Weight Lifted, Part One 👾
On Sanity-Saving Staycations
✍️ August 30, 2023
I can’t sleep.
I check the clock: it’s only three a.m.
My mind is whirring in my dreams again, troubleshooting a massive project that I started yesterday morning.
In 24 hours, I’m going to email twenty-thousand people about something, and I want to get it right.
This was supposed to be my week off—the first full week all summer that I successfully maintained the “Do Not Schedule” block on my calendar.
But something in me decided to take advantage of the quiet time and pull the rip cord: move everyone on my two mailing lists to Substack and make it clear that, for the first time in nearly twenty years of writing and podcasting online, I am now opening the doors to paid subscribers across both platforms.
Heck, evenjoined the day after I started the process with a welcome message for—surely a good sign! The same way it was in 2018 when I spotted her crossing the street leaving lululemon’s flagship store in Flatiron, just an hour before my friend Petra’s book launch party there later that evening.1
At 3:30 a.m., I give up trying to fall back asleep and shuffle downstairs for my must-have morning ritual, reading in the dark with coffee before diving into work.
But my eyes won’t focus on the words in front of me—not on the silly romance thriller, nor on more high-brow fare like The New Yorker.
My mind wanders off too quickly—as if it’s listening to a podcast at 1.5x, tying up technical loose ends. The words on the page are too slow, not urgent enough.
Did I update the About pages? The welcome emails? The website forms? Automations? How will I process all the unsubscribes?
Managing websites for nearly twenty years turns them into rickety old houses: entropy is always at work. Something is always breaking or out of date. Making one improvement reminds me of renovating a country home—flip one switch and reveal ten related other urgent things that need to be addressed or are woefully out-of-date, if not a hundred.
At four a.m., I relent (again). I stop even trying to relax by reading. I bust out my laptop in the pitch-black living room and return to work.
Truth be told, nothing makes me happier than immersing myself in a gargantuan software-related task: doing something so complicated that I can barely see straight. I love it. It shoots me into a flow state where I feel like I’m starring in the 1995 movie Hackers, one of my favorites growing up.
The room disappears as I point-click-point-click-research-research-point-click-copy-paste-export-import-problem-solve-automate.
No one is around, and Ryder is asleep at my feet. It’s just me, solving problems large and small as I move nearly 20,000 people who subscribed to one of my newsletters these last 13+ years, traveling with me from Aweber to MailChimp to Kajabi and now Substack.
We skipped taking a family vacation this summer. But right after I wrote that, my signature symptoms of desperately needing a solo getaway asserted themselves: I cried over something tiny (couldn’t even tell you what), was short-tempered, and couldn’t carry on a conversation with Michael.
I knew my nerves were fried and that I needed a break.
This has been the strangest summer in business: bittersweet doesn’t quite capture it.