10 Lessons on the Road to 33

Birthdays and New Years serve as two natural checkpoints for me. Birthdays act as a time to reflect on what I’ve learned and consider lessons that have resonated strongest over that year of my life. Whereas New Years signal it’s time to set five primary goals and assess how well I did against the previous year’s goals. Most years I publish these reflections, the following are 10 lessons that stood out most over the past year. 

1) Show up, even when it’s inconvenient 

Fighting through canceled flights, delays, and traffic jams to show up for someone when they need it most, even if you’re only there for an hour, matters. Regardless of what plans you might have made for your evening or weekend. The timing of events beyond your control might be inconvenient. But the universe isn’t on your agenda. And there isn’t some perfect version of the future where your life is free of challenges. The challenges and obstacles are what give life meaning. You can point to those as your excuse, or you can show up anyway when it matters most. 

2) Commitment adds meaning

Just as obstacles add meaning, so too does commitment—whether your relationships, career, hobbies, you name it. Directions in life are mutually exclusive. In my early 20s, I optimized for optionality and never committed to anything. Many of these things were unfulfilling and left me restless. But once I started to cross options off my list and double down on the people and things I cared about most, life became far more rewarding.

Getting married to my favorite person in the world this summer after six years together has continued to deepen our relationship. The same goes for my career and the way it has been accelerated by committing to problems I care about solving and the vision we’ve crafted around solving those. 

3) You don’t have to agree with the entirety of someone’s opinions

Almost everyone has good ideas and bad ideas. And you don’t have to agree with the entirety of them. One good idea doesn’t mean every idea that a person has is worthwhile. Just as one bad idea doesn’t mean the entirety of that person’s ideas are garbage. This lesson shows up frequently for me in books. When I was younger, I would take the entirety of an author’s ideas in a book as truth. Now I find myself more often disagreeing with certain aspects, and that’s fine. This ability to balance multiple opposing views and perspectives is what leads to improved critical thinking. This also speaks to the danger of ideologies and blindly accepting a docket of opinions without thinking for yourself. Guard yourself against this at all costs. 

4) More music, less everything else

During the pandemic, this got away from me. I didn’t have my regular outlets at coffee shops or commutes to let go and listen to music. It was all work, all the time. And in the brief moments when I wasn’t working, we were watching Netflix. But music is the thing that allows me to reach a state of relaxed concentration where I do my best work. Making more time for this, creating focus blocks throughout my day to tune everything else out, and starting my day with music while reading or writing in the morning makes me happier. And the same goes for evenings at home. Just turning on music instead of the TV feels more rewarding than whatever show we might be watching. 

5) Focus on what’s within your control

As long as I’m around, I don’t think I’ll ever shut up about this. Focus more on yourself. Every second you spend projecting or losing yourself in imaginary conversations consumed by others’ opinions is truly wasted. Focus back on yourself. Most people waste away consumed by distractions without ever searching within. If there’s any sort of secret in this life, it’s figuring out what you want out of life, reframing that as an internal goal you can actually influence, and pursuing it with everything you’ve got. 

6) Happiness is knowing less about what’s going on in most people’s lives, not more

Comparison is the death of joy. Most people are far too connected and could use more distance. I can only speak to my life, but I am far happier when I know less about people outside of my closest group of friends and family. And that’s a group of about 10 people. Beyond that, it’s just noise. 

Certainly, you must care for your community. But your capacity to give a shit is limited. You have to pick your battles. Anyone who claims they can keep up with everyone and every cause is virtue signaling. Instead, focus on yourself and your family, fight for your cause, and ignore the bullshit. There’s only one way out of the noise most people find themselves consumed by—distance yourself.

7) In-person interactions hold company’s together

I’ve worked fully remote at different points in my career. I’ve never actively sought it out, it’s just worked out that way and I was rather indifferent to it. But over the course of the pandemic, I’ve changed my stance entirely. If your intention is to create an enduring company of top performers who band together to overcome challenging moments, co-located teams will crush remote teams. Fully remote teams sacrifice camaraderie, morale, and meaning in the name of short-term productivity. My expectation is that most fully remote teams will self-destruct over the next few years because they won’t be able to absorb the higher turnover caused by a lack of human connection. 

8) Appeal to Your audience’s self-interest

Whether it’s a presentation, email, article, you name it, most people start by focusing on what they want to say. That’s exactly the wrong path if you’re hoping to land your message. Instead, ALWAYS start by putting yourself in your audience’s position and emphasizing the benefit from their perspective. Addressing the ‘What’s in it for me?’ question within the first 30 seconds is the only way to capture attention, disarm, and influence.

9) your first responsibility is to shut up and listen

I’m surprised at how common this problem is. A new hire joins the company, insecure and eager to prove their value, they immediately jump to providing feedback and solutions without having any context of the business, the product, or the team. And in doing so, they immediately erode any semblance of trust and have to work twice as hard to rebuild that over months. Seems like a fun way to start. This seems especially rampant in senior leaders who come into companies and should know this lesson better than anyone else, but they turn out to be the worst offenders. 

During your first 30 days at any company, just shut up and listen. Regardless of what level you’re coming in at. True confidence can look like keeping your mouth shut and simply listening. This will help you build deep relationships that will serve you far better than attempting to offer up empty feedback that lacks context and only draws attention to your attempts to overcompensate.

10) to command respect, be fearless

Timidity kills careers. Jump into the deep end. Raise your hand. Aspire to always have skin in the game and never act like you’re above the work. Regardless if you’re a middle manager, executive, or individual contributor, the work matters. You certainly have to know how to delegate. Otherwise, you’ll drown. But there will be occasional points where you must go deep on the subject and fight alongside your team in the trenches. If you avoid this second piece, you will never command respect from your team.