The 23 Lessons I Learned on the Way to 23

Between becoming the 22-year-old with their sh*t together, and now turning 23, I’ve had to face some hard realities.

One, of course, is that ‘having your sh*t together’ isn’t a state that you just unlock and keep. It requires you to consistently toe the line. To tirelessly continue to grow up. Sometimes faster and sooner than you’d like.

Nevertheless, my year was once again packed with many lessons that I found myself wanting to oust, in hopes of getting as much from reflecting upon them as I did last year.

And whilst it didn’t seem entirely appropriate to draw attention to myself on my birthday this year (something I address at the end of this piece), I wanted to make a habit of noting the lessons that were mostly hard-won — in the hopes that when read in a better time, they might even save someone some trouble.


1 – Think of yourself as a brand asset and do what you can to make yourself a smart investment for others. Just remember, like a luxury brand, you are known not just for what you do, but also for what you don’t do.

2 – Be focused on a solution that has high value to others. Be rigorous in assessing it, and be utterly obsessive in figuring out how you can be the very best at servicing a particular set of needs.

3 – Become an owner in all that you do. But as you do, be prepared to reinvent yourself sooner than you may be comfortable with. And for where there is a lack of comfort, fill it with immense courage. For true ownership can only come from within.

4 – If you wish to be uniquely valuable: adopt the Toolbox Strategy. This means that as a mentor of mine once advised, you should “think of your career as a toolbox: your job is to fill it with as many tools as possible.” For years, I believed being valuable required creating the largest possible circle of competence. But I have now come to see that by adopting the Toolbox Strategy, each skill and area of knowledge that you acquire gives you another circle. The unique value that you can then offer is, in fact, derived not from the circles themselves, but rather from the Venn diagrams you create as the perimeters of your circles’ overlap.

5 – Slow yourself to notice the tactics your mind uses to shield you from danger. Sit in it. Observe whatever concoction your mind developed — until it ultimately diminishes. Recognise that you are almost always better off confronting the very thing your mind is protecting you from.

6 – Don’t edit whilst you write. Don’t edit whilst you create. Don’t even edit whilst you think! Let your creativity move beyond the boundaries of perfection, and trust that you will eventually return to your wild creation with the precision and refined approach of an expert bonsai craftsman.

7 – Create a routined cue to jump-start you into your difficult days. At the beginning of every single game, Michael Jordan and the rest of his teammates in the Chicago Bulls would gather in a circle and chant “What time is it?, Game time!” — demanding, from themselves, a sense of focus and commitment to winning. Do the same for yourself and earn your championship ring by defeating your own enemy — distraction.

8 – Aim for your life to feel the way a John Barry’s James Bond soundtrack sounds. Sophisticated, smooth, and yet, continuously full of suspense.

9 – In all things that matter to you, aim to appear effortless. Just remember, this is something that requires much effort to achieve.

10 – Don’t feel committed to finishing a book. Reading 30–50% of many books in order to seek out the one or two that completely change your life, is far more effective a strategy than reading 100% of a few books that don’t add much to you. Relieve yourself of the pressure conducted by your friend who once read a whole book by the pool in Spain last summer.

11 – If you work in a team, get everyone in-sync as often as you can. There is nothing quite like an interconnected team with one-mind. To achieve such a state more frequently, develop a sensitive disposition for misalignment and pay notice to when there unresolved differences amongst your teammates.

12 – Place your efforts behind people who are already in motion, rather than those who simply say they want to be.

13 – If you have a friend who wants to achieve something as much as you do, schedule a weekly check-in with them to hold each other accountable. In the best of cases, you’re both there to help each other clearly define your next moves. And in some cases, you’re simply there for each other when it gets hard. Both are invaluable.

14 – Write notes whilst taking phone calls. Develop your own shorthand to be economical; and after the call, convert what you’ve written in note-form into a more comprehensive journal entry for greater retention. For no matter how engaging a conversation is; without tracking the trunk of the tree, you’re likely to get lost in the branches.

15 – Don’t depend on one relationship to give you everything. No matter how special someone may be; relying on them to be the sole facilitator of your every need can run you into unnecessary complications. This is true for your family, close friends, mentors, business partners, students, and lovers.

16 – As Dave Chapelle’s own mother once told him: “Sometimes you need to be a lion, to be the lamb that you really are.”

17 – If you’ve never watched Mad Men, do so now. If you’ve already watched it, rewatch it. This will give you a better understanding of the difference between truly meeting your needs and simply meeting expectations placed upon you. And with that understanding, you will be happier. A thing like that!

18 – But seriously, talk to more strangers.

19 – (One for the lockdown) — Ask yourself: “When I think back to this time, to what will be a significant moment in history, what do I want to remember having done?

20 – In a report that examines the practices of top-performing CEOs, McKinsey & Co. state that ‘external hired CEOs are more likely to move with boldness and speed than those promoted within an organisation.’ This is, in part, because an outsider possesses a fresh perspective that grounds them in their present reality; enabling them to develop a policy of future-action that has little ties to tired, legacy policies. When solving a problem of your own, examine it with the eyes of an outsider — because no matter how great a track-record you possess; what brought you here, might not take you there.

21 – Do your own research, and dedicate your every waking moment to do so. Travel to and from your every appointment with a hypothesis or question in mind. It is not enough to simply browse, hoping that some answer will ‘find you’. You must engage deeply with your reality — noting even the intangibles as you do so. Research with intent, and discover that everything is worth investigating.

22 – Your life is a story and as Donald Miller writes: “if a story doesn’t have negative turns, it’s not an interesting story.”

23 – “Stop measuring days by degree of productivity and start experiencing them by degree of presence.” — Alan Watts


In a year like this, it feels somewhat wrong to celebrate such a seemingly-arbitrary thing as a birthday. There are far too many, more important, goings-on that can’t just be placed on hold for someone to joyously proclaim that this day is for them.

And yet, amidst hard times filled with uncertainty, and as our own inescapable impermanence is brought out of the hazy unconscious; remaining still for a moment to acknowledge that our years are numbered can be immensely powerful.

Upon meditating on ones own mortality, immense gratitude can be felt. It’s what helps put the ‘happy’ back into ‘Happy Birthday’, as you remember that if there is any good missing from the world, it’s always within you — and that if you are able to sit with the fear of death for long enough, you may even become courageous enough to bring a little bit of it back into the world.

Ignore the apparent wisdom of crowds. Despite them being in as high in demand as toilet paper, you don’t also need a Nintendo Switch. These times aren’t something to entertain away. This is an opportunity. A chance to delve deeper. For us all to face our toughest lessons, and become better in a world that so desperately needs — better.

This article was originally published on

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