Out of Office: Stories to Guide Success for Remote Work — Ryan Rogers
Remote work unexpectedly became standard in 2020. While working remotely can be empowering and productive, without the right infrastructure or approach, it can also be terrible. These interviews explore individual remote work experiences in the hopes that through sharing what works and what doesn’t you can find new ideas to try out for yourself or your team.
Ryan Rogers (He/She/They) is a standup comedian and creative director with a specialty in copywriting, who lives in New Orleans. He has had several remote roles, including a decade+ relationship with a creative agency in Texas, and more recently as an associate creative director for Pandora and Creative Director at Chegg.
Topics we explore:
- Advantages of controlling your work environment through remote work
- Importance of clear communication to build successful remote working relationships
- Establishing boundaries and prioritizing time off prevent burnout
- Mental health and remote working
“I’ve had to learn some hard lessons in the last year because I’ve worked with companies who don’t have the infrastructure to manage remote work. And they just kind of learned as they went. And I found that very difficult. As opposed to the ones that I’ve worked with forever, remotely.”
At the start of the covid pandemic, Ryan moved back to New Orleans, transitioning into a remote role with Pandora before taking a job at Chegg to be their first remote creative team member. Today Ryan is splitting his time between freelance creative director/copywriter and standup comedian and says “I’m the happiest I’ve ever been.”
With your experience of in-person, remote, and freelance creative roles, what’s a way working remotely really clicked for you?
“A lot of companies will work in Google-Suite, working in collaborative cloud docs. It’s so much easier, than the War Room, right? You get everything down, tag people in Slack or whatever, ‘hey, take a look at what I did’. They respond in real time, things just get done quicker. I think that version of collaboration is so much more helpful and so much more efficient. And it’s all already captured. You don’t have to go through that 1980/90s style of ‘Oh, it’s in the War Room. Now we’re going to take pictures, now someone’s going to transcribe it’. You skip all of that. I’ve already got the best of my ideas down. You tell me what you think. And you collaborate. Now we can actually build the deck from this and get it ready for pitch. It’s just so much more streamlined.
Every creative agency I’ve ever worked at has had a form of open floor plan. I find them incredibly distracting which is hard with high-stress work. How does control over your environment impact your ability to do your job?
I find remote work for creative to be so much easier because the way I work is I like to do a brain dump, have alone time, do it in a space that’s comfortable for me… I think there’s so much value in being in a safe space to do it. And the office at a desk or a conference room is bottom of the totem pole for a lot of us.
Now if I have 30 minutes here to knock out taglines, I can go to a coffee shop to do that. Or I have a little porch right here, I know I can step out in my leggings or whatever, with my coffee and just like go. I feel less pressure on myself to develop creative ideas within the scope of a workday if I make sure that I have time to play in the sandbox.
I keep thinking about the most distilled form of a creative, let’s say a painter. You wouldn’t give that painter constraints in order to get their best work. You wouldn’t say ‘you have to do it in this space, please do this work in this space’. No, you have to give them free rein to develop ideas and actually channel inspiration.
In in-person work, you have these physical cues and casual interactions to understand and connect with people. How has that been working remotely for you?
I came into a company, I was the first remote hire on their creative team, they were very excited about that, I was very excited about that. The big drawback was, I didn’t get to know these people. And I left the company not having really known them after nine months. It just kind of sucked because the power dynamics were pretty rigid, because me as the only remote worker, I didn’t get the opportunity to know these people outside the office over a beer or a coffee or whatever.
Everything was extremely businesslike all the time. And anytime that there was criticism, feedback, critique, it could be taken the wrong way.
I wish we would have done some early exercises about communication style, the way we received feedback, setting boundaries, all important stuff that we never did. And I hope they learned some lessons there, because we left with no hard feelings, but it was just one of those things where we all could have done a lot better to make sure that this is a successful working relationship.
Relationships take time to build, but successful remote relationships require investing early in understanding communication styles and preferences. I find communicating clear boundaries and establishing accountability essential, what has your experience been?
I would not recommend long-distance relationships unless you have a very clear and very accountable communication cadence setup.
My husband and I went long-distance after a month of knowing each other. So we didn’t know each other’s communication styles when we started this crazy journey, and thankfully, it worked out and we got hitched four years later. But you don’t have the opportunity to learn as you go along, you just don’t, especially in a business setting. You kind of have to know, at least triggers and boundaries and things like that upfront.
If it’s day to day 40 hours plus a week, embedded, real full-time remote work set those expectations early and hold people accountable. You have to let people know, ‘guys, this was something that I raised early on, I tried to kind of uphold it. I don’t think it’s being met’. And just kind of be that person. It’s tough. You have to overcommunicate because you don’t have the freedom to take this person outside of a conference room and have a quick chat.
Even with direct reports you still need to be very clear about how you like to receive feedback. I learned the hard way that I had to ask those questions interviewing potential candidates. I didn’t ask a lot of the traditional interview questions, I asked more about ‘how do you like to receive feedback?’ ‘What’s an instance of you reacting negatively to feedback? How did you manage that?’ I wanted to know that because it’s all communication, you’re basically in a long-distance relationship.
Remote work becoming widespread has smashed through the wall that many businesses maintained separating work and personal. I believe there’s a real opportunity here for companies to retain people longer with this exposure to “whole-person”, would you agree?
As a creative, I’m someone that has to bring my personality into the workplace, I can’t be like a lot of people I’ve met, I have to be a big personality. And as a queer person, I have to show up in the workplace as a queer person, and be this person all the time. So I don’t really have the privilege or the benefit, because of the way my brain is wired, to not be ‘whole person’.
