Hey, I am Darcy Boles, a People Experience Leader and Architect of Company Culture. I live and breathe the inner workings of culture creation and intentionally help shape work culture on value pillars that support teammates to be human.

I'm a Remote Pioneer – I work from the beach, my home, a camper van, or a coffee shop, wherever there's surf, sun, and wifi – I'm there. Lover of all dogs (although mine is the best), people, travel, cultures, and the distributed workforce. I am committed to never working any other way than remotely and was named one of the top 50 Remote Thought Leaders in 2019.

Current Location?

Encinitas, CA

Current Gig?

Director of Culture and Innovation at TaxJar

Current Computer, Mobile, etc?

Macbook Air

Where can we follow you on the Internet?


Tell us a little bit about your background & how did you get started with remote work?

I had spent quite a few years working for a global travel company but wasn’t permitted to work remotely, which I just found silly (because I love to travel!).

I hit a point where my option was either move to “where it’s all happening (SF) at the time, or rely on a dim future in my career (or so many said). I decided I wasn’t willing to give up my home, friends, or community to move to a city to better my career, so I just quit.

I had no idea what was next. I moved to the Sierra Nevada mountain range in Lake Tahoe, CA, and did some soul searching.

I realized how deeply I missed teamwork and working on solutions to tough problems with brilliant people

Once that clicked for me, I started getting connected online with people who shared those values and found TaxJar, a fully remote SaaS company, and got deeply connected within the remote community. I’ve never looked back.

Take us through your typical weekday?

I get up around 7:30 am and am dedicated to my morning routine, which consists of stretching, gratitude journaling, meditation, or Wim Hof Breathing. I then hang out and check in on my emails/pings. I generally start meetings around nine, usually lasting until about 1 pm PST due to quite a bit of crossover with my East Coast teammates.

Later in the afternoon is my heads-down work time, and I generally take a break for a long walk or a surf in the late afternoon. Sometimes, I’ll pop back online in the evening after dinner, dependent on what projects are in the works, but I have to be careful not to overwork myself!

What job responsibilities do you have?

Great Question! I’m on a People Experience team with eight fabulous individuals. My team focuses on the lifecycle of the People Experience at TaxJar.

My focus areas are in the realm of codifying our operating system as a remote company and setting all current and future teammates up for success working within a values-driven remote environment.

What’s your workspace setup like?

We live in a teeny tiny 350 sq ft garden apartment, so I built my desk against our kitchen wall next to the fridge (which doubles as a whiteboard!). I have a mounted dual monitor and still go old school with a corded mouse and headphones.

If I don’t have a crazy busy week, sometimes I’ll work from our camper set up a standing desk. One of the many benefits of remote work is being able to work from anywhere you want. We found out this as of the primary reasons why people quit their jobs and start remote work. ‌

What apps, gadgets, or tools can’t you live without?

Oh man, Basecamp (because our team basically lives in it), My Mac note application (I’m a writer, so I have so many thoughts all the time), and a lacrosse ball that sits under my desk so I can massage my feet when I get stressed out. We suggest a look at the best headphones for remote work to get some tunes going while working.

What’s your favourite travel hack?

VELCRO. My boyfriend and I do a ton of traveling in our camper van and have discovered strong velcro to store gadgets, knick-knacks, and even sticking our charging stations to the truck walls, so they don’t move around when off-roading has been a total game changer!

How do you keep track of what you need to prioritise?

Well thought out yearly and quarterly roadmaps, to-do lists within Basecamp and on my fridge, and check-in with my team every week to ensure we’re aligned with what needs to get done and review any roadblocks, and re-prioritize if required.‌

Aside: We also recommend following a daily routine and maintaining a to-do list while working remotely. You can turn the productivity ship around by following simple tips.

What are you reading currently? What do you recommend?

I just finished Dr.Edith Eger’s book The Choice, and it may now be my favorite book I’ve ever read. IMO, there are few better books for the times we are in, and she reinforces the resiliency of the human spirit and that we always have the power of choice in our minds and lives.

Advice for someone who is looking to switch to a remote job?‌

Do your research! With any job, remote or not, it’s essential to learn more about the company culture and values of the company you are interested in.

Ask yourself, do I align with these values? Would it feel right for me to work here?

When searching for remote-specific roles, you understand the tools or environment in which the company operates. Learn the tools before you do the job.
Never used Slack, Basecamp, or Zoom before? Most tools have free trials so you can do much work on your own, setting yourself up for success when working remotely or for a remote organization.

What qualities would you recommend are a must-have for a person seeking a remote job?

A highly effective communicator, someone who can write clearly and concisely so that people from all different walks of life can understand. Someone who is self-aware and humble, can give and take directions well and set themselves up for success when provided with expectations.

Any courses or material people can refer to when they are looking for a remote job?

Sure! I just had the pleasure of contributing to the book Remote Teams Work, which is a great handbook to help anyone understand the inner workings of a remote organization on a deeper level.

Remote-How also has some amazing courses and resources for candidates looking to learn more about remote roles and how to succeed in finding one and thrive in a remote role.

What, according to you, are the pros and cons of remote work?

Pros: More time to focus on things that matter to me, more intentionality in my work, less BS + wasted time, less environmental impact, more ability to work with a diversified team that holds different perspectives and knowledge, an opportunity to work with more people who don’t look like me, ability to think more about problems and roadblocks instead of just having to respond right away in a meeting room, honestly for me - the pros are endless.

Cons: The natural tendency is to work too much when your office comes with you; your screen time increases a lot. I also definitely miss constant human in-person interaction because I’m an extrovert, but that can also be solved with going to co-working places, coffee shops, etc.(the feeling is just extra amplified for me right now in the amid such conditions).

‌Want to work remotely like Darcy? Go over our guide to see how companies hire remote employees and learn essential qualities a remote employee must-have. We have also created a list of top 20 companies hiring remotely in 2020. Join like-minded people at our LinkedIn community.