The Remote Show

Show Notes:

Darcy's links:



TaxJar a Stripe Company website

Referenced materials:

Chip Conley

Eudaimonic wellbeing

Meaningful Work Lab


Tyler Sellhorn (00:02):
Hello, everyone. My name is Tyler Sellhorn, and welcome to another episode of The Remote Show, where we discuss everything to do with remote work with the people who know it best. Thanks so much for listening. The Remote Show is brought to you by We Work Remotely, the largest community of remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire. Today, we are blessed to be learning out loud with Darcy Boles. Darcy is the director of culture and innovation at TaxJar, a Stripe company. She's a people person, dog person, an avid lover and student of what drives people to truly live the life they want to live. She's passionate about eudaemonic wellbeing, and building a strong company culture with a heart of shared values. So Darcy, tell us about these past four years that you've been building a truly awesome remote culture at TaxJar.
Darcy Boles (00:54):
Oh my gosh. Tyler, thank you so much for having me. I'm stoked to be here, coming to you from San Diego, California. Yeah, it's been amazing, so I'll start with a little bit of my journey. I worked in the hospitality industry for a really long time, and I have always been kind of an avid lover of hosting and creating an experience of belonging and just an experience that kind of works for everybody, and especially with a focus on autonomy. And obviously, what can we speak more of to an amazing remote culture than having an autonomous remote culture where employees are trusted and they trust one another to get their work done, and you can really design your life around your work, versus your work around your life? That doesn't mean that it's flighty and you're at the beach all the time.
Darcy Boles (01:38):
It just means yeah, I can go pick up my kids. I don't have kids. Or, I can surf in the morning, or I can maybe do something scary, like go to lunch for two hours and make myself a long lunch in the middle of the day. Oh my God. God forbid I would do that. And so that was kind of the impetus for me really looking into the remote world. And building it at TaxJar for the past four years, and recently acquired by Stripe, has just been such an incredible learning experience. I mean, I joined TaxJar... I think it was the beginning of 2018, so this was pre-pandemic. Remote was an other. It was a... Maybe you're working, maybe you're not. It was hard to have people take us seriously for a long time, and we're a really serious company.
Darcy Boles (02:21):
We have an incredible product, we have really smart people, and we're serving incredible customers globally. And there's no reason that we can't be doing that from places that really serve us as human beings. So our eudaemonic wellbeing is allowing us to be able to do the best work of our careers in the place that works for us. So that's a little kind of high-level view of what it's been like. And I would say so much learning has happened. I mean, in remote, there's just a magical thing that happens, because you're able to hire so many different people with different belief systems and different experiences around the world, around the states, wherever you might hire from. But it's those shared values that really hold the glue together, and the trust is the glue that binds that team. And that has been just so incredible to watch develop who really thrives in that environment and certain cultures, and who doesn't.
Tyler Sellhorn (03:19):
So fun to hear you pulling forward those lessons that you learned in earlier career experiences into this remote space. You mentioned hosting and producing a feeling of belonging, and imbuing a sense of autonomy, and not just a sense, but really delegating the authority of autonomy to others and giving trust. I guess maybe the thing that I'd like to pull out of your opening statement there is just to kind of say... What does it look like for you on a day-to-day basis to build your work around your life, rather than the other way around?
Darcy Boles (03:55):
Yeah. I mean, I will say still after almost four years, is it is still, in some ways, a daily challenge to give myself the value of permission. And I think a lot of us struggle with that. And it's something I hear from new employees, veteran remote employees, people who are just exploring the remote workforce. But what it looks like for me is being incredibly intentional and accountable to myself around putting a two-hour block on my calendar of yoga or surfing in a time that obviously I don't have scheduled meetings or I don't need to be accountable with my team during that time, and sticking to it. And not just staying tied to my computer because I'm at home, or there's one more thing to do. There really is that deep, deep sense of self-permission that I think comes with time.
Darcy Boles (04:53):
It really comes with time and assimilation into a fully-remote environment. That's a real thing. When I talk to newer and employees who join TaxJar, now a Stripe company, I'll say, "What's your biggest piece of advice as a new employee?" And I'm always like, "Give yourself the permission to start learning how you work best." It could take six months for somebody to even give themselves permission to go on a bike ride at 10:00 AM. But once they do and maybe go a few times, you almost start getting into a rhythm, and you actually have to test yourself.
Darcy Boles (05:28):
