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The 100th Milestone: Reflecting on Lessons in Leadership, Life, and Legacy

This thought letter about future proofing life and work is now 100 letters old. Launched as a gift of ideas and conversation that was 100% opt-in, completely free and covering a range of topics and mindsets around creating better futures for yourself, your organizations and the planet. 

Through my speaking and social media as well as you generously forwarding it to others (thank you!). Now thousands of people around the world from the CEOs and boards of the world’s largest companies to entrepreneurs in Idaho to young changemakers in Asia read, respond, and connect. People have said they feel seen and heard, found new ideas or have respectfully disagreed with me about leadership and life lessons.

Thank you for your support. πŸ™

What have I learned that might be valuable to you?

Much of the past years have been unlearning the past structures of career, organization and leadership so that I could see better. As Mizuta Masahide, 17th century Japanese poet and samurai evokes in his haiku, "Barn's burnt down -- now I can see the moon."

Three moons, in fact:

πŸŒ™People matter.
Obvious? Maybe. Easy? No.

Over the past decade, exacerbated by the pandemic, the work zeitgeist went from shareholder maximization, efficiency and economies of scale to a need for a frankly messier adaptability to cope with complexity and become an “antifragile organization” that could learn from failures. The pandemic supercharged that for sure as thin margin businesses and supply chains collapsed. Frameworks and theories proliferated around how we could get back a sense of control. 

In tandem, a growing cadre of people fueling our businesses started to feel a joyless sense of over optimization. This seemed like an American Silicon-Valley hacker meets Puritan work ethic prizing efficiency and control. If you Google “morning routine” it returns 35 million articles with the recipe for success.

Increasingly people are finding out that the success recipe just doesn’t taste that good (and it doesn’t feed that many people). Even in Asia and especially hard-working China, people woke up to the sense that, as the New Yorker reported in 2021,

"...workers, having scaled and optimized their lives, sense that they have become just like their devices: interchangeable and emblazoned with a sheen of productivity, for no real higher purpose."

We are collectively waking up to the reality that when we don’t matter or are not treated with regard for who we are beyond the transaction, be that the sales quota or prestige college admission or social media like, life loses buoyancy.

And frankly, we don’t really know what to do about it. This will be one of the crucial keys underlying how we build the future of work. 

πŸŒ™Collective Success Matters.

Our achievement culture, which allowed humanity to go from pyramids to skyscrapers and to the moon, has also left a lot of people feeling left behind, not included and othered.

I love the idea that everyone has a unique gift waiting to be unleashed with the right support. However, the last few years left me wondering if unlocking individual potential is useful to solve the world’s pressing problems, including isolation and exclusion.

As my esteemed colleague James Andrade once said to me, in a world of rapid change and commoditized information, “the notion that any single person or sequestered group of corporate employees will hold complete expertise is not realistic. Rather people will rely on the social equivalent of neural networks to have a deep understanding of a given subject area” and solve problems.  

Creating structures to harness collective intelligence, measured by success that considers the fate of 7 billion people rather than a few lucky souls, is a trend I see across my work on boards, in companies, and in the community.

Which brings me to my next conviction after 100 letters, hours of teaching, coaching, convening and quiet reflection and 50+ open-to-the-public Masterclasses on everything from disruption, and conversational AI to happiness and helping the next generation matter.

πŸŒ™ Conversations matter.

The lifeblood of collective success and individual flourishing has at its base our ability to relate and connect to one another. To have productive conflicts and conversations that allow us to transcend easy answers and hardened perspectives.

This is really, really hard. 

If you want to know how hard it is, I challenge you to go into your next board meeting or family dinner and ask what the top 3 most important priorities are and see if you are all speaking the same language.

In the past it was easier. We had more linear careers, specific hierarchies, known roles and clear expectations. Today things are more fluid with great possibilities and a multitude of distraction and confusion. In order for us to stay grounded we have to reflect and identify our deeply rooted values. 

And then talk, share, connect, have conversations that allow us to find common ground, discuss our differences, show up again and again and again for more.

We have been wringing our hands over generative AI without recognizing that technology always changes but understanding humans and behavior is immutable. 

Rather than writing letters of concern about technology, when will the world’s citizens sign an open letter for us to have better conversations?

I, for one, will be one of the first to sign on.

If you would like to introduce someone to my writing and thinking please share or forward this blogpost. Let’s continue to grow together into the future.


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