Severance as seed

Reflections on the strange past couple of years working in Big Tech and what I’m up to next

Working at a large tech company while AI crashed onto the scene was a strange experience. For the last couple of years, the drumbeat from the top was extremely clear:

• AI will fundamentally change the business

• AI will fundamentally change outcomes for customers

• AI will fundamentally change how we deliver products that enable those outcomes for customers

• We should all be using AI, all the time, for everything, to increase velocity

• And on and on and on...

None of this is terribly surprising. But the funny part, to me, was the huge gap between the stated mandate and operational reality. Transformation is easy to declare, but tricky to execute. The legal, security, finance and procurement departments all needed time to adapt. While they sorted out the logistics, people debated the merit and viability of using AI to transform their work. An adage emerged: “You won’t be replaced by AI. But you will be replaced by someone who knows how to use AI.”

As a design director leading an org of 17, I took this seriously. I didn’t want anyone on my teams to get replaced or left behind (Jules from the future side note: hahahaha). I was responsible for encouraging my org to increase their exposure to AI tooling and to model what experimentation and exploration could look like. I wanted to jump straight in to start building my own experience... but we didn’t yet have access.

Self-study

While I waited for the company to catch up, I decided to make headway on my own time. I’d long straddled the line between front-end development and product design, so it was fun for me to tinker on personal projects on nights and weekends with the extra set of hands AI provided. I built a tool to track my running progress, extracting Strava data and rearranging it into the exact configuration I wanted to see. I made Figma plugins to automate tedious aspects of personal design work I was playing around with. And then, during the 2025 winter break, I finally opened Claude Code and had my “oh, shit” moment.

It felt like a switch flipped.

Using a side project as a testing ground, I started building features that would have ordinarily required technical skill outside my grasp. After a couple of days, my ability to create increased by what seemed like a hundredfold. I was having a ton of fun, feeling both incredibly energized and incredibly rusty, deep in the weeds on product design details. I could squint at the future and see just how drastically these tools might change how designers approach their practice.

Having felt these possibilities, I dreaded going back to work in the new year, sitting in the same old meetings and working at the same old pace.

“The design process is dead”

In March, design leader Jenny Wen went on Lenny Rachitsky’s podcast to talk about her work at Anthropic. It’s a great episode and I recommend listening to the whole thing because Jenny goes into a lot of detail on how she sees the design process changing (or dying) with AI. But the part that stuck with me was her take on returning to IC work: that this particular moment calls for getting your hands dirty, picking up new hard skills, and building empathy for what it takes to evolve into an AI-native designer in this new era.

Her episode came up a lot in our design leadership meetings. We talked about the implications her conclusions might have for our team and how we, as leaders, could get closer to the work. Privately, I thought about my own experience during winter break and wondered if I should consider getting back on the IC track myself.

Sabbatical-ing

As it turns out, I didn’t have to wrestle with that question for long because I got laid off in May. The layoffs were bittersweet: after 9 years at one company, I was feeling burned out and ready for a break. Now, because of an “unbelieveable-to-everyone-in-my-life-who-doesn’t-work-in-tech” severance policy, I have the time and space to actually take a beat. While I’m planning to do. For at least the next six months.

There’s a lot I want to do with this time off. I want to travel, and become fluent in Portuguese, and run a marathon, and clicker train my cats, and relearn how to breathe (literally). I want to cook more and figure out how to feed myself in a sustainable and healthy way. I want to, for the rest of this sabbatical, never have a sad desk lunch.

And yet...

My severance check feels like a mini seed round burning a hole in my pocket. I’m curious, incredibly curious, whether all of the changes of this era might make it possible for me to work on my own stuff, winter break style, for the foreseeable future.

The Anti-Founder Founder Club

I’m lucky to have a few extremely talented founder friends, and I really admire their grit, vision and tenacity. But personally, I’ve never been attracted to entrepreneurship. Building your own product sounds fun, but raising money or starting a company to do it has never appealed to me.

So it’s very surprising to have arrived at the conclusion that building my own product is the natural next step. I’m hoping there’s room for a new kind of company: a tech small business that thrives with a team of 1 or 2. A sustainable, indie app where scaling to millions of users is not the goal.

It’s been hard and humbling already, but I can’t think of a better way to get back to being close to the work. In this next chapter, I’ll be closer to the work than I’ve ever been: designing everything from product flows to branding to emails, providing customer support and figuring out how to actually build a business. There’s are still a lot of blanks to fill in and I’m incredibly excited to be in Learning Mode rather than Founder Mode.

I plan to document that journey, once a week or so, for at least the next six months. While I’m working, I’m also going to hold myself accountable to my sabbatical cooking goal by sharing something I’ve made for lunch with each post. Maybe that’s an odd combo, but it makes perfect sense to me.

Holding many truths at once

On a personal note, I’m working on my ability to hold opposing truths at the same time. So here goes:

I’m happy I was laid off, and I’m still grieving the wonderful work community I was once a part of.

I feel incredibly grateful and privileged to have the resources to pursue this path, and I’m worried I’ll regret spending my time and severance this way if I’m not able to find a job if needed next year.

It feels amazing to have so much agency on how to work and what to work on, and I already miss working and bouncing ideas around with a team.

I’m spending more time building than I ever have, and I feel like I’m getting worse at the actual design part.

I’m nervous I won’t be able to pull it off, and I think I’ll regret it forever if I don’t try.

Lunch

This week for lunch, I tried to recreate the excellent Turkey, Bacon and Avocado sandwich from Heirloom Market at Comstock Ferre in Wethersfield, Connecticut.

See you next week!