“True life comes when we’re willing to admit that we’ve
reached the end of ourselves.” When I decided to retire from entrepreneurship, there was a noticeable grieving process. Which makes sense, since grief is the human response to the death of something we’ve formed a bond with. And if you ask anyone who’s ever owned a business before, that bond is like none other. For most entrepreneurs, it’s hard to tell where they end and the enterprise begins. So in a way, a career transition is like a death. The death of a job, the death of a lifestyle and the death of a mindset. And I remember all of the stages of grieving manifesting themselves. First I tried to deny it, holding onto beliefs that were too convenient to be killed. Then I became angry, beating myself up and harboring resentment for others. Next came bargaining, in which I scrambled around with a hammer, trying to turn everything into a nail. Then came depression, where getting out of bed was a legitimate challenge. And eventually came acceptance, when I wrote a letter of resignation to myself and experienced a euphoric lightness of being. Inspired by drops like stars.
“Customers develop solutions for their communications problems that we never thought of before.” Contrary to cynical opinion, smart companies like Twilio aren’t using social media to get other people to do their job. They’re taking a risk by being vulnerable, collaborative and honest. They’re getting the best out of users, not by telling them what to do, but by creating a space for them to do it. I’m surprised more companies didn’t learn that lesson four years ago when Jeff Jarvis first wrote about being a platform. It’s not about going digital, it’s about enabling people. It’s about making it easy for them to build value. And it’s about getting out of the way so they can make use of everything they are. The cool part is, once organizations start viewing themselves as platforms, not companies, the collective posture of their culture changes for the better.
“Yearning to be heard and remembered in the face of so much annihilation.” Performance is second nature to me. Since I was a kid, I’ve always been motivated by a captive audience. Even if there’s only one butt in the seat, I can’t help but put on a show. And overall, that predisposition has served me well both personally and professionally. On the other hand, my greatest strength is often my greatest weakness. And sometimes the need to perform backfires. Sometimes it even ricochets. Like when I’m so focused on being funny, I forget to be honest. Or when I’m so excited about writing eloquently, I forget to communicate clearly. That doesn’t just affect me, it affects the people around me. That’s what happens when you see people as audience members, not human beings. Inspired by a book about friendship during the recession.
“Later is like the horizon, it recedes when you approach.” The key to time management is assuming there’s never a good time to do anything. Once you operate on that assumption for a few months, you quickly knock out most of the productivity excuses that get in the way. Because it’s not about finding time, it’s not even about making time, it’s about stealing it. Grabbing tiny moments from the crowded day and making a meal out of them. How do you think I write all those books? Once sentence at a time. And that’s not a cliche, either. I literally write sentences, all day. It’s the essential act of my profession. And if you do the math, it adds up quickly. Five words a sentence, twenty sentences a day, thirty days a month, twelve months a year. That’s thirty thousand words. That’s a book. Inspired by a mindfuck of a book called Dead Sleep.