Sharing some big news as I turn 28 🥳

Nothing quite like ringing in a new year with a big career change

This week’s content is going to be a little more sentimental than usual. Some of you may have picked up on on this over the past month, but tomorrow is my last day at TestBox. 

Two months ago when I shared this news with the TestBox team, I thought briefly that perhaps I’ve gotten older and wiser and therefore am better at letting go, and maybe this would be an easy transition…

How wrong I was. 

Tomorrow brings the TestBox chapter of my life to a close. Everyone always talks about the startup journey and how awesome it is because you learn so much and make so many friends along the way. Even though I never doubted for a moment that this would be my experience as well, I am still in awe at the depth of relationships that I’ve built. I never expected to experience such a wide range of emotions at work: truly the highest of highs and the lowest of lows. I’ve found friends with whom I’ve laughed, learned, cried, eaten, and traveled with, and I couldn’t feel luckier about this.

I joined TestBox in February of 2021 when the world looked very different.

We were still deep in the pandemic and everything was happening on a fully remote basis. Sam and I had our first conversation about TestBox sitting ten feet apart from each other in his living room, with masks on for an entire three hours. I think everyone has their new “coming of age” story for how they emerged from the pandemic, and for me, TestBox is always going to be a foundational part of my emergence from lockdown. It was with our team that we navigated the in-between of half-masking, testing daily and taking lots of precautions when we got together in person and then eventually made our transition to the new normal that is life in 2023. 

Along the way, I have also learned a lot about myself and pondered the role of work in my life.

In the past 2.5 years, as I’ve written about before, I’ve worn a lot of different hats. I came into this role not knowing what to expect and honestly, each chapter of TestBox has brought with it many surprises. 

Prior to TestBox, I had very clear boundaries on work. It was very easy to leave a bad day at work – for me, working in client services made this particularly doable. It was easy to separate out my value from a frustrated client’s judgment, because I could be confident that my work was high quality even if it didn’t make a client happy (generally from my own team’s validation). If my team was unhappy with my work, it was fairly straightforward to get feedback from them and iterate on what I was doing until it got better. 

When I started at TestBox, we were building a team from scratch. We were just seven people on my first day. We’re now almost twenty. I built a lot of our processes and along the way, defined certain pillars of our team culture: how we collaborated, how we prioritized and problem solved, and how we interacted with each other as people. I quickly learned not just about the logistics of running a company and keeping people employed, but also the emotional side of such a big responsibility.

Ten months in, I planned our first team onsite ever. It was pretty amazing to finally meet most of the team in person. I had planned a jam packed week with lots of meetings to make the most of our time together as well as fun dinners and evening activities to get to know each other better. Halfway through the week, I got feedback that the team was finding the schedule overwhelming and too intense. They wanted more time to decompress. I was so upset to get this feedback about something I’d spent so much time and energy planning. When I received the feedback scores for the onsite afterwards, I was in tears at how they weren’t all 5 out of 5s. (I know, cry me a river.) 

I share this to illustrate a pivotal moment for myself. I learned in this moment that the work I was doing at TestBox wasn’t just work anymore. I was pouring myself into the things I was planning and creating and it meant I was unlocking new levels of quality and thoughtfulness and detail in my output. On the flip side, it also meant I was now feeling more defined by my work than ever before. When things didn’t go well, I took it a lot more personally. I didn’t really know how to handle this at the start. 

Over the next few months, I began to learn how to draw some boundaries for myself to make the job more sustainable. I also identified specific areas of my work where I was going to conscientiously lean into being 150% myself and give it my all. I chose the domains where doing that was going to differentially improve my output (e.g. suggesting that we write each member of the team cards for our company anniversary, investing in our team onsite planning each quarter, and co-creating team structures with the rest of the exec team to find everyone the best place on the team for them). In the spirit of this blog/newsletter, I’m going to take a moment to celebrate myself – I learned to use my magic touch (from bringing my full self into the work) where it was the most impactful.

As I grappled with having a job where being me was what made me good at it (which felt very different from what made me a “good” management consultant), I really questioned what role I wanted work to have in my life. Prior to TestBox, I was someone who was proud of my work but also didn’t define my whole existence through my career. Somehow, when I talked about TestBox to others, it felt more and more like an integral part of who I was. I wanted to tell them about TestBox and what I was doing, because it felt important to my story as me. 

This was a very new feeling. It was scary. 

I was pretty sure before this that I was someone who really saw work as a means to an end – to finance the life I wanted to live. Suddenly, my work seemed to be so much more than just that. I started to ponder all sorts of crazy questions like, “Should I be a career woman? I never saw myself doing that before” and “Have I been bodysnatched? I didn’t think I could love working this much.” 

There were many late nights where I’d lie there awake, wondering what this meant for me and the wonderful life plan I’d made for myself. Over time, I’ve wavered back and forth on what I want the role of my work to be in my life. On the one hand, I will be the first to admit that I’ve never derived as much satisfaction and fulfillment from work as I did in the best moments at TestBox. It exceeded my expectations by a lot. On the other hand, this also came at a hefty cost – when things didn’t go well, the outside-of-work-hours were filled with a lot of emotion and weight. It followed me in ways I wish it didn’t. On the whole, I struggled with finding the right balance of doing a good job and making it sustainable for myself in the long term. 

I wish I could say that as I sit here writing this, listening to my breakup song (yes, I have a breakup song for leaving this job), I still don’t have the answer for what I want the role of my work to be in my life. 

As it stands, I have no formal plans beyond my last day of work tomorrow. 

I turn 28 today and I’m excited to be 28, mildly certain of myself and who I am and what I stand for, and almost (f)unemployed!!! I’m looking forward to living my life as just me for a while and seeing where it goes. I’m calling this the start of my adult gap year.

As I get into my adult gap year (or maybe half year, who knows!) I’m going to let myself get bored, find new hobbies, maybe pick up a few side gigs, and generally just be myself, whoever that is. In the near future, I’m looking forward to subscribing to Netflix again and seeing how many hours I can watch before I can’t stand it anymore, taking spontaneous trips (I sort of want to go to the airport and ask a ticket agent “what’s the cheapest round trip you’ve got right now?” and go wherever that takes me), maybe fostering guide dog puppies, and sitting in cafes and reading trashy novels. Because I do enjoy keeping busy, I’m also making myself available for any startups that may be looking for a Fractional COO. (Please feel free to reach out if you or someone you know is looking for some strategic and/or operational support.)

Annnnd maybe after a while, I’ll start to ponder big life questions such as what I want the role of my work to be in my life. I’ll be sharing revelations and musings here as usual. For those of you who’ve grown used to the work-focused content, I hope you’re ready for the ride that we’re going on over the next while. 

Tl;dr

Tomorrow is my last day at TestBox after 2.5 years. It’s a bittersweet moment and I’m grateful for everything I learned. I’m looking forward to taking time to figure out what I want to do next. I’ll be sharing my musings on this journey here.