A RETROSPECTIVE
The Crossroads: Reflections on Change and Growth
The year was 2019. I was in a stable job at a big insurance company, building and managing an app with a small team in their marketing department. I was a product manager and had been there for 2.5 years. I wasn’t making the most money I’d ever earned, but the job was fairly low stress, and as it needed to track the near-real-time location of our tow trucks when someone requested a service (similar to an app like DoorDash).
Why am I explaining all this? Well, 2019 was the year COVID-19 hit, disrupting my life and the lives of countless others across the world. The reason I’m writing this is because I found myself at a crossroads. I was pulled out of my normal, everyday decision-making routine and forced to make some really hard choices that would change my life forever. I want to share this story because, with a new president entering office in a week, I feel like I’m at another crossroads. Companies I once loved are turning sour and entering what we like to call in our house their “evil villain era.”
Anyway, I digress. This is not going to be a political post, but rather an exploration of what we do when dramatic shifts occur and how to manage them.
Rewinding to 2019: The Start of Remote Work
Let’s rewind a bit. I was in this job, and by April 2020, we were all working remotely. I began to ask myself: What if I don’t go back to an office for a year—or even two years? Would I be able to sustain this? What new habits would I need to form? What modifications to my home setup would I need to make? Thankfully, I worked with a team that was already skilled at remote work, and they were pros at navigating these challenges.
I started to adjust my at-home setup and routines. I also began to reflect on what I truly wanted out of my work. If you strip away the in-person interactions of office life, all that remains is the work itself. So the work has to be that much more important and enjoyable, I thought to myself. This was a huge shift for me. I realized I liked the people at my company more than I liked the work, and this realization made me start looking around for new opportunities.
That’s when I found an incredible mental health startup. YES! I saw that mental health in this country was deteriorating rapidly—mine included—and that more energy was needed to help people. This company specifically focused on providing access to mental health benefits in remote areas of the U.S., particularly in Texas, through a government contract. Their mission really resonated with me, and I wanted to be part of it. So, I left my steady job to join this tiny startup, which consisted of just seven people.
Jumping into Startup Life
Now, I was at this startup, reporting directly to the CEO. As is typical in these situations, there wasn’t enough time or people to get everything done. It was an extremely ambitious project, and I was dropped right into the thick of it. I was excited, but what I missed during the interview process was the chance to meet the team in person. I only did Zoom calls, and it’s hard to get a real feel for people or culture through video.
I remember the old days when you’d go into the office for interviews and get an instant sense of the company’s vibe. That’s lost now, and we’re forced to guess how it might be or rely on online reviews, which are often unhelpful for small startups with limited visibility.
To back up a bit, I took a job where I hadn’t met anyone in person, was dropped into a very challenging situation, and had to figure it out on my own. Needless to say, it didn’t work out. My biggest takeaway from this experience? (This might be a bit controversial.) Don’t take jobs where you report directly to the CEO. It’s not an attack on CEOs, but in my experience, they rarely have the time to manage you properly because they’re too busy running the entire company. I also like a bit more structure, and CEOs generally won’t provide that. You’ll end up flying by the seat of your pants. As someone once told me, “You’re going to fly really close to the sun,” and if you don’t have the tenacity CEOs do, you will get burned.
Lessons Learned
Lesson one: Don’t take roles where you report directly to the CEO unless you thrive in a highly unstructured environment.
Lesson two: Government and medical contracts are extremely hard. The amount of technology and compliance required to manage medical records is no joke. You need a team that understands audits, compliance training, and robust infrastructure to ensure nothing jeopardizes audits or change management. A team of seven people should have been a red flag to me, but since I wasn’t familiar with the space, I didn’t notice it initially.
Reassessing Priorities
I wanted to revisit the main point I mentioned earlier: my mission at the beginning of all this was to work for a company solving interesting problems. That box was checked—I loved the work. But what I missed was compatibility with the people. When you work remotely, team compatibility becomes crucial because you rely on communication methods that can be stressful (dopamine-driven) rather than connection-focused (oxytocin-driven, like in-person interactions). This makes compatibility even more important.
One big takeaway here is that if I join another small startup, I need to meet my manager and some of the team in person before accepting the job. Compatibility is non-negotiable.
The Metaverse Era
That brings us to the next phase: my first stint of not working. This happened after four months at the startup. Shit happens—it’s okay. There was no severance since we mutually agreed it wasn’t a good fit (though I’m not sure if that means I was fired or I quit, as they did offer me another position that I declined).
Anyway, that leads us to Chapter 2: The Metaverse Era. Honestly, sometimes I feel like parts of my career could be an episode of Silicon Valley (the HBO series). My friend was working at an avatar company in LA, and I ended up joining them. These were first-time founders, incredibly ambitious, and focused on building an avatar ecosystem similar to Ready Player One. They had celebrity partnerships, an app, a website, and a big dream.
This team grew at a blistering pace. They leaned into digital expression through relentless creativity, enabling authentic expression among younger audiences. It was an exciting, innovative environment, and I felt like I’d found my people. Many of them were misfits, just like me. Most had dropped out of school, and I really vibed with that energy.
