Jeff Keen

It’s been a while since your last interview, and I know you’ve been busy, but I wanted to check in and see how things have been going for you?

It’s kind of none of your business?

You’re the one who agreed to this interview, and this is your website.

I thought you were just being nice and wanted to check in on me.

No, I’m farming you for content.

Hold on, are we already rolling? I didn’t know we were recording yet.

Yeah we’ve been recording this whole time.

Good to see you, Adam! Thrilled to be here for another check in.

You made it sound like in your 2022 interview that you were just around the corner from recording an album, officially making your community radio side project Dubbletrack a primary source of income, and were looking for a full time job that was doing something more manager-y? How did that all go?

Well… I did temporarily get a full time job! True to my word. It was semi-managery in that I mentored a couple of interns, and it did have some challenging design and development work, which was fulfilling. But it was also a reminder that for all the things I love about full time work (community, collaborative problem solving, learning from others) it has its downsides too (every day??)

That’s a pretty diplomatic answer.

And it shows real growth on my part, doesn’t it?

You’ve come a long way from your early blogging days of coming home from work and complaining about your day at work.

What an innocent time, when being anonymous on the internet was the default.

Hard to be anonymous on a website with your full name as the domain name, but I get what you mean. Do you still have those old blogs published somewhere?

I don’t, but I have them saved privately and every five years or so I like to go back and revisit how I used to be. Sometimes I find funny stories I’m glad I recorded, and other times I find horrifying hot takes on things that give me full body cringe. A lot of times it wasn’t even what I said, but how I said it. I found a series of blog posts in the early 2000s where I decided that saying “fuggin’” was cool.

I’m so sorry. Are finding the gems that make the suffering worth it? Some people might just delete them all.

Oh, I forget about horrors pretty quickly after the full body cringe, and I’d probably not be such a personal archivist if I didn’t have that capability. Can you imagine having in the front of your mind all the stupid things you’ve ever said? I would not survive.

But seriously, revisiting old stories I’ve forgotten and getting to sit back with my 20-years-younger self and remembering how he used to see the world… it’s mostly good.

What’s a funny thing you’d forgotten?

I found a little gem from 2004 that really cracked me up:

Recently Mark and I had to give our apartment written notice that we would not be continuing our lease. On the provided form there was a section titled “Reason you’re moving”. Although we could have gone into the details about our life-situations and our thoughts on how stupid our management is, we chose to keep it simple. We said: “We cannot be caged. We were born to ramble.”

Apparently this wasn’t good enough. “… Thank you in advance for your cooperation and good luck in your new home. I am also curious, if you would, please tell me where you are moving and other than being born to ramble as the reason to move.” - Management.

Wow, you’ve always kinda been like this, haven’t you?

Yeah! Isn’t that fun? I love seeing examples of people as their young selves being exactly who they turned out to be. And not that I was even that young in this example, but still, it’s fun.

What about a serious thing you forgot about?

Reading rants about girlfriends I wasn’t getting along with—woof to that being a public blog post and not a private journal. I was just so sure that I wasn’t part of the problem when I was in my 20s. Also caught a bit of ol’ “when you’re wearing rose-colored glasses, all the red flags just look like flags”. Anyway, knowing how things turned out and finding a detailed report of the landscape immediately before things went sideways: what a thrilling exercise in personal archaelogy.

Also, casual references to my living parents that hit me different now that they’re long gone. Oh! Many words spent on all the anxieties I had right before I quit my job and sold all my stuff to move to New York City without a job lined up. Reading it now is actually calming—I remember myself as unconcerned, fearless even, back then. But no, I was nervous and did it anyway. I’ve been here the whole time. I just forgot.

Any of that make you wish you could go back and tell yourself something?

That is a fun game, but I don’t have a good answer for what I’d say because I’m pretty thrilled with where I’ve ended up, and who knows where I’d be if I chose a different fork in the road? It’s fun to wonder how things would have been had I actually enjoyed my college major, or if I didn’t get married at 25 out of fear of losing a relationship, but who knows if the alternate path would’ve taught me all the things I needed to know to get me here?

I feel like we could have taken an alternate path in this interview about 15 minutes ago.

You trying to change the subject?

Yeah, let’s keep it light. You’re getting a little “I’m 14 and I’m deep.”

I’m 45 and I’m a little shallow.

So since 2022, how’s life on the internet?

I’ve been doing my thing, and my doing my thing I mean not really posting on the public internet. I’ve been spending the majority of my time working on Dubbletrack, which has been a journey and a continuing lesson in the pitfalls of maintaining a work/life balance when work feels like fun and balance is a metric I decide.

That sounds like a loophole.

A loophole designed by who? Burnout itself? Capitalism? Hustle culture?

It has been really fulfilling when I get a handle on giving myself some guardrails and aren’t in state of self-induced burnout. I have been a fan of radio for the longest time, and it feels great to have built a product that people love, for a community I care about, and to then to become a volunteer DJ and use the software I built myself. It’s a fun set of problems to solve, and I love that I’m making a difference in community radio rather than helping some billionaire buy a bigger yacht by optimizing an algorithm used to better target an ad, or whatever.

How many yachts is too many? Does anyone actually know?

They’re still searching for that upper limit, and they won’t stop until they find it.

How long have you had a radio show, and do your friends listen?

The best ones do. I started hosting The Hot Pocket in December of 2023. You won’t believe how fast time flies when you commit to playing an hour of music every Friday at 11am. Friday -> Friday feels like two days.

So that must help with the burnout, I guess?

I mean, it is a scheduled hobby, and when I’m really tuned into it… it’s a lot of fun to share the music I’ve been feeling and getting lost in the sauce. I always used to love picking out a good set on a bar jukebox and watch the mood of the bar turn around, and DJing on the radio is a similar feeling.

What else are you doing to stay sane in this modern age?

Well I’m trying to refresh my silly side projects again (like this one), for one.

trackingnumber.fyi doesn’t seem that silly.

No not that one. There are others. Chill out

I was just telling Zoe that I was doing this interview, and she seriously said “Do you want me to talk to you about deadlines?”

Is that basically her saying “Get back to work”?

I know, right! Feels that way, but I asked for this. I do actually have a deadline that I need to get stuff done for. The problem is she knows about my secret foolproof system of completing tasks eventually

That’s not “Lowest priority first”, is it?

Oh so you know it!

Yes, I’m familiar. But I’m the lowest priority?

Let’s keep this about me.