What it takes to “win” is different than what it takes to “win ugly.” In sports what it means to win ugly can be something like:

• Winning a close, physical game

• Winning in bad weather or difficult conditions

• Winning without superstars

• Winning after overcoming a deficit or when your team is particularly outmatched

• Winning by just doing what needs to be done, even if it’s not fancy or flashy

But winning ugly is also a useful metaphor outside sports:

• In a marriage: keeping a relationship alive during adversity (e.g., during a global pandemic) or after a major loss

• In parenting: staying patient during bedtime when a child is overtired and throwing a tantrum

• In public service: improving across-the-board quality of life for citizens after the city government, which has been under-invested in for decades, goes through bankruptcy (I’m biased because I worked in it, but the Duggan Administration Detroit is my thinly veiled example here)

• At work: finding a way to reinvent an old-school company that’s not large, prestigious, or cash-infused enough to simply buy “elite” talent

The point of all these examples is to suggest that it’s easier to succeed when circumstances are good, such as when: there’s no adversity, the problem and solution are well understood, you’re on a team of superstars, or you’re flush with cash. It’s something quite different to succeed when the terrain is treacherous.

I’ve been thinking about the idea of winning ugly lately because as a parent, the fee wins we’ve had lately have been ugly ones.

Generally speaking, I’ve come to believe that winning ugly is important because it seems like when the stakes are highest and failure is not an option - like during a global pandemic, or when a city has unprecedented levels of violent crime, or when the economy is in free fall, or a family is on the verge of collapse after a tragedy - there’s usually no way to win except winning ugly.

I’d even say winning ugly is essential - because every team, family, company, and community falls upon hard times. In the medium to long run, it’s guaranteed. But honestly, I don’t think most people look at this capability when assessing talent for someone they’re interviewing for a job, or even when filling out their NCAA bracket. 

Moreover, as I’ve reflected on it, I’ve realized that my whole life, I’ve been coached, actively, to avoid ugly situations. I was sent to lots of enrichment classes where I had a lot of teachers and extra help to learn things (not ugly). I had easy access to great facilities, like tennis courts, classrooms, computer labs, and weight rooms (not ugly). I was encouraged to take prep classes for standardized tests (not ugly). I was raised to think that the way to achieve dreams was to attend an Ivy League school (not ugly).

If I did all these things I could get a job at a prestigious firm that was established, and make a lot of money, and live a successful life.

What I’ve realized, is that this suburban middle class dream depends on putting yourself in ideal situations. The whole strategy hinges on positioning - you work hard and invest a lot so you can position yourself for the next opportunity. If you’re in a good position, you’re more likely to succeed, and therefore set yourself up for the next thing, and so on.

If you don’t think winning ugly matters, this is no problem. But if you do believe it’s important to know how to pull through when it’s tough, the problem is that the way you learn to win ugly is to put yourself into tough situations, not easy ones. The problem with how I (and many of us) were raised is that we didn’t have a lot of chances to learn to win ugly.

I, for example, learned to win ugly in city government, at the Detroit Police Department…in my late twenties and thirties.

There, we caught no breaks. Every single improvement in crime levels we had to scrap for. Every success seemed to come with at least 2 or 3 obstacles to overcome. We didn’t have slush fund of cash for new projects. We didn’t have a ton of staff - even my commanding officers had to get in the weeds on reviewing press briefings, grant applications, or showing up to crime scenes. Just about any improvement I was part of was winning ugly. 

By my observation here’s what people who know how to win ugly do different:

No work is beneath anyone: if you’re winning ugly, even the highest ranking person does the unglamourous work sometimes. You can’t win ugly unless every single person on the team is willing to roll up their sleeves and do the quintessential acts of diving for loose balls, grabbing the coffee, sweeping the floor, or fixing the copy machine. 

Unleashing superpowers: If you are trying to win ugly, that means you have to squeeze every last bit of talent and effort out of your team. That requires knowing your team and finding ways to match the mission with the hidden skills that they aren’t using that can bring disproportionate results. People who win ugly doesn’t just look for hidden talents, they look for superpowers and bend over backwards to unleash them.

Discomfort with ambiguity: A lot of MBA-types talk about how it’s important to be “comfortable with ambiguity”. That’s okay when you have a lot of resources and time. But that doesn’t work if you’re trying to win ugly. Rather, you move to create clarity as quickly as possible so that the team doesn’t waste the limited time or resources you have.

Pivot hard while staying the course: When you’re winning ugly, you can’t stick with bad plans for very long. People who have won ugly know that you don’t throw good money after bad, and you change course - hard if you need to - once you have a strong inclination that the mission will fail. At the same time, winning ugly means sticking with the game plan that you know will work and driving people to execute it relentlessly. Winning ugly requires navigating this paradox of extreme adjustment and extreme persistence.

Tap into deep purpose: Winning ugly is not fun. In fact, it sucks. It’s really hard and it’s really uncomfortable. Only people who love punishment would opt to win ugly, 99% of the time you win ugly because there’s no other way. Because of this reality, to win ugly you have to have access an unshakeable, core-to-the-soul, type or purpose. You have to have deep convictions for the mission and make them tremendously explicit to everyone on the team. That’s the only way to keep the team focused and motivated to persist through the absolute garbage you have to sometimes walk through to win ugly. Teams don’t push to win when it’s ugly if their motivation is fickle.

Doing the unorthodox: People who can win pretty have the luxury of doing what’s already been done. People who win ugly don’t just embrace doing unconventional things, they know they have no other choice.

Be Unflappable: I’ve listed this list because it’s fairly obvious. When it’s a chaotic environment, people who know how to win ugly stay calm even when they move with tremendous velocity. This doesn’t necessarily mean they don’t get angry. In my experience, winning ugly often involves a lot of cursing and heated discussions. But not excuses.

Sure, I think it’s possible to use this mental model when forming a team or even when interviewing to fill a job: someone may have a lot of success, but can they win ugly?

But more than that, I am my own audience when writing this piece. I don’t want to be the sort of husband, father, citizen, or professional that only succeeds because of positioning. At the end of my life, I don’t want to think of myself as someone who only succeeded because I avoided important problems that were hard.

And, I don’t want to teach our sons to win by positioning. I want them to succeed and reach their dreams, yes, but I don’t want to take away their opportunity to build inner-strength, either. This is perhaps the most difficult paradox of parenting (and coaching at work) that I’ve experienced: wanting our kids (or the people we coach) to have success and have upward mobility, but also letting them struggle and fail so they can learn from it, and win ugly the next time.