38 Lessons Learned in 38 Years
Today is my birthday. Here's what I've learned as I reflect on this past year.
Each birthday, I reflect back on what life has taught me. Read my prior lists here: ages 35, 36, and 37.
This past year, I feel like I’ve started to come into my own as an online creator. (After 15 years of writing online, this is the first year I’ve even called myself a “writer” or “creator.” It always felt strange to claim that title, but I’m finally coming around to it.)
Since my 37th birthday one year ago, I’ve launched a Substack publication, begun posting consistently on LinkedIn, recorded my first online videos, published my 300th post on my website, got paid to give my first corporate talk (then gave 10 more), and started to frequently make guest appearances on leadership podcasts.
I’ve also suffered a ton of self-doubt and often questioned whether I have what it takes compared to other creators who seem to be better, smarter, or more successful. (More info below about how I’m dealing with the comparison game.)
Looking back, here are 38 lessons I’ve learned this year, split out by topic.
Re: How to Live
1. You always have a choice between one of two focuses: (1) what you want and (2) what you have.
#1 is ambitious. It can lead to high performance but also sadness.
#2 is grateful. It leads to joy.
To live a great life, build your house in Camp #2 with occasional glimpses at Camp #1.
2. Compare little things, not big ones. James Clear puts this well:
“To improve, compare little things: marketing strategies, exercise technique, writing tactics.
To be miserable, compare big things: career path, marriage, net worth.
Comparison is the thief of joy when applied broadly, but the teacher of skills when applied narrowly.” -James Clear
3. Life is about direction, not speed. Accomplishing something important often takes way longer than you think it will. But what matters is whether you’ve chosen the correct path, not how fast you’re moving on that path. (HT:
)4. Emotions aren't bad, but not being able to control them is. In many situations, the person who keeps their cool will win. (Examples: negotiations, sports, debates, etc.)
Re: How to Communicate
5. Connection > Eloquence. Sometimes, the best thing you can do as a speaker is share a goofy story that is only remotely connected to your topic but connects with the audience on a human level. (This goes for both 1-on-1 conversations as well as for public speeches in front of hundreds.)
6. Ask "Do you want to be helped, heard, or hugged?" I default to giving advice too quickly. Sometimes people just want to be heard. Rather than trying to fix everyone else's problems, ask them what they need most from that conversation.
7. The more you're paying attention to yourself, the less you're paying attention to other people. That means that the more comfortable you are being yourself, the closer you can get to other people. (HT:
on Barrett Brooks’s “Good Work” podcast)8. There’s a surprising power in naming things. Memorable phrases can fuel connection and provide clarity. I’ve seen this show up in multiple random places:
Friends have talked to me about terms like “SUB system” or “Being > Doing” that I’ve coined in past articles. Those phrases gave us a shared language.
- ’s article about languishing during the pandemic was shared thousands of times because it put a word to something many were feeling.
On the heartwarming Netflix show “Love on the Spectrum,” several autistic individuals said they were relieved when given their autism diagnosis because it gave them a label for what they had been experiencing.
9. Lean into your weird. Show the world your unique self. I recently had the chance to hear a bunch of talented speakers speak at a conference. But the most memorable speaker was someone I noticed in the room of 400 attendees hours before she took the stage. Why? Because she was dressed differently than anyone else at the conference.
In a sea of business-casual khakis, button-down shirts, and fancy blouses,
was outfitted in fluorescent clothes and a headband. Here’s a pic of Liz:
Liz has built a million-dollar email marketing business and was even a contestant on Survivor, which is why she rocks a bandana. Talk about a unique brand! But what attracts me most to people like Liz is the way she completely owns who she is. That’s powerful. I want to be more like that.
"Normal is forgotten. Only weird survives." -
10. Don’t say the boring stuff. Novelist Elmore Leonard said, “Try to leave out all the parts readers skip.” I’ve thought about that a lot recently on podcast interviews. If the interviewer asks about my habits, I omit everything other people do and zero in on what makes me unique. That’s why I talk so much in interviews about my biannual solo retreats and my habit of reading 2-3 hours at night while sucking down an energy drink. Jump to the interesting stuff.
"If you're not telling secrets, who cares?" -Mike Birbiglia
Re: How to Be Productive
11. Practice radical incrementalism. If you want to do something BIG, just bite off a tiny bit each day. Big things get accomplished through small, consistent actions. Follow the Latin adage of festina lente: Make haste slowly.
12. Just do the thing. If you’re trying to create something (write a book, create a presentation, build a product, etc.), there are hundreds of ways you may procrastinate. Some of the most devious methods feel productive: researching the thing, reading about the thing, talking to people about the thing, etc. But none of those are doing the thing. Gauge your success by how much time you spend actually doing the thing.