But there was one thing I hadn’t anticipated: the company pivoted into the crypto web3 space without me realizing it. Initially, it was pitched as a metaverse company, but by the time I joined, we were selling NFTs. This was 2020, during the NFT boom, and we did well—so well that Bob Iger, Disney’s CEO, invested and joined our board.
Despite the success, my career growth hit a ceiling. As the company scaled, leadership brought in big-name VPs with Fortune 500 and Ivy League credentials instead of promoting internally. I saw the writing on the wall. I needed upward mobility, so I moved to a game company working on web3 tech, hoping for better opportunities.
Takeaway
The Metaverse Era taught me a lot about aligning personal growth with a company’s direction. While the creativity and energy of the team were inspiring, the unexpected pivot to NFTs and the lack of internal promotion opportunities made it clear that the company’s growth trajectory didn’t match my own career goals.
This phase reinforced the importance of understanding not just a company’s current mission, but also its future direction. It’s crucial to ask questions during the hiring process and to evaluate whether there’s room for you to grow within the organization as it evolves. Sometimes, no matter how exciting a company seems, it’s okay to move on when your paths no longer align.
Back in Gaming
Here I was, back in gaming, publishing games for brands like the NFL. It seemed like a perfect fit, right? Just wait.
I ended up at a huge startup that felt more like a giant corporation than a startup. It had finance reviews, roadmap meetings, a massive data team, and dozens of product managers (I was the only PM at my last two companies). It was run by ex-AAA studio GMs, which is why it felt so big.
The team was talented, and the offer was generous, but the company grew too fast. The market shifted, and layoffs came. I knew I had to stay for at least two years to avoid making my resume look shaky, but sadly, I was back on the job market after 18 months.
Lesson learned: even great companies can falter under rapid growth. When you see red flags like unchecked expansion, pay attention—even if the offer is tempting.
Takeaway
The lesson here is that even when things look perfect on the surface, unchecked growth can destabilize even the most promising environments. While I loved the team and the work, I ignored the warning signs of rapid expansion and over-hiring. I learned to pay closer attention to red flags during the interview process and trust my instincts about whether a company’s growth is sustainable. When you see cracks in the foundation, it’s often better to step back and reassess than to stay and hope for the best.
Into the Crypto Abyss
Next up: the real crypto company experience. This was exactly what I imagined crypto would be—engineers who didn’t reveal their names or faces on camera. I never got used to that. I’m a people person, and it felt impersonal to work with faceless colleagues.
That said, the founders and CTO were fantastic. I met them in person at GDC (Game Developers Conference), and their intentions seemed genuine. Crypto companies often get a bad rap, but this one had solid tech and a great team. The problem was timing and fit. After they acquired another startup, the CEO of that startup took over most of the product responsibilities, and my role became redundant.
Another challenge was their culture: no meetings, all asynchronous, with very lightweight agile practices. It just wasn’t my style.
Takeaway
Sometimes, even with good intentions, things just don’t work out. The timing wasn’t right, and the culture wasn’t a fit for me. What I learned is that no matter how strong the team or the tech is, you have to consider whether the operating model and environment align with your needs. It’s okay to acknowledge when something isn’t working and move on with no hard feelings—sometimes, it really is just bad luck.
The Present: Stillness and Simplicity
And now, here we are. Over the last three months, I’ve embraced stillness. I recently read Stillness Is the Key, and it reshaped my perspective. I learned the value of doing nothing—not doom-scrolling, but truly sitting quietly, observing my thoughts.
I started running without headphones, just listening to my footsteps for hours. It’s been a meditative experience. This phase of my life is about curiosity, stillness, and peace—accepting where I am while removing things that don’t align with my goals.
For example, I’ve drastically reduced my social media use. I now only use YouTube, TikTok, and Strava. I stopped checking LinkedIn, Instagram, and Facebook altogether. This has cleared my headspace and helped me align my actions with my values.
Building with My Hands
This is the era of IRL for me. I’ve been focusing on real-life experiences—paying for moments, going on trips, and building things with my hands. Some tech investors say, “bits, not atoms,” but I say the opposite. Building with your hands is deeply fulfilling. Whether it’s pottery, carpentry, or painting, anything you can look at and say, “I made that,” brings immense joy.
I’ve also prioritized in-person relationships. Compliment someone face-to-face, make them smile, and share something personal. My therapist told me when I was 10, “You don’t let people in. You need to share your feelings.” That advice still resonates, and writing these blogs is part of my mission to connect more deeply with others.
Final Reflections
As I look back on these transformative years, I realize that managing dramatic shifts requires both adaptability and introspection. It’s about asking yourself tough questions, embracing the unknown, and being willing to make hard decisions. Change can be uncomfortable, but it also creates opportunities for growth and clarity. By staying aligned with your values and learning from each experience, you can navigate even the most challenging crossroads.
The last four years have been transformative. I hope my story inspires you to reflect on your own journey. Consider what you can add or remove from your life to grow into a better version of yourself. Let’s embrace change, build meaningful relationships, and focus on what truly matters.
