The elusive pursuit of getting it (all) done

Growing up, my French-speaking parents always warned me about having “plus de gueule que de sac.”

While the Google translation is entertaining, English has its own version: “Having eyes bigger than your stomach.” Growing up, this idiom always stayed with me, whether it was at the all-you-can-eat hotel buffet or a post-soccer practice McDonalds run.

This week, I sat down with Nathan Barry the Founder and CEO of ConvertKit. As a fellow boot-strapped entrepreneur I’ve been deeply inspired by Nathan’s ethos, vision, pragmatism and humility. Here’s a brief exchange from our talk:

Nathan: What’s the hardest part of being a solo creator?
Khe: The lack of scale. Every morning I wake up with 100 things I want to accomplish, yet only get 2 done.
Nathan: Ummm. You know that never goes away?

And Nathan knows what’s up. He’s got a team of 60+ generating $27 mm in ARR (yes, bootstrapped).

Yet even those epic numbers don’t quell the affliction of having eyes bigger than your stomach. So what does?

Relentless prioritization

Every morning when we sit down at our desks and check our email, we’re already swimming against the tide of our own self sabotaging behaviors. There’s the Mere Urgency Effect which leads us to choose

objectively worse options (email) over objectively better options (client presentations) when “the unimportant tasks are characterized by spurious urgency (e.g. an illusion of expiration).”

Then there’s the Present Bias which explains our tendency to “give stronger weights to payoffs that are closer to the present” (i.e. the reason we procrastinate, eat too much sugar, and don’t invest in our retirement accounts).

A simple anti-dote to this self-sabotage is the relentless prioritization on your highest leverage, highest skilled activities – your $10,000/hr work. Before you get sucked into the ping-pong of email and Slack, carve out and ruthlessly protect 25 minutes for your $10K work, which can include creating internal training programs, institutionalizing company knowledge, recruiting future leaders or deliberately crafting a 5 year vision. These tasks are (unsexy) activities that will inevitably compound over the long-term.

Recalibrated expectations

What if we applied a classic Munger-style inversion to this affliction? Instead of focusing on the 98 tasks we cannot accomplish, what if we focused on the minimum effective dosage? This approach was recommended to by Molly Crockett, a psychology professor at Yale. Crockett described her own system as follows:

I tend to be very overwhelmed and demoralized by what I have to do, so I created a system where I have a [two column] list of things that require a lot of mental bandwith and a list of things I can do at the end of the day when my energy is depleted. There’s an easy column and a hard one. My daily goal, which is ridiculously low, is one item from each category.

Crockett “sets the bar really low in order to not get demoralized” yet regularly clears that hurdle in spades. This enables her to tap into her own momentum, while avoiding downward spirals and the associated self-loathing:

If it’s before lunch time and I’ve already done one from each column, then I find that motivating and get more done. But if I set a less achievable goal of 3-4 from each column, I’d halfway through the day realize that this wouldn’t happen and then it’s like “well, I broke my diet, so I might as well have two beers and chocolate cake” type of situation.

The real reason

But let’s jump to the real talk. RadReaders know that the productivity hacks and tricks only scratch the surface on the deeper existential questions. The two approaches above merely treat the symptom, versus diagnosing the root cause.

At its core, I suspect these feelings of insatiability are intricately tied to the feeling that we’re one bonus payment away from feeling financially secure, that we’re always running out of time and that the elusive promotion will bring us abiding happiness. As Oliver Burkeman writes in his 8 Secrets to a (fairly) fulfilling life, maybe the remedy is simple acceptance that “There will always be too much to do – and this realisation is liberating.

Burkeman explains that “thanks to capitalism, technology and human ambition, these demands keep increasing, while your capacities remain largely fixed.” That implies that our desires to get it all done are doomed from the get-go.

Thankfully, there’s a silver lining – only one path out of this conundrum:

The upside is that you needn’t berate yourself for failing to do it all, since doing it all is structurally impossible. The only viable solution is to make a shift: from a life spent trying not to neglect anything, to one spent proactively and consciously choosing what to neglect, in favour of what matters most.

So whether that list contains two, 200, or 2,000 items – find what matters most, yet accept that it all won’t get done.

And that’s totally ok.

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