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Binging on Derek Sivers Interviews

Since learning about Sivers from my early days in consulting, he was a core influence on forming my values and principles for life. I admit the initial attraction, like for any relationship, was probably due to similarities in thought. On my annual audio pilgrimage to re-listen to his interviews with Tim Ferriss, I found Sivers came out from his…media slumber?…and had a string of interviews he did in 2020. Lucky me. 

Focus via Buridan’s Donkey. It’s the parable of the donkey that can’t decide between water on one side to quench its first versus the hay on the other side to quench its hunger. It eventually dies from its inability to decide. Related to this is the need to decide and focus on something to do something well. Half-assing two things may be the equivalent of one’s effort/time dying like the donkey. As Sivers points out, if I want to do 5 different things with my life, I could break things up to spend 10 years doing each. At 30, that would mean I’ll get to do all 5 things by the time I’m 80. Having tried to build a career of coaching entrepreneurs for the past year, it’s something I’ve slowly gotten around to saying “I can do this at 50.” This mindset’s been quite helpful lately in re-focusing my efforts to the more foundational careers/skillsets that might be aligned to my immediate situation like age, career capital, etc...

Identities Expire. Books end. Relationships end (Sivers’s story on how he and his partner ended a 6.5-year marriage is fascinating). Job titles end when one leaves. Identities have an end too. It’s whether the individual allows the self to evolve or hold on to the past. For example, a CEO may have been an entrepreneur in the past. An entrepreneur who sold a company might be an investor…but for her to call herself an entrepreneur now….well, she better be in the middle of starting a company. Holding onto past identities might inhibit us from focusing on doing things now… a fixed mindset that deals in the absolutes from the past. 

Professional > Authentic. If you want to get paid or respected for it, be a professional. That means showing up even when you don’t. It’s also delivering what you promised on. Not doing things based on your whim. Those are for hobbies no one cares about. "Honesty is like nudity in that it works best with loved ones.” Be a professional and hide your nudity. There’s a time and place.

Traveling. Mind > Person. If you truly wish to travel somewhere to learn the culture, then ask yourself if 20 hours of talking with people who live there (even better if they immigrated there so they can give contrasting views) versus 20 hours of taking pictures of sites will teach you more. I wager the best is in the middle with a tilt towards conversations with locals, learning the language, and studying the country’s economics a bit before actually traveling to the place. Devoid that, “travel” seems to be another word to brag about one’s life. A nice test to conduct is to ask if one would travel to a new place even if one couldn’t tell anyone about it, and couldn’t share any photos of the travel. Whether it’s truly an act of traveling for the self. 

Additional takeaways for now and future use:

Statements that are like directives:

  • “Whatever scares you go do it.”

  • “Doing the bold thing is always worth it.”

  • “Being present is overrated.”

  • “Women love sex."

  • “Don’t be a donkey."

  • "You don't know what you want until you try it."

Some questions to add to my toolbox:

  • What would you hate not doing?

  • Who are your heroes?

  • Are you driven by satisfaction or dissatisfaction?

  • What’s great about this?