Doing things that matter

Why checklists distract you

Our minds operate on shortcuts. When we try to determine whether we’ve been productive, it’s easy to mistake output for outcome. For those that thrive off checklists, there’s a dopamine rush that comes with checking off a lot of boxes. But too much box checking can leave us with little real progress to speak of.

Box checking incentivizes us to do the easy thing that get us to the next hit. It locks us into focusing on the things that can be fit within a check box rather than let our minds wander into the unknown. And it values output over outcome. Between school and my formative years as a management consultant, it’s taken me years to break out of the compulsive habit to stick to a checklist.

Half-life is the time it takes for a quantity to reduce to half its initial value. While it’s most commonly applied to radioactive substances, it also extends surprisingly well to building products.

Most things we do require an upfront investment before we see any impact. That impact also tends to fade over time, but the speed at which it fades falls on a vast spectrum from trivial to history-making.

Quickfire AB tests may generate short-lived metric wins, but its impact pales in comparison to features that change the trajectory of a business. Tweaking the margins is never going to remake a story. But it sure feels great in the moment to see immediate results.

We can get trapped into chasing low-hanging fruits because of a focus on short-term returns. When the expectation is to ship multiple features in a week, the incentive is to work on easy things.

A constant pressure to raise more capital also caused us to turn a blind eye to solving bigger problems in favor of guaranteed wins. For example, we put off fixing gross miscategorizations in our marketplace for over a year because it would take a major overhaul of our infrastructure for onboarding supply. Even when we did pursue it, our appetite for a multi-month investment was constantly put to the test.

In the end, we lifted revenue by 20%+ through this dedicated effort, exceeding our grandest aspirations. The silver lining in pursuing and pulling off important things that matter is you never look back. When you get to the other side, people have a hard time imagining what life was like before.  

Even Amazon made several baby steps towards Amazon Prime before biting the bullet and launching a game-changing product. Knowing people’s distaste for shipping fees capped their growth, Amazon first tried to show the savings in checkout. Then it tried Super Saving Shipping, which unlocked free shipping on orders of $25+, only to realize that customers were limiting their order frequency to meet the threshold.

Finally, they took a swing for the fences and created Prime — an iconic launch with incredible staying power.

While individuals and teams need a healthy portfolio of straightforward wins and big swings, it’s important to not get hooked on overdoing the former because it feels good on the psyche. It’s important to ask: how long will this matter for? And is it that worth the time we’re putting in?

These questions apply to our personal lives too. Getting the latest TMZ dirt or watching the Kardashians may be satisfying in the moment, but its half-life is very short-lived, unfortunately. The impact of reading a good book, however, endures for much longer.

Doing things that matter years from now is hard because our monkey brain seeks immediate gratification, half-lives are challenging to grasp, and they tend to be the things that others have given up on. But as the saying goes, it’s the sides of the mountains which sustain life, not the top.

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