Jordan Koschei – Senior Product Designer at askSpoke

Jordan Koschei – Senior Product Designer at askSpoke
Picture by Hovsep Agop

Can you introduce yourself?

Hi! My name is Jordan Koschei, and I’m the senior product designer at askSpoke. The company’s based in San Francisco, but I work from a town called Beacon in the beautiful Hudson Valley, about 50 miles north of New York City.

How did you start working remotely and why?

I’ve always worked remotely, though my jobs have grown increasingly more remote as I’ve progressed.

I always knew I wanted to end up back in the Hudson Valley, where I grew up, but conventional wisdom says my line of work mostly happens in San Francisco and New York. After college, I figured I had a choice — toil away in obscurity but live where I want, or give up the place I want to live in exchange for (potentially) a great career.

I decided to prioritize life overwork and headed back to the Hudson Valley, where I cobbled together just enough freelance work to call myself a web designer without feeling like a fraud. Thankfully, that was around the time that remote work started to become more widespread — Slack became a thing, ubiquitous broadband made video conferencing mainstream, and the idea of working for a company in a different city became feasible.

After a few years of freelancing, I realized I hated it, and a local company reached out to see if I’d come work for them. They were an hour away from where I lived, so I agreed, under the stipulation, I wouldn’t have to come to the office all the time. That was my first remote job. After that, I worked for a company in Brooklyn (2 hours away), followed by a company in Dallas (2 time zones away), and now a company in San Francisco (a continent away).

What is your typical day like? 

I get up at around 6 to walk the dog, get ready for the day, and help my wife get her things together for work. On a good day, I’ll spend some time studying my Bible and doing things to help me remember that there are things deeper and more important than the day-to-day concerns of work.
I usually start work at around 8:30, either at my home office or at a nearby coffee shop. I always tell myself I’ll do deep work first and worry about the reactive stuff later… and then compulsively check Slack, email, Twitter, etc.
Most of the company is based in San Francisco, so I have around 3 hours to work uninterrupted by meetings and pings. I try to get a lot of deep work done in the morning, and then take meetings in the afternoon when my coworkers are online. Work consists of:

  • Designing in Figma
  • Writing design docs in Google Docs
  • Lots of calls/meetings in Zoom
  • Thinking about strategy and bigger-picture things regarding askSpoke’s design direction
  • Some assorted management tasks

I go offline by 5:30 pm each evening — that’s a hard stop, so I can help make dinner, enjoy time with my wife, and have a nice quiet evening. On some nights I’ll tinker on side projects or read, and then it’s bed by 10:30 or 11:00.

How do you stay efficient and engaged while working remotely?

Two things have helped me immensely.
The first is to write everything down. I used to be really bad at this, and I’d be both unproductive and anxious most of the time. Then I started using Things as my task manager and obsessively logging every since action item on my plate, as granularly as I can. This has several benefits:

  • I no longer have to trust my own memory.
  • I no longer waste mental bandwidth trying to remember things.
  • I’m no longer confronted with amorphous, stress-inducing tasks like “Design the settings page.” Instead, I have bite-size, easy-to-perform tasks like “Take screenshots of 3 settings pages I like” or “Respond to this one comment in Google Docs [with link]” that doesn’t require any thought. Instead of wondering how to begin, I can just jump into checking tasks off my list, saving my mental energy for the really meaty problems.

One word of caution, though: if you decide to have a system for tracking tasks, you have to track every task, otherwise you’ll be constantly wondering if you’re forgotten something.

The second thing that’s helped me stay efficient and engaged is to not pretend I work in an office. Lean into the nature of working remotely. Need to run some errands? That’s okay, go run those errands. Want a change of scenery? Go work from a coffee shop. It’s okay if someone calls you and it’s a little noisy behind you. Best of all, if I’m not feeling productive, I give myself permission to not be productive. If nothing’s getting done, I can just walk downstairs and do some dishes or walk the dog or something. Usually, I’ll find myself refreshed for the next time I have energy, whether that’s a few hours later or the next day.

What are the tools and workflow that you’re using to get things done?

I use Figma as my primary design tool, and use it for both simple wireframes and high-fidelity mockups. Our design system is getting more and more robust, so there are less friction making wireframes that look like mocks. It’s great! I was a Sketch user before I started at askSpoke, but now I’m a convert.

So much of design isn’t visual, and I think my primary output is probably writing. I collect my thoughts in Google Docs — a couple of pages of mockups and explanations for small features, and the occasional novel for large features. They aren’t formal documents as much as specs that describe how a feature should work, its expected behaviour in different cases, how it scales for different pricing plans and user permissions, etc. Everything is tied back to the initial problem we’re trying to solve.

I often say that a good design doc is as little design doc as possible. I’m allergic to unnecessary process; if I’m writing a doc, it’s because something needs to be written down, not because I want to pad a page count with extra words.
Lately, we’ve been moving more of our product and engineering planning into Notion, which feels more modern than Google Docs. The document paradigm is sort of skeuomorphic — it reflects the pre-web reality of everything needing to be represented on pieces of paper that could be moved around from desk to desk. Notion feels more native to the web, with discrete pieces of information that can be linked and recombined and treated as nodes in an ever-expanding network.

We also use Linear, which has been great for tracking issues between design, product, and engineering.

How do you think remote work will evolve in the future?

I think there will be a lot more of it. Companies want the best talent, which isn’t necessarily the same as the best talent available within 20 miles. Why not hire someone from three timezones away, or an ocean away, or someplace that’s not the same city as your company happens to be headquartered? Companies that restrict themselves to local talent will find themselves at a disadvantage.

Within the next five years, I think it’ll no longer turn heads to say you work for a company completely elsewhere, at least among knowledge workers in countries with strong tech infrastructure.

