What I did on my summer vacation
Reflections & learnings from my time on sabbatical
In July 2026, I left Chegg after nearly 6 years. It was something I initiated, to which they agreed, and we planned my departure for several months. As I entered 2026, I was unsure of what I wanted from the future time I might spend there, while feeling good about the work I’d done to date. But I was also, increasingly clearly, burned out. This wasn’t so much a Chegg thing as it was that I’d worked nonstop my entire career without a break longer than 22 consecutive days.
Of course, knowing for months when my last day would be, and being the person who loves a plan, I made lots of plans. I made macro plans for what I wanted each month, based on what I expected would be 6 months off before I started a new job. I made financial plans for what we could afford before I needed to find a new job. I also planned what I thought my new “free day” would look like, hour by hour.
As they say, LOL.
I guess some of it worked out and some of it didn’t. I’m now about 3.5 months in, and I have learned so much about myself and my ideas. I’ve also learned and reflected a lot about how I thought about and planned this time.
One thing I knew I’d spend time on was forming my own opinions about AI. I expected this would be more of a philosophical undertaking, reading, watching, and talking to other people. And I’ve done that. But I’ve also done a lot of playing around. So much more than I expected. I’ve made random apps on the fly for nearly every stray thought that went through my head. It’s been fun, and you can see more about those under the Projects link above.
And I built one for sabbatical planning. Well, maybe not plaaannning so much as pre-reflecting? Putting it on paper. As I’ve come back from being really disconnected and talked to people I worked with or alongside, I caught up with them and told them about my experience these past few months, and I heard it over and over: I wish I could do what you’ve done. I daydream about that much time off.
A year ago, I was in that same place - I wished I could take a bunch of time off too. And now, I have. So I’ve tried to take what I’ve learned and build something that might make the undecided (or the forced-into- it works for layoffs too) take a concrete step or two. Maybe go all the way to taking their daydream seriously.
Two Key Lessons I Learned & Built into Hiatus
Of course I had a plan. Read more, exercise, get outside, find some creative projects, build better habits. Basically, become a healthier, more interesting person. I managed to turn my own break into a project with deliverables, which says a lot. And then I learned these two things, in this order.
1. Wherever you go, there you are.
Removing the demands of a full-time job did not turn me into someone with a different set of habits. I’m still me. More rested, less frayed, but the same person. The overachiever’s big list of Things I Must Do to prove this time was worth it was one of the first things to go. I’ve never felt better about failing to deliver on a project.
What surprised me was how quickly I naturally reconnected with the things I care about outside work. No grand self-discovery required, no big list, just what drew my curiosity and attention in the moment. That person was there all along. She had just lost the ability to focus on things that mattered only to her, without reporting results to anyone else.
2. I did it once; I can do it again.
This is the bigger one. Throughout my career, I went straight from one job to the next, and once I was in a role, I felt enormously responsible for making it work. Fix things, deliver, prove myself, rinse and repeat with each new title, role, or project. Even when I wasn’t especially happy. I like to think I really like to win, but in hindsight, I was probably more scared of losing. Either way, it costs.
Stepping away and seeing that everything was okay changed how I think about what comes next. I don’t need to find the perfect job or commit to something forever. I can take on a good challenge with good people, and if it stops being the right fit, I can choose something else.
I know I’m lucky to have had the safety net to step away, and that’s a big part of why nothing fell apart. Not everyone gets that option. But for me, the cost of leaving turned out to be lower than I assumed. It also makes me more willing to go all in on the right thing, because I’m choosing it more freely each day rather than being tethered to it.
My husband said something during this break that I keep coming back to: “You don’t have to do that much of a good job all the time.”
I’m still ambitious. I’m still - probably more - curious. I still want to do work that matters. I just don’t have to prove it every minute of every day.
What I actually did during the first two months I was off, before I started app-building madness.
Wrote a collection of short stories and experimented with zines, a format that never gets old, even when we do. In a world of AI, there’s something increasingly meaningful about work that is local, personal, printed, and made by hand.
Spent whole afternoons shelf-reading at my local library. (Ask your nearest librarian. It’s a thing.) I also discovered how many people I know have books there with a “Local Author” label.
Swam in a lake until I pruned. Yes, I went to the cottage and had this view for a few days. I do my best thinking while floating.
Read a genuinely unhinged stack of books. (I didn’t say I finished them.)
Watched too much of the World Cup. But didn’t we all?
Spent a month with family in my Canadian hometown. It turns out you can go home again, and the bars are much better than you remembered.
Built out our small art collection and solved an art mystery, which I will not be elaborating on at this time. Art feels more important to me than ever.