The Specialist, the Generalist, and the Non-Conformist

This is the story of three people: Nick, Sara, and Taylor. Each faced the common challenge of deciding what to focus on for their life and work. The challenge was complex and involved lots of variables. What was best for one person might be the wrong choice for someone else, etc. etc. Ultimately, however, all the variables pointed to one big decision:...

2d

Life Lessons from Sylvia Plath

In many ways, Sylvia Plath did not have a charmed life. She suffered from severe depression and was treated with early forms of electroconvulsive therapy, a method that has come a long way since first being introduced in 1940. In The Bell Jar, a semi-autographical novel she wrote the year before she died at the age of thirty, she sought to...

2w

To Stop Comparing Yourself to Others, Decide in Advance What Success Looks Like

There’s a saying, “comparison is misery.” Until fairly recently, I knew that was true, but I didn’t really know what to do about it. Most of the advice I heard was in the vein of, yeah, that’s a problem, don’t compare yourself to others.  This was, of course, unhelpful—just like most advice that simply says “don’t do this thing that’s hard to stop.”...

3w

The Law of Average, or How to Stop Settling for Systems Designed for the Masses

The law of averages states that outcomes and events revert to the mean. Over time, if you roll a pair of dice that are properly made, the result will be random. Even if a low number has come up ten or more times in a row, to believe that the next roll of the dice “must” produce a different outcome than the last is a gambler’s fallacy. You...

4w

How to Make a Personal Roadmap

In the days before smartphones, a map was something you’d use when going on a trip. Gas stations sold them, or sometimes gave them away with advertising included. Maybe these still exist for people who don’t have phones? Who knows. These days, roadmap is more of a startup word. A company (or a team of some kind) publishes a roadmap to show where they’re...

5w

The Little Voice in Your Head

At times in life you come to a crossroads. You have to make a key decision, and you feel conflicted. You’ve made a pros/cons list, you’ve asked a close friend for advice, and you’re still stuck. Let’s assume for the sake of discussion that there’s no way to split the difference. You simply have to decide between two competing choices. This is where...

Jul 2022

The T-Rex Takeover: How We Smashed a Guinness World Record

Ten days ago, I stood on a stage in downtown Portland, Oregon and looked out on a sea of inflatable dinosaur costumes. Over the next two hours, the Dino Czar (more on him in a bit) and I facilitated a program that culminated in a big achievement: a World Record! Three days later, it was on the front page of the Oregonian, and online meme accounts...

Jul 2022

WDS X, A Very Brief Photo Recap 🪄

Last week and weekend I hosted WDS X, the tenth and final installment of an event I started in 2011. WDS is always an emotional experience, and this time was perhaps the most intense of all. Not only was it the first time we’ve been able to host the event in three years, it was also the final WDS. I’m not good with endings, and it will take me some...

Jun 2022

Time Will Pass Either Way

Consider, for a moment, that big thing you want to do. Perhaps it’s a long-held dream, something you’ve been thinking about for years. Or maybe it’s a secret, something you’ve held in your heart without telling anyone. It could be that you’re even a little afraid to acknowledge it to yourself. A big trip to a faraway land A new venture or career...

Jun 2022

Fearful / Greedy

“Be fearful when others are greedy, and greedy when others are fearful.” -Warren Buffett Life is full of advice that is factually accurate but not very helpful. “Don’t get hit by a bus,” for example. There’s wisdom and common sense there! It’s just not helpful or useful information. Most people who get hit by buses don’t plan on it happening when...

Jun 2022