The Fixable Failure That Happens Before We Even Start

If you’re reading these words, it means I finally did it… I finally managed to move this newsletter over to Substack. Hooray! Success!

Except the success I’m celebrating is the direct result of a long series of failures. Funny how that works, huh?

The truth is I started planning this move roughly six months ago. And it was probably always going to be a six month project, but the original deadline I’d set for myself was the end of Duke’s spring break, which was mid-March.

In other words, in my mind this triumphant announcement is showing up roughly five months later than I’d planned.

And those five months weren’t 150 days of me just “not getting to it.” They were a series of starts and stops, second thoughts, and struggles with deliverability. Then there was the actual transfer, which I’d estimated would take an afternoon. After all, how long could it take to copy and paste a few articles from one platform to another?

Spoiler alert: It took a lot longer than an afternoon.

The first thing I’d forgotten is that I’ve been writing this newsletter for over a year, meaning “a few articles” was actually closer to sixty. The second thing I’d forgotten is that the phrase “copy and paste” sounds effortless until you’re actually doing it and remembering how every text editor ever built handles formatting slightly differently. Each weird indentation and random extra spacing took an extra 10-15 seconds to fix, which probably doesn’t sound terrible until you realize there were, conservatively, a thousand of them.

And to be clear, I’m not telling you all this because I want you to marvel at all the time and effort I put into making this email possible. Instead, I’m admitting to a wonderfully human form of miscalculation that takes the shape of Pareto’s Principle.

For those unfamiliar, Pareto’s Principle is often referred to as “the 80-20 rule.” It’s the observation that 80% of the value comes from 20% of the work. However, when it appears in these types of “underestimating the work” failures, it manifests itself as roughly 80% of your time getting consumed by roughly 20% of the work.

In my case, when I imagined the project of moving my newsletter to a new platform, I imagined the big, obvious tasks like copy/pasting articles. But I completely failed to account for the enormous, invisible longtail of tiny edge cases that never show up in our mental estimates but end up devouring the majority of our time.

Simply put, us humans are fantastic at predicting the big stuff, but we’re comically and catastrophically bad at recognizing all the little details. And the result is most of us are terrible at setting proper expectations.

Obviously none of you care about the step-by-step logistics of transferring newsletter platforms. Instead, the reason I’m walking you through my technical misadventures is to share how often, in the middle of my five-month ordeal of missing deadlines and screwing up things that should have been simple, I caught myself feeling like I was failing.

It’s a kind of failure I’m certain all of you reading this can relate to. It’s a failure to meet expectations we set for ourselves, which is a particularly miserable kind of failure because most of us are our own worst critics.

Luckily, it’s also a very solvable kind of failure because failing to meet our own expectations is almost entirely self-manufactured. After all, expectations happen to be some of the very few parts of life we can actually control. Sure, you can’t control how long something really takes, or how many hidden edge cases will appear, but you have enormous control over the expectations you set for yourself, which means you have enormous control of how much failure you’re preparing yourself to experience.

Most people never even try to set those expectations carefully. They just grab an optimistic number based on whatever limited knowledge they have, commit to it, and then spend the entire project feeling badly about their shortcomings.

However, while getting better at the up-front guesses isn’t necessarily easy, and it won’t make your plans more accurate, it is possible. And getting better at setting proper expectations at the beginning of something will eliminate entire categories of failure, in reality, were never actually failures in the first place until you created them for yourself.

Since this issue is about the difference between an actual failure and a poorly set expectation, let’s use it as an opportunity to practice getting better at setting those expectations.

To be clear, I’m not asking you to get more accurate or more pessimistic. Instead, the next time you’re about to start a decent-sized project, I just want you to pause for a few moments at the beginning and deliberately recalibrate your expectations before you begin.

Here are a few questions that can help:

• What’s a pessimistic estimate for how long this will take or how hard it will be, and how does that compare to what I’ve imagined?

• Where’s the hidden 20% in this project? What are the small, boring, forgettable edge cases that are easy-to-overlook but, when combined, will take significant time to manage?

• Is my estimate based on the visible task, or the whole task, including the tiny issues and challenges that are easy to overlook?

• If this ends up taking twice as long as I think, what would have to go wrong, and how likely is that to happen?

• What does “going exactly as it should” for this project realistically look like, and am I measuring against reality or my initial fantasy?

Admittedly, these are going to be hard questions to ask yourself. When we set our minds toward something, we usually want to get to work as quickly as possible, and pausing to recalibrate expectations will feel like a big (and pointless) stall. But if you can convince yourself to do it, you’ll stop feeling like a failure when things go exactly the way they were supposed to.