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Every two weeks, I share my writing on investing, career transitions, meaningful work, parenting, living intentionally, and other topics that engage me.

I'm still trying to figure stuff out.

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Let's Work Together

You may have read my recent essay, “Problem Solving,” which describes how I’m approaching what comes next for me professionally. Since then, and inspired by valuable conversations with key thinking partners, I’ve expanded my search to include fractional and full-time roles.

I love meeting new people and exploring ways I might impact organizations by leveraging my skills and experience. If you think there’s someone I should meet, I welcome an introduction.

For more information, see the updated "How We Can Work Together" section at the bottom of this email.

More and Less

The final days of August hit hard every year. Recently, I heard August described as the Sunday of Summer, which captures the feeling quite well.

But this year, the feeling is particularly intense.

For one reason, our oldest child is entering her senior year of high school, a rite of passage that presages more dramatic changes ahead. Also, our youngest just wrapped up driver's ed, and my wife has taken an expanded role at her job.

As for me, I find myself navigating another career transition. This year, summer in Maine offered more time than usual for relaxation, reflection, and reconnecting with friends. Honestly, the timing worked out quite well.

But now it's time to get cranking. To quote the tagline on my LinkedIn profile, I'm "Ready and hunting for what comes next."

Through journaling and contemplation, I've noticed how this career exploration phase differs wildly from job searches in my 20s. The goalposts were always clear back then, even if they kept moving.

Over time, I sensed there might be more to it all. Social approval mattered less. Doing good work mattered more.

In a 2021 interview with Shane Parrish on The Knowledge Project Podcast, author Josh Kaufman shared his definition of success as "working on projects that I value, and I think are important, with people that I like, in a way that allows me to take care of myself and my family."

I remember hearing that response and making a note, subsequently marked as a favorite I review regularly.

In the domain of professional success, I think he nailed it. For me, at least.

I was 51 when I first heard Kaufman describe success. At that point, I'd worked hard to simplify my life. Still, I suspect his words informed my approach to a more dramatic career pivot a year later, in early 2022.

Achieving the type of success Kaufman describes requires a different approach than it did in my 20s. He confirmed what I already knew inside; the role was less important than the experience.

Fortunately, at that point, I'd been working with a gifted career coach named Kathy Vines for more than a decade. Together, Kathy and I planned my next steps.

This was a great unlock for me. Instead of targeting specific roles, Kathy and I designed the "BIG IF" framework to evaluate a broader range of opportunities. In July of 2023, I wrote about the "BIG IF" in my LinkedIn essay "Evolving Advice on Career Pivots."

To keep things moving, here's a cheat sheet:

While the "BIG IF" framework remains very much intact, two years later, I'm also thinking about the environments and activities that enable me to thrive professionally. And those to avoid (or minimize).

I've found it helpful to create two buckets and write them out as a thinking exercise to clarify these ideas. For example, here are some of my points from each bucket.

I Want More of This:

1. Creative problem-solving: I want to engage more with work that requires innovative thinking and unique solutions. I love finding ways to improve efficiency or processes.
2. Collaboration: I'm seeking opportunities to work closely with high-performing teams, at least occasionally in person, where we can hold each other accountable.
3. Continuous learning: I want a career path that constantly challenges me to acquire new skills and knowledge, building upon my experience. Similarly, I want also to support my colleagues and partners in their growth.

And Less of This:

1. Performative Busy-ness: I want success measured by results or deliverables, not activity or box-checking.
2. Short-term focus: I'm less interested in organizations prioritizing speed over quality and immediate gains over long-term sustainability.
3. Zoom meetings: Of course, I recognize the benefits of meeting online. It's super efficient. But it's draining and an experience I'd prefer to minimize. I'll spend very few days in back-to-back online meetings, so I'll either work remotely with fewer meetings or seek hybrid/in-person roles, even if that requires some travel.

There's a reason I chose "more" and "less" instead of more extreme constraints like "all" and "none." While you can't eliminate all friction from the workplace, you'll likely be more successful with the wind at your back.

This approach has already led me to consider options I might have overlooked if I'd been too focused on finding an exact match to my current skills.

As summer winds down and we face the changes ahead, I'm reminded that career transitions are a natural part of life, like the changing seasons. We can approach these shifts with clarity and purpose by focusing on what we want more of and less of in our lives.

Frameworks, like those above, free us from chasing the elusive 'perfect' job and open us up to a wider range of fulfilling possibilities and experiences.

Whether you're contemplating a career change or any significant life transition, I encourage you to embrace the uncertainty with flexibility. It's not a weakness but an opportunity to grow and discover new aspects of yourself and your potential contributions to the world.

Other Stuff

Insurance Isn't the Only Cost Increasing for Property Owners I recently discovered The TreppWire Podcast. It's a solid resource for data and insights into commercial real estate. The team also publishes a daily email called The Rundown, which is quite good and a quick read (subscribe here). A recent edition focused on trends in multifamily expenses. Since I couldn't find a link to their write-ups, I've included a printed PDF of the 8/20/24 that you can access below.

View the email: Insurance Isn't the Only Cost.pdf (3 mins)

From Darwin to Wall Street: Harnessing Evolutionary Theory for Smarter Investments This clever Enterprising Investor post by Drew Estes applies concepts from evolutionary theory to investing. Specifically, Estes argues that economics mistakenly sought inspiration from physics, a closed equilibrium system. Instead, he encourages investors to explore concepts from biology, like evolutionary theory, which operates in open systems in constant disequilibrium.

​Read the post (7 mins)

What is Coast FIRE? The Ultimate Guide to Semi-Retirement To be clear, this is not my current plan, but it's a path that may appeal to several readers. As described by its author, Nick Maggiulli, Coast FIRE is a retirement strategy focusing on saving enough for your future retirement and then "coasting" until you reach that goal. It allows flexibility and work-life balance without extreme saving measures associated with traditional FIRE methods. The Coast FIRE approach offers financial security and meaningful employment choices before the traditional retirement age.

​Read the article (12 mins)

And a Farewell Photo...

How We Can Work Together

Hi, I’m ​David​. This newsletter is a passion project that helps me stay connected with thoughtful people like you.

I spent 25 years in institutional equities as an analyst, portfolio manager, and salesperson. In 2022, I joined Circa, a seed-stage rent payment startup, as COO. I left Circa in 2024 as part of our successful exit to ​Stake​, a larger private company in the proptech space. Also, since 2019, through ​Cove Investments​, I've been an active multifamily real estate investor for myself and on behalf of others.

Here are three ways we can work together:

1. The Right Full-Time Role: I’m exploring full-time roles working with great people where I can leverage my skills and experience in 1) managing relationships and processes, 2) evaluating, distilling, and communicating complex opportunities in simple terms, and 3) building teams and developing staff. This could be in the investment world broadly defined, but it might also be in a new industry altogether.
2. Fractional Engagements: I’m also available for specific projects and fractional work. If you’re a business leader, investor, advisor, or family office looking for additional resources to help with investment analysis, business operations, due diligence, process optimization, or evaluating new products or opportunities, let’s discuss how I can help.
3. Cove Investments: I’m particularly excited about a new strategy focused on smaller properties in the DC Metro, a massive niche under the radar of most investors. Investment opportunities offered through Cove are only available to accredited investors in my network.

To learn more about any of the above, click ​here​ to schedule a one-on-one call to see if we're a good fit.