Today is my 26th birthday.
To start this celebration on the most depressing note I can think of:
- If my fate is the same as my mom’s (and her mom’s) that means I’m now officially over halfway through my life.
- If I hit the average U.S. life expectancy for a woman that means I’m almost exactly one-third (33%) through with my life.
That said, I feel deeply grateful to be alive today. Not everyone makes it to 26, and I’ll be damned if I squander it wondering when I’m going to die.
I only share this thought because I think it’s important to remember — that we are all headed towards the same end zone. Milestones like birthdays are only important in so much that they give us a reason (however arbitrary) to reassess and redesign.
On every birthday in my twenties I’ve reread this email from my mom:
The words: “everyday with you is a best day for me” get me every time, but that’s besides the point.
The quote in subject line is what I’m after:
“At 20, everything is possible and tomorrow looks friendly.” — Jim Bishop
At 20, I was happily lost, dazed, and confused. I was just deferring all the important decisions and conversations into the future, hoping that it would just work itself out. I didn’t have the slightest inclination as to what may be possible.
And I certainly wasn’t expecting tomorrow to be friendly — I was destined to be extremely hungover, attempting to stomach a Dunkin’ Donuts bagel just in time to start appropriating culture for an excuse to day drink (Cinco De Mayo).
Same pretty much goes for 21, 22, 23, 24, and 25. I mean not the bagel, the hangover, and the appropriation necessarily (I grew out of those things, thankfully) but you get what I mean.
The majority of my twenties have been painted black by the grief of my one-of-a-kind mom. The one who sent this incredibly kind email, and who, from wherever she is now, is still guiding me forward.
I’ve wondered every year since: could she have possibly known, I’d be sitting here reading it again trying to pull some wisdom from her words?
Probably not. I certainly couldn’t have expected to.
But I’m lucky I can. Because today, on my 26th birthday, six full years after receiving the above email, everything finally does seem possible and tomorrow looks almost sickeningly friendly.
With that, I want to share a 26 item list (go figure) of some important lessons I’ve learned in my 20s because of the struggle, the grief, and everything else:
- “Nothing either good or bad, but thinking makes it so.” Shakespeare said that. So did the Stoics. So did like every smart person to ever live. This is such a powerful belief to have — to be able to step back and see every event in your life as neutral. This is not a moral statement; it’s more about personal perspective. My favorite thing is to ask: “What have you gained from this awful thing?” For example, my mom dying helped me reach a level of compassion that I never would have otherwise.
- Vulnerability is strength. Every good thing in my life has come out of writing the things I don’t think I am able or sharing the truths I don’t think I can speak. Every great friendship I have has been built upon a story or two that is deeply personal. Surface level conversation is abundant in this world; vulnerability and honesty are rare. This makes them valuable.
- You can overcome any obstacle with the right toolkit. When something feels impossible, it’s because you aren’t experienced or knowledgeable enough to handle it yet. Don’t stop there. You can build up the emotional, physical, intellectual, and mental resilience you need. A different mindset, belief, book, idea, or conversation could be the solution.
- “You cannot underestimate the unimportance of practically everything.” John Maxwell said this. I think of it often, especially when I start to get overwhelmed by small details — like running two minutes late to a meeting or losing an article of clothing. In the scheme of things, does any of this matter? Not in the slightest. All my needs are met. I have a good life. Why waste the energy?
- Food is fuel (and medicine). I follow a very strict diet — low carb, no sugar, no processed foods, etc. I don’t even think of it as a “diet” though; it’s just the way I eat now. Some people think it’s crazy (maybe it is). But to me, never feeling “hangry” and having all engines firing (95% of the time) far outweighs my desire for pizza. I want to show up everyday at my best — ready to serve. I have realized I cannot do that if I am crushing donuts.
- Social media and caffeine are just like any other drug. They’re an addictive crutch, and to some extent, offer minimal benefit in return. I love coffee sooooooooooooo much (like SO much), but have to monitor my consumption habit closely or I’ll accidentally have four cups in a day and then wonder why I can’t sleep. Same for social. I try to remember that every time I log onto Instagram or Facebook, I’m up against a multi-billion dollar empire that is investing substantial amounts of money into figuring out how to keep me distracted.
- Never go more than three days without exercising. I definitely stole this from somewhere or someone. My mom used to run 6–7 days per week because she swore it made her a better mother. I understand that now, and really don’t like going a day without exercising, but have to sometimes just to recover. After one or two days without exercising, I start to feel like a sloth, my nutrition starts to drop off, and my productivity goes down; it can all be turned around with a good sweat.
- “Discipline is freedom.” This is the title of one of ex-Navy Seal Commander, Jocko Willink’s, NYT bestsellers (which I haven’t actually read). But this premise… I agree with it 100%. One of the goals of life should be to stop mentally negotiating with yourself. When you say you’re going to do something — like go to the gym at 6pm for instance — you should be able to consider it done before 6pm even arrives.
- The “thinking mind” — the roommate in your head that insists on compulsively talking all the time — is not you. Meditation has a lot of hype lately. It’s great for many reasons, but in my opinion, the real benefit, is understanding this idea. You are NOT your thoughts. You are watching them in a 4D theater, which makes you think you are them. But when you can disengage and sit back, you realize almost everything can be manipulated and redesigned for your benefit.
