#5 🧗♂️🧩🛍🏋️♂️🎙♟
Grown-up mountain, contributing in the right role & team, new employee onboarding, the future of shopping malls, podcast with Substack CEO and 3D Chess
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Today I have some longer mini-posts, ranging from maturing as a thinker to the future of shopping malls. There’s also a survey and some videos. I hope you enjoy it 😀
Also, in the last post I mentioned our trip to Mendocino with a group of friends a couple weeks ago in a town called Ukiah just two hours north of SF. It’s quiet and full of nature. We rented an Airbnb on a big piece of property and spent the weekend doing arts and crafts, light hiking, watching silly movies like Shrek and Airplane!, playing board games and enjoying hanging around the outdoor fire pit.
Here’s a shot of our setup from my friend Eric’s drone (which I got to fly for the first time and it was surprisingly easy):
What’s not depicted is me falling into the freezing pool later that night - fully dressed and in 40 degree weather - while trying to reach the stairs from the fire pit on the bottom right side of the photo. I woke up the next morning to find my AirPods at the bottom of the pool 🤦🏻♂️
Luckily, Eric works at Apple and got me a discount on a new pair. Thanks, Eric! 🙏
🧗♂️ Climbing Grown-up Mountain
Tim Urban from WaitButWhy shared this graph recently that really resonated with me. It’s a journey from high conviction / low knowledge (Child’s Hill), down to low conviction / low knowledge (Insecure Canyon), and on to higher knowledge with higher conviction (Grown-up Mountain).
Looking back, I was in Child’s Hill until around the age of 23. I thought I knew everything and was very confident about it. Then I had a very humbling experience starting a company and making all kinds of mistakes. In reality, I knew very little.
When I shut down my startup, I stumbled down Insecure Canyon. I took a low-paying job at a startup and felt pretty embarrassed about my failed attempt at even getting a startup off the ground.
Over the last seven years in SF, I’ve been steadily working my way up Grown-Up Mountain. I’m building up knowledge and confidence in a gradual way. It feels like building on solid foundations. I love saying “I don’t know” when I don’t understand something and ask lots of questions.
I have no plans of ever reaching the top of Grown-Up Mountain. I think of it more as a decades-long journey across Grown-Up Mountain Ridge.
This framework captures the long-term, sustainable path for maturing as a thinker.
Child’s Hill? Good riddance.
🧩 Contributing in the right team and role
I think it’s impossible for someone to find meaning through contribution if they’re not in the right role on the right team.
In other words, meaningful contribution is enabled by playing a specific role on a team that values and appreciates the unique strengths you bring to the table.
Think of Toy Story. The toys need Andy, Andy needs the toys, and the toys need each other. They each have a unique role to play. Buzz Lightyear can’t truly play Woody’s role and vice versa.
Or the Avengers. They know they’re stronger together when they play to their strengths. Individually, they’re weaker. In unclear roles, they fight one another. We even had a civil war chapter in the Captain America storyline. The Avengers can only beat the bad guys when they’re coordinated as a team. That’s why the Avengers came together in the first place - the biggest challenges can’t be tackled individually.
I regularly question whether I’m playing to my strengths, in the right role, on the right team. I used to think that this question would come up only if I was unhappy. I know now that’s not the case; it’s always there. Even when things are going well.
Questioning how I’m doing and looking for areas to improve is just an ongoing conversation in my head. It doesn’t mean anything is wrong. It’s just continuous self-inquiry. It’s a loop I’m always running in the background.
I know a lot of people who repress this type of reflection rather than embracing it and fully exploring the answers. Some see criticism of the present as unproductive and as a result rationalize staying where they are without honestly questioning it.
To be clear, staying where you are is, indeed, often the right move. But not always. And the exceptions make the questioning worthwhile.
The important thing is being open to an honest internal dialogue with yourself about whether you can do better in a different role, on a different team, or a combination of the two.
🙋🏻♂️…⌛️…👨🏻🔧 New employee onboarding
I’ve been digging into the new employee onboarding problem space. If you’ve been involved with onboarding in any capacity at a startup, it would mean a lot to me if you took 5 minutes to complete this survey.
A new employee’s onboarding path in startups looks something like this (some of the middle steps can be shuffled around and the drop-offs aren’t at the right scale):
offer letter extended
offer letter signed
shows up on start date
confirms work eligibility w/ ID
sets up direct deposit / payroll
enrolls in benefits
Gets access to tools
makes contribution as employee
contributes consistently
helps others contribute consistently
Many employees don’t advance all the way through the “happy path”. I believe most of the time it’s not the employee’s fault; I see it as the company’s responsibility to set employees up to be successful. And unfortunately companies often don’t know how to set up employees to be successful.
Another issue in fast-growing startups is that often people are hired into roles that nobody knows how to do yet. So it’s not about onboarding them into an existing role, but about setting them up to define what that job means at the company.
In addition, hyper-growth startups that double headcount every year end up having new people onboarding new people. This can work well with deliberate planning and thoughtfulness but is definitely a risk with onboarding large volumes of new employees in a short timeframe.
If you’d like to share your thoughts with me, please take the survey 👇
🛍🏋️♂️The future of shopping malls
I’ve been seeing fitness studios popping up everywhere. Crossfit gyms, bootcamps, yoga studios, etc. The size of the studio determines the cap of members. There’s a boxing gym on our street that costs ~ $300/month. Which feels crazy to me.
The growth trajectory of e-commerce makes it likely that people will no longer be going to physical stores for most of their shopping in 10-20 years. This shift is already underway. There’s even a term for abandoned malls: dead malls.
As I think about these two trends - growth in demand for gyms and death of shopping malls - I can see a future where these empty malls are re-purposed into indoor physical activity hubs, full of CrossFit gyms, yoga studios, indoor parks, etc.
Since gyms needs to be easily accessible as part of one’s routine and most dead malls aren’t within walking distance from dense population centers, my prediction is that this will most likely impact suburbs where people can reach the malls within 10-15 minute drives. People in major cities like SF or YC won’t even know it’s happening.
To be clear, this is an optimistic outlook: using massive indoor spaces for recreation and fun rather than for endless consumption.
🎙Podcast with Substack CEO
I recently listened to a podcast with the founder/CEO of Substack, the service I use to publish this newsletter. It’s always interesting to get into the mind of the person who created something I value using. If you want to learn more about this newsletter platform, you’ll enjoy this conversation.
+ Jason Calacanis (the host) is one of my favorite people in tech. He’s honest and says what’s on his mind without worrying about being politically correct.
♟ 3D Chess
I learned how to play chess a few years ago and enjoy playing every chance I get. Chess time is time to think competitively. It really puts my brain to work.
I’ve heard people talk recently about “3D chess” and asked myself, isn’t regular chess already 3D chess since a knight can jump over pieces?
So I googled it.
And I found this gem from Vice/HBO. Turns out 3D chess is a real thing. But it’s not quite what I expected.
Note: the brief intro in the video alludes to politics but I’m not making any kind of statement about politics. This isn’t a political newsletter.
🎶 Song I’ve had on repeat this week
That’s it for this one - thanks for reading! If you’re new here, feel free to check out prior posts:
#4 Remote work, R&R, George-inspired tweets & books 👨💻⛰🦮📚
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