Faux Interview

Content Warning: Self-indulgent

I’m having trouble getting around to writing new material. Lately I’ve been spending my time immersed mostly in programming and job applications¹, and after so many months of relatively uninterrupted left-braining, I’m gun-shy when it comes to prose. More recently I’ve had a few fleeting moments of creative inspiration, but the thoughts are quickly jumbled or cramped. Meanwhile, a folder on my desktop has slowly been filling with fragments and false-starts…

I decided responding to prompts would be a good way to get my thoughts going and break out of the rut. The idea crystallized while listening to a podcast I’ve gotten really into lately, the Tim Ferriss Show.² I’ve listened through enough episodes at this point where I think I know his voice and rhythms fairly well, and I’ve basically memorized his usual “rapid-fire” questions asked at the end of each interview, so writing up an imagined interview should be pretty easy. Also helpful is the fact that interview-style responses mean I can be a less fussy about the writing itself.

So without further ado, here’s a goofy fake interview vaguely in the style of a Tim Ferriss podcast.

What have you been up to in the past year or so? #

I’ve been fun-employed! Sorta. In brief: I left my job, went to school for a few months, kept learning stuff, applied to jobs, and recently moved out of NYC. Good stuff.

Where’d you go to school

A software “bootcamp” based in Manhattan called The Flatiron School.

What did you do before that?

I worked at a startup that builds software tools for digital health companies. It’s a mix between Heroku and Turbo Tax, if you’re familiar with any of those. Basically it helped companies get to market faster and navigate the requirements of HIPAA. But the product was generalized enough that eventually they plan to target other regulated industries involving sensitive data, like finance.

So why did you leave?

In short, I wanted to actually become a software developer and I wouldn’t be able to do that there. It was a phenomenal company (they’re still doing quite well) and I left on totally amicable terms, but I wasn’t able to learn and do what I wanted as effectively as I’d need to. I mean, they were supportive, but when you’re that small of a company it’s just harder.

How big was the company?

While I was there the company was between 7 and 10 people, all but one of whom were software devs. And their caliber was off-the-charts good. Plus we were a fully distributed team. All that meant that when I asked a question, I was Slack messaging someone between 3 and 7 hours away, whose time could probably be billed at like $3 a minute or more if they consulted. So you really only wanted to ask questions that were mission-critical, and everything else was the FITFO protocol.

So, why did you want to be a developer? Why not technical account management or customer success or those kind of hybrid roles you see at SaaS companies?

Having been a philosophy major and a music performance minor, I missed the creative aspects of what I had spent 4 years doing. Programming to me felt like a phenomenal combination of both, being creative, rigorous, logically driven, but with a practical product resulting from your labor. I had been getting increasingly stoked about tech throughout my brief career, and the stuff I liked the most was the scripty, code-y, creative bits. The more I learned, the more I wanted to know (and the less I felt like I knew). Also, some intense family stuff happened 6 months prior to my departure–the sort of thing that makes you think more seriously about how you spend the time you’re given.

So as all that was percolating in my head, it was also hard to get better at the thing I wanted to do more of, which was writing code, helping design and create features for something people loved, you know, all that. Eventually I realized if I was gonna do it, I had to just leave and do it.

If not now, when?

Exactly. So I spent September through December at the Flatiron school.

And then since January, I’ve been engaged in what you might charitably call self-directed grad school, with a mix of self-study, side projects, and job applications. I was also working out a lot, trying to get healthy and run again.

What do your workouts look like? Are you training for anything?

I’m a runner, but I’ve been struggling through near perpetual injury for years. No races yet.

So currently it’s a mix of stuff. I lift, I cycle, I swim, and ocassionally do yoga or rock climb. Having had a bunch of injuries pretty much everywhere, I’ve become fairly omnivorous with my fitness approach. Once I get healthy enough to train properly, the goal will be to blow up my stale mile PR I set in high school. (I want to run under 4:20).

Running is still rough going, but I’m staying fit. Plus I landed a job which is one big goal I can now cross of the list. The next goal (besides “be good at my job”) will be picking up my horn again and getting back into “shape” there. I practiced for the first time in months the other day.

Do you have any morning routines? #

It’s funny, I’ve always thrived on routine even though I seem to be mediocre at maintaining it. But at one point I think I had it dialed in, right down to the things I would say to myself when I woke up, how I’d push my door open, and when I’d put the coffee on. Currently it’s a bit more flexible.

Can you walk through maybe one iteration of it?

Sure. I try to wake up early, before 7 unless I’ve been out. The first thing I do is think to myself “feet on the floor.” It’s an easy goal, and it gives the moment immediate momentum. Otherwise grabbing your phone and lounging in bed is all too easy. After that I try to bang out a few push ups and pull ups on my hang-board to wake up.

Then I open my door, draw my curtains, put on water for coffee…sometimes I’ll take a quick cold shower while it’s heating. Then I’ll stretch a bit–usually a really abridged yoga thing–and then pray for about 5 minutes. I find that if I don’t move around a little before praying then my mind is either too sleepy or too distracted stay focused.

