Inspired by Ryan Holiday, I’ve made a practice of listing a few things I’ve learned over last year on my birthday. Here’s 37 and 38. And here are a few things I’ve learned in the last year.
Chaos
We’re living amidst more turmoil than any time in several generations. And, despite being relentlessly optimistic, I think things are going to get worse before they get better. I wish that weren’t true – I’d love to build my business and raise my family in peace. But the next decade, and likely the rest of our lives, are going to be chaotic. Assuming that, the question becomes: how do we stay resilient?
AI is here
To paraphrase William Gibson, “It’s just not evenly distributed yet.” I’ve known AI is important for years now. At Responsive Conference, we’ve curated about AI since 2019! But I hit an inflection point this spring and now I’ll talk about the coming AI storm to anyone who will listen. Among my peers, it is trite to say that AI won’t replace people but instead people using AI will replace people. That phrase is true – as far as it goes. But it doesn’t do justice to the amount of change and disruption that I believe is coming.
Adaptability
Fellow entrepreneurs have been asking me how I feel that my business of the last six years, Zander Media, may be replaced by AI. As someone who’s reinvented himself and his career more than a dozen times in the last fifteen years, I’m more prepared than most to adapt to change. That’s what it means to be an entrepreneur – and also a prepper.
Adaptability is among the most important skills in this century.
Optimism is a competitive advantage
If these first two items sound bleak – they are. I don’t think we’re headed into a gentle time in human history. Thus, optimism is even more important than ever. As Kevin Kelly wrote in Excellent Advice for Living: optimism is worth 25 IQ points. When we show up with optimism and enthusiasm, people are more likely to listen, to follow our advice, and to change. (Optimism is actually a secret to selling.)
Durable skills
During my first few months in San Francisco in 2008, a woman asked me what my “hard skills” were – and then had to define the term for me to mean technical skills like software engineering or graphic design. I responded that all of my marketable skills were soft skills – persuasion, storytelling, talking to people, and selling.
Recently, someone introduced me to the term “durable skills” and I like that one better. All my skills are still soft – or durable skills – and I’m good with that.
Sales
There’s a story my dad tells about driving with my grandfather through the Central Valley of California long after my grandfather had retired. My grandpa asked that they stop through a small town and stop by a specific depot. The adult children of the proprietor came out crying, “It’s the candy man! It’s the candy man!” Apparently my grandfather used to bring those kids candy in their youth, as a part of his route as a door-to-door salesman selling tractor hitches..
The ability to sell – not to manipulate, but to persuade – is a superpower. As BJ Fogg says: “Help people do things they already want to do.” Sales and persuasion are going to be important in the years ahead.
The Trades
A friend of mine recently left his senior position at a name-brand technology company, borrowed money, and bought an established plumbing company. An old colleague makes more as an appliance repair man than he ever did as a personal trainer. The Trades, and being able to work, quite practically with your hands, is going to become more important – and more lucrative – in the coming years.
Get into real estate
This one is personal. I don’t think most people should treat real estate as business, even if they want to own property. But I went down a real estate rabbit hole this spring. I’m going to dabble in buying and selling real property for the rest of my life.
Daily habits
I haven’t had my cold plunge available for most of 2025. (The horror!) For a few months, I exercised 45 minutes a day, instead of my more typical two hours. I’ve fallen out of keeping a journal. But my daily habits are so strong, historically, that I’ve been able to build them back with ease. When things are going a bit off the rails, I can easily get back to the basics because they’re well known habits.
Discipline doesn’t have to be punitive
Growing up, I was criticized for not being disciplined. As an adult, people tell me how disciplined I am. No surprise, then, that I’ve always struggled with the idea of discipline.
The word "discipline" originates from the Latin word disciplina, which means "instruction, teaching, knowledge, and learning." It is derived from the Latin root discere, which means "to learn". Over time, discipline has come to mean punishment and correction, but the core meaning remains rooted in learning and self-control.
Exercise every day
This isn’t new to me. I’ve been exercising every day since I was 19 years old. I was reminded again this spring – amidst a couple of very challenging weeks – that when I get enough exercise every day, life is better. In particular, I like finding a specific routine (currently: a 5 mile loop through the Oakland hills) and doing that on autopilot. My girlfriend was surprised to hear that I “work” during those runs – mentally processing a lot of loose ends.
Do hard things
I really like doing difficult things. When I’m feeling stuck at work, running a really hard hill makes everything better. When I have a difficult day ahead of me, a few minutes in my cold plunge makes the day easier.
