Cailyn Hansen

90 Days Unemployed

Today marks 90 days since I quit my job as a senior engineering manager at Duolingo leading the Notifications team. I want to take a moment to share a bit more about my reasons for leaving (I’ve been asked that a lot), give a snapshot of what’s kept me busy, preview what might be next, and, perhaps with too much self-importance, share some learnings.

Why I left?

The comfortable answer—the answer that makes sense—is that I was burnt out. I needed a break, a way to step back and refocus, a reset, to recharge. And that’s true, but it’s not the full story, doesn’t capture the full emotion. Work, for better or worse, was a space that I invested a lot of energy. At first, it was the people, the friendships, the care I had for others, the desire to enact change, and the commitment to be vocal. As the years went by, and only in hindsight, that focus, that drive, changed. It morphed.

Success—that version of success marked by promotions and raises and validation from externally legitimate sources—became my north star. I woke up thinking about experiments to move DAUs and went to bed thinking about how to scale my team’s impact. The internal metrics dashboard was the most visited site on any device I owned with internet access. And maybe because of it, maybe because of the effort I gave, maybe luck, or most likely because of how awesome and impressive my team was, we shipped a bunch of DAUs, increased KPIs across the board, and improved long-term reliability. By all those metrics, we, and thus I, succeeded.

What did I trade for that though? My sleep, my free time, my capacity to show up for my reports in the ways they needed, my community, my ability to engage with the large and scary things in the world, my headspace for literally anything else. But, most notably, I traded my ability to keep going, to keep caring. I had a fancy new title and absolutely no ability (nor desire) to keep performing at the caliber that got me there. Perhaps the synthesis is I need better work-life balance. I think it’s deeper than that though….

I live by a motto: Be Bold. Take Risks. Make Change. It’s been on every resume and every version of my website for the past seven years. In the final months, I realized I drifted from this core principle of my life. I needed to find my way back. I needed to care again. And I felt the only way forward was to throw myself into the deep end of unemployment and figure it out. I gave myself six months. We’re halfway there.

What’s happened?

I’ve spent nearly one third of the time so far outside of NYC (My cat expressed his displeasure by learning to open our front door). My travels were split between Canada, Taiwan, and Miami. I saw a rare gull near Niagara Falls, spent all day birding on a land-reclamation peninsula in Lake Ontario, had some of the best food of my life in Tainan and a small village outside of Puzi, participated in a tea ceremony in Daxueshan, had some long (and difficult) conversations with family in a too-cold Coral Gables, and experienced my first long-distance Amtrak on the Floridian.

Reading, and especially writing, have become more regular and consistent for me. I started journalling, reworked previous pieces, threw a personal record amount of words into text documents, and explored new formats and genres.

I began too many projects and finished some of them. (For all my birding friends, check out https://birds.cailynhansen.com for a beta test!) I updated my website a bunch of times. I spent way too many hours trying to figure out an old Raspberry Pi I had. I tried to stay up-to-date on the hundred different AI tools and breakthroughs and smoke and mirrors.

But I also stressed about finances, made a budget, then re-made it twice. I was checking my brokerage account five to seven times a day at one point making sure this 6-months-unemployed plan was going to work. The day-to-day fluctuations were never going to affect my ability to continue this, but I had to unlearn this deeply conditioned scarcity mindset that told me I needed continual wealth accumulation to live.

Hours (like a lot of hours) went by watching YouTube, sleeping in, scrolling through LinkedIn worried I was making a mistake around my career. More were spent baking various breads, listening to countless episodes of podcasts while aimlessly walking through the city, playing games with friends. But perhaps most notably through all that, I stared into space worrying about not being “productive”. Have I fully gotten over that feeling? No, but I’m working on separating my worth from my output.

The additional time has also allowed me to get angry, feel defeated, rant, scream at the world, but also to protest, to organize, to provide mutual aid, to work on figuring out how to make change. I’ve reflected on old ideas and integrated new beliefs. Snippets of grand dreams and small hopes have circulated around.

