Erin Sharp - Part 1 / Spouse of Remote Worker

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Jonathan This is episode three, with part one with our special guest, my wife, Erin Sharp.

Ari Now, this episode is sponsored by Cultivate Now. Cultivate Now cares about remote work and helping distributed teams thrive and individuals succeed with a remote career. To learn more, visit

Jonathan Welcome, Ari.

Ari How are you doing, Jonathan?

Jonathan I am doing well. So, this episode is a lot of fun for me because I had a chance to sit down with my wife and talk about remote work. And I have my perceptions of how it goes and she has her perceptions on how she experiences it, and they don’t always line up, so it was very insightful for me.

Ari It’s always good to see how the other half deals with the unique position of remote work.

Jonathan It really is. And so it’s been a lot of fun and I was proud of my wife for being willing to sit down and do that. And so we’ll go ahead and play the interview now and then come back after the first half of it is completed.


Jonathan Welcome! I’m Jonathan Sharp and I’m here with my wife, Erin.

Erin Hello, everyone!

Jonathan And our three dogs are over on the couch, lounging. And so a little bit of background about ourselves, us together: We’ve been married for 11 years and, of that, eight of those years I have worked remote, worked from home. And we’ve worked in a number of different places, but at that time I was working in a corporate job, in the cube farm. You were... You were...

Erin Very pregnant.

Jonathan You were very pregnant, yes.

Erin Yeah.

Jonathan That’s a key fact.

Erin [Laughs]

Jonathan And one day I kind of came to you and said, “Hey, what do you think about if I worked from home?” And, really, the motivation behind me asking that was I wanted to be closer to our family. This was going to be a big change for us. We were about ready to be new parents and we talked about it a bit, and what did you say?

Erin Well, being asked what I thought of you working from home would’ve been similar to being asked: “What would you think if we were to move to Mars?” I mean, I couldn’t formulate an opinion. Really, I had nothing to base my understanding or knowledge of a husband coming home and working from home. So, I was excited and clueless.

Jonathan [Laughs] And at that time, did you know anyone else—like, any of our friends or acquaintances or anyone else—that was working from home, really?

Erin Um, I’m thinking, and I really can’t recall anyone.

Jonathan Yeah. At that time, I knew two other people that I had worked with in the past—I work in the tech industry—and they had transitioned to remote jobs. But up until that point, I really hadn’t heard of many people at all working remote from home in a full-time capacity. It was...

Erin Right, dedicated to home, you know.

Jonathan Yeah.

Erin I mean, every once in a while you’d hear a story about, like, let’s say a wife was really ill and there was kids at home, and the husband would come home and work from home while he helped his wife take care of the house and the kids for, like, a day, but nothing long term.

Jonathan Yeah, yeah. It was definitely not the normal, default situation...

Erin Correct.

Jonathan ...of what that was like. So, for us, we decided, you know, I want to work from home. It would be a good thing for our family. Our daughter was born two weeks later. I went into work and I turned in my letter of resignation. I wish you had been there to see the look on my boss’ face because he was always up for joking and that type of thing, and I handed him my letter and he looked at it and he thought it was a total joke, and so he laughed at me. He’s like, “Oh, that was a good one.” And I said, “No, I’m serious. I’m resigning.” And then he goes, “Oh. Didn’t you just have a baby?” [Chuckles] I was like, “Yes, we do!”

Erin [Chuckles] “We sure did!”

Jonathan So, it may have been feasible to write it off as sleep deprivation or something at that point, but that was what we were committing to. And three weeks later, I walked out of work, out of that job for the last time. And my assumptions and thoughts of working from home was that this was going to be great, this was going to be an empowering thing, that you, Erin, my wife, had the same assumptions of what I needed to do for work, and that it was just going to be that romanticism that creeps up about the topic usually. And that was kind of not the case at first, I think. And we’ll get into kind of more the what I mapped out as four seasons of a remote journey, but there’s this ideal of what it’s like, and then there’s reality, and we’ve experienced a lot of that. So, over the past eight years, there really have kind of been four seasons to working remote for me, and the first one was really in a freelance capacity. So, what that means is I was doing a lot of project-based work. I had a number of clients, a number of projects going on at the same time, and not a real steady, predictable source of income. There’s a lot of variability in that. And then there was a period of about a year...about nine months, I would say, where I worked on-site for a contract, and that was a period of a lot of stability. So, I kind of jumped back into the on-site world for a bit. And then there was a period where I was really an entrepreneur and started a company with another developer, and that was about two and a half, three years in length. And then more recently, since exiting that venture, I’ve been a full-time contractor, and so that’s been basically one client at a time in a full-time or close to full-time capacity, and a lot more predictability and stability with that. So, of those four seasons, the first one, when I left my corporate job, was really freelancing. And what did...what were your thoughts about that period of time?

