It Didn't Look Like Success

Shortly after the iPhone came out, and apps were just starting to take off, I was part of the leadership team at an interactive marketing and communications company.

We had an idea. We called it You Buy and I’ll Fly, a localized errand service, the kind of thing where you could ask someone nearby to pick something up or run something over for you.

At the time, we were serving the financial services industry. That was our business. Bank clients, financial communications, that world. An errand-running app didn’t look like something a company like ours did.

So we let it die on the vine.

A few years later, I watched companies like TaskRabbit and eventually DoorDash build enormous businesses around a basic behavior that felt very familiar: using technology to connect people who needed something done with someone willing to do it.

I don’t know whether You Buy and I’ll Fly would have worked. There were probably a hundred reasons it might not have.

What has stayed with me is that we never really found out. We didn’t walk away because we’d tested the idea and discovered it wasn’t viable. We walked away in part because it didn’t look like the kind of thing a company like ours did.

It didn’t fit our picture of where success for our company was supposed to come from.

The violinist in the subway

In January 2007, Joshua Bell, one of the world’s great violinists, stood near a Washington, D.C. Metro station during morning rush hour and played for 43 minutes.

No stage. No announcement. Wearing jeans, a T-shirt, and a baseball cap.

During that time, 1,097 people passed by. Only seven stopped for at least a minute. Excluding a $20 bill from someone who recognized him, Bell collected $32.17.

Three days earlier, he’d filled Boston’s Symphony Hall, where good seats sold for $100.

The violinist hadn’t changed. The context had.

We don’t always see what’s actually there

In that setting, Bell looked like another street musician.

I think something similar happened to us with You Buy and I’ll Fly. We were a company serving financial institutions. An errand-running app didn’t fit the picture we’d developed of what our company did. So instead of only evaluating the opportunity, we were also evaluating how well the opportunity fit our existing picture of ourselves.

There is an important distinction. Sometimes the thing in front of us isn’t wrong. It just doesn’t look like what we’ve learned to recognize as right.

Saying no isn’t the problem

None of this means every idea deserves to be pursued.

Organizations have limited time, money, people, and attention. Good leadership requires saying no. Sometimes an idea doesn’t fit the mission. Sometimes the economics don’t work. Sometimes the organization doesn’t have the capacity. And sometimes “not yet” is the right answer.

The problem isn’t saying no. It’s saying no before we’ve actually looked at the opportunity in front of us with fresh and clear eyes.

Looking back, I don’t know whether You Buy and I’ll Fly deserved a yes. Maybe a small test would have exposed flaws we hadn’t considered. Maybe we would have learned quickly that the economics didn’t work.

But we hadn’t earned the no. We hadn’t given the idea the opportunity to be ruled out on its merits. Our immediate perception of what fit our company had done some of the evaluating for us.

That’s the part I think about now.

Sometimes the opportunities that don’t immediately look like a fit are worth testing, not because we should become something we’re not, but because they might reveal something about what we could become.

Youth sports has its own version of this

I think this matters especially in youth sports right now because the industry is changing quickly, and we’re all forming ideas about what the next version of a successful organization is supposed to look like.

Youth sports has accumulated its own signals for what success is supposed to look like. More teams. Bigger facilities. National tournament schedules. A certain kind of social media presence. The programs everyone points to as the sophisticated ones.

None of those things are inherently bad. Some may be exactly what an organization needs. But another club’s evidence of success isn’t necessarily a blueprint for yours.

The problem comes when those visible markers become the basis for how we make our judgments. We stop asking whether something serves the athletes and families we’re trying to serve and start asking whether it looks like what successful organizations are supposed to do.

We can do the same thing with people. The coach without the résumé. The player without the expected physical profile. The program that attracts a different group of athletes than we imagined. The idea nobody else around us seems to be pursuing.

Professionalizing your club should make you better at evaluating opportunities on their merits: whether they advance the mission, create value for the people you serve, and move you toward the organization you’re trying to build. It shouldn’t mean getting better at copying what the other clubs around you look like from the outside.

Where this leaves you

Joshua Bell didn’t stop being Joshua Bell when he stepped into that Metro station.

What changed was the context around him. And the context changed how people perceived what was right in front of them.

I wonder how often we do the same thing.

How much talent have we overlooked because it didn’t arrive with the résumé we expected?

How many good ideas have we let die on the vine because they didn’t look like the kind of thing we already do?

How many decisions have we made because they looked like what successful organizations are supposed to do rather than because they were right for the organization we’re trying to build?

And the harder question: what is right in front of us right now that we aren’t seeing clearly because it doesn’t look like what we’ve learned to call success?

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