4 years ago, I published my first newsletter on the internet.
I started my personal newsletter, “Writing to Wisdom”, to reflect on my thoughts once a week. My original intention was, as the name suggests, to become wiser through writing. My original idea was: “wisdom is built through reflection, and reflection happens through the active processing of thoughts, also known as writing.”
So for about half a year, I pretty consistently spent 2-3 hours every Sunday morning writing down my newsletter of the week. Some better, some worse.
But then, in the middle of 2023, I stopped.
Why did I stop?
It wasn’t an active decision. Looking back, if I had to tell this story about myself, I’d say I stopped writing in my spare time because I started to make a living from writing for other people. Writing for myself didn’t pay me, so I deprioritized it.
To some degree, that may have been a good decision at the moment. I was trying to get Letter Leverage (my writing agency) off the ground with my then-Co-Founder, and I needed to focus.
But as I reflect upon it right now, it feels like a mistake.
Writing to reflect is kind of like resting your mind. The paradox is that the more you exercise, the more your body needs to rest to perform at its highest level. In the same way, the more you experience, the more you need to reflect to derive insights and maintain clarity.
I felt a sense of synchronicity 2 hours ago, when I listened to Dan Garner (a fitness coach) utter the same idea that led me to start writing 4 years ago. Paraphrasing:
“There’s a difference between someone who’s experienced and someone who’s wise. An experienced person may have lived that day a thousand times. But they only become wise if they combine their experience with reflection to draw lessons from it. We’ve all seen a person who’s made the same mistake 10 years in a row. They’re experienced, not wise.”
What nobody told me about entrepreneurship is that clarity is the most important asset you can have, because it allows you to see clearly what to work on, with whom to work on it, and how to do it. More importantly, a lesson I’ve learned is that nobody wants to lead themselves, because if they did, they’d have to think through every decision they make. Even scarier, they’d face 100% accountability for the mistakes they made. When I was still in school, I dreamt of the freedom to “design my own day” and “be free to do whatever I want”. I’ve been there for 2 years now, and it’s hard, because when you have the freedom to do anything you want, you’re always questioning whether you did the right thing. It’s just like the digital nomad paradox - digital nomads can live anywhere, but that makes it tough for them to commit to living somewhere, because they’re juggling a dozen trade-offs at any given moment.
Written reflection keeps you sane in two ways. First, it helps you add structure to your thoughts. I read a quote recently which was something in the likes of “if you’re not putting your thoughts on paper, you’re just fake thinking”, and I think there’s something to that. Second, it creates a historical track record for your decisions and self-actualization. I’m happy I documented my decision to start my own firm (my intention was “entrepreneurship is gamified self-development”, and I was right about that!), just as I’m happy I documented my decisions to go to college (it would be fun) and dropping out of college (it wasn’t fun) just 3 months later.
Two or so months ago, I spoke with Mark MacLeod, who was the first CFO at Shopify. He’s coached VC-backed founders for 20+ years through uncertain times, and now runs his own community, Limitless.ceo, which I’m a part of (and strongly recommend).
He was asking me how I’m feeling at the moment. I told him about my business accelerating to the moon, how there was opportunity around me everywhere, and all the things I was about to do. He gave me a piece of advice that felt counterintuitive at the time, but that I’ve been grateful for since:
“When everything around you is speeding up, you need to slow down. When you’re getting pulled into all directions, you need to find strong footing and ground yourself.”
It took me a few weeks to understand his message.
The big irony of entrepreneurship is that you need to care a LOT about your company to grow it, but you also need to be detached from it to make sound decisions. I used to be completely attached. To this day, my iPhone home screen has the iMessage app removed from it. It’s because 3 years ago, I’d fear seeing that small white number of messages increase and know a client texted me during the weekend. It would completely pull me out of my peace and put me into fight-or-flight mode.
When business is volatile, you need grounding around yourself. Whether that’s relationships, exercise, a hobby, or something else. The reason why is twofold. First, when your business is going through hell, you want to have things to remind you that “it’s just business”. Second, when your business is skyrocketing, you need things to remind yourself that “it’s just business.” The second one is arguably more important; deriving dopamine only from business growth or big deals is one of the surest ways to alienate yourself from everyone who isn’t a founder and guarantee misery. Reflection, breathwork, and writing pull us out of the day-to-day to remember the bigger picture. And I have yet to see a founder burn out who had their family, social life, and physical health together.
That’s why I’m returning to Writing to Wisdom. Because it’ll force me to reflect in public once a week. Because it’ll leave a trail for me to understand the person I’ve become in 3 years. Because it’ll allow me to understand myself better.
Time to pick up the pen again
Nils