Do you eat breakfast?

If I’m planning on working out later in the day, yeah. If I work out that morning, I’ll skip breakfast until later.

What do you usually have?

Either a shake or oatmeal–as long as I have some nuts and a banana in it, I’m happy. Actually, really if I have coffee and a banana in some form I’m usually pretty happy.

So yeah, my routine I guess is coffee, prayer, sometimes a workout. But mostly coffee.

What books have you gifted the most? #

I’ve never really gifted books. Although maybe I should start, since I have often given nothing in the past…


Yeah, I’m known in my family as being kind of a shoddy gift-giver, so much that it’s become a running joke for me to find creative ways to give no actual thing….

Also I have weird book tastes. Like, I’ve read the Silmarillion several times, and I would gift that book to pretty much nobody.

Can you explain what that is for people listening who might not know?

Oh sure. It’s what you could call the prequel to Lord of the Rings. Tolkien wrote a huge set of myths, including a creation story, and something very close to the story of Atlantis. It’s beautiful, but parts of it read a little like the Bible or greek epic poems, with long genealogies and great big events described with sparse dialog and sometimes little detail. (As an example, a fight between Sauron and a super powerful elf-king is covered in about a paragraph or two, and one of the paragraphs is a poem).

Got it. It sounds like you’d have to be very into the legends and the history.


So not much on the book-gifting front? Have you yourself been gifted any books that were impactful?

Well, I do like to share articles, though.

What’s an article you’ve shared recently

You have to read How to Hack an Election, it’ll totally change your perspective on the viability of democracy in the digital age. I’ve also been really into the Slate Star Codex blog. If you wanna get really political, but also really scientific and have the stomach for rigorous philosophy papers, I’d check out Robert P. George’s article Embryo Ethics. You may disagree with his conclusions, but one thing is for sure: the guy did his biology homework.

Do you have any favorite movies or documentaries? #

I think I’ve watched The Matrix 10 times.

The trilogy?

Oh, no just the first (and best) one.

Any documentaries?

Yeah, Manufactured Landscapes was really striking. It’s by this photographer, Edward Burtynsky. It paints a very stark picture of how humans are altering the face of the planet, but without being preachy. Like, one photo is just a huge rusty red river coming out of a mine in Ontario. Some of the images are pretty hellish, actually. But there’s not much dialogue, and very little music; the photography speaks for itself.

It’s a cool format though, since it’s a great way to get everybody on board with being more environmental. If people think climate change is a bunch of malarkey, then this at least gives us common cause: buy less, reuse more, etc. You don’t really need that iPhone upgrade do you? It’s just going to end up at an e-waste dump in some Chinese village and ruin the water table more.

What is one thing you believe that others think is crazy? #

Oh man, great question….

Well some of the things I believe are controversial but not crazy. Maybe the most crackpot stuff I’ve started to get into is around AI. I’m really concerned about strong AI in 40-50 years–I think it’s an existential threat. But I’m in good company believing that, with Bill Gates, Stephen Hawking, Elon Musk, and other techies just about equally concerned.

I’m also a Christian, so that means I believe in an omniscient, omnipotent, and omni-benevolent God (despite the well-known conundrums of suffering and divine-hidenness); in Sin (separation from God and God’s purposes); and in this amazing cosmic drama where a guy named Jesus not only lived and died, but came back from the dead in this ultimate act of forgiveness. I mean, I don’t pretend this stuff doesn’t sound crazy. But I think it’s true. And I’m in pretty good company there too. Who knows… Well no, I guess we all will eventually.

Yeah once the great machine uprising happens…

Haha, yeah exactly. Maybe the planet finds out in 60 years time. I hope not.

When you think of the word successful, who comes to mind? #

Easy: my parents.

I look at my parents and think: wow, they worked their butts off and hit some pretty big goals. Beautiful home, good family, good job(s), incredible memories… And they each have pretty cool stories too.

My mom was a dancer for a bit, and later an account director at an advertising firm or something like that. But she devoted most of her life to raising 4 kids, though she did do a ton of volunteering and other work on the side too. But when you think of the “score board” you know, like, what are the KPIs of a mother? She crushed it. All four of her kids have kept or deepened the faith she raised us with. All of us went to great colleges and had solid academic careers. Among us is a D1 athlete, a fitness trainer (my sister’s class absolutely murdered me, by the way), an indie band minor rockstar, academic awards, music awards, eagle scout awards, gold awards, and all of us gainfully employed in various cool cities. She’s still waiting on grandkids, but we’ll get there soon enough I’m sure.

So as far as a parent wanting to raise kids with pretty good characters–we’re certainly not perfect–and fine resumés goes, she did an amazing job. And it was never forced. My parents were generally really good at encouraging opportunities, but not making you do things you hated.

And your father?

My Dad to me kind of embodied the American Dream. He grew up in the Bronx, was fairly middle class (or at least he makes it sound that way), and was hustling from day one. He had a dog grooming business, a prescription drug delivery service–

Drug delivery? Was he HIPAA compliant?

