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Hi! I'm David.

Beyond the Cove - Sustainable Planning, High P/Es, and A Few Billion Dollars


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Happy New Year in advance!
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Many thanks for your interest and support in 2024. I don't take your attention for granted. If you have a moment, please drop me a line to share what you like, ideas for essay topics to explore, or any suggestions to improve this newsletter.

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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Sustainable Planning

In my final newsletter essay of 2023, I shared how I simplified my annual review process by removing the complexity caused by overthinking.

Here’s the basic process I recommended a year ago:

  • Look Back: Reflect on what worked and what could have been better
  • Look Ahead: Choose 2-3 high-leverage goals for the year
  • Plan: Identify habits, systems, and projects to support each goal and schedule quarterly check-ins to track progress

I’ve used this approach for years, and it remains valuable for reflecting on what worked well and what could have been better.

One thing that could have worked better was how I incorporated my annual review into the rest of the year.

Here's the funny thing about best-laid plans: they have a way of gathering digital dust in our perfectly organized note-taking apps.

As I moved through 2024, I noticed something that probably sounds familiar.

Despite my streamlined approach, I wasn't referring to my plans as often as I should. They were like fancy exercise equipment relegated to the darkest corner of the basement, present but not entirely living up to its potential.

I completed my quarterly check-ins and corrected the course as needed, but the process felt abstracted from my daily life. I needed a way to incorporate my goals and plan into the regular flow.

The problem wasn't with the planningbut with the daily execution. I needed something to bridge the gap between my annual plans and daily decisions.

Something memorable that wouldn’t rely on checking my notes.

A North Star

That's when I realized I only needed one tweak.

I needed a compass.

A single word that could serve as a North Star for the year ahead. A word that would instantly reconnect me with my deeper intentions without pulling up a document or checking a to-do list.

Sustainable

After careful consideration, I chose "sustainable" as my touchstone word.

It's not the sexiest word. It doesn't have the aspirational ring of "excellence" or the bold promise of "transformation."

That’s the point.

At this stage, I'm more interested in creating durable, quality outcomes that can compound over time. "Sustainable" resonates with what I want to create across many projects and areas, with a new job and daily routine.

Here are just a few examples of how this should work:

Health

Despite a flexible schedule for most of the year, I didn’t make as much progress as I’d like. There were fits and starts, but my weight and fitness metrics held in a tight range, just beyond my target. Then the holidays arrived.

Now, I have work to do.

With a 35-minute commute added to the mix, I’ll need to be more disciplined this year to make progress that will serve me well for the next decade.

This year, I'm focusing on eating and exercise habits I can maintain for the long haul. No more "beast mode" workouts that leave me unable to move for days, hating exercise, or injured.

Instead, I'm embracing consistent, moderate exercise and meal planning that fits naturally into my daily routine.

Career and Work

After years in high-pressure jobs relying on a single, significant event - a bonus, property transaction, or business exit - I’ve chosen a more stable role. In my new role, the pay and hours will be less demanding but more predictable.

Still, I’ll have ample opportunity to develop new skills and positively impact my clients’ lives.

Here, "sustainable" means finding my rhythm in this new environment. It means being selective about extra projects, especially in these first crucial months. It means maintaining my writing and real estate commitments but at a pace that doesn't leave me exhausted.

Most importantly, it means resisting the temptation to prove myself by saying "yes" to everything. I've been there. That path leads to burnout.

Personal Finance

The math of 2025 is sobering: my daughter's college tuition bills begin arriving this summer (followed by my son's in 2027), just as I'm adjusting to a more modest salary. Fortunately, we've prepared for this, but still, it's stressful to deplete savings and burn cash.

Here, "sustainable" isn't just about budgeting. It's about reimagining our family's financial framework. It means having hard conversations about lifestyle changes, being creative about other income, and making peace with drawing down some savings.

The goal isn't to weather this period by white-knuckling it through extreme frugality. Instead, the goal is to find a sustainable new normal for both kids' college years and beyond.

A Simple Filter

The beauty of a single-word filter is its immediacy. There is no need to pull up documents or review lists.

Just one question: "Is this sustainable?"

It's already proving useful.

Last week, I was running late and debated skipping a 30-minute workout before work. Instead, it guided me toward a more realistic 20-minute session.

That was fine. Plus, it avoided the risk of having to reschedule the rescheduled workout. You get the point.

This simple filter cuts through the noise in the chaos of daily decisions.

There's something fitting about using "sustainable" as the test. If this approach doesn't work, I'll know quickly and adjust accordingly.

That's my experiment for 2025.

Your Word

I've shared my 2025 word, but I'm more interested in yours.

What single word captures your intentions for the year ahead? What would help you make better decisions in the moment?

If you'd like to explore this together, I'll set up periodic email check-ins to share our progress and adjust as needed. No cost, no upsell. Just a small group keeping each other accountable.

Click below to join me.

Sometimes, the simplest changes, like distilling our intentions into a single word, can make the most profound difference.

Let's see where this takes us.

Other Stuff

The Best Tools for the Job For readers without large research budgets, here's a helpful collection of mostly free tools and data sources for investment research published by the newsletter Market Sentiment.

​Read the post (7 mins)

A high P/E is not a stock market sell signal ⚠️ In this season of forecasts, many prognosticators have flagged valuation concerns, typically using the S&P 500 forward P/E as a proxy. That's an overly simplistic approach that also may not be especially helpful. In this take, the financial newsletter TKer by Sam Ro offers a credible, optimistic outlook based on a bullish outlook for healthy earnings growth. I enjoyed the reference to this Steve Cohen quote refuting the value of shorting based on relatively high P/E multiples, "Everyone owns a calculator. Math is not an edge." FWIW, I don't place much value in shorter-term market predictions, but I find thoughtful insights and frameworks helpful to inform and challenge my own thinking.

​Read the essay (17 mins)

How to Make a Few Billion Dollars Terrible title. Great business book. Brad Jacobs has founded seven businesses, each with a market cap of over one billion dollars, including United Rentals, United Waste, and XPO Logistics. He's walked the walk and then some. This book is a rare, insightful business book stuffed with practical advice on hiring, running great meetings, and fostering open communication. I was led to this book after hearing David Senra's Founder's Podcast episode reflecting on the book and his breakfast with Jacobs. I also enjoyed Shane Parrish's interview with Jacobs on The Knowledge Project Podcast.

​Read the book (not an affiliate link)

And a Farewell Photo...

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Hi! I'm David.

Every two weeks, I share my thoughts about investing, career transitions, meaningful work, parenting, living intentionally, and other topics that engage me. I'm in my fifties and still trying to figure stuff out.

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