travels.of.tara

July 10, 2026

Transitions can be hard, and this one has stretched out for so many months that I’ve been itching to get a move on already. I gave too much notice at work: about 11 months when I first breached that I was thinking about it to my supervisor, 6 months confirming to her that I’d be doing it, 5 months telling my boss, and 3-4 months telling my coworkers and colleagues. It’s been a lot of emotions I can only now describe as senioritis.

Of course, the process wasn’t that neat. It’s been a messy, complex mish-mosh signified by avoiding confrontation and uncertainty around the value of my work. Now, as I’m just two weeks away from my last day and as my to-do list trickles down to organizing files and saving documents, I’m preparing to actually reflect on the last eight years.

I never intended to stay at my job for eight years. After leaving a stressful but meaningful job working for a local elected official for four years, I told myself I’d take the next two years to chill out at a nonprofit, working fewer hours and making a higher salary, before pushing myself back into government. Everything was going according to plan. My coworkers were kind and drama-free, I began to pursue hobbies, and I was on a two-year lobby ban so I couldn’t even legally do some of my job requirements. Still, after a while I started to get bored and feel underutilized, and I recall hitting a breaking point that involved crying to a coworker in a Starbucks and realizing that it was probably time to start looking. It was February 2020.

So, yeah. Covid changed everything. I think our society has chosen not to reflect too much on that time, burying a long, mass trauma. I struggle with it even now. I remember feeling very strongly that I didn’t want to make any major life decisions or changes, settling into a comfort zone that was so uncomfortable. Cleaning out my office computer files the other day I found a screenshot of a staff meeting where we were all in beach theme: virtual backgrounds, cocktails, plants, and sunglasses. We had truly lost our minds. 

And somewhere along the way, I got two title bumps and a couple of raises. I started working on some new campaigns that seemed to interest and engage me. Office culture became hybrid and flexible and that really worked for me. I accrued a lot of vacation time and got to travel often. Sometimes I would think about leaving again, but the frustrations were few and far between, and I loved the healthy work-life balance I had struck. So I stayed.

As a teenager and into college, I always said that my greatest nightmare was working the same job for my entire career, as my father had done as a music teacher in NYC public schools. I am prone to boredom and I love learning and working through challenges. Retirement security doesn’t exist the way it did in my dad’s time, so it makes sense that I’d prioritize enjoying my job through frequent change over job security.

As the years ticked on into the 2020s, I thought of this from time to time. Rather than rationalize that it was ok to change the plan if things were working, it only served to terrify me that I was falling into a rut of too much routine and brainrot.

But as the comfort zone is prone to do, it took a lot to shake myself out of it. In 2023, several close friends were very sick, and I once again coped with adversity by clinging to the same-ness. In 2024, I felt good again, and let work be easy while focusing on enjoying my personal life. And then the first half of 2025 happened, a really hard time that I can now reflect on with such gratitude.

So many bad things converged in a short amount of time. Much of it had to do with the beginning of Trump’s second term. Everyone in my circle was miserable, coping with the many horrible things happening in our country. At the same time, my supervisor went on parental leave, leaving me to cover much of her job. While the workload itself wasn’t a big problem, I found myself on the frontlines of dealing with a nonprofit constituency that was in a chaotic panic (rightfully so) and taking it out on us, harshly criticizing the way we did our work. For the first time since the pandemic my coworkers were all stressed and our work began to feel a bit toxic. And as this chaos reigned, I simultaneously fell into bouts of boredom with the work, sighing that it was the same year after year with few positive results. I fell into a despair that advocacy doesn’t really matter, an existential bug that occasionally makes its way to the surface. Another word for all this might have been burnout.

Nothing like a bad time to make you start thinking about a change. And that’s what happened. I went on a solo hiking trip to Arizona that April, mid-stress, that I now am comfortable calling life-changing. I let myself spend hours thinking and dreaming and ideating on what my future could look like. It was the first time I entertained the possibility of taking some time away to seriously travel. I even wrote out my first budget to see what it might take. I thought about other career paths, combining my interests into something that could help others while making me feel more fulfilled. I thought about writing and sabbaticals. I thought about love and risks. I just thought. I felt better.

I got through the rest of the work busy season in June. That summer I took a romantic risk that didn’t pan out, and it shattered me for a little while. I wrote a lot through it all and kept dreaming, not content to let April’s momentum die. For I was in my risk-taking era.

One year ago, I went to the Adirondacks with my family, as I do every year. I took a notebook on a short hike, one I’ve done many times before. I found an isolated spot on a rock hovering over a wide creek, and found myself writing out a script that I planned to present to my supervisor when I got back. The content was messy; the idea was still messy. I wanted to do something travel related on a timeline that would begin the next summer, and I wanted to see what might be possible. Could I keep my job and take a sabbatical? Work remotely out of the country for a while? Go part-time? There was no precedent for any of these things, so I knew it wouldn’t be an easy answer. But the newly bold risk-taker in me included an ultimatum in that first script: I am doing this. If I can’t make it work with keeping my job, then I will leave.

