What Will You Regret Most?

At a Glance:

• Our biggest regrets as founders and leaders

• Why this is the foundation of advantage now

• Getting started

The biggest regrets of the dying, as documented by palliative care nurse Bronnie Ware in her book "The Top Five Regrets of the Dying", are as follows:

1. "I wish I’d had the courage to live a life true to myself, not the life others expected of me."

2. "I wish I hadn’t worked so hard."

3. "I wish I’d had the courage to express my feelings."

4. "I wish I had stayed in touch with my friends."

5. "I wish I had let myself be happier."

How Leaders Lose Their Way

This may seem harsh to compare leaders to the dying, but bear with me. Business people who have “been through the ringer” have an oddly similar set of regrets:

1. “I wish I’d built the business I wanted, not the one others told me to build.”

2. “I wish I’d had a more balanced life.”

3. “I wish I had been more honest, especially with myself.”

4. “I wish I had let myself enjoy the journey.”

5. “I wish I’d known the cost of success (or failure).”

Capitalism doesn’t teach us these things. It doesn’t care. At least, it hasn’t.

I was on a podcast with my Dad this past week and the host asked my advice on being a good son. It’s the same if you want to be a good business partner, romantic partner, parent, sibling, or any other role.

Work on yourself first.

Why That Matters Now

As my next book will make clear, people are catching on. They’re seeking organizations that make them feel alive. AI is democratizing the landscape. What’s left is human connection, not assholes.

That starts with leaders who show up for themselves. When they do that, they show up for others: vulnerable, authentic, kind (not “nice”), curious, empathetic, supportive, and deeply inspirational.

That’s becoming what attracts buyers and workers, breaks through difficult situations, and electrifies companies.

What it Means

This doesn’t mean kowtowing to trophy-craving sponges demanding free massages. It means working on yourself to become a steward of purpose, fueled by creative superstars.

And it’s not “another task” to add to the list. It surrounds your activities, breathing life into the mundane, and making the whole network feel the energy of aliveness.

It’s a decision. Simply by committing, huge leaps can be made, some relatively quickly. Also, when this work is done as a team, it unlocks stuck emotions, resolves hard conversations and decisions, and fuels innovation.

Harvard Business School said two-thirds of business failures can be traced to issues like burnout, stress, and mental health. My math is more like 90%. We need a new approach.

I’m incredibly lucky to work at this intersection of inner work and outer results. It’s wildly rewarding, AND I get to see the world improving instead of deriving my energy from news feeds.

People are changing. Moats are becoming more human. Capitalism is starting to shift.

Start by looking inward. Talk to the “you” on your deathbed. How does that version of you feel about you today? How is the story of your life playing out?

With love, 

Dave  

(PS - I asked AI for a picture of me talking to myself on my deathbed. Super creepy and I seem really angry at my old self for some reason. Ping me and I’ll send it to you 😆.)

Seeing results from showing up more fully? Hit reply - I'd love to hear your story.

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