Ashlie Crooks
Writing

Reinvention as a Tool

August 21, 2026

This started as a talk at DevFest Wisconsin on August 19, 2026. It was my first conference talk. What follows is roughly what I said, rearranged for reading.

The organizers asked me to open with a time I was excluded, and I didn't have to go back very far. I went to a single-track conference earlier this year. The community prides itself on being friendly and inclusive, and every single person I talked to was friendly. That did not add up to feeling included.

I'm autistic and I have social anxiety. Years of retail acclimated me to talking to strangers one-on-one, so I can walk up to a person and tell them they gave a great talk and that I learned something from it. The second that person is standing with another person, I lose the ability entirely. So this is a gentle reminder that nobody being actively excluded does not automatically make a thing inclusive.

Someone held the door open

I opened with a live poll asking the room whether they knew Hilary Stohs-Krause. Thirty-eight people voted and 61% said no, which was honestly the better answer, because it meant I got to tell them.

Hilary is on the DevFest board. We met about ten years ago when a friend introduced us over email in the context of Madison Women in Tech, and then in person very shortly after, at a board game event I was hosting. At that point I was not a woman in tech. I became one, and then officially joined the group.

I don't think anyone can know all there is to know about Hilary. She's a serious cat person, she loves board games, and she loves connecting people. She's also one of the coolest people I know. Over the years she has been both a friend and a mentor. She was one of the deciding factors in taking my last job, and working with her was one of the most rewarding parts of my career.

Hilary is someone who holds the door open for people. That's a metaphor I keep coming back to, so hold onto it. I've gotten where I am partly through reinvention and partly because people like Hilary believed in me and gave me a chance. It is not an exaggeration to say I gave that talk because of her, both her example and her encouragement.

The road I didn't take

The second poll asked who in the room had a degree in Computer Science.

I have a creative writing degree, and I got my first tech job after 40.

For a long time I thought that was the thing that made me a fraud. Not the work. I could do the work. It was that everyone around me seemed to have arrived by a road I hadn't taken, and I couldn't shake the sense that I'd come in through a side door.

Thirty-six people answered:

Half that room was in exactly my position.

I had spent years quietly certain I was the exception in every room I walked into. The first time I actually asked a room, the side door turned out to be the main entrance.

Around the same time I read a post from Women Who Code saying that 75% of women executives have experienced imposter syndrome. Not juniors. Executives. The people who by every visible measure had already made it. The reframe that came with it is the one I keep returning to.

Imposter syndrome isn't loudest when you're underqualified. It's loudest when you're underrepresented.

That "do I actually belong here" feeling shows up hardest when you look around and you're the only one who looks like you, whether that's because you're a woman, a person of color, or because you took a different route to get here.

I quit

Ten years ago I was miserable. I was the Prepared Foods Team Leader at Whole Foods, and after nearly two decades in retail I was ready for something else.

My partner John suggested I try FreeCodeCamp. Within the first few lessons I was having flashbacks to the mid-90s, right-clicking on websites to read the source and figure out how they'd done something. (Spoiler: it was tables. It was always tables.) Very quickly I realized that not only was I good at web development, I enjoyed it.

I kept learning on the side while things at work got worse. Heavy pushes toward premade foods while still hitting target margins during labor crunches. After one particularly bad week, I did the only reasonable thing and quit.

John had just started a new job with good benefits, which gave me the room to leave. I wish I could tell you the transition from retail to tech was smooth. It was not. I kept going with FreeCodeCamp until I ran out of completed modules, which at the time meant HTML, CSS, and JavaScript. The React modules hadn't been built yet, and I could not find anything that would effectively teach me the newest, hottest JavaScript library.

It turned out I wasn't the only one. Jose Pérez Aguinaga had written a famous piece about exactly this. Babel, Webpack, Browserify, Gulp, Grunt. I couldn't figure out any of it.

So instead of fighting dozens of tutorials that contradicted each other, I turned back toward something comfortable and familiar. I dreamt about food carts and board game cafes. I signed up for a local startup accelerator, since defunct, with the idea of opening a cafe. About halfway through the two-month program I realized I should be building websites, because I was sitting in a room full of people who needed to communicate with their customers. My first freelance clients came out of that cohort.

Teaching is how you find out what you know

Freelancing was miserable in a different way. I hated selling myself. I had been great at selling in a retail setting, especially when I believed in the thing, but networking and convincing people to hand me money was another matter entirely.

I kept a few clients and picked up several part-time jobs, including a couple at Maydm, a local nonprofit that prepares underrepresented youth for careers in STEM. I started there as an afterschool web development instructor, and I will tell you that there is no better way to find out whether you actually understand something than trying to teach it to a room full of junior high kids. I also worked as their WordPress contractor, and eventually got asked to help develop curriculum, which was one of the most challenging and most fulfilling things I've done.