I have learned, at least for myself., well maybe, I'd work really well from this coffee shop. Or I've learned a lot about traveling while working remotely. I know I have to give myself two full days to get settled. So I will fly somewhere on a Saturday, so I least have Sunday. And maybe I'll take Monday off to get fully settled so I know my internet's good, I have all my stuff with me. It's not just go fly to wherever, or go on a bike ride here or there. You actually have to take the time to design your life around your work. And it takes energy, it takes thought, and takes practice.
Tyler Sellhorn (06:04):
Thanks for going deep on that. I know for myself, I'm a dad, and there are parts of the day that I'm needed by my family. And those things are on my work calendar.
Darcy Boles (06:16):
Yes. Yes, exactly. And communicating that to your team. I think that's the other piece of this, is clear communication. Also, clear communication only comes with set expectations, and those two things go hand in hand. If I have a crazy week or something, a product release or something massive that's coming up, I know that I might not be able to be as flexible, and so I then communicate that to my friends and family or my travel plans or whatever that might be. So again, it all is kind of this living, breathing ecosystem, but communication is at its core.
Tyler Sellhorn (06:49):
Really great. Okay, you mentioned having joined TaxJar in the pre-pandemic days. It's always exciting for myself as a 2019 " remoter," as I call us-
Darcy Boles (07:01):
I know.
Tyler Sellhorn (07:03):
... to kind of think about that zoomed-out sort of view of the different epochs, time periods of what we're doing here. Give us kind of the compare and contrast of 2019 and before remote, then this moment that we're kind of still sort of in of the pandemic, and then look ahead for us and what you think might be in the future. Do that compare and contrast for us. 2019, right now, and 2022 and beyond.
Darcy Boles (07:28):
Great question. So I would say I have this deep affection for you, Tyler, and all our fellow 2019 remoters who were all kind of building and helping to build these fully remote companies. There were very few of us. I mean, I would say at the time, 25 of us maybe, maybe 30. And I'm sure there are other people out there, of course, and so I'm sure I'm forgetting people. But there was kind of this small group of people where I remember reaching out to certain CEOs of other remote companies and be like, "How did you deal with this issue?" And they'd be like, "How did you deal with this issue?" And none of us had competing products, and there was this deep, deep-
Darcy Boles (08:03):
... deal with this issue. None of us had competing products. There was this deep, deep sense of knowledge sharing and all being on the same plane of, we're trying to create a different operating rhythm in the workplace, a different way to look at work, and looking at the people behind the product. How do we look at this holistically?
Darcy Boles (08:18):
I think that was a massive theme that was, in 2019, shunned, frankly, by a lot of companies and shunned by a lot of CEOs. I don't think it was shunned because people didn't want to do it, I think that they just hadn't had either an experience in the past that had brought them to their knees that really made them want to do it, they hadn't been in a personal situation that they'd realized that it could work. The pandemic almost shined this light on that 2019 remote crew, and was like, "Oh, my God. This actually might work. Hold on. Let me just think differently about it."
Darcy Boles (09:03):
I think that moves us into that 2020 and now 2021, where people's brains ... It's actually neuroplasticity, where people are starting to practice, and starting to realize and think differently, and, frankly, I believe at a higher level of consciousness, that, "Oh, my gosh. Wow. What if we do focus on eudemonic wellbeing? What if we do actually, frankly, do the hard work to sunset some of our Industrial Revolution policies and look forward into creating a better world for our customers, for our people, for our product?" Creating more of that stakeholder mindset and that win-win situation for everybody.
Darcy Boles (09:48):
I think right now we're in a fuzzy period. I think a lot of companies are going to struggle quite a bit when they choose to go back to the office or choose to do hybrid, but I also don't think that that's a bad thing. I think it's a whole learning process, and the companies that haven't been fully remote or are unwilling to ... It's kind of like teaching a toddler to walk. We're going to all get through it, and we're going to get through it through knowledge sharing.
Darcy Boles (10:14):
Certain companies are going to learn that it works really well for them, and certain companies are going to learn that it doesn't work for them, and that's okay. I think that's the onus on the leadership teams and holistically on teams to decide, "How does this serve our customers? How does this serve our employees? How does this holistically serve the future of the business?"
Tyler Sellhorn (10:34):
Really cool. I think, even for those that are going to remain in the office-first team, this moment of remote, shout out to [Darren 00:10:45], and [Sid 00:10:47], and [Matt 00:10:47], and all those guys and gals, and all the different folks that have been leading the way for us here when we had this suddenly remote moment. Just that there is a forcing function, as Darren says, to being intentional, even those that are going to choose to go back to the office. Because we're remote right now, you have to decide. That's what you just said, right?
Darcy Boles (11:09):
Tyler Sellhorn (11:09):
I agree wholeheartedly that that's what's going to be required of organizations.
Tyler Sellhorn (11:13):
Okay. I love this word, and you've said it a couple of times now, so you have to unpack it a bit. Eudemonic wellbeing.
