Tackling Your Skill Debt

On finding ways to rekindle the practice of rotting skills

In the product design world, we’re all accustomed to the concept of tech debt and design debt. As we skyrocket towards the next product release (while putting out fires along the way), we inevitably sacrifice some quality and consequently accumulate a pile of things to improve later.

So we track these extra things to do — refactor some code, tweak an animation, make a component reusable, standardize some UI copy— and ideally sprinkle these items throughout future sprints and releases. We do this because without the practice of continually addressing the debt, we’re left with an unobtainable mountain of it.

I think we need to be applying this thinking towards our own personal skill debts, too. (Or at least I need to work on it! 😅)

Let’s Talk About Skill Debt

Like with tech & design debt, in everyday life we forge ahead towards our next goals (while dealing with life’s twists and turns), surely accumulating a pile of things to do later — clean the shower, sew that button, write that thank you letter, buy more toilet paper. Most of us, thankfully, are pretty ok at managing those to-do’s before finding themselves on Mt. Unobtainable Sh*t To Do. (Well, most the time, hopefully).

Skill debt is so easily overlooked because it’s not about what’s lingering as a to-do, but what’s lost in place of the to-do’s.

But what about all the things diminishing in that time, that wouldn’t be on the to-do list? What about all the talents we don’t make time for? The crafts we’ve found shortcuts to replace? The learned abilities we like to keep trying, but barely practice anymore? That’s what I’m calling “skill debt.” Skill debt is so easily overlooked because it’s not about what’s lingering as a to-do, but what’s lost in place of the to-do’s. It’s the empty crater you didn’t know was developing until it feels too late to fill.

A vast, empty crater with distant mountains, ominous clouds and peeking sunlight in the background
A vast, empty crater with distant mountains, ominous clouds and peeking sunlight in the background
Photo by Robert Bye on Unsplash

Doing Something About It

This first post, for me, is a step towards tackling some of my own skill debt. And hopefully it’s a thought-starter to tackle some skill debt of your own. For me, personally, here’s some of my current skill debt eroding away like a sinkhole at the bottom of the crater…

  • Hand-sketching and doodling — Whether it’s whiteboarding at work or a game of Telestrations, those A’s in fine arts classes are starting to look more like they’re from grade school 😬
  • Running — Consistently improving 5-mile runs have sadly deteriorated to consistent excuses for why not to run 🤦‍♀️
  • Writing — It’s like my ability to quickly write intelligent, meaningful, concise compositions has backwards-matured post-college essay-writing 😱
  • Wireframing, the craft Sure, the proficiency isn’t “lost” in 10 years of doing it…but I must admit the craft sure has dwindled. UI kits and libraries have helped us jump from hand-sketched to mid/high-fidelity much faster, and the speed of product development has conjured scrappy shortcuts. In that, I notice myself admiring the beautifully-crafted wireframes of junior-mid level teammates who devote that time to polish in the low/mid-fidelity. 🤩
  • Italian language — Once fairly proficient molti anni fa, now strapped to a few phrases (most fluently around ordering wine 😳)

The bad news is that there’s a lot more skill debt than just this. The good news is that there are attainable steps I could take to rekindle any of these. So I’m prioritizing the ones which matter most to me, like writing, and starting to experiment with how I might build better habits in keeping up the practice of these skills.

My Method for Getting Started

Here’s the simple thought process I found helpful to prioritize what really matters to me, and figure out what to do about it. I’ll walk through an example…

  1. What skill is withering away? In this case, writing.
  2. Do I care about reviving it? Yes! I’ve enjoyed writing as a hobby back to the 2nd grade “What do you want to be when you grow up?” unit, where I was the one weirdo kid who wanted to be a writer. Plus, it takes me waaaay too long to write up an email these days, and I bet it’d help me orally articulate my thinking better, too.
  3. What has stopped me from doing this anymore? Besides the time… I don’t find writing as rewarding without readers, so personal journaling isn’t for me. And the thought of a dreamy long-term endeavor like writing a novel or doing weekly letter-writing for the rest of 2020 feels too overwhelming to even start!
  4. What’s one thing I can do today to kickstart it back up? Back when I was studying abroad in Italy, I sure enjoyed blogging about my life and adventures. There was no regimented long-term schedule to overwhelm me, but I felt compelled to publish my thoughts because it was there with an audience. So I’m going to publish a first post in a new blog— one grounded on my thoughts and experiences as a product designer.
  5. …Ok, I did it! How am I feeling now? What can I do next? Welp, can’t say this one yet. But knowing myself, pressing that “Publish” button is going to surge a nervous-excited sense of commitment, and make me think more about my next content. I’ll be back! (And if I’m not, come yell at me).

Steps #4 and #5 are the big ones. It’s where this shifts from a mere reflection to an action-oriented goal-setting experience that sets the foundation of habit-building. And it starts with one attainable step to take now as opposed to a major long-term commitmenta mini-goal which builds off past experiences and follows through with a moment to reflect, reassess, and restart with the next mini-goal. (This is inspired by some of the behavior change work we do at WW)!

It was something Julie Zhuo said in a Design Better Podcast that really triggered my motivation for actioning on my writing skill debt through writing on Medium:

I tried to set that goal to be more about action than about quality, or results, or whatnot, just so I could force myself to do it. I still love setting goals like that because sometimes, before you get too hung up on is this good, are people going to read it, is this really what I want to say, does it represent my voice, et cetera, because we can be very perfectionist sometimes. All of those concerns can just block us from even starting.

I’m not setting out to become a best-in-class writer or lock myself into a long-term, regimented path forward: I’m challenging myself to just write…and continue prioritizing time for it.

In this Medium blog, I intend to write loosely about my thoughts and experiences in product design things that shape both my professional and personal life. I might share tactical tips I’ve learned, perspectives I’m tinkering with, behavior change design experiments I’m trying out, design community conversations I’m interested in, and who knows what else. Word by word, post by post, my hollowing crater of skill debt starts leveling up today.

Principal Product Designer @ WW (formerly Weight Watchers)