I teared up getting off the train on my way home from Circle Day.
I'd spent the day around people who, like me, had built some part of their lives and careers around Squarespace.
And on the way home, I found myself reflecting. Not just on the day, but on all the years I'd spent Squarespacing.
Why am I still doing this?
Where does this brand loyalty come from?
It's almost embarrassing to admit.
It's not as if I have some special relationship with the company. And there are plenty of other platforms I could use to do the same things.
So it's not really about the technology.
And then I started remembering.
Sitting in my cubicle, spinning around in my chair, thinking, I need a portfolio for my videography business.
Building that portfolio on Squarespace.
Landing my first creative internship and having the people there be impressed with the website I'd built.
Looking at the possibility of leaving my job and thinking, I need to update my Squarespace.
Actually leaving my job and realizing I could make money building websites for other businesses.
Sitting on the toilet and getting the email that I'd been accepted into the Squarespace Specialist Directory.
Landing my first clients. Learning how to customize Squarespace templates. Figuring out what people needed and how to give it to them.
And eventually, coming out of depression and finding something I could build on.
I've told that part of the story before.
At a time when I felt like my life wasn't going anywhere, Squarespace gave me something to devote myself to. Something I was interested in, something I could get better at, and eventually, something people were willing to pay me for.
Over time, the work changed.
I went from building websites to selling customizations and plugins. From working with individual clients to creating products, sharing what I was learning, and helping other people build businesses around Squarespace.
And somewhere along the way, what started as a website builder became the foundation for much of my career as a creative entrepreneur.
Not because I planned it that way.
I just kept following the opportunities that presented themselves.
Why haven't I moved on?
That's the question I keep coming back to.
Why am I still here?
Why have I spent so many years working within this particular ecosystem when there are so many other things I could be doing?
Well, I have done other things.
Plenty of them.
And I'll probably do plenty more.
But I'd be lying if I said Squarespace hasn't played a pivotal role in my life.
Thinking about it now, I realize how many different versions of myself have passed through this platform.
The guy trying to become a videographer.
The guy trying to leave his job.
The guy figuring out how to make money working for himself.
The guy learning to sell products instead of his time.
The guy trying to find his way out of depression.
And the guy who, all these years later, is still finding new things to explore, new problems to solve, and new people to connect with.
Squarespace has been there through all of it.
Not because the software never frustrated me. It certainly has.
Not because there weren't better tools for particular jobs.
And not because I think everyone should be using Squarespace.
I know it's just a website builder.
But it's also the website builder I happened to find at a time in my life when I needed somewhere to go.
And I kept finding new opportunities from there.
So maybe that's what I was feeling when I got off that train.
I'm not particularly attached to the technology.
I'm sentimental about what it made possible in my life.
And after all these years, I'm still curious about what I might be able to build next.
