I think I’m good at building things. I don’t think I’m good at marketing them. I’m sure, at least, that I’m not passionate about that part—which makes it really hard to be good at it.
After we sold DoneDone in September 2024, the product I’ve worked exclusively on since 2018, I drove down the road of solo-software development. I had built a product in a few months called DnsDigest, but then came the marketing part.
Of course, instead of marketing it, I decided to start on another.
I was very excited about the second product, but as I was envisioning the road ahead of getting this to market, and the urgency to start making money again (my exit from DoneDone was not a windfall, more a slight breeze-fall), I started to lose steam.
That was early March, when a position opened up at 37signals titled “Web App Product Designer”.
When I got the email and read the description, I found my next move.
In truth, I’ve never considered myself a designer. I like building all of a thing. But here was a chance to concentrate on the design part while still having my hands in front-end code.
I was ready to trade in breadth for focus and depth.
A designer who builds. Working with a team of self-managers. Autonomy and trust. A chance to focus on one part of the stack. To not have to market! And a very good salary. All the things I wanted and needed right then.
Plus, it’s 37signals.
If you’re around my age (46) and began your professional career on the web, 37signals is that underground band you felt cool listening to before everyone else did.
They’re a clear-cut success now, with a handful of “hits”. A few decades in, they still have a fervent following. And like all bands that reach a certain level of success, they have their share of detractors.
And I love all of this about them. That they continue to do what they believe despite what popular-thinking-of-the-day may tell them. That they are so gut-driven.
Now, here was this position that I felt fit me so well—the right time and place to actually join the band I grew up listening to.
So for three weeks in March, I dropped the project I was working on to focus all of my available time and effort on my application.
I gave it everything. Curated my best work. Went high-level and in-the-weeds. Noodled over every word. When I submitted my pitch a few hours before the deadline, I felt that kind of great exhaustion that comes with making something you’re proud of and having nothing left to give.
All that work paid off. In a sea of nearly 1,500 applicants, I got through two rounds of interviews and was given a “take-home” assignment—something they give only to a few applicants. Then, another interview after that.
An observation: The one thing I instantly noticed about their style of interview is the degree to which they sit back and want to listen to you talk, uninterrupted. There’s a comforting slowness to the pace of the discussion. So very them!
In the end, I got painfully close. But I fell just short.
For my final project, they wanted to see a bit more range in design. And as I looked back on my work, I can’t disagree. I played it a bit conservatively, and frankly, designing novel things requires a muscle I need to exercise more than I have.
But I know I have it in me. Maybe this experience will be the catalyst to start working that part a lot more.
But damn—
I really wanted this job. As I got closer to the finish line, when long shot morphed into very real possibility, the want grew too.
It took me a couple weeks to pick myself up.
Even though I didn’t get the job, I got to make a few things and, perhaps, discovered what I really want to do next.
Here’s the custom portfolio I built for the application. I spent a lot of time on it because I wanted the job, of course. But as I kept iterating the thing, it became something else. An opportunity to reflect on my past work. A pause in my life to curate my career. A reflection on what brings me satisfaction.
This was my cover letter. But it became more than a cover letter to me. It was almost a letter to myself. Why do I want this? Do I even want this? It evolved into my own Jerry Maguire mission statement. (That’s a movie from 1996 that someone my age will still quote from as if it came out last year).
Note: I think we should throw away the term “cover letter”, which alludes to the overly effusive, boilerplate letter that you’d put over your paper resume back in the day. It’s really a “personal pitch”. An explanation of why you want this particular job.
I mention this because the importance 37signals places on a cover letter briefly became a hot topic again. Like any programmer would attest, I think part of the problem is the naming.
I love building things on the internet. In the past, I spent my hours on all of it. Soup-to-nuts as they say.
But with the progress and uncertainty AI brings, the toll that “soup-to-nuts” building takes, and simply having less stretches of free time to do things (I have two kids, the primary homemaker, and we live in a multi-generational home where I’m often helping out both young and less young), I need to create a role that fits my reality of today with my still-strong desire to build.
I want to keep making things. Maybe with a focus on design. Perhaps designing more things, less deeply. Or maybe as deeply, with a new set of tools.
I don’t know what this all looks like just yet. I’ve gone a couple of directions since last year that have narrowed the spectrum a bit.
I’ll keep going and find out.