How do you stay in touch with your team?

We use Slack constantly (though it’s okay, and expected, to keep it in do-not-disturb after hours), and have frequent meetings and spontaneous syncs via Zoom. We do an annual offsite, too, so everyone gets to be in the same place at least once a year.

What do you enjoy most about working remotely?

The freedom! I can live where I want and work where I want, even if those aren’t in the same place. I can leave during the day if I need to, and enjoy more personal time since I don’t have a commute.

What is your office/workspace look like? 

I use a 2018 15” MacBook Pro and a 27” Acer monitor. My office is pretty basic — beyond keeping it clean and tidy and generally pleasant, I care about my physical setup less than my software setup. Or, to put it bluntly: I can work from anywhere if I have my computer and the right software, but if I don’t have those things, the nicest office in the world wouldn’t help me.

That being said, there are some nice-to-haves that I like to keep around my workplace. I have a large print poster of the Belafonte from the Wes Anderson movie The Life Aquatic with Steve Zissou. I also have a framed rendition of Hyrule Castle from Ocarina of Time. And I like to keep my bookshelf close by so I can turn around and see the books I really care about. All things that inspire me.

What are the challenges of being a remote worker?

It can be isolating. Most of my coworkers work in the SF office, and when I go to visit, I enjoy the camaraderie and inside jokes and general sense of community. They make a big effort to make sure we remote workers are always included, but some things are just hard to do through a screen.

Staying focused is always a challenge, and I’ll never lose the sense of guilt I get when I step out midday to run an errand. (I know that’s absurd, especially considering that nobody cares at all, and people step away for various reasons all the time. Don’t ever work for a company that monitors your time, cares about how long you’re in your chair or acts like you’re a high schooler who needs a hall pass to leave their desk.)

Do you have any side projects? Can you speak about them?

I run Creative Hudson Valley, an online publication where I interview people doing interesting creative work in my region. So far we’ve had an Oscar nominee, a famed indie musician, several designers, and a principal dancer of the American Ballet Theatre. Coming up soon we’ve got a young engineer and entrepreneur who’s upending the prosthetics industry, a social media influencer, and a husband-and-wife design team whose work you definitely know.

I often say that the Hudson Valley is where people go when they graduate from New York City; this project is my attempt to demonstrate that to people who don’t believe me. Stay tuned for some more interesting interviews later this year — I’m working on getting at least one of the Avengers who lives nearby (but no promises).

How do you combat feelings of loneliness, isolation and burnout?

Get out of the house. I like to work from coffee shops frequently, and some of the nearby college libraries if it’s summer and they’re mostly empty. It’s important to stay engaged with the community and to see people, too — we’re not adapted to having all of our relationships mediated through a screen.

I go to church and volunteer there every Sunday, and I’m part of the Hudson Valley Tech Meetup, a local community group that hosts events with tech talks and more. In the summers I’m the emcee for Stockade FC, a local semi-pro soccer team started by Foursquare founder Dennis Crowley.

I also highly, highly recommend taking a weekly Sabbath — once a week, take a day completely off. Working remotely, it’s really easy for your weekends to feel like your weeks, but we simply aren’t built to live like that. To borrow a cliché: we’re human beings, not human doings. We’re not robots, meant to flit from task to task.

What is special about the place where you live?

The Hudson Valley is the best-kept secret on the East Coast. It’s been the centre of so much culture, and a lot of people don’t even realize it. Woodstock happened here. Lots of pivotal moments of the American Revolution happened here. The Culinary Institute of America is located here, and lots of students fall in love with the area and stay, so we have a culinary scene that can rival a major city’s.

The natural beauty is unmatched, and the region is dotted with towns and small cities that each have their own character. I live in Beacon, which feels like an extension of Brooklyn (and was recently ranked “Coolest Small Town in America!”); before this, I was in New Paltz, which is a bohemian arts community/hippie college town. A few towns away is Rhinebeck, a charming village that’s also headquarters of a world-changing robotics company, not to mention a coffee shop co-owned by local residents Paul Rudd, Jeffrey Dean Morgan, and Hillarie Burton.

Lots of heavy-hitters from the New York tech scene have settled up here. Now that remote work is widespread, you have people who are at the apex of their careers moving here to raise their families outside of the city, but still doing amazing work. Dennis Crowley, the founder of Foursquare, started a local semi-pro soccer team that’s gotten pretty big.

A Hudson Valley Tech Meetup event

Besides work, how do you like to spend your time?

I spend a lot of time with my wife and dog! I also enjoy frequenting local coffee shops and the occasional brewery, trying new restaurants and old favourites, and exploring some of the cool towns nearby. I read a lot (you can see my reading for the last few years on my website), and try to go to art museums as much as possible. The proximity to New York City is helpful — some of the best museums in the world, less than 90 minutes away. In the summers, as I mentioned, I’m the stadium emcee for Stockade FC — I get to yell “GOOOOALLLLLLL” into the microphone with varying degrees of enthusiasm depending on which team scored.

Local soccer draws a huge crowd

Do you have any recommendations for those who want to work remotely too? 

Get very, very good at remote communication. If you can write clearly, you’re already most of the way there. Being able to write good emails and Slack messages, knowing when a well-placed emoji will help convey your meaning, being able to intuit when to switch to live communication like a video chat… all that is very helpful.

Also, get comfortable with over-communicating. Communicate to the point where it feels obnoxious; let your team know what you’re up to, go into more detail than feels necessary, and don’t assume that something that’s obvious to you is obvious to them. From your perspective, it’ll feel like over-communicating, but from their perspective, it’ll feel like you’re a good teammate who cares about keeping them in the loop. This has been the most helpful thing in my remote career.

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