Essay

15 Lessons I Learned Before Turning 31

31 feels slightly less monumental than 30. Last year, I reflected on the most important lessons learned over the course of my 20s. But there are no off-years in life. If you’re doing it right, each one offers new experiences and opportunities to grow.

Every year I create checkpoints to consider lessons learned, challenges I’ve faced, and progress I’ve made. Birthdays are one of those triggers to step back and administer a healthy dose of perspective. 

I’ve found that the true test of how much I’ve learned in the previous year is considering myself at that same point in time 365 days ago. If I laugh at how stupid I was, that’s a good sign. Investor, Ray Dalio, shares a similar sentiment, “It seems to me that if you look back on yourself a year ago and aren't shocked by how stupid you were, you haven't learned much.”

The years I’ve been able to look back and contemplate how much I’ve learned, despite laughing at the expense of my younger self, have been the most rewarding.

This year was an important one for me. Although it’s not as big of a milestone as 30, this year was full of little victories, failures, and lessons. I’ve learned as much as I ever have in a single year. Here are some of the most important lessons that have stuck with me.

1) What matters most is the ability to bounce back

There will be times you fail to rise to the occasion. What matters most is the ability to bounce back. It’s one of the most critical skills you can build in life.

I’ve learned this time and time again in my career. You can’t expect perfect conditions each step of the way. Things are going to break, you’re going to run into ignorant people, and there will be times that you face an onslaught of obstacles with no end in sight. What matters is that you find a way to come back with a fresh perspective each day, ready to try again. 

The best teams I know embrace imperfections beyond their control and contribute something meaningful anyway. The worst teams self-destruct because they’re too busy obsessing over inconveniences. 

2) Experiences can still surprise you

I’ve been fortunate enough to have traveled to dozens of beautiful places across the world. I believe the more you travel, the more perspective you build – an invaluable gift in life. But the catch is that the more you travel, the more you seem to lose the novelty of first-time experiences. 

I will never have the same feeling that I did the first time I went dogsledding in the arctic circle, kayaking in the Milford Sound, or camping in the Vietnamese jungle inside Hang En cave.

But this year, I went to South Africa and was surprised to discover that elusive feeling in the raw experience of a safari and in the bliss of the beautiful countryside of Babylonstoren, one of the oldest Cape Dutch farms. If you keep an open mind and maintain an appreciation for life in all its forms, experiences will never cease to amaze you.

3) Convenience is worth paying for

Five years ago, “frugal” would have been one of the best adjectives to describe me. Over the past few years I’ve let that go in favor of convenience. And this comes from learning to value my time properly. 

My routine for years has been to write at a coffee shop on Saturday afternoons. But I would always cut that short to head across town to pick up groceries, an absolute nightmare on weekends. This year, instead of interrupting myself during this time, I’ve started using a grocery delivery service. 

On average, I save two hours of uninterrupted focus time. And it only costs me five extra dollars. At a certain point, you have to learn that time is the most valuable thing you have. 

4) Reversibility matters more than certainty in your decisions 

Time is far more valuable than a marginally better solution. To help make faster decisions, I’ve started asking myself, “How reversible is this decision?” If it’s easily reversible, I make it right there. Assessing decisions based on reversibility, rather than certainty of the potential outcome, has improved my decision making significantly. 

Slow, deliberate decision-making can be a significant advantage in avoiding massive mistakes. But the reality is that most decisions you make on a daily basis aren’t permanent in nature. There’s a time and place to use this level of deep thought and consideration. Not when it comes to picking a restaurant for dinner or testing a new layout for the landing page of your website. 

5) Success doesn’t come from preventing things from falling through the cracks

This is about building a systems mentality. In other words, developing the ability to step back and consider the interconnected whole – the structures, patterns, and cycles – instead of being blinded by a single event or moment in time. This frees you to focus your limited time and energy on what matters most. Success doesn’t come from being better at preventing things from falling through the cracks. It comes from knowing what to let fall through. 

You can identify those who have failed to build a systems mentality by how overwhelmed they get by minutiae – especially when the stakes are at their highest. They become fixated on insignificant things, gripping for control in their foolish quest for perfection. They’re unable to let the little things go.

6) Four things separate you from the top of your field

When I started my career in product, those above me seemed almost lightyears ahead in terms of their intelligence and abilities. I wouldn’t put myself anywhere close to the same category. But the more interactions I have with executives and senior leaders, the more I’m convinced that they aren’t infinitely smarter. The real difference is in their risk-taking, network, growth mindset, and a healthy dose of luck. It’s a good reminder that you’re not that far off. 

7) Don’t get pulled into races that you’re not willing to run

If I don’t create room for reflection, I often find myself getting pulled into other people’s aspirations and playing stupid games for stupid prizes – struggling to position myself on the corporate ladder, equating meetings with productivity, or seeking validation through arbitrary certifications and recognition. 