Darcy Boles (11:20):
Tyler Sellhorn (11:20):
What does that mean to you?
Darcy Boles (11:24):
Eudemonic wellbeing is basically a Greek philosophy surrounding fulfillment of life and meaning. The difference between eudemania and happiness is actually pain, and it's okay to have pain. Eudemonic wellbeing is the holistic view and the holistic feeling and meaning that we feel when we're doing things that we love.
Darcy Boles (11:48):
But we're also going through the wave that is life. Being able to be in the flow of our zone of genius, but also be okay with a lot of the things that we cannot control. Learning how to live in that space, that space of eudemania, that space of fulfillment, not just happiness or sadness.
Tyler Sellhorn (12:10):
Okay. What I'm hearing you say, when you say eudemonic wellbeing, you're saying we're going to take on the full experience of what it's like to work at TaxJar, or to be in the world at all. Embrace all of it, and receive it as something that we can pursue fulfillment out of. Not only happiness, or only joy, but also sadness, but also pain. That those things ... You don't get to have one side of that coin without the other.
Darcy Boles (12:50):
Exactly. You don't get to have one side of that coin without the other. I think also I'll touch a little bit on self-determination theory, which is really how ... My mentor has taught me ... Amazing mentor. She's the CEO of a company called Meaningful Work Labs. Done a lot of work together. She really taught me about self-determination theory.
Darcy Boles (13:09):
We've been building at TaxJar for the last four years around three pillars. Those three psychological pillars are the need for autonomy, the need for belonging, and the need for mastery or competency in what you do for a living. You got to feel like you're getting better at something.
Darcy Boles (13:28):
Of course we want to create better products. Of course we want to feel like we belong. Of course we want to have autonomy. That sounds very simple, but if you look at a culture and designing it around those three things, that can also be parallel to how you're looking at eudemonic wellbeing. You can have autonomy, but you can still be sad and you can still be happy. Autonomy puts you in that middle place of being able to navigate that. That makes sense?
Tyler Sellhorn (13:51):
Yes. What I'm hearing you say is that one of the requirements of eudemonic wellbeing is agency.
Darcy Boles (13:59):
Yeah. For sure.
Tyler Sellhorn (14:01):
We have to take charge of our situation. Organizations like TaxJar, organizations like Yac, my day job, we're inviting people to be a part of this shared project that we're working on together. It's up to that individual to decide, "Okay. Yes. I am going to be a part of that today, and every day," or not. The power rests in the individual. That's what we're saying, is that autonomy, belonging, and mastery can be designed in the workplace, but to take it on for oneself is up to that individual.
Darcy Boles (14:35):
It's up to that individual, but it's also, from a design standpoint, if an organization, let's say, is designed to have super micromanagy principles, it's going to be much more difficult for that individual to take on those three pillars because the permission isn't granted for them to be there.
Darcy Boles (14:52):
That's actually something I always encourage job seekers to dig into in their interviews, is, really, ask about what the culture is like. How much autonomy do you have? How can you best thrive in this organization? Because, again, not all cultures are made for all people. There's very different organizations for very different people. It all depends on knowing yourself, knowing what makes you happy, but knowing that, and I want to just really harp on this, we all share those three psychological needs of autonomy, belonging, and mastery.
Darcy Boles (15:29):
When you're looking for a job, for all the job seekers out there, really start thinking about that, what those things mean to you. Where do you want to have mastery? Because that'll really help you to decide what role you're looking for. How much autonomy do you really want? Some people actually need somebody checking in on them a little bit more. Where is it that's going to make you feel like you really belong?
Tyler Sellhorn (15:50):
Yeah. We need intention as individuals choosing to seek out jobs. What kind of job do we want? Make it the one that fits you, and do your due diligence as well to find out whether it's the right fit for you. Okay.
Tyler Sellhorn (16:03):
To find out whether it's the right fit for you. Okay, one of the questions that I love to ask remote leaders is, how do remote companies demonstrate and show that they are offering an opportunity for autonomy, belonging, and mastery in their remote workplace? How do we communicate that in a way that can be received by a job candidate? That, oh this is the type of organization that I want to be at? What are those signals that we as job seekers can look and find about jobs that we're seeking? What are those questions that you tell job seekers to ask?
Darcy Boles (16:35):
Yeah, absolutely. So I would say first off it starts with employer brand and public facing materials. So I was so excited when the Stripe acquisition happened because there is actually, on the engineering blog on Stripe, there's an engineering remote hub. And it was so cool to read that story. So I think storytelling is huge, storytelling through blogs, storytelling through employer brand. Checkout all of the jobs pages, dig in, see if there's any social media pages and try to understand what the way of life in that company is. It really does come back to the job descriptions and it comes back to saying, "Here is exactly what's going to be expected of you. And here's what we're going to give to you in relation to that." So really we're looking at it or I'd be looking at it as a job seeker as, what is my mutual value proposition? What is the mutual value proposition of the company to me?