And I’m able to be that person unapologetically and really transparently. And it’s helpful. For those people who do have passions outside of the office, outside of whatever their role is, I would highly recommend you lean into that.
Because now you can’t hide your children or your dogs, I mean you can try or you could, but why do that vs be more of an interesting person. People want to work with people they like, and they want to work with people who are passionate and have a life outside of work. I know I do.
The pandemic has also been extremely difficult on mental health and burnout. The “we have a hotline to support mental health benefit” doesn’t give the personal investment people need. Can you share some of your journey with this?
I was diagnosed a little over a year ago, major recurrent depression disorder, which I didn’t really know or treat… I got to the point before I left [Chegg], where I would put on a hoodie on the morning, lay in bed with a hoodie on, on my phone until I had a Zoom meeting, take the hoodie off, do the Zoom meeting, get back in bed, it’s all I had. It was bad. It was a rough, rough patch. And what I wish I would have done better is ask for time off. I needed time off.
I went straight from one job to another to another to another, constant state of change for 15 years. And I’m 33, I’ve been doing this since I was a teenager and I’ve never taken a break. Never. And I got to that [breaking] point, especially with COVID.
It was incredibly uncomfortable for me to ask for time off. I even went to HR and asked about what kind of policy I could get for a mental health break and they told me what was available and it was attractive. And I was like ‘I can’t leave the company high and dry during this rebrand’. They would have been fine without me for a little while. They existed long before I got there.
That should be a big red flag for any manager or HR, if an employee is asking, most likely they need it. Don’t let that drop off your radar. More than ever, PTO isn’t something that should be apologetic or create a burden.
It used to be a badge of honor to not take your PTO.
I thought it was so notable for me to leave work, eat something, go for a run, and come back to the office. My creative director did it at the same office. And [now] the world, I believe, is shifting or has shifted so that taking time off is a good thing. I’m still kind of on my sabbatical now. Do I have the crazy benefits and income that I did at Chegg? Hell no, however I’m the happiest I’ve ever been. I have the privilege to have some money saved up to be able to do this, not forever, but for a little while. I didn’t think it would be this long, but honestly, I don’t want it to end. I’m firing on all cylinders and when I have to come to the table for creative jobs, I’m the best version of myself.
[The agency in Texas] It’s been so successful because I was able to just be like, ‘I’m gonna put all of my crazy shit on Instagram. You’re gonna see exactly who I am. I’m not going to edit it’. I’m going to say ‘no’ to deadlines and then somewhere inside me, I retreated. And now I learned the hard way that you have to figure the mental health stuff out, or else you’re going to suffer more than everyone else, but you’re going to put them in a bad place too, because they’re your employer.
Wellness and mental health are not linear. Sometimes, I’m going to have off days too. I’m going to work sometimes, sometimes I’m going to need to shut the computer down and get in the car. I had to do this once, I shut my computer down, got in the car and I drove to Bay St. Louis, Mississippi and sat on the beach for a day. Literally, I was like ‘I have burned myself out. They’re not getting good work. I have done a bad job about boundaries. They don’t have the infrastructure to deal with me as a remote worker. I’m out’. And I put everyone in a bad situation.
And no, it should never come to that, but people should have the wherewithal to be really transparent about what their needs are with remote. Because like I said, you don’t know that person. You don’t know them outside of the Zoom calls. So you have to be as transparent and as authentic with your needs as humanly possible.
Where did mixing your ‘whole-person’ with the autonomy and control you have working remote lead you?
We’ve had a tough year, like we went to buy a house and it fell through. We had a lot of personal challenges outside of work, being candid, I wanted to work more on my mental health. I’m in addiction recovery as well and have been for quite some time. And I think all of those things kind of culminated in me getting let go from Chegg, and it forced me[to ask] ‘what do you really want to do now? You can easily get another job just like this. There’s recruiters knocking on your LinkedIn right now. Just get another one. It’ll pay good. You’ll get to do a lot of the same. You’ll probably burn out in a year and you’ll go somewhere else.’
But I really thought hard about what I wanted to do. And I went to an open mic one night, and I just watched the show and I was like, I could do this and probably better. And I did. I started the next day. I wrote a set that night, went up on stage the next day, and I’ve been doing it full time for seven months. I go up on stage every single night. I run my own show now. I’m touring this year, it’s going very well.
I just feel like there’s so much of an opportunity right now with remote work to make it a more pleasurable experience. Because at the end of the day, a lot of creatives don’t want to go to the meeting, they don’t want to get on Zoom, like leave me alone. Let me just write, let me just design. You can make it more pleasant and [let them] know that they are in a safe space to build and be heard. As that’s key. I’m assuming fatigue is extremely real for everyone, creatives especially, you will burn people out immediately. You have to be protective of people’s time. And you have to be protective of them saying no, that has to be a viable option for them.
This piece was edited down from its original interview by Jenna Hasenkampf and approved by Ryan Rogers prior to publication.
Ryan Rogers (He/She/They) is a New Orleans-based comedian & writer who’s performed across the US & Mexico. A proud member of the LGBTQIA+ community, Ryan uses his queer experience to create side-splitting humor about identity, sex, sobriety & gender relationships.
Experience Ryan’s comedy and see his upcoming show schedule here.
Check out Ryan’s creative portfolio and inquire about services here.
Jenna Hasenkampf (She/Her) is (currently) a Massachusetts-based writer, Mom, and Managing Director for MKG Marketing, a remote digital marketing agency. She’s worked in in-person creative agencies in San Francisco and New Orleans and is now all about that Remote life.
If you’re interested in sharing your experience with remote work or leading a remote team please reach out.