This is one of the most difficult skills to develop, sorting through the noise and determining what’s your own. As a human being, you are highly impressionable. This is great when it comes to social cohesion, but terrible when it comes to realizing your own aspirations. It’s okay if you don’t want the same things as everyone else. Just make sure you aren’t getting pulled into races that you’re not willing to run.

8) People are amazingly consistent in their behaviors

Another way of saying this is that everyone gets what’s coming to them – for better or worse. It’s just a matter of time. Habits and behaviors projected over the course of years dictate future conditions and outcomes. The trouble is that when you’re young and could use this advice the most, your perspective of time is too shallow to really grasp the lesson.

I see examples of talented, hardworking people catching breaks every month. I also see examples of grown adults clinging to the same identity they had in college who are paying dearly for short-sighted decisions in their careers, health, and relationships.

Use this as motivation to focus on getting the conditions right, developing better habits, and playing the long game. With this mindset, it’s just a matter of time before you start catching breaks. 

9) Compound interest from reading is no joke

After five years of reading 50+ nonfiction books each year, it’s only within the past few months that I’ve felt like I’ve been able to make seamless connections and pull relevant stories on demand. Once you form these connections, you propel yourself forward with a wealth of vicarious experience. 

This is critical to so many areas of life – mastering a multidisciplinary approach, identifying your guiding principles, outthinking misguided people. Without reading, you have to learn this all from direct experience. But books provide you with lifetimes of experience and perspective that you can call upon at will. 

10) Stories > instructions

Stop telling people what to do. Unless you’re running a laboratory, people don’t give a shit about instructions. Stories are the best way to communicate. If you let people interpret things for themselves, you get better results. Especially in fields that demand creative thinking. 

Of course, there are obvious exceptions and integrity matters. But you see the power of this in presentations. Speakers who use stories are able to capture the imagination of their audience. That’s what resonates with people. The same thing goes for brainstorming, design sprints, whiteboarding, and every meeting you have.

Everyone craves stories because that’s how we make sense of the world and piece together our own ideas.

11) Improv makes you a better human

I signed up for improv classes to help improve my public speaking skills. I wasn’t sure what to expect but I wanted to take a non-traditional approach. Fortunately, this has been one of the most profound experiences of my entire year. There are so many positive takeaways and important lessons that I’m planning to write a full article on the experience. 

The short version is that improv will get you out of your own head, train you to be a better listener, and wreck your comfort zone. 

If you aren’t listening with every ounce of your being, you will fail. You can’t fall back on normal cognitive patterns and predictions that you use in everyday conversations. And the constant discomfort during class forces you to embrace and accept the fact that you’re going to look like a dumbass on stage. There’s no way around it. It’s an empowering realization. I’ve since given up my attempts at perfection during presentations, which has helped me relax and improve my delivery.

12) Routine is essential to creativity

The more automatic my habits and routine become, the more energy I can pour into being creative. Ever since I carved out dedicated time and space for writing, my craft has improved significantly. Most mornings I start writing at 6:30 AM. Since I’ve built this habit over years, when I sit down at my desk in the morning I’m able to shift into a creative mindset without a colossal effort.

I often think of this quote from Gustav Flaubert, “Be regular and orderly in your life, so that you may be violent and original in your work.” With that being said, there is a golden mean. I have to challenge this routine on occasion to make sure it’s still working for me and I’m not becoming too rigid in my approach.

13) Drawdown periods matter

I’m excited to release my first e-book next month. But it was no small undertaking. It required five months of sustained effort. Before jumping off I had to make room for a drawdown period where I was able to prepare, rest, and reflect before starting. I knew I would need every ounce of energy I had if I wanted to get my thinking clean and bring the best version of the idea to life. 

This drawdown period was essential in helping me create a buffer where I was able to piece together and discover my own thoughts on the subject. It was an escape from being bombarded by influences and outside noise. The bigger the project, the more important it has been for me to settle my mind leading up to it. 

14) Time your vacations to avoid burnout

Over the past few years, I’ve kept track of when I start to feel like I'm burning out in a given year. And I've noticed it always occurs around the same time. So this year, I planned vacations and weekend getaways to avoid falling into the same pattern – February, May, July, August, and November.

As ridiculous as it sounds, one of my New Year’s resolutions was to take five vacations. It was a way to self enforce breaks when I would otherwise attempt to be a hero and power through things. This has made a huge difference in my wellbeing, the quality of my work, and overcoming the burnout I’ve faced in recent years. 

15) Purpose starts with meaning

Over the past year, I’ve had conversations with many people struggling with purpose. I love being able to share these deep conversations and I sympathize. That was the first ten years of my adult life – forever tiptoeing on the edge of an existential crisis. Some days I still wonder what the hell I’m doing. Purpose is such an overwhelming thing. 

But what I’ve learned, and what I try to share in these conversations, is that purpose is just the series of pieces you find meaning in. Look for where you find meaning in your day to day. By doing more of those things, you move purpose within reach. And if the quest for purpose ever becomes too much, settle for doing meaningful things instead. 

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