👋 Hello Friend,

This newsletter explores investing, career transitions, parenting, and other topics that engage me. You'll receive a shiny new edition in your inbox every two weeks.

None of my writing should be considered advice, investment or otherwise. I learn best through the writing process and conversations with others. In that spirit, I'd love to hear your thoughts.

Three Powerful Levers

Thank you for joining me at “Beyond the Cove.” Knowing that you might read my words inspires a more serious effort. I’m grateful for your interest, attention, and partnership in this process.

At this time of year, in the final edition, some reflection feels inevitable. But especially this year. 2022 has been one of the most transformative years in my adult life.

Professionally, I pivoted dramatically, leaving the safety of >25 years in institutional equities, a world I knew well, for a leap into the unknown. By April, I joined Circa, an early-stage proptech startup focused on reinventing rent, as COO. The work is dynamic, challenging, and meaningful but also fraught with existential risk.

And on the personal side, I haven’t felt better in decades. Since late summer, I’ve been drinking A LOT less. I’m exercising regularly. I’m also sleeping much better, and most days, I wake up early, without an alarm, feeling rested. It also helps that I’ve lost 25 pounds from my peak weight in late 2019.

To be clear, it’s not like I have anything figured out. There’s plenty of work still to do. Just ask my kids.

Still, I felt a profound and positive mindset shift this year. It was as if I finally had a decent set of tools. I'm sharing what worked for me in the hope it might help others.

Three Levers

More than anything else, these three activities have helped tremendously in the past year: conversations, writing, and taking action.

• Conversations - Partners, friends, former colleagues, and coaches have all been tremendously helpful. For example, I have a weekly mastermind meeting with two friends who are also former colleagues. We hold each other accountable, offer support when needed, and serve as sounding boards for idea generation. Getting thoughts out of your head and into the light of day often changes your perspective. And objective feedback and fresh perspectives inform and expose gaps in knowledge.
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• Writing - Whether it’s a journaling practice, a letter or email to a friend, a memo at work, or a newsletter, writing remains a powerful tool for understanding ourselves. The contemplation required by the writing process enables a deeper understanding of one’s ideas.
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• Taking Action - In perhaps the most dramatic shift, I’ve forced myself to take action in the face of uncertainty. Fear of the unknown threatens the ego and can be paralyzing. I’ve found that it’s better to dive in with the trust that confidence will build through action. A flexible strategy can be liberating. Start with a tiny step and iterate along the way.

A Mindset Shift

All these approaches helped me ask myself tough questions and reflect, leading to an overdue change in perspective. The hard work exposed the absurd reality that I seemed focused on some elusive ideal state down the road. I was working toward something, unaware that my life was happening every day in real time.

Making peace with the present hasn’t been easy. And it’s been tough to come to terms with the reality that I won’t do or accomplish everything I planned.

In his excellent book Four Thousand Weeks, Oliver Burkeman eloquently describes this struggle. Burkeman writes,

In the final months of 2022, I finally understood that the point isn't to set myself up for something else, that this isn’t a dress rehearsal. While perhaps overdue, this realization is both valid and welcome.

Conclusion

As you work through your inevitable challenges, consider having some honest conversations with others you trust, writing, and taking appropriate action in the face of uncertainty. Yes, it's uncomfortable, especially at first. But that's probably the best indicator that you're right on track.

Happy holidays to you and your loved ones.

Other stuff

Apartment Transactions Plummet October transactions are down 52% YoY, which reflects volatility in debt markets that make lenders more risk averse. Fewer transactions also make price discovery more difficult, which doesn't help bridge wide gaps in price expectations between buyers and sellers. The environment is unlikely to change materially until debt markets stabilize.

​Read the article (2 mins)

Ideas That Changed My Life In this brief post, Morgan Housel reflects on a handful of powerful ideas that have influenced his thinking. Here's the list, though the rationale for each makes the short post worth a read.

• Everyone belongs to a tribe and underestimates how influential that tribe is on their thinking.
• Everything’s been done before. The scenes change but the behaviors and outcomes don’t.
• Multi-discipline learning
• Self-interest can lead people to believe and justify nearly anything
• Room for error is underappreciated and misunderstood,
• Sustainable sources of competitive advantage, and
• Your personal experiences make up maybe 0.00000001% of what’s happened in the world but maybe 80% of how you think the world works.

​Read the post (4 mins)

The Ultimate Guide to Summarizing Books: How to Distill Ideas to Accelerate Your Learning 2022 was a massive year for Tiago Forte with the launch of his book "Building a Second Brain," which codified the ideas of the popular BASB online course. While I don't love everything about Tiago's approach, this post was an excellent resource on the valuable process of summarizing books.

​Read the article (23 mins)

Part 1 Pmarca Guide to Career Planning: Opportunity Kudos to Fictive Kin for preserving a treasure trove of 2007 posts from Marc Andreessen that had since been removed. Within the collection is a guide on career planning that begins with an awesome one-two punch: "The first rule of career planning: Do not plan your career...The second rule of career planning: Instead of planning your career, focus on developing skills and pursuing opportunities." Of course, haters will dismiss Andreessen for this firm's aggressive move into crypto at the top. Still, those with a more open mind will find some terrific nuggets in this archive that dig into venture, startups, and music. Despite his flaws, I remain a fan of Andreessen and remember feeling moved by his optimistic and inspirational essay " It's Time to Build, " written during the depths of the pandemic.

​Read the post (9 mins)

And a Farewell Photo...