#69: Everything is Somewhat Broken
A lens through which to view the art and science of building or improving anything
I have been wanting to write this letter for the last six weeks. It’s because there was some moment when I realized what I’m about to share, and it was a bit of a “mental unlock.” It didn’t fully rock my world or anything, but it added a nice mental model to the ol’ noggin arsenal. I’ll try explain more now. I’m going to come back to this theme a few times, because I’m certain I won’t nail how I think about this fully in a short letter.
Psst: Don’t let the title fool you into thinking this letter is going to be drowning in negativity. I think it’ll be quite the opposite.
Start time: 4:01pm (taking a break from Homegrown for a bit)
TL;DR — Embracing the reality that all things have room for *real* improvement is what creates the possibility that tomorrow might be better than today
I’ve always been preoccupied with the concept of entropy, or in laymen’s terms the likelihood for disorder to occur.
Entropy is all around us, things are always moving towards states of change and disorder.
Your kitchen is a great example of this. Think about that feeling you get when your counters are clean, there’s not a single dirty dish in sight, and that candle burns with your favorite scent. Does this state last forever? Hell no. Soon, that entire carton of ice cream just had to be eaten, and a bowl appears. Then a glass for your water. Then a pan for the pasta… Before you know it, the components that were once in an orderly state, are now taking up all of your counter space. And it will take work to get it back into an orderly state. Only for disorder to occur again. This is the nature of things.
The very same pattern is happening everywhere else in your life, too. Things take work to maintain — relationships, your health, that product you’re working on at work… Without attention and care, things atrophy. Tools decay / depreciate. Products lose their relevance and sales drop. Your relationships may start to show signs of decay. It all takes effort and the bravery to change.
If you accept this premise — that all things take work to maintain or improve — then a next logical question is:
Screw it, I’m having a beer while I write this. Hold please. … Alright, it’s 4:10pm now
Ahem, the next logical question is: how do you improve things, given that disorder / decay are always happening? Where do you begin?
How do you make things better? Of the many ways to approach this question of how to make something better, the way I have started to prefer is to embrace the stone-cold reality that said thing has room for improvement. That, to some degree, every thing around you is broken, you just might not fully realize it yet.
People who have worked with me probably grow sick of hearing me say, “there is always margin (of improvement) to uncover!!” Our jobs are to mercilessly discover where to improve. … Like a Formula One racing team finding that .015% adjustment to downforce and realizing that the car will now go .002 seconds faster is what we’re constantly hunting and building for. Maybe that minor adjustment on its own won’t win you the race, but stacking improvements like this over and over and over again, day after day, week after week sure might. ((Go read Exonomist #44 — “Companies as Experiments…” — there’s a paragraph about how winning companies stack innovations. This last sentence is basically the same idea)).
Let me pause to create a bit of a logical chain, using your team at work as the main object.
Do you think your team is perfect? Of course not. So, you agree that your team is imperfect? You agree that something is not, plainly put, optimal? —>
Because your team isn’t perfect / optimal, this means that something is not working
When something is not working, we oftentimes use the word “broken” to describe the lack of that thing’s functionality
Just because something is broken doesn’t mean it’s entirely broken. It might just be somewhat broken.
And it is better for us to accept that some things are somewhat broken, so that we might discover the way to make it better. We should also accept that sometimes things are essentially completed broken, and beyond repair.
In other words, your team might be freaking amazing. You love how people communicate, you enjoy being around them, but invariably as your team goes through systems and situations that all have a tendency to decay / move towards disorder, things break. Weaknesses appear. You nurture the good stuff, while investing time on improvement the not-so-good stuff. This is management.
And sometimes, this means that the composition of your team must change, because something — or some dynamic — is so broken as to be beyond repairing or, to borrow from the world of automobiles, totaled
So, my somewhat-modest proposal is that we should all accept that the things we work on our broken, to *some* degree
Let me give you an example of how this has been valuable lately for me. As we’ve built up our company, we’re constantly building new things. New products, new features, new approaches, new messaging, new, new, new, new. All the time we’re testing new things, and as we deploy new things we get feedback. Sometimes that feedback is good, sometimes it’s not-so-good. The parts that aren’t good signal that something might be broken, but the parts that are merely good also aren’t perfect, which means they might also be a somewhat broken. This way of thinking allows us to constantly re-assess every part of our model, which allows us to experiment with sometimes-bold changes frequently. These experimentations give us learnings, these learnings are helping us to win, more, faster.
