I spent the latter half of this week at an incredible retreat center called 1440 Multiversity in Scotts Valley, California (the sunrise photo this week is from the trip). My friend and the co-founder of New Story, Brett Hagler, hosted a small event called Camp Redwood for social impact founders and senior leaders.
I served as emcee for the event to help the group consolidate their learnings and connect on a meaningful level with other founders in the room. I’d say it was a huge success. I came home inspired to double down on working with and telling the stories of founders working to solve big problems.
And I’m a day late on the newsletter because the plane ride home to Portland wasn’t long enough to get my writing done. So, sorry (kind of), but better a day late than never!
Let’s get to it.
A quote to make you think from a book worth reading
“The more you know about another person’s journey, the less possible it is to distrust or dislike that person. Want to know how to build relational trust? Learn more about each other. Learn it through simple questions that can be tucked into the doing of work, creating workplaces that not only employ people but honor the soul in the process.”
– Parker Palmer, as quoted in Reinventing Organizations by Frederic Laloux
…
This book stretched my thinking on operating organizations. Some of the theories in the book worked in practice during my time at ConvertKit. Some of the theories I immediately wanted to try (but don’t currently have an org to try them on). And some of the theories I’m skeptical will work in practice even though they’re great in concept.
Anything that stretches my existing mental model on leadership, org structure, and relationships at work is worth reading. If you pick it up, let me know what you think!
Three links to encourage deep thought and breakthrough growth
1 Choose Good Quests by Trae Stephens and Markie Wagner | Read time: 11min
“There are important challenges facing humanity that no one is working on, including critical, and even existential challenges. In other words, if you are an exceptionally capable person, failure to pursue a good quest is not neutral. It constitutes a loss for humanity.”
This article perfectly captures a thing I’ve been trying to communicate for a long time. We need more talented, intelligent, experienced people taking big swings at hard problems. Someone should solve the water crisis. Someone should invent a plastic alternative that doesn’t kill us slowly. Someone should create water filtration that doesn’t leave us consuming millions of particles of nanoplastics.
Everything we have ever made needs to be reinvented to be sustainable, favorable to human health, and non-destructive to Earth’s ecosystems. Pick anything that is used often and it should be reinvented by someone smart in the next 100 years.
Question to consider as you read: Are you working on a good quest? If not, what would it take to switch to a good quest? (I asked myself that question as I read and it left me with a pit in my stomach)
2 Optimism by Packy McCormick | Read time: 28min
“Optimism isn’t a belief that everything will go well all the time. It’s a belief that despite the inevitable challenges, we will make progress. We need more of it.”
I don’t know whether it’s that we’re coming off a pandemic or I’ve lived in Portland too long or I hang out with mostly parents of young kids who are in the sleepless slog like me or Twitter sounds a lot like Eor from Winnie the Pooh or that I was so frustrated at my last real job because we weren’t actually trying to reach our potential as company, but I’m done with pessimism and cynicism. Pessimism is paralyzing, based in fear and helplessness, and it doesn’t lead to progress.
Here in this community, I’m committed to thinking about the future from a place of agency and ambition. There are thousands of hard problems to solve and we’re going to encourage each other to solve them.
Question to consider as you read: What problem or problems in the world scare you to the point of paralysis? What would it take for you to believe in a better future in which that problem is solved? How could you contribute to solving it?
3 Cities and Ambition by Paul Graham | Read time: 18min
“You might think that if you had enough strength of mind to do great things, you’d be able to transcend your environment. Where you live should make at most a couple percent difference. But if you look at the historical evidence, it seems to matter more than that. Most people who did great things were clumped together in a few places where that sort of thing was done at the time.”
I’ve been thinking a lot about how the places we live shape the thoughts and ambitions we have. In this essay (from 2008!), Paul Graham lays out the major messages of key cities in the US like New York, LA, Silicon Valley, and Cambridge. Then he makes an argument for why — especially in the core earning years of your career — you should live in a city that sends a message aligned to what you’ve set out to achieve.
Question to consider as you read: What message does your city or community send? Does that align with the change you’re trying to create with your career? How could create a community within your city to create an intentional bubble of encouragement towards your goals?
