Category Archives: Career

Be A Volunteer

April 24, 2022
Career, Leadership
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Once you get to the point in your career where you realize a) you’ll be just fine financially (because your resume kicks ass), b) your company doesn’t give a sh*t about you, and c) you know what the Right Thing to do is, act like a volunteer.Continue reading →

Open Office Hours with Charlie

December 22, 2020
Business, Career, Clarity of Thought, Customer & Product, Leadership, Organization & People, Startups, Technology & Execution
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Last month I offered “office hours” to anyone who wanted to chat with me. It was an experiment to see a) if interesting people would reach out, b) if I could be useful to these people, and c) if I’d be exposed to domains where I could spend more of my time in the future. All three hypotheses have turned out true. Thank you to all of you who utilized this so far! I still …Continue reading →

Customer, Business, Technology, Organization (CBTO)

April 21, 2018
Business, Career, Clarity of Thought, Customer & Product, Leadership, Organization & People, Technology & Execution
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CBTO = Customer + Business + Technology + OrganizationContinue reading →

Merit Badges – A Mental Model for Success

April 1, 2018
Career, Clarity of Thought, Leadership
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A long-time mentor of mine, Chris Phillips, taught me the Merit Badge mental model. This mental model has given me clarity and peace of mind over the years when navigating big career decisions. What’s the Merit Badge mental model for measuring success? The concept of a Merit Badge comes from the Boy Scouts. The idea being a scout can only earn a particular merit badge (actually a patch that gets sewn onto a vest) by …Continue reading →

Find Work That Does Not Feel Like Work

March 24, 2014
Career, Leadership
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The first thing I ask people who are looking for a new job is “What work do you want to do in your ideal job?” It is interesting how few people answer this question. Almost everybody wants to answer different questions like “What do you want to work on?” or “What kind of work environment are you looking for?” They respond with answers like “I want to work on a small dynamic team with other …Continue reading →

The Job Decision Matrix

April 26, 2012
Career, Clarity of Thought, Organization & People
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Thinking clearly about what is important to you can be hard, but without clarity on what is important to you making a job, the decision is fraught with danger. As I have traveled along my personal career trajectory I created a tool that has helped me with this. I call it the Job Decision Matrix. The Job Decision Matrix will help identify what is actually important to you at this point in your career. Gaining …Continue reading →

You are Thinking of Your Career Trajectory Wrong

April 8, 2012
Career, Clarity of Thought, Leadership, Organization & People, Startups
15 Comments

Most people think about their career trajectory as being like a bell-curve or that of a cannon ball fired from a cannon. Something like this: For 99% of all successful people, this is completely the wrong way to think about it. For that other 1% (the Bill Gates & Mark Zuckerbergs of the world) it might work. For the rest of us, there’s a mental model that will help keep you sane, help you appreciate …Continue reading →