It started quietly. A text message. My business partner’s long-time dog passed away.
Shortly after that, another heavy piece of news. His uncle died.
Then, a Slack notification popped up on my screen. I clicked open the DM. Instead of a quick business update, the words hit me like a physical blow.
“Dan… she didn’t make it.”
Just like that, a long-time member of my Dragon 100 family – a woman I respected deeply, someone I was very close with… was gone. Cancer.
Three deaths in 14 days.
This heavy season comes on the heels of losing my cousin in Hong Kong. He wasn’t just a cousin; he was the closest person to me. We were essentially brothers. He is just… gone.
As you get older, the people you love just start dying around you. The notifications on your phone slowly transition from wedding invitations to funeral arrangements. It is a profound, paralyzing kind of pain. It strips away all the noise, the business strategies, and the ego, forcing you to stare directly at the hourglass.
Remembering a dear friend and long-time Dragon 100 member. A heavy reminder that we can build all the business Certainty in the world, but our time here is strictly limited.
I am writing this issue of Certainty Insider entirely for myself. It is a reflection on the brutal, beautiful truths I’ve had to learn the hard way. If you are grinding away at a business right now, ignoring your life to build your net worth, I urge you to pause and read this.
1. The 20 / 40 / 60 Rule
It feels like it was just yesterday that I was 20, grinding in a tiny apartment, trying to prove my worth to the world. Now, I am 44.
“Life is a blink” is a cliché right up until you are the one blinking.
There is a famous quote that perfectly maps the human ego:
When you’re 20, you care what everyone thinks about you.
When you’re 40, you stop caring what everyone thinks about you.
When you’re 60, you realize no one was ever thinking about you in the first place.
I spent way too much of my life agonizing over what people thought of me, especially as a public figure. Am I saying the right thing? Do I look right? Will this video get more views?
I don’t look anymore. I haven’t looked at my stats in years. I don’t check my watch time, I don’t obsess over likes, and I don’t read the comments. I finally learned that what others think of me has very little to do with me, and everything to do with them. I will say things that provoke people, and they will hate me. I will say things that inspire people, and they will love me. I cannot control it, so I stopped trying.
But while life is ruthlessly short, it is also incredibly long. If you stay focused, you can accomplish vastly more than you ever thought possible. I never could have imagined in my 20s what I would go on to build in my 30s and 40s.
2. Your Brain is a Soap Opera Writer
As human beings, our brains are the ultimate soap opera writers. They are non-stop “What If” machines, constantly fabricating wild scenarios and tragic endings that do not exist.
What if the economy crashes? What if the launch fails? What if my employees leave? What if I lose it all?
We spend our waking lives consumed by low-grade, constant anxiety. But when real tragedy strikes, you realize how pathetic those business worries actually were. Most of the shit we lose sleep over never actually happens.
I have spent years actively conditioning my own psyche to reject this trap. When the anxiety spikes, I force my focus entirely onto gratitude. It is a psychological law: fear and gratitude cannot co-exist in the mind at the exact same time. You cannot be terrified of losing your empire while simultaneously feeling deep gratitude for having built it.
Stop hallucinating your own tragedies.
3. The “Dying Breath” Delusion
Whenever you watch a movie and a character is bleeding out on the battlefield, what is the first thing they say?
“Tell my wife I love her. Tell my kids I’m proud of them.”
With our dying breath, all we want to do is express love. So why do we wait? Why do we assume the people around us just “know” how we feel?
Do not delay it. Say what needs to be said right now.
“Dan, you’ve said ‘I love you’ three times today,” Jennie will laugh from across the living room.
“I know,” I tell her. “And I’m going to say it again.”
I say it to my mom every single time I see her. I even look at my two dogs, Mochi and Cookie, and tell them out loud. Say it now. Say it every day.
4. The Tower of Pisa Regret
A few years ago, I was standing in front of the Leaning Tower of Pisa. There was an older couple nearby, probably in their mid-70s, traveling with a tourist group. The wife was moving very slowly, leaning heavily on her cane.
I overheard the husband look up at the tower and sigh.
“I wish we could go up,” he whispered. “If we were 30 years younger, maybe we could.”
His wife gently patted his arm. “Now, we just take a photo from the bottom.”
That moment hit me like a physical blow. Money can be recouped. Cartilage cannot. Jennie and I are very fortunate to have traveled the world while we are still young enough to actually climb the towers. Do not wait until your bank account is overflowing if it means your knees no longer work.
At the top of the Leaning Tower of Pisa with Jennie.
And document it. Take the photos. Take the videos. Print them out physically. How often do you sit at a family dinner and think, “I wish I had a photo of this”? So take the damn photo.
With my cousin. We were essentially brothers. You never know when a photograph will become the only thing you have left of someone you love.
When you get older and your physical world begins to shrink, your memories are the only things that stay vivid.
5. The Illusion of Net Worth
I spent way too much time, effort, and attention chasing material wealth and fame. I spent an embarrassing amount of money on fancy cars, massive houses, and designer clothes, all to impress other people because of my own internal insecurities.
I got rid of almost all of it. I haven’t bought a luxury item in three years.
As entrepreneurs, we obsess over our net worth. We tally up the business equity, the real estate portfolio, the bank accounts, and the expensive art.
But the brutal truth is this: You do not actually “own” any of it.
We come into this world with nothing, and we leave with nothing. We are just temporary managers of capital and assets. That plot of land you are so proud of? Someone else owned it before you, and someone else will own it long after you are gone.
The absolute most valuable thing your money can buy is Time. Time with your family. Time with yourself. Time to pursue the interests that actually bring you joy. Time to sit in quiet reflection. Time to write.
You can always build another business. You cannot build another body, and you cannot buy back a single second of the clock.
We spend our entire lives as entrepreneurs trying to eliminate risk.
We write standard operating procedures. We scale platforms. We stockpile cash. We obsess over building Certainty in our businesses so we can finally feel safe.
But when the Slack notification pops up, or the text message arrives in the middle of the night, you are violently reminded of the ultimate truth.
There is only one absolute Certainty in this life: Death.
Dan Lok
Certainty Capitalist™