Keeping Possession, Courage-Patience, and Permission

I once read an article written by an American watching a European soccer match for the first time. It was about ~10 years ago but I can’t seem to find it on the internet. In any event, the author wrote about how different soccer is from “American” sports like basketball, baseball, and football. For example, soccer’s running clock and (at the time) lack of video-replay refereeing emphasizes flow over accuracy. But I think the author’s most insightful observation was about keeping possession, and how in soccer, passing the ball backwards isn’t necessarily a retreat.

Most elite soccer teams today are built around keeping possession of the ball for as much of the match as possible – e.g., it’s not unusual to see Barcelona have 70%+ possession (meaning in a 90 minute match, they would have held the ball for over an hour!). This is impossible in, say, basketball, where there’s a 24-second shot clock, or football, where every drive ends with either a score or a turnover. Here’s a great example: in this clip, Manchester City make 44 (!) consecutive passes, ending with a tap-in goal for Ilkay Gundogan:

Notice the number of sideways and backwards passes. How patient the build-up play is. And how disciplined each player is in either (a) picking out the right pass, or (b) waiting for a better option to present itself. They don’t try to force the issue by attempting an impossible pass or run. They just wait until the opposing team loses its shape, and when that window opens, they pounce. (By the way, that “opposing team” is Manchester United, a team I’ve been a fan of since I watched this guy play on TV in the 90s; I tried very hard to find a clip to post here that *didn’t* involve United losing – to City of all people – but alas, this was the best one, and I’m committed to my readers, so…)

Interestingly, the popularity of possession-based football is a pretty recent phenomena. For most of English soccer’s history, teams favored a direct and physical style of play that emphasized ambitious passes over the tops of defenders, hard tackles, and fast, risky runs down the flanks. But then came Pep, and things changed. Pep Guardiola is the manager of Manchester City (the team in the clip above). Before City, he managed Bayern Munich and Barcelona, two of the most dominant and iconic teams in European Football. (Some people wonder how their life would have turned out with “the one that got away”. I wonder how my life would have turned out if Pep Guardiola had succeeded Sir Alex Ferguson as manager of Manchester United instead of David Moyes.)

Before Pep, possession-based football was easy to pigeon-hole as either a niche idea or an exotic luxury; something only Barcelona could pull off because they had Messi, Xavi, and Iniesta in their squad. But at both Bayern and City, Pep inherited “classic” teams and quickly turned them into possession-based powerhouses. Lots of people have written detailed analyses of Pep’s methods and tactics. But what I see in Pep is something that I call courage-patience. Specifically, I think what makes Pep such a great manager is that his courage-patience give his players permission to play the game their way, even when that might take them further away from the goal.


One Pep’s first big moves at City was to get rid of their goalkeeper Joe Hart, a long-time City player and fan favorite, and replace him with Ederson, a somewhat unproven and unknown Brazilian who until then had been playing in the relative obscurity of the Portuguese league. The reason? Because Ederson was a better passer of the football. That’s right: Pep is so committed to possession-based football that he even requires his goalie to be regularly involved in passing the football.

Playing football this way is risky. When goalies make mistakes, they tend to be very serious, which is why teams would normally keep the ball as far away from their own goalie as possible. For this reason, it’s not enough that Ederson happens to be a great passer. It also takes both courage and patience on Pep’s part; courage to take risks, and patience not to overcorect when things go wrong. I think these two go together, which is why I call it courage-patience.

For example, lots of people invest in the stock market, which requires courage, but sell their holdings when the markets go down, because they don’t have the patience to sit still and ride out the volatility. Without the patience to just sit still, they overcorrect, and sell their assets when they’re at their cheapest. Meanwhile, the courage-patient few reap outsized returns: the S&P is up ~5x today from its low in 2009. By contrast, here’s a video of Ederson trying to intercept a pass and making a mistake:

And here’s a quote from Pep:

I’m sorry, but until my last day as a coach, I will try to play from my goalkeeper.

Pep Guardiola


Let’s say you’re on a first date in a bar in [insert city full of ambitious young people]. Your date asks you what you do for work. You say you’re taking some time off to figure out what you want to do. For how long, your date asks. I don’t know, you reply. Awkward silence follows. I’d imagine Ederson would have gotten a similar reaction in Portugal if he told the media he was an average goalie but awesome at passing.

While I haven’t been on a first date since Obama’s first term, I have gotten that same awkward silence when I’ve told people how I’ve been spending my time roaming through various ideas and curiosities with no particular destination in mind. It feels like there’s strong societal pressure to fit people into a neat little box that’s moving forward linearly, like widgets on a factory line. Being outside of the box, or worse, “not making progress” (gaspshockhorror!) breaks the model, and invites questions, quizzical looks, and judgment (real or imagined).

For a long time, I internalized this pressure and fit myself to the model. I defined myself in a box (“founder”) and pointed to linear progress as the yardstick of my value (revenue growth, fundraising, more employees). When situations changed and I was no longer in that box, I built new ones for myself (“founder looking for next thing”, “investor”, “home cook”) and duly started measuring myself along the same, linear-type progressions (“how close am I to ‘the next big thing?'”, “how many companies in my portfolio?”, “how instaworthy was that dish?”). With this came my old friends Anxiety, Frustration, and Impatience (kind of like the Seven Dwarves but fewer in number and less jolly), because I always felt like I was losing at someone else’s game.

Why didn’t I just stop? I think it’s because I had been operating under the assumption that doing so required something that I didn’t have – a vague amalgam of money, status, and power. For example, without a giant pile of cash to serve as a financial safety net, “not making progress” felt irresponsible, almost rebellious; like not doing my homework to go play outside; a frivolous, selfish (and thus “bad”) thing. Ergo, I should go back to the box, get back on the line, and charge aggressively toward the goal, for then I shall have earned the freedom to transcend the game. In hindsight, I think I was looking to these things as a proxy for what I really needed: permission. I just wanted someone to tell me it was OK to live in a world of my own creation, even if that meant going on a journey that was (a) non-obvious to me, (b) non-obvious to an independent observer, (c) involved an uncertain route and destination, (d) contrary to prevailing wisdom, or (e) all of the above.

A breakthrough came when I realized that I could give myself this permission, and that I didn’t need someone or something else to do it for me. Giving myself permission to play my own game has been one of the most liberating things I’ve ever done for myself, because it’s turned off the voice in my head that used to say “you’ve got to make progress”. I imagine this is the same kind of permission that Guardiola gives his players – to hold onto the ball, make the sideways or backwards pass, and resist the temptation to always drive forward.

I think the line between courage-patience and mere obstinacy is an interesting one and worth exploring. I suspect the distinction may be that when presented with new information, the courage-patient seeks to filter signal (needs courage to act on) from noise (needs patience to let it pass), while the obstinate selectively hears only that portion of the information that fits their mold. I also think the concept of courage-patience is closely linked to investing, especially investment horizons/duration, and cash. For example, I’d imagine many investors (myself included) struggle with the idea of holding onto large amounts of cash in the bull market we’re in, even if they also believe we’re on the verge of a recession. The sentiment among many investors I’ve talked to is that it’s generally “bad” to have cash “sitting on the sidelines”. Meanwhile, a handful of the smartest (courage-patient?) friends I know are sitting on lots of cash. They’re in good company – Warren Buffet is sitting on over $128BN in cash at Berkshire. Like Pep, they’re holding onto the ball, patiently waiting, unafraid of playing a sideways pass.