What do you optimize for?

Once a year, I spend a weekend with my “tribe” at the World Domination Summit in Portland Oregon. There are any number of reasons I keep coming back… community, conversations, the speakers, great parties, Portland itself… perhaps the most valuable are the occasional ideas that force me to reconsider my life and priorities.

This year it wasn’t until the closing speaker that such an idea seized my mind and wouldn’t let go. Derek Sivers was talking about his experience building CD Baby and came to the point in the story where he sold the company. He told us that it was an easy decision, because he always defaults to freedom… whenever faced with a decision, freedom is what he optimizes his life for.

I decided I should write down the obvious question: What am I optimizing my life for? Continue reading

Crossing the Chasm

“Don’t be afraid to take a big step. You can’t cross a chasm in two small jumps.”
— David Lloyd George


Grand Canyon, Mather Point Rainbow. NPS, Public Domain.

I completely agree… sometimes you just have to take a big leap of faith and trust that things will work out.


What if you could build yourself a 30 foot bridge? What if there’s another part of that chasm that’s only 10’ across? What if you can train yourself to be a better jumper? Rent an airplane?

You still might fall, but the odds just got a lot better.

Continue reading

Purpose, Method, End State (Part 2): Your Career Plan

In  Purpose, Method, End State (Part 1), I talked about modern military orders and their three core sections.  We saw how this method of planning works,in an example for the NGO Leadership Initiatives.

This simple Why-How-Result template is a powerful way to think about your career as well.

Here’s what my own career plan looked like a few years ago:

  • Purpose (Why): I want my work to be focused on making the world a better place. I want to broaden and deepen my expertise, leverage my experience into new opportunities to learn and grow, and continue to develop my career narrative.
  • Method (How): I do paid and unpaid disaster relief and international humanitarian work, gaining experience, developing my skills, and building a network. I’m building a business and the team to help manage it, while continuing to develop my skills and reputation as a military officer.
  • End State (Result): I am established as an entrepreneur, a respected humanitarian professional and military leader, able to pick and choose the opportunities that are right for me.

Continue reading

Freedom, Structure and Creativity

Something I’ve learned from 15 years of work, lots of years of school and a host of other personal and professional experiences…

Creativity requires time & space but, at least in my case, it also benefits from some structure, drive, and collaboration. Taking off a day or a week, a month, or even a year is great for me – BUT if I don’t keep coming back and doing the work, I won’t have problems worth thinking about or solving.  Challenges are a massive driver of creativity, within the pressures of a set structure.

I think that life shouldn’t be too easy, and we are at our best when we’re a little uncomfortable… Continue reading

Side Hustle: Success Across Pursuits

Planning your time as a “side hustling” entrepreneur…

I’ve seen a ton of templates and scheduling plans to help “maximize your creativity.” They are all interesting and potentially valuable. Unfortunately for anyone trying to build something while they’re still employed full-time, however, they’re mostly written for people who control the majority of their time.

What if you have to spend 8-10 hours a day, 5 days a week doing a job unconnected to your creative drive, or the business you’re trying to build? How do you structure your time around your “real job”?

Tough question. Continue reading

Do you feel bigger than your dream job, or does your dream job seem bigger than you?

Change is hard and uncomfortable, but it’s the only way to get to something better than what we have now, even if it means changing our idea of a dream job. There’s also no shame in admitting that we aren’t happy where we are. Even a “dream job” can lose its lustre. What was perfect for someone else, or even a slightly younger version of yourself, might be perfectly awful for you now.

Continue reading


This week I’ll be traveling… to a place that I’ve been enough times that it feels a little like home. I’ve spent a fair amount of my professional life traveling, often in parts of the world that most people couldn’t find on a map. I’ve sometimes felt more at home arriving somewhere totally new than I did walking through my front door.

What is it about developing countries and travel that starts to feel so familiar? Continue reading