200: Resilience → Outliers

200: Resilience → Outliers


On the 200th edition, my newsletter is changing it's name, topic, and cadence!

Welcome to the 200th edition of this newsletter!

This newsletter has gone through multiple iterations. The first edition started on Substack with just 10 subscribers during COVID under the title Making Connections. Four years later, we cross the 200th edition on Ghost under the banner of Cultivating Resilience.

For 200 weeks I've written about creative risk taking, difficult transitions, and the power of courage. During that time, I went from venture-backed founder, to product leader at a Big Tech firm, to independent executive coach and author.

Now it's time for the newsletter to evolve again.

From Resilience to Outliers

I named this newsletter Cultivating Resilience on the 50th edition (May 2021) to focus on the idea of transitioning into new identities and forging new paths in the face of adversity. It felt like an urgent need at the time, and I also published a series of pieces over the next year on Every that detailed my Resilience Rules framework.

But I've realized that resilience isn't necessarily the best theme for a newsletter. Subscribing to a newsletter is a commitment—to engage with a topic for a long time. I've found that people often seek resilience at specific times in their life:

  • After a layoff
  • When experiencing burnout
  • During a rough patch at their company
  • A general period of languishing or overwhelm

Resilience isn't an identity (e.g. runner, writer, founder), nor is it an evergreen concept that you're always seeking more info on (e.g. AI, mindfulness, ).

While written for the venture-backed founder, I'd argue that much of my best advice and insight on resilience can be found in The Path to Pivot.

Perhaps one day I'll do a follow up (eg The Path to Pivot —Career Edition) for knowledge professionals facing a crisis of meaning. But for now, this singular work + my many essays on the topic can do a lot of heavy lifting for folks looking for resources on resilience.

So we're changing it up.

The newsletter will be renamed The Outlier Advantage

You've seen me write about outliers—the high variance founders, builders, and creatives who defy convention and seek breakout success on their own terms—in previous editions:

My goal is to attract people who feel different, out of place, or just unseen. What Steve Jobs once named "the crazy ones", "misfits", "rebels" What Seth Godin might call "ruckus makers" and what authority figures would likely term "troublemakers" and "rough around the edges".

I want to give these outliers a home. A place to come back to for inspiration, community, strategies, resources, and evergreen hub of discovery.

And even if you don't identify as an outlier, you might still want learn the unconventional lessons, strategies, and stories of those who do.

I also find the weekly cadence of essays both too frequent and not frequent enough:

  • Sometimes I have a lot to say and the weekly cadence is frustrating because its too in frequent to get all my ideas out there while they are fresh.
  • Other times I have to really dig deep to product a quality and relevant essay into your inbox.

If you follow Josh Spector you know this is the format he uses in his daily (!!) newsletter For the Interested. Subject line ties into the content, easy to jump out.

I'm going to try for 3x a week (Mon, Wed, Sat)

This new frequency and cadence doesn't mean I'm moving solely into curation. I will be frequently linking to things I've written / authored elsewhere on the internet:

The goal is to see this newsletter as a jump off point to great ideas about success as a high variance achiever, whether from me directly, or from others that inspire me.

I get that 3x per week is a lot. And some of you might be fed up by this and unsubscribe. I understand. The goal is a lighter-weight send where things are easier to skim and you ultimately hear from me more often.

One Final Round Up?

At the end of 2022, I did a retrospective on my favorite and most popular articles of the year. Didn't get to do one in 2023 but here's a quick round up here.

  • Notes on wisdom
    • Timeless wisdom on research, storytelling, project management and changemaking (CR153)
    • How to be a Dark Horse—notes from a great book for outliers (CR141)
    • How to do great work—a Paul Graham mindmap (CR190)
    • Lessons from The Psychology of Money (CR145)
  • Doing Good
    • Rebuilding a computer lab in SF Chinatown (CR175)
    • How a volunteer trip underscored the importance of showing up (CR161)
  • Meta / Facebook
    • On my departure from Meta—my badge video and 25 thoughts (CR 155)
    • The way Meta makes use of metrics—lessons learned as a PM (CR154)
    • How Meta manages for high achievement (CR158)
  • My Courage Series
    • Courage is the first and most important virtue (CR139)
    • Physical Courage (CR164)
    • Emotional Courage (CR165)
    • Professional Courage (CR172)
  • My outlier series
    • Being an outlier—getting a PIP in Kindergarten (CR179)
    • Strong Suit - how to make your outlier obsessions an advantage (CR181)
    • Kryptonite—managing your weaknesses as an outlier (CR182)
    • My own outlier interview (more to come on these!) (CR186)

Now what?

Now that I've made this announcement, I feel pressure to start posting in the new format. It's probably going to take me a few weeks to get fully up and running and on the new cadence so I ask for your patience as I enter this new phase!

As always, I am open to your thoughts, feedback, and suggestions.


Thank you for being a member of Cultivating Resilience / The Outlier Advantage. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

How I Can Help You

🧢 Executive Coaching: 1:1 coaching for outlier founders & executives that unlock transformational growth over 4+ month engagements (schedule a call)

🛠️ Participatory Workshops: Interactive seminars designed to learn and practice crucial skills for navigating complex transitions—storytelling, emotional intelligence, experimentation and more.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.

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