Alongside that I volunteered for YWeb Career Academy, a program the local YWCA built to prepare underrepresented people for careers in tech. I tutored, and I ran mock technical interviews.

I was maybe six months ahead of some of the people I was interviewing. Some were career changers like me, with degrees unrelated to computer science. Some had no degree at all and had only ever worked retail.

The thing I kept telling them in feedback was that skills transfer. I already knew the soft skills I'd built in leadership would carry over, things like communication, empathy, training, mentoring. What I didn't understand yet was how much else would come with them.

Triaging bugs on a live system, for example. A SQL query is nothing next to the stress of a line out the door on the Wednesday before Thanksgiving.

The first real job

As much as I loved Maydm, I was ready to have one single job. I started applying for anything and everything, and I got to in-person interviews with two local companies.

The first was a more traditional engineering role: dozens of cis white men in an office where I would have been the first woman. The second was a small team, just a backend developer and a designer who went on to become the team lead.

That team lead was Joe Baz, and he gets a shout-out here too. Months after I was hired, Joe told me two things. They had been set on hiring someone underrepresented in tech, and I had been their first choice after the technical interview.

What I didn't recognize at the time was that I had been building the reinvention skill itself. All those false starts that didn't quite take, all the earlier skills, were still there. They were layering onto what I was learning rather than being replaced by it.

My interviewing experience turned out to be worth a lot when we decided to hire a junior developer, and again we went looking for someone underrepresented in tech. I led the hiring round, weighed in on candidates, and we hired the best one: a young Black man who had just finished an in-person bootcamp. When I trained him I fell back on years of training team members in retail. He taught me React hooks and GraphQL. That went both directions, which is how it's supposed to work.

With each job after that I added more: full-stack, Postgres, Ruby on Rails. I loved learning Rails. That job also let me give John a break, and I got to have a househusband for a while.

I quit. Again.

A year ago I was miserable again.

Early in the year I updated my resume and started looking, then gave up because it felt too bleak. Every week there was another announcement of mass layoffs from another company going all-in on AI. But by the end of the year it was clear the situation wasn't sustainable for me. John had just started a job with better benefits than mine, and we decided the best thing I could do was leave.

So I quit a stable job in the middle of one of the worst markets software developers have seen, and took some time to work out what I wanted to do next.

The archive

The last poll asked how people were already using AI. Thirty-six answers:

Exactly one person in the room said they weren't using it at all. Whatever else is true about this moment, that audience had already made up its mind.

John had signed up for a Claude account and shared it with me. I'd introduced him to Obsidian the year before, and he had the genuinely good idea of connecting the two, since Obsidian is just plain markdown files on disk. I followed his lead and started building an executive coaching system that now largely runs my daily life.

Something I found out along the way is that Claude can be a real tool for people who struggle with executive dysfunction. Obsidian gives it an enormous library of context about me. It reminds me about upcoming appointments. It reminds me about projects I started one day and lost interest in the next. Most of all it reminds me of the things I actually want to do with my time, which is the part that tends to get lost.

I've written about how that system works in more detail in Claude Code + Obsidian: Executive Function as a Service.

Reinvention 2: Electric Boogaloo

From there I started building with AI as part of how I genuinely develop, rather than as a party trick. I have Claude check out branches and write entire features while I read and review the code. I wrote my own Claude skills. I built my own agents and workflows.

I had Claude write me lessons to learn Python by building things I actually wanted to build. I started learning Godot, because I had an idea for a cozy game set in a cat cafe.

Remember the cafe I wanted to open, back when I was avoiding Webpack? Nothing is lost. Everything is still here.

This reinvention has been scarier in some ways, largely because I know it's happening. I am actively choosing who I become, and deliberately choosing things that frighten me, like becoming a person who goes to conferences where she knows nobody, and then a person who speaks at them.

Here's the part I find beautiful, though. If this reinvention doesn't take, if I never want to give another conference talk as long as I live, I am still someone who gives conference talks, because I stood up in that room and gave one.

A commit, not a force-push

That's the thing worth holding onto. Reinvention is another commit in your history, another layer on the person you're building. It is not a force-push. You don't overwrite what came before, and you couldn't if you tried. Yes, it is scary, and it will keep being scary. At the end of it you are still you, with new skills sitting on top of the ones you already had.

And if you're not looking to reinvent yourself, if you're genuinely happy where you are, then look for chances to hold the door open for someone else. Help somebody find their first tech job, or their next one.

The slides are still up at devfest.ashliecrooks.dev. They're worth a click for one reason: the three polls are archived with the room's real votes, so you can see the actual bars instead of my summary of them. I built the polling app for this talk rather than using an off-the-shelf one, so the deck reads the results live and branches to a different slide depending on how the room answers. Arrow keys to navigate.