Keaton Taylor – Product Designer at Envoy

Keaton Taylor – Product Designer at Envoy

Can you introduce yourself?

Hi. I’m Keaton Taylor – husband and dad of 4 living and working remotely from Ashland, KY, USA. I’m a product designer at Envoy – I work on the Billing platform team.

How did you start working remotely and why?

Honestly, It started because I took a contract role at a marketing agency in Arlington, TX, and they let me work from home three days a week. When that contract ended, I was terrified because I had two kids and needed work. I was interviewing, but I did what everyone does and sent out a tweet. An acquaintance was looking for a designer for his studio and was open to remote. Consequently, we did a contract-to-hire thing, and I started full time the following February. That was 2013.


The best way I can sum up why I work remotely is that I’ve seen all four of my kids take their first steps, which not everyone can say. It’s definitely a privilege, and I try really hard not to take it for granted. 

What is your typical day like?

A “Typical Day” is hard to plan out when you have 4 kids. I won’t mention times because it varies depending on the amount and severity of the faecal matter/blood/screaming I am awakened up. Generally speaking, I wake up before the kids. Always head downstairs and make a pot of coffee first. Usually, I check the news to see what kind of foolish things are happening in the US, check my personal email, and sip on some of the said coffee. I’ll take coffee up to my partner, Then head back downstairs to make the baby’s milk and wait for the onslaught of children. At this point, I would typically start making either scrambled eggs or oatmeal for breakfast. Depending on the occasion, we might head over to Jolly Pirate Donuts and grab a few honey glazed. The kids are here now. They’re eating breakfast. I’m headed upstairs to shower and/or get dressed and grab the baby. The baby needs her breakfast. She has almond milk in a sippy cup and runs around, screaming and laughing. After milk, I give her food and watch her throw it on the floor like an animal. 


I usually head to my office upstairs around 9 am. Start with meditation in Headspace and then start looking at what the day is going to bring. I’ll look in on design Twitter and see who’s mad at who today and how/if I can add value to any conversation happening. Meetings in the mornings are pretty sparse because I’m on the East Coast, and most of my team is in San Francisco. Generally, I work peacefully until early late morning/early afternoon and then get into standup meetings, planning meetings, and 1:1’s. I usually take a break a little after 1 pm and to check in on my partner and our kids’ homeschooling progress and grab a bite to eat. The rest of my afternoon is usually cross-functional meetings, task-work, and feedback sessions with our team. 


I sprinkle in family walks, reading time (I’ve been using Blinkist to digest some of the seemingly less exciting books that I want to read). Sanity breaks to make sure I’m as useful as possible for my team. I struggle with anxiety, as well. It’s super important for me to have the space to take 10 – 20 minutes here and there.  Some days I need to step away and meditate or do breathing exercises. I’m lucky to work on a team where I can say that and do what I need to do. My manager is incredible, and she works very hard to build that kind of psychological safety into our culture. 

How do you stay efficient and engaged while working remotely?

I start work before most people get to the office in SF. That has its drawbacks but overall it allows me to focus really clearly on what needs to get done before meetings or heads down time starts. I’m in a unique position where I have an office with doors that close in the house I’m living in and that’s really helpful. My biggest help in overcoming distractions is my partner. she’s a champion mom and best friend.

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

At Envoy we use Sketch and Abstract to design and version control our work. We use Zeplin for feedback from cross functional partners. The usual collaboration tools, Slack and Zoom for talking through things. We have an amazing data ops team that helps us a ton with Looker and analytics questions. 


Personally, I have a few things I use that make things a little easier. I have a little menu bar app called Next Meeting that I love. I use my iPad Pro and Apple Pencil to quickly sketch out ideas and flows. I use a lot of stock apps for my day to day work. 


Workflow varies but most of the time I’m working closely with my PM Kate, who is based in NYC and is amazing. We will take a spec or problem back to our designers and engineering partners and we work through spec to crit to implementation refining our solutions along the way as needed, while maintaining a “Great Enough” mindset. 