I also reached out to dozens of old contacts and friends. I’ve reconnected with people I thought I would never talk to again. And I’ve cold emailed several people doing interesting things and asked to learn more and connect. I’ve been ghosted but I’ve also said yes to introductions and meetups that I was nervous to accept (internal thoughts screaming, “I’m definitely not cool enough”).

A lot has happened in 90 days. And there’s a lot more I didn’t do. I have to remind myself there isn’t a playbook for this. Part of the fun (and certainly the challenge) is to figure out how to make sense of all of this and make this meaningful—whatever that looks like… to me.

What’s next?

Admittedly, there’s still a lot of unknowns and uncertainty and there’s going to be false starts and wrong turns. Neither three months, three years, nor three decades feels like enough time to “figure it out”.

First, I’m not going to commit to a quota of essays written, books read, git commits authored, projects updated. I’m going to de-metric my life. To honor this (and the amount of time I spent staring at metrics dashboards), I’m launching my newest digital art project: https://metrics.cailynhansen.com. Here’s to irony!

I’m coalescing around a set of ideas of what I want as my next chapter. I know it’s not tech. This isn’t me abandoning anything technical (I don’t think I could even if I wanted) but not putting that at the center of what I do. I learned that too often my “side interests” fall to the wayside of my primary focus. I’m ready to make tech that side interest.

It is fairly common knowledge that I am a strong advocate of transformative justice and generative conflict. Some folks know that I’ve worked to develop systems to respond to harm based on these ideas in various groups before. Others have heard me excitedly talk about my love of science fiction, especially Afrofuturist fiction and Octavia Butler. Few know that I’ve ruminated on combining these together for several years now. I’ve decided to make that a reality.

I want to study literature’s affective capacity to explore ideas of justice outside of the carceral logic of the criminal legal system. I hope to understand the social barriers to adoption of such approaches and explore the generative potential of narrative story telling and science fiction in overcoming these barriers. In particular, I aim to apply this in collaboration with high school and college students to provide tools to support their building of the social infrastructure that encourages individuals and communities to re-imagine conflict response and harm reparation. I want to embrace the idea, termed by Walidah Imarisha, of “visionary fiction”. (Also everyone should read emergent strategy.)

This perhaps looks like grad school (of various possibilities/lenses), or getting involved with local organizations already doing a lot of this work, or building out something new with others. I’m taking my next 90 days to refine this and narrow in. If you’re in this space, have ideas around it, or are also interested, let me know. I would love to discuss it with you.

Lastly, I am working to succeed—succeed at my version of success. This is not the success of metrics, promotions, accolades. No, this is the success of being bold, taking risks, making change. This is caring. This is commitment to supporting the communities of which I am part. This is to stop worrying what success is. This is to know I haven’t succeeded, but I am committed to trying.

Personal insights you didn’t request *(and will probably disagree with but hey just maybe find some resonance with)*

Sometimes, not always, perhaps better if never, but depending on what calls you, you will feel the need to share what’s important to you. Is this something I should publish on my website for future employers to see and decide that they probably don’t want to hire me? Oh, almost certainly not. So, why, why share this, why risk it? Because… because I’m tired of a world, of an organization of our lives and labor, that is unable to see past ourselves, our own comfort, our individual-ness, our reduction to points on a yard stick. I share this because it’s more than a “truth” for me. It’s an invitation, a plea, a (perhaps desperate) hope that I’m not alone in wanting this, in desiring a better way of relating, a better future.

I know no other way to build community than to offer myself, to express vulnerability, to take a risk that what I have to share and offer will not only be un-reciprocated but weaponized against me. It is in this space of uncertainty and fear but also hope and longing that we model that which we so earnestly believe.

The world you want—whatever that is—is one you’re going to have to build and build it together with others. None of us can (nor, I believe, should) do it alone. We will have to offer ourselves, face that fear, weather rebuke, learn from our mistakes, but also experience that joyous feeling of building something that is more than the sum of its parts. Find and surround yourself with the people who will be there to build it with you.

As I close, I reflect on the past nearly seven years of working in corporate environments. I played the game. And I was good at it. I’m ready to change the game altogether.