Darcy Boles (17:32):
So that is definitely a question I would be asking companies if you are interviewing for roles right now is, what are the expectations of me in this role specifically remotely and looking at asynchronous communication and autonomy? And in return, what am I going to receive from the company and how is this a two way street? And how are we building this together? Because the energy that I put in and the energy that the company puts in, that when equalizes is magical, it's magical.
Darcy Boles (18:04):
But again, it takes intention. And so being really intentional as a hiring manager in writing job descriptions, that actually line out the expectations and write down the culture. So, so many cultures out there are not written down. It's like, "Oh, the culture is great. Or the culture sucks." Or whatever, but write it down. What are the expectations of human behavior? Again, my mentor has... This will stay with me forever, words, make worlds. They really do. And in a remote environment, word choice and crafting language that encompasses the feeling of the culture and behavior of expectations is a skillset. But it is something every company needs to invest in and to start codifying.
Tyler Sellhorn (18:54):
Yeah. I've started sharing this joke with remote friends, if you're a country music fan, like I am, George Strait is one of the, turns out, one of the patron saints of remote work. Because he said, "Baby, write this down." Okay. For any of you out there that are country music fans you'll laugh along with me. Or you can just laugh at me because I told that joke. Okay so let's flip that around. So you're a job seeker, how can I communicate myself as ready for a legitimately remote job? How do I say yes Tax Jar, I am ready to be an awesome part of your shared values. I'm ready to be a part of this organization that has all kinds of different people in it. I'm really interested in being given permission to do the life building, in addition to the working at Tax Jar, how do I say that?
Darcy Boles (19:49):
Authenticity. I think authenticity is huge. We've all worked in organizations where our coworkers may or may not have been authentic and the ones who are the ones we tend to gel with generally a little bit more. So I think authenticity is huge. I think in order to be able to really showcase yourself in an authentic way though as well, research comes before that. So researching everything that the company has publicly available. Try to see if you have any connections on LinkedIn or first degree, second degree connections, connect with them. See if you can just pick their brain, if they're willing. To understand more about how the culture works and then reflect that back on yourself.
Darcy Boles (20:35):
And then you're able to have the information to then be able to write a cover letter or apply to a role of saying, one my skill set fits the role because that's a requirement, we can't forget that, that's 50% of the job right there. Making sure your skillset fits and then looking at yourself and saying, "Here's where I see my personal values align. Here's how I see myself actually making this company better as a part of the team." I don't want to hear, at least if I'm a hiring manager, all of the things you've done in the past. That's great. What I want to know is how are you going to take those skills and the values that you share and how are you going to make this company better that you're applying to? Because that's really the key.
Tyler Sellhorn (21:21):
Yeah. Well, I want to say thank you to you Darcy back in early 2019, when I was on my remote sojourn walkabout, you answered a cold invite on LinkedIn to say, "Yes, I will connect with you Tyler Sellhorn teacher of algebra to 12 year olds looking for a remote job. Yeah I'll say what's up." And I'm so grateful for you and others that have been learning out loud as we're working on this thing together. It's really great.
Tyler Sellhorn (21:49):
Okay so you mentioned shared values again, and I'm curious, what is it about codifying those value systems, codifying that culture? You said, words make worlds, right? You, you quoted your mentor on that. And can you go deep on that? How do we, even in a virtual environment, even in a remote team, how do we build that together?
Darcy Boles (22:12):
Yeah. It is a hard, interesting, fascinating, and important process that takes delicacy, time and body. And this might sound fluffy, but it's not. It's actually really serious, is it is a translation of collective feeling and culture at its core is the collective consciousness of what a group of people says, feels, thinks and does. You're always going to have subcultures. You're always going to have some people, especially in larger companies, that it's not a match and they're there to get their job done. Look, it's a reality. It's okay. It's okay. And I think we forget that that's okay. But in order to really scale culture, we've got to take the time to spend on codifying operating principles or values. So then we're able to understand how the environment operates. Write those down, so the more that company grows and the further that company gets away from the founders, from that core group of people, those feelings and expectations are translated in employer brand and on day one of onboarding.
Darcy Boles (23:31):