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

I think we’ll see more and more companies and organizations moving in the direction of remote work or at least satellite offices in smaller and less cost-prohibitive areas.

How do you stay in touch with your team?

We have a solid culture of communication rituals at Envoy. I believe wholeheartedly in aggressive communication and radical candour. We do one team-wide group show and tell and two discipline-focused critiques per week. Monday, we do a sprint planning meeting, and we have a bi-weekly all-hands to discuss team goals and need-to-know information. That’s all really helpful for general communication, but then we also keep in touch through Slack and 1:1’s. 

The most important way we stay in touch is getting different teams together about once per quarter to work together, in-person at our office in San Francisco.

What do you enjoy most about working remotely?

Being able to make breakfast and lunch for my kids. Full stop.

What is your office/workspace look like?

Keaton Taylor’s Workspace

15” MacBook Pro

12.9” iPad Pro w/ Apple Pencil 2

iPhone 8+

LG Ultrafine 5k Monitor

Dell 4k monitor 

Pilot G2 0.7mm (don’t @ me) 

Various gridded notebooks (Muji, Field Notes, grocery store)

Vivo Dual arm monitor mount

Jarvis Adjustable Standing Desk

Gorilla Grip Anti-fatigue mat

Rode PSA1 mic boom

Blue Yeti + Blue shock mount

Ikea Desk Lamp

Envoy mug by MiiR

What are the challenges of being a remote worker?

They’re numerous. If you’re living in a low cost of living area, there is usually not a great design culture around you to tap in to. You have a team of people you work with plus an entire company you have the opportunity to see maybe 4 times a year (if you’re lucky?). Loneliness and burnout from working more than you probably should. The ability to just shut your brain down and not wander back to your laptop and grind for a bit. I think most of those things pass with time and experience, but they resurface for me now and again.  

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

I have four kids, an excellent partner, and an anxious little dog. We have friends scattered all over the world we try to keep up with and family very close to us. Professional loneliness is something I think is here to stay. Still, I fill that void with my family and friends instead. Could I go further, faster if I lived in SF or NYC? Probably. I’d likely also miss my kids’ breakfast, lunch, dinner, and even bedtime some days. Knowing that I get to see them all through those things and more is all the combat I need, frankly. 

What is special about the place where you live?

We’re living in the next town over from where my partner grew up. She knows people here. Some of her high school friends are here working in foster care and just really doing fantastic work. The cost of living is insanely low, and we’re in the Appalachian country, so it’s beautiful and untouched in many ways. There are significant drawbacks, but the people are friendly, and the scenery is gorgeous. There are tons of hiking trails and paths all over because of how mountainous the region can be. It rains a lot here in the winter – which I love. 

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

Hiking with the kids in Kentucky and West Virginia. We just bought a Thule Sapling for our 16 month old. 

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

I actually just wrote an article with some pretty solid advice over at https://envoy.design, so if you have a chance, check that out. I think in general remote work is worth checking out. It’s not right for everyone at every level, but I think it’s pretty amazing. Go into it with clear goals and an open mind, and see if it fits your working style. 
The main things I would recommend are to:

  1. Have the discipline to get up and treat a remote workday the same way you would an on-site workday. Get a quick shower, put some pants on and fill up that coffee cup before you hit the kitchen table, or office, or couch, or whatever. 
  2. Make clear and straightforward expectations at home and at work for when you’re working and not working, so that everyone understands your schedule and your needs. 
  3. Travel as often as you can. Go to conferences or to the HQ in BigCity, USA. Take your family to the zoo in another city. Just get out and kill the cabin fever. 

I don’t have any books or podcasts specifically about remote work to recommend because it’s such a personal thing. I’m not sure other peoples’ experiences are an accurate gauge for what your own experience will be. If you have the opportunity, try it! 

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