Maybe it’s a study in contrast, but doing hard things really does seem like a secret to success.
Limit social media
I deleted TikTok a few years ago. I haven’t been posting on Instagram almost at all in 2025. For sure, this is to my professional detriment. But my mental health is so much better! Social media is a mixed bag – there are good and bad things about it, for sure – but I’m healthier without it.
Limit screens, generally
I’ve watched two movies so far this year and no television shows. I have a time limit on all of my most-used apps on my phone. When I’m not working or researching real estate, I’m doing my best to avoid screens. And life is better!
Community is strength
When I brought back Responsive Conference after a pandemic-hiatus in 2024, the deciding factor was because I appreciated the value of people gathering in person. For the same reason, I’ve been hosting a monthly potluck to gather people together socially. Humans are meant to operate within a community. Community is strength.
Get a dog (they’ll teach you about presence)
My dog Riley is eight years old. I’m traveling this week, and thinking about her. She’s my best teacher on one important topic: presence.
I’ve done a lot of meditation, and dabbled in a variety of “presence” practices. But nothing has been more useful for practicing presence than having a dog as my daily companion.
I was listening to this Conversation with Tyler with Anthropic co-founder Jack Clark. Tyler asked Jack when we’ll be able to communicate with dogs, and what they’ll have to say. Jack said we probably already know what dogs will say: “Walk!” “Food!” and “I love you!”
Find your rabbit holes
I’ve always been someone who dives deep down rabbit holes. This spring, I spent about a thousand hours on real estate.
As my friend Marie is fond of explaining, the word amateur comes from the Latin “amare” meaning to love. It used to refer to someone who does something purely for the love of it. I think it is really healthy for humans to specialize and to practice out of love.
History > News
Twice over the last year, I’ve developed the bad habit of listening to several political podcasts as I’m waking up in the morning. I’d wake up and immediately start listening to The Daily, followed by other political podcasts. Predictably, I felt depressed for the rest of the day.
I’m learning to limit my consumption. No podcasts or news before 10am or after 6pm. Instead, when I want to think about what’s going on in the world, I turn to history. There’s some comfort in recognizing how much chaos and violence the human race has been through.
Write to think
Writing is hard. Even after writing more than 200,000 words over the last two years, it doesn’t seem to be much easier. But I am a better writer. And my thinking is quite a bit more clear.
Writing isn't the only way to train critical thinking (BrainHQ is also great), but it is one of the best ways I know.
You know more than you think you do
I’ve been writing Snafu for two years and am always surprised that I have more ideas to write about. Over the last six weeks, I’ve been leading a weekly workshop about a more authentic approach to selling. As I prepare for the workshop each week, I’m consistently surprised by how much I have to say – way more than I can teach in an hour a week! We all know more than we think!
Avoid “Grass is greener on the other side”
I’ve noticed a habit among entrepreneurs to chase a new idea, project, or business when the better course of action is to double down on the current business. I’ve done this a lot across a dozen industries in the last decade!
It is important to avoid sunk cost fallacy! Don’t keep going if you’re just digging the hole deeper. But also don’t jump to something new just because it looks more appealing than the hard work in front of you.
Keep going
Luck accumulates to the persistent. Just keep showing up.
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3 things I’ve loved this week
Quote I’m thinking about
“The future is already here – it's just not very evenly distributed” -William Gibson
I’m astonished how many ideas I discovered reading science fiction in high school have come true in the last few decades. But perhaps none capture the truth of the last few years like this quote by William Gibson.
Idea I’m wholehearted embracing
“Treat sugar like a recreational drug.”
My friend was just reading about Pegan Diet (an awkward portmanteau between Paleo and Vegan) and stumbled across this phrase. It 100% fits with my experience and beliefs about sugar.
Escapism book I’m enjoying
Flybot by Dennis E. Tailor
Best known for the Bobiverse series, I’ve recommended Dennis E. Tailor’s Outland before. Flybot might be my new favorite of his books.
Set in the near future, a tinkerer accidentally releases a superintelligent AI, which quickly spirals into unexpected and existential challenges.
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When you're ready, here's how I can help
Get good at selling
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The course is going really well and I'll be starting another one soon. If you're interested, join the waitlist here.
Tell your story
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Read these books
Responsive: What It Takes to Create a Thriving Organization is a book for any startup founder or enterprise change lead who wants to improve their organization. And if you want to learn to do a handstand, read out How to Do a Handstand.
Join us in September
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Until next week,
Robin
