Issue No.10

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By Richard Huffaker

If you've read any of the previous After Hours newsletters I've written, you know that long before I came to Quo, I was a very early employee at a company called Weebly.

I started at Weebly at a transitional time in my life. I'd just come out of a six-year relationship that had defined most of my twenties. I was about to turn 30. And I was extremely focused on my career, which is a nice and fuzzy way to say I was still trying to figure out what to do with my life while working non-stop.

Weebly was going through its own transitional period right as I started, hitting a wild and unexpected growth spurt. A relatively small but steadily growing operation with a few thousand paying customers tripled its revenue in a couple of months and would 10x it by the end of the year. Tripling the revenue means triple the people to talk to for the person handling customer communication. That was me.

For over a year, the shape of my day was this: I answered support emails. I answered sales emails. Sometimes the phone would ring and I'd answer it too, annoyed that it took me away from all the emails I needed to answer (usually around 500 a day, every single day). Sometimes I slept.

The email queue was never-ending. At the time, I would've told you I was just working hard. Looking back on it now, I wouldn't be quite so kind. I was obsessed with work. I thought if I stopped, everything would fall apart. I grew up very poor and had come from a trailer park in Tennessee to San Francisco, determined not to remain poor. I thought nonstop work was the only way I could achieve that, when all I was actually achieving was a slow-motion personal collapse for a company that was doing well and didn't need me to sacrifice my mental health to be a good employee.

But I didn't know how to stop. I was answering emails on Christmas Eve at midnight. Answering emails from my phone in the TSA line at the airport. When I wasn't working, I felt guilty and just thought about all the work I needed to be doing. I was burned out, but I wouldn't have said so at the time.

This might have gone on forever, but one of the young founders (they were all 25, which was kinda annoying to then 30-year-old Richard) pulled me aside and said I'd been on edge, and everyone could tell how stressed I was. Until then, I hadn't noticed how little of me existed outside of the inbox. We then set out to fix the problem and did so, a story I've told in a previous newsletter.

I think about that time now, many years later, and I barely remember any of it. All I did was work. I can tell you a lot about the operational side of it: the emails, the hiring, the eventual fix. But I can tell you almost nothing about the year itself. That's what obsession with work does. It takes your time, and then it takes the memory of it.

If I could go back and tell my 30-year-old self one thing, it'd be this: boundaries are as much a part of the job as anything else. They're what let you have a job that isn't your whole life.

The hour when you close your laptop, the day when the customer can't reach you, and the stretch when the business is running without you at the center of it: those are the parts you'll remember. Without them, the year just becomes work.

Turn your computer off for two days, and it'll still be there when you come back. Let a teammate pick up, and the customer's calls still get answered. Start with one day off this week. See what you get back. The ordinary boundary you set on a Wednesday afternoon is the one that keeps work from swallowing the rest of your life.

Three things to try this week

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Justine Delgadillo

Here are three small moves that make it easier to take real time off. None of them takes longer than a coffee break to set up.

1. Try a shared inbox so you can take an afternoon off.

A shared inbox lets a teammate pick up calls and texts from your number, so you can step away without your customers noticing anything has changed. Internal threads let you leave context on any conversation that needs it, and voicemails and calls sync automatically for everyone with access. This playbook covers the setup and how to use it to delegate handling conversations.

2. Set up an auto-reply so customers hear back, even when you're off.

The best auto-reply text messages are short and specific about when you'll be back, who's covering, and how a customer can reach that person if their question can't wait. You can adapt something like this to your own voice:

Then you can set up your auto-reply to send a different message based on whether you get a text, call, or voice message — no manual sending required.

3. Build an "I'm away" call flow before you need it.

A temporary call flow is an alternate version of your call routing that you can switch to whenever your usual setup doesn't fit, be it a vacation, a long meeting, or an unexpected afternoon off. Build it once, then switch to it in seconds when you need it. You can also schedule it to switch back to your default flow automatically. That way, you don't have to remember to change it later. This guide covers the setup.

Richard recommends

What to read, listen to, or watch when work won't shut off

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Richard Huffaker

Below is a short list of things I've turned to when the boundary was harder to enforce than I thought it'd be, along with a few I wish had existed when I was 30. The list includes two books, a newsletter, a podcast episode, a short YouTube video, and a TED Talk.

Company of One by Paul Jarvis (book): A small-by-design guide for owners who don't want to scale themselves out of having a life outside of work.

Burnout: The Secret to Unlocking the Stress Cycle by Emily and Amelia Nagoski (book): The science of finishing a stress response, which most of us never do. Useful if you've ever wondered why a "relaxing weekend" didn't relax you.

The Tim Ferriss Show #373 — "Jerry Colonna, The Coach With the Spider Tattoo" (podcast ep, ~2 hrs): A former investor-turned-CEO coach, in conversation about why high performance and inner turmoil so often live together.

Oliver Burkeman's The Imperfectionist (newsletter): a twice-monthly email to read over coffee, with smart takes on the limits of optimization culture.

The School of Life — "The Importance of a Breakdown" (YouTube, ~6 min): Six minutes, calmly animated, philosophical instead of self-help.

"The Art of Stillness" by Pico Iyer (TED Talk, ~15 min): Short, beautiful, and the rare productivity-adjacent talk you can recommend without cringing.