- Depression is a natural, yet impermanent result of deep grief. You can’t fully prepare for grief. But you can note that depression is a natural result ahead of time. I didn’t do this and I wish I did. I was convinced for a few years that I was irrecovably “broken.” But that was just depression talking.
- State → Story → Strategy. This idea is from Tony Robbins. When you are trying to make a massive change, your instinct is to implement some new strategy — a productivity tool or diet. This makes so much sense in the moment, but rarely ever works. Why? Because it feels like a drag. And we do things based off emotion, not intel. If you address your emotional state first, and then the story that’s playing out such as, “I suck because I procrastinate all the time,” you can actually create results.
- You can’t pour from an empty cup. My girlfriend used to say this to me all the time, but it didn’t really resonate until I filled my cup back up. I thought I didn’t have limits and could take it all on. But that’s dumb. We all have limits — emotional, physical, and mental. We have to respect them and take time to rest and recover. I’m still working on this.
- People are always doing the best they possibly can with whatever beliefs, skills, knowledge, experience, and physiology they’re working with. Everyone has a story. They have a belief that makes them want to snub you for credit on that project. They have a reason for yelling in the checkout line or cutting you off in traffic. The thing is: we are all doing our best with what we have. Why else would we do anything?
- “You are the average of the 5 people you spend the most time with.” And not just people, either. You are quite literally the ideas you think about, the podcasts you listen to, the books you read, and televisions shows you watch. Your beliefs, ideals, and values come from the people around you and are reconfirmed by the news channels you watch. If you don’t like where you’re headed, begin exposing yourself to new inputs: people, ideas, belief systems, etc.
- Don’t do for the sake of doing. I‘m all about crushing to-do lists. But how often do you question whether any of those things actually matter? Figure out what will move the needle forward — in your relationships, career, and life — and then do those things. Focus your energy and attention on what may have a disproportionate long-term impact or make you happy in the moment. And remember: it’s human being, not human doing.
- Be the person with the questions, not the answers. You can’t possibly know everything. If you’re being paid to have the answers, then sure, have them. But otherwise, the direction of life is going to be determined by what you’re willing to ask. Life gets exponentially more interesting when you start listening as much as you speak.
- Invest in a real phone case. This one is self explanatory, but I’m only writing it here because I can’t seem to figure it out. Maybe now I will.
- Parents are people, too. This is hard to swallow. You grow up with this fictional film playing out where your parents are either villains or superheroes. At some point, you’ll realize — they each have an “origin story” or a reason for why they are the way they are. To love unconditionally is to accept their imperfections and see them as people, too. Because that’s what they are.
- Nobody really cares. Everyone is so concerned with what they have going on that they’ll barely pay attention to you. Your ego wants you to believe otherwise; stop listening. Do some karaoke. Go to the party in your workout clothes. Switch careers. Have some humility and remember that you are just a tiny spec in a seemingly infinite universe full of people who are innately self-centered.
- The external is just a vehicle. The money you have, the career you’re in, the way you dress— it’s all just reflective of what’s going on inside. It’s the chance to manifest in the world what it means to be you — your purpose in this world. It’s an opportunity to learn, grow, and discover. There is no other reason to be or do.
- My future self is always happy when I do it now. The dishes, laundry, client work, whatever. Whenever I don’t want to do something — I try to remember that my future self will be VERY happy that I did it now, so she doesn’t have to do it. This motivates me not to procrastinate.
- Read. Read. Read. The average CEO reads 52 books per year. That’s one per week. Why? Because they know to get ahead and stay ahead you have to be learning. I’ve found that reading is the best way to learn (for me personally) not that it can outperform experience. On that note, Haruki Murakami wrote: “If you only read the books that everyone else is reading, you can only think what everyone else is thinking.” Read obscure things. Read things that stretch the limits of your mind.
- “Without a goal you can’t score.” LOL. Don’t you love cliché quotes like this? Me too. Clichés are often cliché because they’re true. Without a goal, you’re stuck in the matrix. Living day to day, waiting for the weekend. With a goal, you are compelled by growth and a mission to move forward. You have to have a goal — a big goal. And it has to be almost sickeningly specific or else you can’t achieve it.
- Have principles. I read Ray Dalio’s book Principles this year and it totally changed my life. We all have rules — for how we make decisions, prioritize, and operate in the world. But how often do you think about yours or write yours down?
- It doesn’t matter if what you believe is true. Do I know if my mom still exists? No. Do I believe she does? Yes. Why? Because it’s easier for me to function if I believe she does than to entertain the alternative. What matters more than the truth of your beliefs is what you activate them for and if the result is net positive for the world around you. That is to say believing in God, for example, has both positive and negative potential outcomes. It can be used as fuel to kill people or to help people. It’s in that choice in activating the belief really matters, not whether God is real or not.
- I may not think any of this still stands in a year (and I’m okay with that). I once heard someone say, “If you aren’t embarrassed by the person you were a year ago, you’re probably not growing quickly enough.” I think that’s true. I also think it’s silly to be so certain of myself that I’m fooled into believing that every single thing I have outlined here is going to be true in my life forever. That’s the thing about life: we can’t know what’s going to happen. For the first time in a long time, that’s an exciting prospect, not a burden.