So you get into an environment where you know that if the culture works this way, that it's safe to walk away from your computer for a few hours. That it's safe to speak up. You have to tell me in onboarding that it's safe to do those things, or I'm going to assume that it's not safe because so many of us have had terrible work experiences. So writing down that culture of expectations is essential to the success of that employee that you just hired.
Tyler Sellhorn (24:02):
Yeah. We have to tell ourselves, we have to tell each other, and we have to tell candidates, we have to tell new people. What it is, how it is that we work together.
Darcy Boles (24:15):
Yes. We have to. You can't assume it, specifically in remote. Because I will never forget Tyler. This is a story that I will probably tell for the rest of my life. When I first started at TaxJar, I remember having an employee come to me via ping and saying, " Hey, is it okay? What do I need to do if I need to go to the bathroom in the middle of the day?" And I said, "Oh my God, this is the moment. This is the moment where we forget." Again, we're hiring remotely from all different walks of life, from organizations where there may have been very theory-strict rules in place, punch in and punch out. We're still living a lot in the world of work in the industrial revolution that way of working. And that is not at the fault of the employee. We have an opportunity working remotely and building newer companies in this newer age of being able to never, never assume and always assume good intent.
Darcy Boles (25:11):
And so writing those things down, it might sound so simple. Of course, you can go to the bathroom, you can go watch a movie for all I care in the middle of the day as long as you get your work done. It doesn't matter to me. But some individuals don't know that unless you tell them and you have to unlock, I call it unlocking the value of permission.
Tyler Sellhorn (25:31):
Yeah. Unlocking the value of permission. And just like you were saying earlier, permission to oneself to put it on your work calendar, the things that are going to help you be your best.
Darcy Boles (25:44):
Be your best. Because you are hired to do probably a pretty hard job. We're not building baby toys at TaxJar Stripe company. It's a hard product and we're all collectively working together. And I want to be my best self when I'm there for my team. I want the head space to be able to work on really hard problems. And sometimes that means, yeah, putting certain things on my calendar, in support of that.
Tyler Sellhorn (26:10):
Yeah. No judgment to anyone who is in a baby toy manufacturing.
Darcy Boles (26:14):
I'm sorry. No judgment. There's absolutely no judgment. And I'm sure some of it is incredibly difficult.
Tyler Sellhorn (26:20):
Well, I don't know, just as a dad, I'm grateful to the hard work that baby toy manufacturers have put in. Okay. I want to talk about collective feeling. And I want to zoom out past TaxJar. So I'm going to ask this question. So when you're thinking about what's next. Let's think 2022 and beyond. What is the collective feeling that you'd hope for us to be building as a remote culture broadly. We've expanded the tent, there's a whole bunch more folks here with us. It's not 2019 anymore in the remote work world. What is the collective feeling you'd like for us to build towards together?
Darcy Boles (26:59):
Good question. At the core of kind of the future of remote, I hope we're building a healthier and more sustainable community and world for everyone. And I think that starts at the individual level. So I'll use an example. Since I've started working remotely, now my local coffee shop knows my name. I put more money into my local community. I go to my community garden and water in the morning. I'm able to connect so much deeper with the physical space that I live versus commuting. That's one kind of more macro level that I think I'd love to see. A larger level that I'd like to see. I'd like to see us tackle climate change. I'd like to see us tackle understanding of different cultures because we're working so broadly with our global teams remotely.
Darcy Boles (27:53):
And I think that, that's an underlying thing that we'll start to see come up is when we're working on global teams, which a lot of us have already done. But not really in this true remote capacity, is the belonging piece that I mentioned before of a deeper understanding of how different cultures actually experience one another on Zoom. Share different tactics of how their cultures approach problems. And start to have a much larger shared consciousness and understanding and feeling of one another's experience in the world and in support of that build products that better society.
Tyler Sellhorn (28:34):
I am here for it. Let's continue to be working and building towards a sustainable remote working future together. Darcy, I'm so thankful for all the things that you've done in the service of that already. And I'm excited to be continuing on together.
Darcy Boles (28:48):
I'm so stoked.
Tyler Sellhorn (28:50):
Blessings, thank you for coming today.
Darcy Boles (28:51):
Thank you so much, Tyler.
Tyler Sellhorn (28:54):
Thanks so much again for listening to the show and be sure to check out, weworkremotely.com for the latest remote jobs. And if you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do so. As always, if you have someone we should talk to, any advice you have, or if you'd like to advertise on the podcast, please reach out to us at [email protected], that's [email protected]. Thanks so much for listening and we'll talk to you next time. 

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