Writing

On Legacy & B2B SaaS

2025-05-21

On Saturday, I sat around the TV with my partner and his family as we watched a tribute segment for Greg Millen before the hockey game. He was an NHL goaltender turned broadcaster, well known for things beyond my realm of knowledge. This got me thinking about what I've done with my life so far and where I'm heading - typical reflections when you hear about a distant passing. Prompted by the nationally televised memorial, I started thinking about these questions in the context of legacy.

As a kid, I had aspirations of doing something good with my life, dreaming of virtuous career paths like a teacher or the author of a really good book series. The capitalism bug got me and I believed an impactful job was synonymous with fulfillment and meaning. At some point though, the idea of devoting myself to a career in pursuit of fulfillment lost its appeal and I swung to the other end of the spectrum. I yearned for a completely inconsequential job where I could turn my brain off after 5 (or go home early without anyone noticing) and my career would be the least interesting thing about me when people met me. I pushed away ideas of career ambition and instead dreamt of building a rich personal life filled with friends and family I could be present for, hobbies I could take seriously. The mindset extended beyond work as I scoffed at notions of grind culture and pouring your all into a passion project. I wanted all of my passions and interests to exist outside of any type of work framework, so I spent little time examining what I enjoyed doing and what that implied when it came to my strengths and motivations.

I'm not sure why this switch happened some time in university where I entered with an above average level of self-confidence and eager to take advantage of every opportunity. My best guess is, over time, my fear of rejection and failure intensified and the stakes felt, and still feel, too high to emotionally invest in my future or the world at large. It's a stupid and obvious conclusion, but one I'm sure has become especially common these days. It's so easy to risk very little and just pick the things that make you the least unhappy. In my case, when I look back, I see that I was choosing opportunities that would give me a semblance of stability for the foreseeable future - opportunities where I knew exactly where I would be and what I would be doing for the next year. A lot of this was motivated by very valid reasons and fears but I still wish I had taken some risks anyway.

The ironic part is that in trying to reject societal values around work, I've ended up at the heart of Big Work itself: B2B SaaS. I guess it's what I wanted - to be a faceless cog in a machine simply along for the ride for better or for worse, indulging in trivial benefits like snacks at the office and getting to wake up seconds before my first meeting. From here, I could go anywhere, but it doesn't feel quite how I imagined. It sort of feels like I'm going nowhere at all. I could write a whole other piece on how this is normal, how my Girls rewatch is hitting me hard (read: "I have work, and then I have a dinner thing, and then I am busy trying to become who I am"), and how I'm catching onto the feeling lost in your 20s experience. I know that somehow and eventually, I'll be okay; I'll end up somewhere. I think the point I'm getting to is that I've realized I want to make sure I end up somewhere good. Somewhere that, when I die, I'll be content with laying a piece of my legacy.

My favourite quote, and one I try to carry with me each day, is "How we spend our days is, of course, how we spend our lives" by Annie Dillard. As I stand at the precipice of graduation and the great unknown, I'm thinking a lot about what my days (and by extension, my life) look like. If I were to die a year or two from now, what could I say my life amounted to based on the seeds I'm planting daily now? I feel both paralyzed and desperate to take action when the thought hits me, scared that all of the best opportunities with my name inscribed on them are passing me by. What if I missed my opportunity to start something good? What if the opportunity is now and I'm doing nothing about it? What if the opportunity is due to arrive next year and I've done nothing to prepare for it?

I used to think that the idea of "legacy" was reserved for people indisputably changing the world - leaders, innovators, change-makers. I certainly don't believe that impact can be accurately measured by scale or numbers. Legacy can mean a lot of things like being there for your family and friends and trying to be someone you like. Obviously, legacy isn't solely about career either. In fact, I believe work is only 1 tiny piece of the larger Legacy Puzzle. But as a 23 (going on 24) year old on her third internship, yearning for financial and career stability and taking a good hard look at life post-education, you can see why it's on my mind a lot. For now, my work-life has come to represent my life-life.

Here is what I know:

  • I want to contribute to a bigger picture. This could be in the form of a community or mission. I want to be a part of something that makes other people feel optimistic about the future.
  • I'm not someone aiming to change the whole world. Not because I don't think I can, but it just doesn't fill me with the sparkly feeling in my chest when I try to imagine it. I feel like I'm not supposed to admit that I don't want to start some revolution because it's what good and ambitious people should want to do. But if anything, the concept feels very detached and void of any tangible meaning to me.
  • I want to do more than bring my immediate friends and family joy. I want to leave an impression on people who don't know me at all and people who never will but feel the trickle-down effects of my efforts.
  • I want to be challenged. I want to spend hours and hours on a project, chase rabbit holes, practice a skill for hours just to feel like I know what I'm doing only a little bit but excited to learn even more. As much as I want passion to overtake me and act as the driving force, I also think there's something really beautiful about practicing discipline and commitment. I hope to have a bit of both.

What I gather from my reflections is that I want to dedicate my time to something real. To me, real falls somewhere in between playing the long game and instant gratification. It takes thought and intention, and produces tangible impact. Trying to change the world feels too detached in a similar way that only aiming to influence those around me does. Real can look like a lot of things: being part of an organization whose purpose and mission I believe works towards a meaningful cause, working in roles with responsibilities that satisfy my day-to-day cravings, or things as simple as reading a book that makes my brain feel a little bit bigger and taking my time to cook a meal for myself. All of these things, given our current conditions, feel like the closest ways to ground myself back to earth - to remind myself of what I'm doing here and why I choose to get up every morning. They encompass both the big picture and minutiae that make up Life, capital L. I say "given our current conditions" because modern work in itself is the farthest thing from grounding, but a girl's gotta cope somehow (I know that the rat race is only one of many paths, but most of the time I don't feel like I have a choice).

The rest are question marks. Maybe I'll spend the rest of my life trying to fill in the gaps, chasing new endeavors and people, planting seeds that will only come into full fruition when I'm on my death bed. I wish there was a guidebook on how to navigate your 20s (or just being a person on this earth in general) beyond reminders that "it's okay to not have it completely figured out yet" and "there's still time". When will I know that my legacy has been built, or at the very least, that the first brick has been laid?