"Even 30 minutes spent actually doing the thing today are more valuable than hundreds of purely hypothetical hours in the future." -
13. For many things, the long road IS the short road. It takes a lot of time to do something great, so many people look for a shortcut. Rather than putting in the time to get fit, they take a diet pill. Rather than building a real audience, they pay for fake views or followers. But shortcuts don’t often lead to long-term growth. The long path (i.e., doing the hard work) ends up being more fulfilling and also more sustainable.
"The best way to become something is to do the work required to become something." -Gary Vaynerchuk
14. Work with slow productivity. Cal Newport coined this phrase in his newest book, and he breaks it down into three steps:
Do fewer things
Work at a natural pace
Obsess over quality
I love this model because it avoids the trap of viewing busyness as a badge of honor. True value is created not by completing a bunch of aimless tasks but by completing a select few that truly move the needle.
"Don't mistake activity for achievement." -John Wooden
15. Build a reputation for solving tough problems. The rarest type of employee is one who will run through brick walls to get something done. That also makes them the hardest type of person to replace…and one of the highest-paid.
16. Shorten the feedback loop for the metrics you care about most. My most important metric is email subscribers: people who choose to get my ideas in their inbox. For the longest time, the only report I’d get about that metric was a weekly summary email. This year, I shifted to getting an instant alert every time I gain a new subscriber. Now I can see in real-time which initiatives are/aren’t working to generate subscribers. What’s your most important metric? How can you tighten the feedback loop?
17. Don’t hunt small game just because it’s easier to kill. Big goals tend to be intimidating and hard to visualize. In contrast, small goals are simple and easy to wrap your mind around. We tend to focus on the small ones because it feels good to check items off a list. But remember, one of the easiest ways to underperform your abilities is to shoot for small targets.
“We are kept from our goal not by obstacles but by a clear path to a lesser goal.”
-Robert Brault
18. Some habits are keys that unlock hundreds of other habits: get 7-8 hours of sleep, exercise, spend time in nature, schedule frequent dinners with close friends, etc. Prioritize keystone habits and they’ll help you topple many other dominoes.
Re: How to Take Action
19. There’s immense power in explicitly deciding to NOT do something. Whether setting personal goals or business goals, create a “not doing now” list. Doing so explicitly gives you permission to deprioritize many things that don’t matter—or at least things that don’t matter right now.
20. If you’re trying to make it in a given field (writing, music, entrepreneurship, etc.), prepare for a LONG road. Good things take longer than you think: finishing your novel, finding the right job, breaking through with your business idea. Because of this, it's important to do three things:
Set reasonable expectations for yourself.
Start today.
Enjoy the journey.
"Nearly everything awesome takes longer than you think. Get started and don't worry about the clock." -James Clear
21. You'll learn best by taking action, not thinking more. It’s very rare to know all of the steps between now and your ultimate goal. You can’t see around every corner. Just start walking the path and you’ll learn more with each new step.
"As you start to walk on the way, the way appears. Clarity doesn't come before action. It comes from action." -Rumi
22. Every year, run hundreds of small experiments. If you’re not sure if something will work, find a way to test it for a specific amount of time. Then tweak. Then test. Then tweak. Then test again. Do more of whatever works and stop anything that doesn’t. (This is especially helpful online: social media, digital ads, etc.)
’s book Tiny Experiments is a great how-to manual for doing this.“When we use trial and error, we set in motion a series of growth loops where progress emerges in conversation with our environment.” -Anne-Laure Le Cunff
23. Increase your luck surface area. In many fields, it’s impossible to know what will work and what won’t. But you can still put yourself in a position to get lucky. How? Perfect your craft, publish more, practice more, pitch more, put yourself out there more.
“I believe in hard work and luck, and that the first often leads to the second.” -J.K. Rowling
Re: How to Create Something of Quality
24. Be worthy of remark. We throw around the term “remarkable” without considering what it means: something worthy of passing along to your best friend, partner, coworker, or sibling. That’s a high bar. Something has to be really freakin good for me to tell someone else about it. If you’re creating something, set that as your goal: it should be worthy of remark.
25. “Be so good they can’t ignore you.” Comedian Steve Martin said this, and Cal Newport popularized it in a book of the same name. Whether you’re trying to get promoted, break through as a musician, or get a publication to cover your new product, it’s easy to complain that people aren’t noticing your work. But that’s not the real problem. The problem is you’re not good enough yet. Focus on your craft, not the crowd.
