Almost 4 years ago I asked myself two questions that changed my life:

Are you happy? No.
Do you know how to be? No.

That opened a clean slate. My assumptions weren't serving me what I wanted, 'happiness', so I started questioning them, and continue to.

At the time I was a full time drunk. My first 4 fingers of bourbon followed the alarm clock. My 2nd were added to my coffee from one of the bottles sitting proudly on my desk in my silicon valley office.

Turned out, it wasn't serving me. I'll be sober 4 years soon.

Over lunch a colleague told me about his divorce, and that he was finally going to climb Kilimanjaro.

My assumptions told me that wasn't my thing, so I made myself say "May I join you?"

We wouldn't have called each other friends at that point.

We would now after that summit.

From 15,000' base-camp to the ~20,000' summit the oxygen gets rather thin. I was a smoker, 20 years, pack a day, no intent to quit. I smoked for 7 days around the mountain and up-to base-camp. I couldn't smoke summit day. I was miserable, wanting to quit the whole time, I didn't.

We took one photo at the summit and I literally jogged/slid on gravel from the summit back to sub 15K feet so that I could breath again. My trip down was 45 minutes, the rest of the group joined me ~3 hours later. I smoked my last smoke at that base-camp. It didn't serve me.

My caffeine intake increased throughout this time until I was drinking 4 cups of coffee, a few sodas, and a liter of ice tea a day. I was jittery, unfocused, and sleeping poorly. It wasn't serving me. I stopped buying myself tea and sodas. Now, 2-3 cups of coffee per day.

Through this I still had holes in me that needed to be filled while I worked on them. Where alcohol filled them before, work filled them now. The mental toll was palpable, it wasn't serving me. I was done working for toxic people who were making more money from my work than me.

Last year I decided to change that, and co-founded a company. I will see this company fail before I see it treat it's people the way I've seen others treat their teams. Because it serves me. I get more out of my teams fulfillment and our customers delight than I do from more $$$.

Bootstrapping a company during a pandemic can be a touch stressful, so I poured more work in. As my anxiety increased my work increased. It wasn't serving me, but I thought it was serving the company. Then I realized, if I'm not healthy, not happy, I can't help.

I began working out 3-days a week for 1 hour, and have increased slowly to 6 hours weekly. I'm now in the best shape of my life. More importantly, I'm happier, more energetic, focused, and capable.

By taking 6 hours a week back, I made the hours I give better. It's serving me.

Then deeper, I'd always focused on being 'tough', 'masculine', 'hard.' Being called an asshole was easy, actually feeling was hard, and had the potential to hurt me, so I hid in plain sight behind a wall of self-induced bull-shit. Surprise, it wasn't serving me. So I'm changing.

I've learned one tangible, tactical thing you can take away from this long-winded nonsense.

You don't need the answers to everything. You only need the right question. Is it serving me?

If your assumption is correct, it won't falter.