For a long time, I treated conflicting emotions like evidence that I was doing something wrong. Now I think they're just evidence that life is complicated. ⬇️

I was 19 years old, interning on the floor of the Chicago Board Options Exchange, when my boss left for lunch. Before he walked away, he said: "Build up my Amazon position, but don't lose any money." 1/3

My love for art didn't start with me. My mom had a full-time job, two kids in sports, and still found time to run a calligraphy business on the side. She still lights up when she finds a painting, sculpture, or anything beautifully creative. 1/3

My wife thought she was daring me to do something once. She underestimated my commitment. While we were visiting family, she dared me to work the phrase "good sir" into my conversation with the guard at the gate. 1/3

I didn’t notice the last time I had to cut food into tiny bites.Or tie someone’s skates.Or read the same bedtime story for the hundredth time. I just stopped doing them.And didn’t even realize it. ⬇️

The most meaningful email I've received this year wasn't about business. It was from a hockey player I coached years ago. He told me where he'd decided to go to college. Then he thanked me for everything I'd done for him. I smiled. Then I read the last sentence.

I completely missed my cue at my daughter's party. The DJ played one of her team's competition songs, but one of the girls was home sick. Since I'd spent years watching them compete, they decided I should step in and take her place. The girls assured me, "You'll know when it's your cue." ⬇️

I love asking people what they do for a living. Apparently my wife does not. Someone asked her what I do. Her response: "I can try." Honestly, that's fair.

I’ve become fascinated by the moments that don’t seem important until years later. They rarely announce themselves. They’re usually just ordinary days.

Kids notice everything. How we react when something goes wrong. How we talk about people who aren’t in the room. Even the moments we don’t realize they’re watching.

I’ve coached a lot of kids over the years. One of them will always be “$100 Kid.” His parents offered him $100 if he scored a goal. He laughed because he didn’t think it would ever happen, but I wanted him to see he was capable of more than he realized. He scored that game and earned every penny.

My son got his college dorm room assignment. For some reason, that made everything feel real. It feels like yesterday we were picking out his backpack for kindergarten. Now we’re talking about roommates and move-in day. I didn’t expect a room assignment to hit me quite this hard.

The first sale is exciting. The second one is everything. I still remember exactly what my first customer ordered. I also remember when they came back and ordered again. That’s when something changed. It wasn’t just confidence. It was motivation. If one customer came back, why couldn’t another?

My kids probably won’t remember the email I sent at 8:00 p.m. Or the invoice I paid yesterday. They’ll probably remember the game we made up together. Or the random Friday in July when something happened at dinner and we laughed until our stomachs hurt.

One thing nobody tells you about getting older is that the systems that helped you make friends disappear. Nobody assigns you to a classroom. Nobody signs you up for a team. Nobody arranges a playdate. The need for friendship never goes away. The opportunities just don’t create themselves anymore.

🧵 One day at hockey practice, I pulled a marker out of my pocket and started drawing on the ice. The kids looked at me like I’d completely lost my mind. A couple even asked what I was doing.

My daughter discovered my LinkedIn posts, and at first, it was awkward. Then she started scrolling. 1/2

🧵 I once took a meeting with two guys who claimed they’d developed an incredible heat-resistant coating. They brought samples. They brought a torch. They were ready to prove it worked.

🧵If you asked me to describe an average workday from ten years ago, I couldn’t do it.

🧵 My brother and I once had a Diet Coke drinking contest on a flight from Chicago to Phoenix. I won with six cans. Never again.

🧵 Once a year, I’d make my hockey team take off their skates, put on gym shoes, and get back on the ice. Full pads. Every kid thought I’d lost my mind.

There is nothing scarier than teaching your kids how to drive. The “oh sh*t” handle on the passenger side of my car is doing a lot of work right now.

🧵 I keep a signed Sandy Koufax baseball on my desk even though I’m a Cubs fan.

Some people are exhausted because they’ve been working too hard. Others are exhausted because they’ve been building a life that no longer fits.

One day at hockey practice, a kid showed up with chicken nuggets in his jacket pocket. Not in a container. Not wrapped. Just… in his pocket.

🧵 My grandfather spent half a Cubs game trying to get someone to give me a baseball. I was 15, sitting a few rows behind the Rockies dugout. Every time a coach wandered toward the top step, my grandfather would wave and call out to him. He was absolutely convinced it was going to work.

Before we got married, my wife used to tell people she was dating “the pen guy.” She wasn’t wrong. When I’m working through a big decision or trying to untangle a messy problem, I still reach for a fountain pen before I reach for my laptop.

Some of the things I’ve spent the most time trying to fix weren’t actually problems. I was just tired. It’s surprisingly difficult to tell the difference sometimes.

I spent years watching my daughter dance. Then one day, I decided to try it myself. It didn’t take long to realize that dance is a lot harder than it looks. And it’s a lot easier to appreciate what someone does after you’ve tried doing it yourself.

I caught up with a friend recently and learned he’d landed three new clients in a week. It didn’t help my business, it didn’t change my life, but it did improve my day. There’s something energizing about seeing good things happen to people you care about.