before that day.

I came over a hill and saw the field laid out in front of me. Wet, rocky descent. Most of the runners ahead of me were picking their way down carefully, cutting wide around the rocks, slowing to find footing.

I took the inside line.

I was usually a middle-of-the-pack runner. I trained for track and was naturally faster as a sprinter, which doesn't always translate to cross country. But that day, on that hill, threading through the rocks where everyone else slowed down, I started passing people.

I came in third. I'd never come in third in a race like that. I was covered in mud and shaking from the cold when I crossed the finish line. There was hot apple cider and donuts inside the school. We took hot showers, got back on the bus, and went home, and I sat there the whole way home knowing something I hadn't known when I'd gotten off the bus that morning.

I was a good downhill runner.

And the line you take matters more than how fast you can run.

I didn't know it at the time, but I'd spend the next thirty-five years applying that lesson to systems, businesses, and now the practices of the coaches I work with.

The breakthrough drill is one of the first things you learn. So is the inside line. Every race comes back to the same principle: the runner who takes the shortest path covers less distance than the runner running the same time but wider.

It sounds obvious on paper. It's not obvious in a race. A race is full of decisions you make in fractions of a second, often without consciously making them: where to put your foot, whether to pass on the inside or the outside, whether to cut through two runners or go around them, whether to slow down on a wet descent or trust your line and keep moving.

The runners who win, or in my case the runners who pass middle-of-the-packers like me on a bad-weather day, aren't always the fastest. They're the ones who chose better lines, second after second, over and over, all the way through the course.

And here's the part that took me years to fully see: the cost of a wide line isn't a single dramatic mistake. It's a thousand small ones, added up. Four feet wide on every turn, across a 5K, is nothing you can feel as it happens. By the marathon distance, it's a different race.

The thing that makes this lesson hard to apply outside running is that, in running, it shows up in seconds and feet. In other parts of life, it shows up in months and years.

I spent twenty-five years building user interfaces for big companies: State Street, Wells Fargo, Janus Capital, and on the consulting side, Disney, Genentech, and Vail Resorts. The work was different at each one, but a pattern repeated.

Inside every team I worked with, there were features that nobody could explain the origin of, workflows that took three more clicks than they needed to, screens that asked for information the user already had given somewhere else, and settings stacked on settings that someone, at some point, must have built for a reason.

None of it was a single bad decision. It was the accumulation of small choices over years, each one obvious in its moment, none of them stepping back to look at the whole.

The runners on the outside line, taking three extra feet at every curve.

What I learned in those years is that systems don't get more complicated because anyone wants them to. They get complicated because every small "let's just add one more thing" feels harmless. The cost shows up at the marathon distance, which in business is a quarter or a year or three years later, when nobody can remember why you have to click through six screens to get to the place you go every day.

Good UI design, the kind I was fighting for in those meetings, wasn't about adding features. It was about taking the inside line: asking which screens could be cut, which steps were leftover from a previous decision that no longer applied, which complexity was real and which was just there.

When I started talking to coaches a couple of years ago, the pattern that struck me first was how familiar it looked.

A typical coach is using:

Ten+ tools, each one chosen for a reason in the moment. None of them designed to talk to the others.

The wide line in your coaching practice is the seven tabs you open to find one client's intake form. It's the Sunday night you spend reconciling what was said in Voxer with what's documented in your CRM. It's the moment three weeks into a beautiful new container with a client when you can't remember which platform you sent the worksheet from.

Every coach I talk to has some version of this. None of them set out to build it. They built one decision at a time, each piece reasonable in isolation, and then they ran the route for years.

The cost shows up in places that look like other problems: burnout, missed follow-ups, clients who slip out the back door, marketing that's working but a backend that can't absorb the leads cleanly. It looks like a marketing problem. It's a wide-line problem.

Taking the inside line isn't free. The line is harder to find. It requires you to step back from the race and look at the course before you run it.

For a coach, that step back means doing something the daily work fights against. You have to stop running long enough to look at the route you've drawn, count where client information lives, name what each tool is actually doing for you and what it isn't, and ask whether the workflow you built three years ago, when you had four clients, is still the right workflow for the practice you have today.

What you find when you look is usually that the route is longer than it needs to be, not by a single dramatic step but by four feet at every turn, year after year.

This is the work my partner Chad and I have been doing on Sidkik. We started by looking at every place a coach's clients touch the practice, and we worked backward from one question: what would the inside line of this look like? Not "what features should we add." What can we cut out of the route entirely so coaches are doing less running for the same result?

That's the bet behind the platform. The same bet I made on the hill thirty-five years ago: that finding the right line matters more than running harder.

If you're a coach reading this, the work isn't to be a faster runner. You're already running.

The work is to step back and look at the line you've been running, and ask whether it's the shortest path between you and the actual work. The actual work is the coaching, the transformation, the client.

A few feet wide at every turn is nothing you can feel as it happens. Across a year, it's a different race. Your exhaustion is already proof.

PS. If you want to step back and look at your own route, join the waitlist for coaches who want a different kind of platform when it's ready. And if you want to start understanding what your clients are actually saying before they walk in the door, try our free Know Your Client tool.