It’s Valentines day and I am in a writing mood. This might just be a barf of thoughts.
People around me will often find I say, “Everything in life is temporary” often, and I still stand by it. Sometimes temporary can mean one hour, 48 months, or 40 years. Things come full stop at some point. For the past few years, I’ve lived what I now call a “portfolio career”. Instead of committing to one company, I’ve moved between projects, contracts, and markets. I’ve built, scaled, advised, and stepped away. Then pursuing the next variety, challenge, and impact rather than stability. It’s not that I didn’t want to commit to one project or company. In fact, I was working for one employer while operating in different companies and projects. But I am aware of the optics of non-committal.
What I didn’t expect in the past 3-4 years was how closely this mirrored my personal life, especially when it came to relationships.
Dating with an expiry
I feel like this sub title makes it sound like death. But it’s not. The thing with living in cities for six months here, a year or so there, I inevitably meet new people. Sometimes, I meet someone who feels significant. And yet, almost from the beginning, I kill the mood by being upfront about how much time I plan to be in the city. I let them know my lifestyle, my work, and the fact that we could be in an exclusive relationship but there’d be an expiration date. Because my time in that city isn’t permanent.
It’s not that I don’t care about them or the connection after my work term ends. It’s that I’ve been in long-distance relationships before, twice, and both times it was so trying that it couldn’t be maintained. The missed small events, conveniences of doing things together, sometimes the time zone strain, the promises that turned into frustrations. After the second long d ended, I decided I don’t want to ever go through it again. So instead, I’ve leaned into the moment: fully present while I’m there, fully aware it will end when I leave. Sounds callous, I know.
The price of my choice
On good days, it feels good to be honest. I don’t make commitments I know I can’t keep. I let the women I’m interested in know where I stand. It sounds cold but I haven’t figured out a better way to approach this. And I know that transparency doesn’t make things easier. But I have to be clear about my intentions rather than leave anyone with false hope. It’s how I respect the connection: if the commitment (although temporary) isn’t possible, I won’t pretend otherwise.
In the past few years, this approach has led to some incredible relationships that were rich. And of course, naturally on other days, I do feel like I’m protecting myself at the cost of something deeper. I have been fortunate enough to have been with women who were open to still being with me under these conditions. As a result I’m know what grounded, kindness, and growth feels like with someone. And walking away was never easy. Because what could it have been if we continued?
Is it worth it?
The trade-off is the same as in my career. A portfolio path gives me variety, experiences, and growth. But I give up stability, permanence, and the comfort of building one thing over the long haul. I get the highs of new markets, new problems, new wins but I don’t get the safety of a single, steady home base.
In love, the pattern is eerily similar. I’ve had the richness of different connections, cultures, and experiences. They’re meaningful moments and relationships that shaped me. But unlike my career, they’re not portfolios I can flex for my next endeavour.
I think what scares my family and friends is that I enjoy being alone. I’m not concerned if I do end up being alone forever. But I’m also not afraid to admit, there are moments it gets lonely when there’s no one.The quiet nights are nice, until I meet th next girl because that also means the “next goodbye.”
No takeaway
I’m not the type to regret my life decisions. I might think back and wonder but I don’t regret the choices I make. I know these choices have a cost and I’ll pay it. I focus more on the growth, perspective, and freedom as much as the loss: the possible missed chance to build something lasting with someone who might have mattered if I let them in.
Maybe one day, like in my career, I’ll find the right company, or in this case, the right person that makes me stop chasing variety and start building permanence.
The Unspoken Side of Leadership
March 15, 2025