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Every two weeks, I share my writing about investing, career transitions, parenting, and other topics that engage me. I'm just trying to figure stuff out.

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Back to Work

Some days, I just feel like writing.

Last Saturday started out as one of those days.

I followed the usual rituals to get my creative juices flowing. I sat in my regular spot at the kitchen table, watched the sunrise as I sipped my coffee, and then started typing.

I began without a clear plan of attack, which is also normal. I’ll always have a broad topic I want to explore, but the outline and conclusion emerge through the writing process itself.

Since I’m a terrible typist, I have plenty of time to reflect on words and ideas while fixing my errors. I think and revise as I go, accumulating more insight and clarity into my thinking. This messy process is normally a satisfying flow state.

On good writing days, time flies. It’s natural.

On bad writing days, it’s a slog.

Everything seemed set up perfectly. Even my regular morning companion, our dog Ollie, gave me space to crank away. In every way, last Saturday should have been a good writing day.

The day before, I’d chosen my topic: cap rates, the most common valuation metric in real estate. I’d had several conversations over the week with investors, and cap rates came up a few times, so I thought I’d dig into the topic a bit through writing.

Over two hours, I hacked away at a draft as I searched for what exactly about cap rates warranted deeper reflection. Eventually, the essay described how to calculate and apply cap rates and highlighted their limitations in illiquid and idiosyncratic markets.

Sounds awesome, right?

It was awful.

The language lacked emotion. The essay’s structure felt rigid and labored.

The piece had an academic paper's dry, pedantic tone, but without any supporting research or original insight.

I couldn’t finish. I bored myself into submission and stepped away from the laptop.

I no longer felt like writing.

Fortunately, I had a welcome distraction to save me. I had to run some errands, so I hopped into my truck and drove into town.

Instead of clearing my head, the break offered an opportunity to think more about the demise of my great American cap rate essay.

At first, I wondered if the problem was the topic.

While blatantly uncool to state publicly, I find valuation deeply fascinating. I’ll talk about cap rates with anyone at any time. So, while I should have been able to find a relatable approach, I couldn’t seem to do it.

My heart wasn’t in it.

Since I had another hour before I needed to be home, I rerouted my course to the Maine Beer Company. It was crowded with tourists, which is odd for December in Maine, but I found a quiet space at the bar where I sat undisturbed.

Armed with a pen, a notebook, and a freshly poured Peeper Ale, I started journaling. Eventually, I explored my frustrating writing experience from earlier in the day.

As my writing filled the page, the problem became clear. The motivation for the cap rate essay emerged from perceived duty rather than genuine connection.

It’d been a while since I’d written about real estate, the one-time focus of this newsletter. For no particular reason, a real estate-themed piece felt overdue, which was arbitrary and self-determined.

With that backdrop and given dramatic moves in bond yields, cap rates seemed like something I should write about. And so I did, with all of the inspiration that comes with obligation.

It shouldn’t be surprising that the writing fell flat.

In my heart, I wanted to explore questions of how we find meaning, especially through the lens of my relationship to work. That’s what’s been in my head. And I think it deserves more attention.

On a practical level, work provides a source of income. But on a deeper level, our experiences through work touch other valuable areas of our humanity. Often deceptively, work also provides a source of connection, inspiration, community, meaning, purpose, identity, fun, and more.

Whether an occupation can or should shoulder such a burden is an important question to ponder for each of us.

My freeform journaling led me to a place of gratitude for the personal relationships I’ve developed over time through work. It wasn’t the activities or projects that endured in my memories, it was the people.

While I’ve written about this subject a few times before, apparently, I’m not done. There’s much more to explore here, both for myself and hopefully in support of others.

I finished my beer and put my writing tools away. It was time to head home.

In hindsight, the cap rates essay missed the mark. I forced it, and it showed. It wasn't cap rates but the human connections forged through work that truly resonated with me.

You can expect more on that topic in future essays. I hope you’ll stick around for the journey.

Other Stuff

The Complete History & Strategy of Costco With the arrival of Costco's first store in Maine, this episode was particularly timely for me. While much of Costco's impressive business model and success is widely understood, the team at Acquired brilliantly recounts Costco's history. I was also stunned by some of the stats they shared. For example, did you know that Costco's house brand, Kirkland Signature, is the largest consumer brand in the world? With sales of $62B, it's larger than Nike! This was hands down one of the most insightful and enjoyable business breakdowns I've heard in a long time.

​Listen to the podcast episode (3 hrs)

The Pathless Path by Paul Millerd For a few years now, I've admired Paul's effort to highlight alternative career paths from afar, mostly through his newsletter and podcast. I admire his honesty, thoughtfulness, compassion, generosity, and independence. Paul, an MIT Sloan grad and McKinsey alum, walked away from the traditional path because it never resonated with him. He wants the world to understand there are options to the default scripts, but he's not trying to convince anyone to change. I finally read his book, and it inspired me to contact Paul directly to thank him for his work. I also bought a bunch to send as gifts and have ten extra copies. Hit reply if you'd like me to send you one.

​Check out the book's website ​

Working with Problems This short blog post from Seth Godin explains the difference between problems and situations and how to identify each.

​Read the post (1 min)

And a Farewell Photo...