#91: Frontier Conversations, Fragility & Remote Futures

😷 Reflections on life, work & what matters

April 25th: Greetings from Las Palmas and day 41 of lockdown here. Grab your coffee and enjoy these Saturday morning Boundless thoughts.

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#1 Beautiful Conversations & The Frontier ⛰

Over the past few weeks I had a number of conversations with people who reached out to me or friends who wanted to reconnect. People tend to reach out for a number of reasons:

  • They know I’m down to go from zero to deep conversation in a few minutes and/or they want someone to ask questions others won’t

  • They want permission to take a scary next step in their life (I usually tell them not to take advice from a stranger on the internet!)

  • They get a kick out of my story and the fact that I have a link for anyone to schedule a conversation and they want to see what happens

As my career drove my 20’s, conversations and curiosity have been the guiding wisdom of my 30’s. This might sound absurd, but I resonate with David Whyte’s articulation of the “conversational nature of reality”

I began to realize that the only places where things were actually real was at this frontier between what you think is you and what you think is not you, that whatever you desire of the world will not come to pass exactly as you will like it. But the other mercy is that whatever the world desires of you will also not come to pass, and what actually occurs is this meeting, this frontier. But it’s astonishing how much time human beings spend away from that frontier, abstracting themselves out of their bodies, out of their direct experience, and out of a deeper, broader, and wider possible future that’s waiting for them if they hold the conversation at that frontier level. Half of what’s about to occur is unknown both inside you and outside you.

Over the past three years and especially the past two years, I’ve spent more time closer to that frontier than ever before, which is equally terrifying and energizing.

My bet is that by injecting chaos, discomfort, creating new things and following the thread of the conversations I’m curious about that I can fill my life with things I actually want to do.

It sounds simple until you realize that this is not how most people think. Money has become such a powerful force in the world that people often think about life in terms of how much money they need to make.

Last week a friend reached out and told me that his goal is to “replace” his long-term income. Yesterday, I talked to a class of students at UConn and one student asked “how do you take your own path if you know that you’ll get more responsibility as you get older?”

I asked him what he meant and essentially the question was about money. Life must get more expensive as you get older, right? You have to get an expensive house and keep ratcheting up your cost of living.

So many people accept this assumption but when challenged don’t need all the things they are pricing in to their decision making.

My cost of living is a fraction of what it was five years ago. Life has gotten “cheaper” but more meaningful. I’ve earned less, but I’ve also had more space and time to follow the conversations that bring me alive like writing this newsletter.

Similarly, I’ve spent the last two weeks working on putting together an “ideas deck” with a collection of fellow independent consultants and also working on an interesting longform essay about the current crisis with another friend.

None of these have a clear path towards making money, but damn are they fun.

One of the things I’ve noticed is that work seems to dominate more of our imagination about life than ever before. I grew up surrounded by “stay-at-home parents” (what a crazy label!), but now almost everyone works. This has led to a narrowing of our imagination to things that can be paid for.

Few people ask me “what’s energizing for you right now?” Many ask “is your business doing well?” “do you have (paid) work?”

The need to make money in today’s world is nearly unavoidable - we live in what some have called a “wage-based world.” But there is a lot more wiggle room than people imagine.

The challenge for most of the people I talk to is not making money, its actually figuring out what they want to do, finding the “conversation” that matters to them.

Finding that conversation is not a challenge of replacing your income, finding that dream job or even following your passion and it doesn’t depend on your being employed or self-employed.

It’s a journey of finding questions worth asking and the one’s worth asking usually don’t have easy answers.

One person I talked to this week is thinking about leaving her good job in search of a new, unknown journey, even amid this crisis.

To the people in her life it probably seems crazy and reckless. But from what I’ve seen, these shifts become no-brainers when a certain imbalance arises: certain pain and uncertain wonder outweigh a certain success.

While I often talk to people in pain, many have not developed a capacity to imagine a different way forward. This “uncertain wonder” is really what Whyte is talking about when he talks about the frontier.

This quote from lawyer turned writer Gretchen Rubin brings this alive:

“I’ve come to a point where I’d rather fail as a writer than succeed as a lawyer, and I need to try and fail or try and succeed, but I need to do it.”

I’ve probably had 30 or 40 conversations with people about all these things over the last few weeks. I guessed at the beginning why these people may be reaching out, but ultimately it doesn’t matter.

These are the conversations I want to be having and help me explore the frontier of what I know, don’t know and what might emerge.

Until next week ✌


#2 Think 🤔…………..then build

A rebuttal to Marc Andreessen’s “It’s Time To Build” from Johannes A. Niederhauser

Without leisure and without idleness we are spiritless, we are numb. There is no poetry in such a world - only effectiveness for the sake of effectiveness. All enjoyment is already only relaxation as if we were an ox under a yoke, a castrated animal carrying a burden it does not see. The question of leisure and idleness, make no mistake, is not some question about what we do in our spare time or now that we are locked in.

Read the full thing here.


💬 “Society grows great when old men plant trees whose shade they know they shall never sit in.” - Greek Proverb


#3 Systems Thinking & Fragility 🍸

#1 An essay worth reading from Bonita Roy and rethinking our current systems and a call for imagination. It starts:

But there is something pernicious I want to point out here: we are experiencing two very different kinds of systems.

When we see all the confusion, incompetency, panic and hysteria on TV, we are witnessing the failure of the centralised system to function in the face of complex challenges. By contrast, the simple ways we have organised, behind the scenes, locally and on the internet, are examples of taking back our own agency, and sovereignty, in the company of people with whom we are actually connected.

#2 Thoughts from Nassim Taleb in the New Yorker

“The state,” he told me, “should not smooth out your life, like a Lebanese mother, but should be there for intervention in negative times, like a rich Lebanese uncle.”

Full essay here


#4 Remote Futures 💻

Seeing more examples of company considering a permanent shift. What’s happening at your company?

Many Universities are making dramatic shifts to distance learning with some announcing plans for the fall already. Would you pay $25k for a semester of distance learning at Northeastern? (my consulting skills course is only $399 😂)

I can see many students taking a sabbatical from the upcoming semester. It will be interesting to see what kinds of experiments emerge especially because most won’t just be able to travel freely instead.


#5 Creator Corner

Random shoutouts to people creating interesting things:

Michael is teaching people Alexander Technique online:


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