People Who Make You Feel More Like You

One of my take-home ideas from the World Domination Summit (WDS) 2014 was: “Spend time with people who make you feel more like you.”

As that idea has proven itself true over the last few years, I’ve added a complimentary thought… Spend your time doing the things that make you feel more like you.” We tend to find a lot more of “our people” and opportunities that are more right for us when we’re doing what we love than when we are doing what we think we ought to.

Sounds simple, right? But how much of our lives do we invest in the things we do because we have to, because someone else wants us to, or that we feel like we “should”?

I don’t believe that it is necessary to renounce conventional ideas of success or ignore the opinions of the people who matter to us.  We need to understand why we are doing things, and if what we’re doing isn’t right for us, we need to stop.

When we are with those people who make us feel more like us…

and we tell them about what we are doing…

how do they respond?

These are people who recognize when you are on the right path and will help keep you there. Some call this your tribe. Finding your tribe takes time and commitment. If you’re anything like me, keeping these people in your life can be a full-time job. My tribe is international, nomadic, and entrepreneurial, which can make them hard to keep track of. That said, the return on investment for me is amazing, hands down the highest return of anything that I do.

About two years ago I gave a great friend that I hadn’t spoken to in a while the rundown of what I was doing with my life. There was silence at the other end of the phone when I described a full-time office job, move to DC, another masters degree, a “grown-up” lifestyle, reasonable work hours… but when I mentioned my new sailboat, trip to Thailand, non-profit board opportunity, and plans for this blog and consulting… “Oh, thank God – you’re still the person I know.”

Developing world travel and work is one place I find my tribe—I need to spend time in this part of the world, where I can take a moto taxi, listen to the power lines faintly sizzle, and forget the some of the realities of my privileged life. The people you find here are fantastic. On the Thailand trip, I met a disaster logistician on the dive boat… taking a break on his way to the Philippines, most recently working in the Congo. We talked a combination of diving, travel and disaster logistics. It didn’t really matter what we talked about. There was the moment of recognition that he was one of my tribe, and it is always so nice to find them.

It’s as easy and as hard as that. Spend your time with people who make you feel more like you, and spend as much time as you can doing things that make you feel more like you. 

It’s a spiral of positive reinforcement.

Have you found your tribe? How do you feel about the path you’re on? Who and what keeps you on the right or the wrong path in your life? Leave a comment!

Why Are You Wasting Your Time Here?

Once upon a time, not so long ago, I worked at a very large organization, full of detail-obsessed people and bureaucratic gridlock.  One day my colleague had had enough, and we spent over an hour talking about our shared frustrations with the organization and its processes.

The conversation eventually turned to her career, where she wanted it to go, the feeling that she was “stuck” and all of the dreams and fears that accompany a big career transition.

Then she said, “So, what’s your plan? Because sometimes I look at you and think… you don’t belong here, what are you doing wasting your time in this organization?” Continue reading

Do You Need a Business Plan?

Does your business plan look something like this?

Ready, Fire, Aim

Fail Fast

Don’t Plan, Do

This is the message that most often gets trumpeted by entrepreneurs.  I agree, to a point.  You shouldn’t let planning get in the way of doing, but let me share a couple sayings that are common in the military:

  • Failure to plan is planning to fail.
  • “The plan is nothing, planning is everything.” – Dwight Eisenhower
  • Planning expands to fill the time available.
  • “A good plan violently executed now is better than a perfect plan executed next week.” – George S. Patton
General Dwight D. Eisenhower, 1 February 1945, public domain

General Dwight D. Eisenhower, 1 February 1945, public domain


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Building Space to Work

I’m an introvert, and easily distracted. I do much better work when I can get into the flow of things long enough to wrap my brain around a question or project to actually make some progress. Having a TV blaring at me or someone constantly interrupting prohibit me from creating much that is useful, or thinking through a tough question.

For me, focused time is essential to productivity. Continue reading

Mentoring up, down, across, from afar, big and small….

What does mentoring mean?

  • How do you find a mentor or mentee?
  • What do you gain from the relationship?

A mentor is someone who helps you understand yourself and your environment, and helps you grow and develop personally and/or professionally. That’s a broad description, and the corollary is that mentors are everywhere. You are undoubtedly a mentor/role model for someone even if you don’t realize it, and it’s foolish to look for a single person to be your “one true mentor.”

At the World Domination Summit in 2013, the first question for Danielle LaPorte (who was awesome) was “will you mentor me?”  Her answer, “No,” was direct and perfect.  She explained that her time is extremely limited, it takes a lot of time to build a relationship, and that was why she writes and creates.  Another way of stating her answer is: “Yes, but through my work, and if you want to use my work to start a conversation and build a relationship, great!”

Some of the best mentoring relationships are with your peers.   Continue reading

Creativity and Getting Out In Front of the Herd

A herd of goats on the road in the Greek highlands. March 2006, public domain.

A herd of goats on the road in the Greek highlands. March 2006, public domain.

When you’re a creative problem-solver and you see interesting and different ways of doing things, sometimes where you want to go is way way out in front of where everyone else is. The problem is that when you express some of these crazy ideas to colleagues and friends, they might not be able to see far enough to understand or embrace your ideas and creativity. They might not be able to get to where you are intellectually from where they are. You need to help them get there with intermediate steps.

You need to get far enough in front that you’re leading the herd, but not so far ahead that you’ve lost the protection of the herd and you get eaten by a lion. Continue reading

Developing Your Risk Taking Muscle

Lots of people will encourage you to take risks, dream big, work for yourself… but what exactly are they encouraging you to do? Is it as a simple as starting your own business, taking that big trip you’ve been dreaming about, quitting your job to pursue your passion, or is there something more fundamental to the idea of risk taking itself?

I maintain that anyone can take entrepreneurial risks, in almost any situation.  You don’t need to start a business, quit your job, or totally reorient your life, if that’s not right for you.

It can be as simple and as hard as asking tough questions, thinking differently, and being willing to press for what you believe in.

I’ve seen military officers take risks by advocating for organizational change, photographers refuse to shoot a job the way that a client says they want it, pilots propose new operating procedures that upset the established way of things… all entrepreneurial actions.

Of course, starting a new business, going out on your own without a safety net, and trying to build something truly new is entrepreneurial, and involves real risk.  However, the key is that you don’t need to start a business in order to be entrepreneurial.  Like many things, entrepreneurial thinking is a skill that can be developed.

How can we develop our entrepreneurial risk taking muscle while we keep our day jobs? Continue reading

My Approach: Understanding and Communicating the Unique You

People may know you, and give great advice, but do you feel understood? Can you clearly communicate who you are and your personal why?

If we’re having trouble getting someone to understand an idea, the fault is generally our own. Usually, the problem is not that the person receiving my message can’t understand or just doesn’t get it, but that I’m not choosing the right words or examples. Even well-respected authors and thinkers sometimes fall short when they focus exclusively on a single metaphor or way of explaining. No matter how powerful their message or metaphor, what they say isn’t going to resonate with everyone. I’ve seen two conference speakers deliver essentially the same message, but each speaker’s perspective resonates with a different segment of the audience, simply because of the words they choose to use and how they deliver essentially the same information. Continue reading

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.

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