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Reframing email // Purpose vs. pointlessness // Tangible progress // Big ones, frogs, and systems

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📕 Happiness by Design by Paul Dolan 📗 Just Fucking Ship by Amy Hoy 

I’m (finally) approaching the last leg of getting back to inbox zero, where every outbound message begins with some sheepish variant of:

I’m so, so fuckin sorry that this took me three months to get to.

(On the bright side, the fact that I’m even sending these apologies means that I’m at least making progress through the pile.)

In Happiness by Design, Paul Dolan lays out a wonderfully helpful 2x2 matrix for evaluating our day-to-day experiences:

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(Aside: now that I’m searching for it, I can’t actually find this diagram in the book, so maybe Dolan just described it in words, and the doodle is from my notes*.)*

Anyway, email has always been a soul-crusher for me, high in both pain and pointlessness. (It’s obviously not so bad in an absolute sense, but that’s how I’ve always experienced it.)

In some cases, soul-crushers can simply be eliminated (e.g., bad boss, bad job, bad commute). In others cases, they’re inescapable (e.g., serious illness, hostile divorce, slavery). 

Email sits somewhere in the middle, where it can be massively reduced through good systems, but never fully eliminated. 

For example, I’ve invested pretty hard in my email process, which I think is just about as optimized as it can get:

Yet I’m still constantly behind and stressed.

My inability to handle email is almost certainly the biggest contributor of unhappiness to my life. (In case you’re concerned, I should clarify that I’m in no way unhappy overall; life is great. But it would be even better if I could crack the email thing.)

Anyway, given that I can’t make email any smaller, the remaining option is to find a way to make it more purposeful.

One of Dolan’s observations is that purpose outweighs pain. For example: running a marathon, raising a child, starting a business, or writing a book all tend to reduce the pleasure (and increase the pain) in one’s life. However, they also add such high doses of purpose that net happiness ends up increasing.

Can I manage that same trick for email? Maybe!

Here’s Amy Hoy in Just Fucking Ship (p46):

When you’re working on a dinner party, you get to see, feel, and smell the fruits of your effort.

There’s nothing as gratifying as watching your work shape up before your very eyes. 

With software, writing, design, teaching —  the process is far less tangible.

But it doesn’t have to be that way.

You can _make_ your work tangible. Create milestones. Give yourself the joy of watching the progress bar move, of saying, “Hey, I finished Something!”, even when it doesn’t feel like it.

Based on Amy’s advice, I’m making my inbox efforts more tangible by dividing emails into four mental categories (based on their emotional difficulty and/or time cost) and then physically marking off progress in each category as I go:

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Two weeks in, the categories that I’m tracking are:

  • “Big ones,” which are emails that require actual thought and effort (as opposed to instant processing)
  • “Systems,” where I’ve invested extra time on something like a delegation process, automated filter, or textexpander shortcut in order to make this sort of message easier to deal with in the future
  • “Frogs,” which are the messages that I’ve been willfully avoiding, since there’s something about them that throws me into a spiral of shame/anxiety/frustration
  • “Serendipity,” which are the messages that aren’t actually mandatory (often outbound), but which might come back as good opportunities or connections in the future

I know that this sounds sort of stupid, but it has been transformational for me, because it has shifted my focus away from the raw number of emails and toward the ones that I’ve been avoiding.

For example, spending 20 minutes to add a system is normally invisible progress — the time is gone, but the number on the inbox hasn’t changed. But by getting to make a mark next to “systems,” I can feel that progress in a way that excites me. I’m now +1 on systems (or -1 on frogs). Which is both a little bit fun (pleasant) and a lot more meaningful (purpose).

In addition to that, I’m also attempting to keep myself focused on the ultimate goal instead of the petty task. For example, I’m not answering emails because “I have to.” I’m doing it in service to my desire to be helpful and present for my customers and readers. And I’m doing it to clear away the stress that’d holding my attention hostage, allowing me to focus more fully on the work I most care about. 

On its own, trying to just tell myself that it was meaningful wasn’t quite enough. 

But by combining that with the salient progress of my marking off the big ones, frogs, systems, and serendipity, it’s starting to turn a corner. 

I’ll let you know if it stands the test of time.

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