Erin It felt a lot like going out and looking for food in a place that we weren’t familiar with, to me, in a sense that there was no direct path of “this is how this will work and this is when it will work and this is how long it will work for”, and so it felt a little bit lost. I think another key part of that was how much others’ take on what we were deciding to do in our professional lives played a role into how we felt about it. I think, at least in our families, we were pioneering the idea of someone working from home, at least the man of the house working from home, and there was a lot of apprehension from close friends and family. And while we all like to be in the mindset of “I’m independent and I don’t need the approval of others”, it does affect our way of thinking if the people who are close to us are questioning our decisions as far as what we’re doing and what we’re pursuing professionally in our jobs.

Jonathan Yeah.

Erin So, that little bit of lost feeling piled on top with the initial family “[Gasps] What are you doing?!” came as a little bit of a surprise to me in the beginning and it really caused me to have a reason to kind of soul search myself and find the strength and the confidence within us and our relationship and our ability to make sound decisions and really own it. And that doesn’t mean that there wasn’t hard days. There certainly was. There certainly is and there will be more, but it was really what we were supposed to do and what we were called to, and it’s been a really great thing for our family.

Jonathan Yeah. Because that first year, I remember when I filed taxes and I had made roughly half of what I had made at my previous job, and I think that was a little bit of a... I was aware of it and we did a really good job of managing the money that we had, but that was a significant pay cut for the approach that we took to this. So, that was kind of the first part of the first season.

Erin It was almost like jumping into cold water.

Jonathan Oh, it definitely was.

Erin Like, you look at it and you’re like, “I can do this! It’s not going to be a big deal.” And then you initially jump in and the shock of it kind of overtakes you a little bit, and so then you got to kind of gather yourself and step forward in confidence.

Jonathan I will never forget that last day that I walked out of that job, and I left and was walking to my car to commute home for the last time, and it was really a surreal experience because it was like, “We really did this. Like, I am not getting paid by them anymore. I don’t have to show up here on Monday again.” But at the same time, for me, it was extremely liberating because I felt like this is... My personality traits and my strengths and really who I am, I felt like this’s connecting with me and what I was looking at with our family. So, after that kind of first year, then I transitioned into a contract on-site for about nine months, and while it was on-site, it was still in the freelancing side of things and contracting side of things, where it was was hourly work and I had a legal entity set up for my business, and the contract that I negotiated was a Corp-to-Corp contract, which means that I managed all my taxes. And so really, this first year-plus, more or less, I was learning how to run a business. And then on the family side of things, we were learning how to be parents.

Erin Yeah. I think that portion of time when you were working more or less out of the home at the job site felt a little bit, looking back in hindsight, like you were getting the hardships of both worlds, both worlds being working out of the home for another business, as well as all the responsibilities and hardships that can come and do come with working for yourself. So, you still had to commute. You still had to play the games that you played, keep bosses happy when they see you face-to-face. You still had to dress up in a certain way. Our cars were still getting the wear and tear from travel and it was still working in traffic and all of that. But at the end of the day, the money that came home was on you. I think one of the biggest things that’s a shocker is most traditional jobs will give you a sick day, a paid sick day or a paid holiday or an insurance package or...

Jonathan Retirement.

Erin All of that stuff. And I guess I just hadn’t thought all the way through it. I just had no way to process all of it all at once. But if you were sick back then and you didn’t go to work, then we just simply didn’t get paid. And the reality of that was incredible. It was heavy and very real. I remember being frustrated at being saddled with all of the responsibilities of being responsible for insurance and, you know, working through some things that maybe a company would give you a break or an option for, but still having to do it out of the home. As a wife and a mom, I was like, wait a minute. I feel like we’re getting the short end of two sticks here.

Jonathan And that’s the thing that, in the situation of freelancing where you’re doing hourly work, if I look back on that early period, the one thing that I got right, I feel, was figuring out what my minimum rate had to be, and that was taking into account taxes and the cost of insurance and vacation time. And what I figured at the time was there’s 2,080 hours in a year roughly, if you’re working 40 hours a week. And I took that number and divided it by half, so around 1,000, and then figured out what I needed to make and really knowing what that is. Because that empowered me to very quickly, when I was evaluating an opportunity, to be like, “Honestly, I can’t go that low on my rate.” There was definitely some periods where there was a hard hustle going on and I was taking whatever work no matter what the rate was. I never told the client that, but you just do what you need to make it happen. But for me, I discovered that, as frustrating as it can be, being self-employed and managing insurance, there’s been one benefit, and that is, as I’ve moved between contracts and that type of thing, our insurance has stayed the same. I know very specifically the cost of insurance and how that impacts our family and have a lot of ownership for it.

Erin Yeah. In that case, it’s been highly educational.

