The Best To-Do List App for the Smart Risk-Taker
Fellow Riskologist, For the last few weeks, we’ve focused on finding and addressing fear so you can move forward with big projects in your life. Before you clear away underlying fears, getting started on a big project can feel like pushing a boulder up a hill while breathing through a straw. But once they’re dealt…
How to Properly Celebrate Your "Badiversary"
Fellow Riskologist, One of the less amazing things about life is that bad things often happen to good people. Sometimes, these are a result of your own poor decision-making. Maybe you made a bad business investment and lost a lot of money or neglected a relationship that fell a part. Maybe you simply miscalculated and…
9 Ways to Tell if You or Someone You Know is an Undiagnosed Awfulizer
Fellow Riskologist, Are you an undiagnosed awfulizer destined to fail at everything you do? Or worse, are you unlikely to try anything even slightly risky because you can only see the worst possible outcome in every scenario? If you read regularly, I’d guess, no, you aren’t. But you probably know someone who is, and that…
Break Any Personal Record With the +1 Theory of Human Achievement
Fellow Riskologist, What holds you back the most? If you have a dream you haven’t realized yet, what keeps you from pursuing it? Typically, it’s a fear of failure. No one wants to set a goal they don’t believe they’ll actually reach. And if you continuously set goals that are too high, you set yourself…
The Day it Becomes Easier to Take Action Than to Wait
Fellow Riskologist, Greetings from rural Nevada, where I’m hanging out for a few days before heading into the mountains for a little backpacking trip. This morning, I woke up and went for a run. Let me tell ya, running in rural Nevada is a bit different from running around my home in SE Portland. There were…
A Brief Guide to Selling A Business: Thoughts From My BrewPony Exit
Fellow Riskologist, Have you ever thought of starting a side business? What about selling one? If you’ve ever started a business in your spare time based on something fun or important to you, then you know two things well: It’s very exciting, and It’s a lot of work. Earlier this year, I invited you all along…
A Smart Risk-Taker is Always Building Assets
Fellow Riskologist, The other day, I was in the middle of a small negotiation with a friend whose business I’m going to help for at least the next six months. It’s exciting work that’s right up my alley, but as we went over the terms of our agreement, something was leaving me just a little…
The 10 Bands Theory of Originality
Fellow Riskologist, What does it take to be truly original? When you think about your favorite artists, musicians, writers—or any other creative type—do you ever ask yourself, “How do they do it?” Would you be surprised to know the answer is they just ripped off their own favorite artists? Would you be more surprised if…
Maybe You Can Say What You Really Think and People Will Still Like You
Fellow Riskologist, I remember as if it were yesterday. Young, college punk Tyler was out walking around Portland on a Saturday night with some students. I didn’t know everyone; I was tagging along with a new friend and his group. As we walked, I pulled a stick of gum from my pocket, popped it in my…
Finally, A Simple Way to Tell Smart Risks From Dumb Ones
Fellow Riskologist, Not long ago, I was riding in the car with my friend, J.D. Roth here in Portland. I don’t remember where we were going or what we were talking about, but I do remember we were stopped at a set of train tracks while a long, slow train rumbled through town. I also…