My supervisor is wonderful; we get each other’s work styles and work together very well. She has always said to me that if I ever plan to leave, give her lots of notice so they can do transition planning. And the conversation went well. She wasn’t the one who could provide answers, but she gave me some new ideas, thoughts on how our executive director would take things, and other things to think about.

We checked in a few more times over the next couple of months. My plan was evolving. I bought a one-way plane ticket to Greece for late July, not knowing how long I would stay there or what that might turn into. I thought about where else I might go in the world. I decided to take a four-week trip over the holidays to Costa Rica (with a combination of office closure, working remotely, and a few vacation days), using it as a test case to see how I did with long-travel and giving myself until I got back to make any final decisions. Unsurprisingly it was great, and on my last day in San Jose I was journaling in my quiet hotel courtyard and found myself saying yes, duh, obviously I am doing this.

At that point, the plan was a 5-month trip with no work, focused on destinations that were too far away to reasonably work remotely due to the time difference. Ideally, work would stop paying me except for my health insurance, and then let me return around the New Year when I would jump right back into busy season. I would have a very similar job function, though perhaps with some more flexibility around travel in the non-busy season. I recognized that the plan was still a little messy, but I had a plan and I was sticking to it.

Around that time I also met with my financial advisor (my cousin Joe) who showed me how relatively easy it would be to do this without ruining my retirement savings, and that gave me the confidence to move ahead. I’m firmly of the belief that money can buy happiness. One of my motivations for a work break is around escaping the ills of modern capitalism that throws you into a perpetual cycle of hard work for pay as your primary motivator. And yet, I’m acutely aware of how I’m only able to do this because of capitalism: because of my salary that paid me what I’m worth, because of the raises I advocated for, and because of the lifestyle choices I’ve made that prioritize travel over daily comforts like having enough storage space or owning a car.

I told my supervisor the plan in January, and we made a plan around when to tell our boss. It ended up happening spur of the moment one evening in early February, just after a big lobby day I had helped plan and when she seemed to be in a good mood. The conversation was friendly, though she was surprised. I talked about how common sabbaticals are, and what my job might look like if and when I returned. She said there was no precedent for anything like this, and she’d have to take some time to figure it out; and that we had time. It ended in a hug.

About a month later, after I’d let things settle, I was ready for another check in. I asked my supervisor about it, and she said something to the effect of, “I understand how you said the conversation went, but our boss’s understanding of the conversation was different, and she understood things to mean that you are leaving.”

Um, ok. Clearly there was some avoidance and fear of confrontation going on. This was a bit of a bombshell for me, because as much as I was willing to risk my job to do this, I really thought they would make it work for me. Eight years is a long time to give up on someone. It felt a little like I was being fired, even though the rational side of myself knew better.

But on the other hand, I really hate uncertainty. And now that was gone. I had a plan! In late July I would leave my job in order to travel. Wow! I couldn’t believe it, I was going to be a backpacker cliché, sailing off into the sunset to find myself. Or something like that. And perhaps, it was a gift, giving me a push to break free of the comfort zone and boredom that I had come to resent. It took a long time to process.  

I worked out more logistics with work, the most pressing being around health insurance, which I would be losing come August 1. I figured out a travel health insurance plan, got a bunch of vaccinations, and over the next few months did tons of preventative and routine doctor visits while I still had insurance (some which turned into bigger headaches and a lot of money: American health care is a huge scam). All the logistics of prepping for this work break have become time-consuming and stressful, as well as distracting from dealing with the deep emotions of transition.

Two other coworkers in my department left this month, one to go to law school and one to move back to her family in another country. Our final goodbye lunch was lovely and sad, and I’m now finally starting to let go of the logistics and lean into the emotional side of things. A lot of people have been saying really nice things about me lately, and I’ve had some nice meals and drinks with people I’ve loved working with. I know that I’ll miss them, but I don’t think that I’ll miss the work. I really don’t know what I’ll miss. Perhaps the structure; perhaps the mission statement and knowing I spend most of my waking hours trying to make New York a better place, even if it’s usually in vain. I also don’t know what I’ll want to do when I get back. While uncertainty is scary, I’m truthfully more excited about it than anything else.

I’m currently in the Adirondacks with my parents, squeezing in a long weekend of spending time with them and relaxing before the big transition. It’s a place where things slow down, and today I find that words can finally spill out of me. Ironically it’s on a work day, a summer Friday where the only work I did was organizing a final list of who to contact to tell them I’m leaving.

These days, I find myself vacillating between pretending I’m already an unemployed lady of leisure and clinging to my last vestiges of structure. So in what may or may not be a coincidence, the clock has struck 2, and the work day is officially over. I’m heading to the lake.