Blog

Plaza San Martin, Buenos Aires. My biggest hurdle growing up was my obsession with what others thought about me. I had to be funny,...

I ask questions for a living. Coaching, podcasts, writing… What makes a low-quality question? In my mind, it’s one that can be answered...

No, I don’t feel older. But I do feel wiser. Here are some things I’ve learned in these 29 years. Hope you find one of them valuable. 1)...

Connor’s bachelor party in the mountains, April 2022. Earlier this week I shared the biggest criticisms I took away from my annual...

Bro love. ❤️ This is Connor. He hated me in middle school, is the reason I run my own business, and has been one of my best friends for...

One of my besties and I do an annual feedback review. The goal is to be as honest and exposing as possible. Crying is encouraged. I try...

West Virginia, 2022. For all of my 20s, I would list family as one of my top priorities. But there was a problem. It wasn’t. From 18-23,...

I’m Dillan, and I’m a recovering shit-talker. When I failed college in 2017, I got a job at the Cheesecake Factory. There I started...

I’ve been connecting with strangers, coaching people, and staying in touch with friends for years. Here’s what I’ve learned about great...

They are: 1) Labels are limits. We give ourselves disempowering labels and attributes all the time. Here are a few I heard from some of...

Lake Gaston, 2013. This photo is of me, my dad, and my grandpa. We’ve been told that each generation is brighter and more handsome than...

My roommate just announced she’ll be moving out in March. This sparked three emotions. I’m super excited and proud of her for leveling up...

A good friend sent me a podcast yesterday. It was a panel of academics sharing research on the relationships of friends. I thought I’d go...

Since attempting suicide in 2017, I’ve been obsessed with living a better life. I’ve even made a career out of helping people improve...

Receiving feedback from our friends, family, and colleagues is one of the quickest ways we can improve ourselves. It can also be...

For the first time since starting my business in 2020, I’m busy. It’s something I never want to be. Many Americans use the word “busy” as...

A few years ago, one of my best friends—the guy I thought would be my best man—cut me out of his life entirely. He stopped returning my...

My friends and readers of this blog know that I’ve been preparing to move to Brooklyn later this year. Mostly because I won’t shut up...

I’m writing a book on creating. Over the past six months, I’ve been interviewing creators and entrepreneurs of all shapes and sizes. Many...

What’s the solution to overwhelm, poor health, and money problems? I have no clue. There are thousands of possible steps one could take...