Ha, definitely not. Back then he knew his customers by name and what they took. It’s funny too because now this is some big disruptive Silicon Valley idea with millions in VC backing. But in the 60s it was a Jewish kid in the Bronx with a bicycle, a list of names, and a friendly drug store owner. He also worked at hobby shop for free just ‘cause it was cool and eventually started to up-sell customers that came in, so the shop owner gave him a cut. He also learned to repair pretty much anything, and that became yet another side gig. On top of all that, we was–and remains–an accomplished jazz piano player and did that in college and throughout law school. He had a couple bands and was a radio DJ as well.

Does he still play?

Not as much as he should. (But I’m not one to talk…)

But he’s never stopped really doing something. He’s a lawyer but with a qualifying asterisk, you know? He’s just very hands-on. He does property management, but does all the remodeling and maintenance work himself. That’s probably his problem and where what’s made him successful is also a drawback. Because he can pretty much do everything, he does do everything–he has a hard time offloading work, and spending money in exchange for time. The kind of stuff you talk about on your show.

Right. The non-renewable resource known as time. Did your dad influence you at all?

Massively. I’d say that some of my dad’s chief pedagogical contributions were developing our penchant for and skill in argument, and jazz–both forms of improvisation, so kind of related.

I think my dad taught me more about essay writing and editing than any teacher, until maybe high school. He taught me to be skeptical of what you read, and what good debate looked like (though less now–we tell him that he needs to listen more). And my musical life and musical taste I can attribute almost entirely to him. Super grateful for all of it. Growing up I fell asleep at night to the sound of him playing jazz ballads on the piano in the living room.

Anyone else come to mind?

Aside from them, I’m kind of an Elon Musk fanboy these days. I’d say he’s pretty successful. Setting goals, hitting them, and inspiring other people….

Who has had the biggest influence on your world view? #

My family members are a gimme. So I’ll say some of the philosophers I’ve read–and in some cases met–in college.

Can you give an example

Sure. If you want to read an interesting blog, check out Ed Feser. I don’t agree with everything he argues for, but I admire his accessible but really rigorous style.

What purchase at or under $100 has most positively impacted your life? #

Another easy one: Alfred, an app for mac osx. I’ve given two presentations on it, and it’s changed the way I use a computer forever. If you don’t have Alfred or some equivalent application launcher, go check it out.

Other than that, maybe my first pair of running shoes?

What advice would you give your 18 y/o self? #

Advice usually comes in the form of “do more of X” or “do less of Y” and I think the most powerful driver there is regret. So using that as a guide, I have a couple things come to mind pretty quickly:

But then again, if I’d done things differently, maybe some things I love now wouldn’t have come to pass…

Is there anything that keeps you up at night? #

I definitely inherited a lot from my parents with respect to my mental life. My dad is always thinking of something, and my mom’s a big planner and verbal processor. It’s why they’re able to do so much and were very successful at juggling the lives of 4 kids on top of their own personal lives. So my mind can be hard to turn off at night.

But like them, it’s also super useful. When I was studying philosophy, anticipating objections to your own argument was crucial. In doing that, you have to imagine and handle a few different threads at once. It’s a bit like Calvin from Calvin and Hobbes, where he builds some small sand castles or snowmen and then stomps them all down, except they’re your own arguments, and whatever is left standing is probably a half-decent thesis.

That ability to assault your own thoughts can manifest in weird ways though, as self-doubt, anxiety, all that. So sometimes negative stuff, or planning, or whatever I was working on, rattles around my head at night.

Do you have any practices to deal with it?

The biggest one I try (and typically fail) at is cutting screen time. No screen an hour before bed. Also, listening to fiction books on tape to fall asleep is magic.

If you could have a gigantic billboard anywhere with anything on it, what would it say? #

Do I have to have one? Can I just take one down?

Hahaha. OK, I’ll say it another way: what would you say if you could deliver a short message to a lot of people.

Honestly, I really don’t trust slogan-able messages most of the time. That’s one reason I don’t love billboards (aside from the fact that they’re aesthetically oppressive). I think we have a lot of problems today because we try too hard to fit wisdom or complex political debates into these pithy little 140-character phrases. But sometimes truth doesn’t soundbite well.

What about that?

What, “Truth doesn’t sound-bite”? Heh, kind of a contradiction. I guess if I had to pick something, I dunno… Maybe “Go outside.” Or “Put away your f-ing phone.” I need to remind myself of that last one, too.

Hahaha. Agreed. The amount of health benefit I’ve gotten from just being in nature is, ahh, not to be underestimated. I think that’s a great note to close on. Listeners, go outside! Colby, thanks so much for the time.

Yeah of course, thanks for being part of my fevered imagination. This has been really fun.

As always, thanks for listening, and keep experimenting

¹ Which finally met success this week, landing a SWE position in Santa Barbara

² Tim Ferriss is an interesting guy. He’s kind of loveable and hateable at the same time, and his palpable self-consciousness can be distracting. But he’s very good at interviewing people, and his guests are often incredible.


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