An idea sparked by my client work to help you lead better
Burnout comes up a lot in my work.
Sometimes a founder is working themselves into the ground and it’s only a matter of time until illness, depression, or simple exhaustion knock them out of the game. This can be the product of a harsh inner critic, self-sacrifice, messages from childhood, fear of being poor (again), fear of failure, comparison to peers, status seeking or any number of other factors.
In these cases, the typical formula is fairly straight forward. Get to the root cause so that the founder becomes more aware of the pattern. Create some boundaries. Work within the boundaries. Add in some new patterns and habits to create the possibility of longevity in the work. Setting a hard bed time, working out more, hiring a chef or food service, seeking therapy, journaling or meditation, and time in nature are common antidotes.
This is not easy, but it is straightforward.
Sometimes a founder or exec reaches a stage of emotional burnout. This type of burnout is much more insidious and often harder to diagnose and turn around.
Most often, emotional burnout is about the leader’s relationship to their team or their mission. They get out of alignment with one or both and then don’t want to confront the obvious but emotionally difficult answer.
Living in the dissonance becomes torture. They might try all of the common antidotes to burnout that comes from working too much that I mentioned above… and none of them work. That makes the emotional burnout even worse.
Emotional burnout is the most likely kind to lead to depression. It ends up feeling like something is wrong with you (or perhaps that’s an old message or pattern that’s being reinforced by your work).
In this case, the most common antidote is to to a) sell or shut down the business, b) leave your role and seek a new one, or c) fire the person or people triggering the misalignment. In rare instances a founder or exec can change their inner world enough to transform their relationship to the work. Even then, a departure often provides the hard reset necessary to fully solidify the inner change.
The third type of burnout happens when you’re more ambitious than the team or organization around you. If the ambition is healthy (which is a big if), working with people who don’t share that ambition can put you in a really bad head space.
When you’re more ambitious than your team or company, each day feels like being a sports car stuck in neutral (without realizing it) while revving the engine to try to get it unstuck. The engine roars but the car doesn’t move. You rev the engine more to try to get it to move. It doesn’t budge. Slowly the engine degrades.
The equivalent at work might be:
- making ambitious goals and clear plans to reach those goals
- proposing endless ideas for how to improve growth metrics or internal efficiency
- generating new product possibilities to meet a common customer complaint
- imagining strategic changes that could 100x your current impact
In many environments, these qualities would be encouraged and rewarded. But in some environments, you might get stonewalled, rejected, or even punished whenever you bring them up. You might get fed excuses for why it’s not possible — “we don’t have the budget” or “you don’t understand the complexities of what you’re suggesting” or “the team can’t handle any more.”
When you have your ideas shut down for long enough and the organization you’re leading or part of is not reaching its goals… it’s easy to internalize the sense of pessimism and failure as your own. If you feel a strong sense of loyalty to the team or commitment to the mission, you might even convince yourself you are the only one who can save this place.
The danger begins when you believe you can be the savior of your company. Or perhaps you even start to view yourself as a martyr, sentenced to suffer on behalf of the group.
The only way I’ve ever seen the third type of burnout get solved is either:
- If you’re an exec, to leave the company and find an environment that values your ambition.
- If you’re the founder, then you have to lead a hard reset on the team you’ve hired.
In either case, you have to ask how you “contributed to creating the conditions you say you don’t want” as my friends at Reboot like to say. As an exec, perhaps you got so excited about the possibility of the title, pay, or mission of the company that you failed to ask hard questions about the culture. As a founder, perhaps you fail to properly resource your ambitions or perhaps you unknowingly discourage people when they offer ambitious ideas.
All three types of burnout matter. But it’s the third type — burning out because you’re more ambitious than the people around you — that we need to talk more about. If you find yourself in that position, don’t settle. Make the hard decisions necessary so that your hard work and commitment can lead to positive change in the world rather than staying stuck in neutral.
Sports cars are meant to go fast. If that’s you, embrace it.
Have a great Sunday! I hope this week is filled with optimism, ambition, and the pursuit of a good quest.
Much love and respect,
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