26. If you put in 10X the effort, you’ll get 100X the outcome. (HT:
) If it normally takes you 5 hours to write an article, it’s tempting to wonder whether you could get that time down to 4 hours. But that’s often the wrong direction to move. What would happen if you put in 50 hours? Would it then be worthy of remark?27. Extreme results only come from extreme actions. The average American watches TV for 3 hours per day and doomscrolls on their phone for 5 hours per day. Don’t be that person. Find something worthy of your time, then pour yourself into it.
"You don't get extreme results without extreme actions. If you do what most people do, you get what most people get. Don't be normal." -Derek Sivers
28. One of the most extreme actions is to be boringly consistent with the little things. One of my life rules is “Improve by being boringly predictable.” Every night between 9 PM and midnight, you can find me at my desk: reading, writing, and journaling. It’s the habit I’d credit for any modicum of success I’ve had in my career.
"Be boring. (It's the only way to get work done.)" -
29. Excellence comes from your unique Venn diagram of skills. You may not be the best in the world at any single thing, but the more skills you can stack on top of each other, the more likely you'll stand out. For example, here are three facts about my life:
I’ve managed teams as large as 160 people.
I’ve worked in startups, small & midsized businesses, and Fortune 50 companies.
I write articles online.
Any one of those facts by itself is ordinary. But I’d bet that only 1 percent of the world has done all three of those things. The Venn diagram of those three things is my sweet spot as a writer, which is why I write this publication about leading and learning.
Re: How to Be Creative
30. For creative projects, focus 90% on what you think and 10% on what others think. It’s stupid to let others define your work. But it’s also ignorant to think that others’ opinions don’t matter at all. Build for you, but listen to feedback to see how others are perceiving your creation.
31. Pay attention to what you pay attention to. If a social media post makes you stop and read, ask yourself why. If someone’s sales pitch makes you actually listen, figure out what they’re doing differently from others. If a talk makes you feel inspired, unpack what the speaker did that was so magical. Then deploy the same tactics in your work.
32. Consume what you want to create. If you want to be an author, read a lot. If you want to be an entrepreneur, build relationships with founders and soak up what they’ve learned. Whatever you consume will eventually come out of you.
→ Note: This doesn’t replace the power of action (lesson #21 above). It complements it.
“You write and speak what you read.” -Ward Farnsworth
33. Push through the dip. Creative work follows a predictable curve. You begin with excitement and often see some initial positive results, but then hit what Seth Godin calls “The Dip”: your results lag behind your effort. Many creative endeavors die in the dip. But if you can push through it, you can often create tremendous results.
34. Share the byproducts of your existing workflow. (HT: Barrett Brooks’s interview with James Clear) The outputs of your natural learning process (book notes, quotes, slide decks, etc.) are—in and of themselves—content you should share with others. We all create more output than we realize. How can you repurpose the byproducts of your learning to serve others?
35. Learn → Curate → Simplify. In a world of endless information, curation is one of the most valuable services you can provide to others. As soon as you learn something, curate the best takeaways and share those. As you share them, you’ll notice you gradually get better at simplifying the message and curating the best bits.
"A wealth of information creates a poverty of attention." -Herbert Simon
36. Learn your ecosystem. This year, I realized I’ve done a horrible job of connecting with other writers. I’ve approached my work as a lone wolf, and I’ve missed out on the fulfillment and benefit of partnering with other creators. Now, I’m studying the ecosystem of other online creators so I can bond with other writers and find ways to help each other.
37. Copy what works. If you’re launching on a new platform, the best way to succeed initially is often to copy the process and format of the top dogs. (And I don’t mean just the biggest creators—I mean the ones who are creating something worthwhile.) For example, if you’re starting on LinkedIn, learn from mavens like Chris Donnelly and
. If you want to start a YouTube channel, follow creators like Ali Abdaal and Deya. Learn from the best and pay attention to what they do.38. Use the dawn of AI as a chance to be MORE human, not less. Lately, I’ve been asking myself how I can stand out while millions of people are cranking out AI-generated articles, book reviews, and online slop. The answer: leaning into the human elements of my work. For me, that means including pictures of my unique book notes system when I write book reviews (like this and this). It means including more personal stories in my email newsletter. And it means pushing harder into authentic human connection by responding to reader comments with thoughtful, heartfelt replies. What about you…how can the dawn of AI fuel your humanity?
It’s been a rich year of learning, and I’m excited for this next year of life. Thanks for reading, and I’d love to hear below which lesson(s) resonated with you most.
Much love,
Bobby
First of all, thank you for the content, Bobby. I read it, I'm rereading it, and I'll read each of these teachings again.
I live in a South American country, and unfortunately, for those who enjoy reading, the difference between what's produced in my country and in the US, for example, is clear.
Your content contributes greatly to reducing this discrepancy by bringing us extremely relevant aspects so we can evolve individually.
Thank you, and long live!
Happy birthday Bobby. Love number 23