Instead of trying to constantly defend why something is perfect, we embrace that it isn’t, and it allows us to be honest about how to make things better. And by employing this nonstop, 24/7, we’re testing and learning faster. And when we get stuck, we call on people we know who are excellent at what they do (shout out to my advisors, Ian and Allen, among many others), who quickly will tell us: “Yeah, that’s not it. You should try ______”
And in those conversations, that were started because we believed something was a little or very broken, we find the foundations of our future.
Embracing the reality that all things have room for *real* improvement is what creates the possibility that tomorrow might be better than today
And look: this stuff is hard! It’s not easy to look someone in the eyes and say, “This isn’t working” …and yet that’s where the real progress occurs. When you do the hard thing, have the hard conversation, and begin to move forward with a more complete view of how to make tomorrow’s outcomes better than today’s.
I was listening to some podcast last year where some VC guy who was completely full of himself uttered a nugget of wisdom, something along the lines of: the times of his career where the most groundbreaking leaps happened was directly correlated with the number of difficult conversations he had. This stuck with me over last year, and sure enough I realized that:
The toughest conversations my (freaking stellar) wife and I have had are the ones where we tend to grow the most
The hardest conversations I’ve had with my cofounders and team are the ones where we’ve realized the biggest jumps in thinking and/or have grown more effective as a unit
That most difficult moment when you need to let the person who is toxic on your team go is the turning point when the rest of the team was finally able to move forward with less of a “tax” on their energy and focus
Some of the most direct and personal feedback I’ve received (which has been a gift) is what led me to feel like shit, but to think about why I felt like shit, and to figure out how I might feel a little less like shit about it over time
In all of the above situations, something was broken, and we had the bravery to confront what wasn’t working. Which leads me to the final idea / suggestion for you to consider (…consider does not mean “utilize” — it means you’ll think about it):
You should find the courage to call out when you think something is broken. Yes, you’re going to likely face some kind of friction or discomfort, but this is usually required to really achieve something meaningful
Of course, there are ways to do this with elegance. You don’t need to go full Elon here and ruin somebody’s psychological foundation in the name of progress; you can call for the fixing of what is a little or very broken in a way that respects the emotional investments others have made into a thing, because nobody likes to have their baby called ugly.
Alright done at about 4:55pm. I don’t think I nailed the messaging here. There’s a potency that isn’t translating from my (admittedly-tired) brain to the page right now, but this is a sufficient starting point.
MD
APPENDIX OF ADDITIONAL THOUGHTS.
This (the fear of being radically transparent in calling out things that aren’t working) is one of the absolute worst parts about big companies by the way. And no, I don’t mean the easy stuff like, “we could be better about adhering to timelines.” While improvements like this are important, I’m alluding to the bigger, riskier stuff like telling that toxic person, in a 1-1, that their behavior is causing real emotional churn for a high number of people, and that you would like to work with them on ways to communicate differently.
At some point, groups grow so large and politics becomes critical to people’s survival / livelihood, which can undermine the incentive for people to actually say the hard thing. God forbid you piss that VP / Partner off, man: what’s going to happen at your year-end review???? What of the state of your alliance with that VP’s team? This isn’t a great setup, and it leads to cycles of mediocrity and strategic paralysis, where people aren’t really innovating anymore. And who can blame them? It’s hard to jeopardize your career foundation, when that foundation is enabling you to live / fundyour life.
Thought leader / founder / investor David Cummings wrote over the weekend about “The Rise of the Forever Lean Startup” (I recommend reading it!). I loved how he talked about the benefits of forever lean teams that don’t grow too big, primarily because in smaller, tighter-knit cultures, it can be easier to reach the levels of candor and psychological safety where you can consistently practice this approach of “Everything is (somewhat) Broken.” This is what I have always strode to build — teams and cultures where very smart people can disagree and criticize, while also enjoying being around one another. It’s a hard thing to achieve at all, let alone maintain, but I know it’s possible.