Jonathan Yeah, absolutely. So, after that onsite period, then it was kind of the season of being an entrepreneur, which was a whole new rodeo in and of itself. And myself and another developer started an enterprise consulting company, and we provided development, training, and support services for jQuery, which is a technology used in web development. And we grew from the two of us up to a team of roughly 23 people, and we were a fully distributed company. We were spread out in 15 different states, and I think a lot of the developers that work of course had families, and if you were to add up all of the people, it was roughly 65 people that existed in this organization. And for me, that was a really exciting time. And that didn’t happen overnight. There was a lot of work with that. But one of the things that came out of that, I was working from home again, but there was a lot of travel, and that impacted our family greatly. And what are your thoughts about that with travel and kind of a lot of variation in schedule?

Erin Well, if someone likes routine and predictability, travel can be a rough road to travel. No pun intended. [Laughs]

Jonathan Do you think it’s easier for someone to travel if they commute every day out of the house and they’re kind of always gone? Versus if they work from home and then they travel and they’re really gone.

Erin Yeah. My personality type likes the never doing anything the same way twice, and so for me, I was okay with the changing. That doesn’t mean that there was not hard parts about it. The part that was hard about you leaving came more specifically to my attention as Noel, our daughter, got older, and she had a hard time with the transition. She would struggle two to three days after you left. “I miss Dad. Where’s Dad? Why can’t Dad be here?” And then we get in a routine of just the two of us and we’d be cooking right along, and right about that time, you’d come home, and then that would be another hard transition, because when there’s one person in charge, then that’s the person that is in charge. When another adult comes home and the roles aren’t quite as clearly defined, it’s hard. And just the differences in how the house runs when you’re home or when you’re not home are loud enough that a little girl could notice. It’s not because your bad or your parenting style or your style of being a husband and a provider of the home is bad. It’s just different. And so, when you have someone in the house that struggles with transition and change, that can be really rough.

Jonathan And really, Noel, our daughter, from early on, that first year, I was home all the time. Then there was that period where I was working onsite, but then I was back home again. And at that stage, she was two and a half, three years old, and was really starting to attach quite strongly. And so, her expectation of what is normal is that Dad is home, he’s working.

Erin Yeah. That’s the way life went. She really hasn’t known it any other way.

Jonathan Yeah. So, that season ended and I exited that endeavor, and since then, I’ve been back to full-time contracting. But things have been a little different this time around. I’ve focused on one contract at a time. I have been fortunate to be able to do that. And there’s been fairly limited travel. I do travel a couple times a year, but overall, it’s been pretty consistent. And I guess one other aspect that’s been unique is we moved.

Erin Yeah.

Jonathan So, when we first started working remote, we were living in the Omaha, Nebraska area, and we had been there I guess four years that we were working remote, and in the past four, we’ve now been in Northern Wisconsin in the small town of Three Lakes, where we have how many stoplights?

Erin None.

Jonathan We had to think about that one there.

Erin Right? Stop signs, but no stop lights.

Jonathan We have lots of those. Yes, no stop lights. But it’s a small rural community and it’s where you grew up.

Erin Yep.

Jonathan And you still have family in this area. And in 2013, we felt that we wanted to move back up here. And our daughter was getting to the age where we wanted to be closer to family. We didn’t have any immediate family in the Omaha area. So, how did working remote kind of impact that?

Erin Well, that made it so it was possible. I don’t think we would have been able to move if it hadn’t been that, really, your job wasn’t impacted at all, other than we needed to have you take some time off to make the trip from Plattsmouth, Nebraska to Three Lakes, Wisconsin. It really opened a lot of doors. As long as where we landed, there was internet, we could go anywhere the internet was. So, that’s been a real huge blessing.

Jonathan Yeah. And so, where we’re at... Three Lakes, Wisconsin is not exactly a technology hub, which is my career and profession, there are jobs up here in web development and that type of thing, but they’re kind of few and far between. There’s a few of them. There’s a handful of them. But bringing the job with us has provided a benefit to our local community, because I’m effectively importing income, because the current contract I’m on is based out of Minneapolis. And so, as I work and generate income, we’re now spending that locally in the community, and so that’s benefiting our community greatly. So, let’s talk about logistics now of working from home. So, I am physically at home every day, and over these past eight years, my home office has kind of been in different parts of the house.

Erin It’s kind of a floating office.

Jonathan It’s a floating office. So, we’re in Omaha, Nebraska. We lived in a house that was roughly 1,700 square feet, and my office was down in the basement in one of the kind of spare rooms. It was kind of off in the far corner of the house. And at another time, it was in our third bedroom on the main floor of the house there. And our current house, which is about 1,100 square feet, it’s been in our third bedroom, and it’s a pretty tiny bedroom. It’s about eight by ten feet. But it’s really in the middle of the house. How has the location of the office impacted us working from home and how has that played out?

Erin I think something that is very apparent to me when you started working from home is all of the people that you worked with were basically in our home during the hours you worked, and the hours you worked varied. And so, there was people theoretically in our home at all hours of the day—and night, sometimes—and so, the feeling that people are here and we need to be mindful of that. If there is a deer in the front yard, all of the people that are working with Jonathan that day are very aware because our dogs don’t let many things cross our front yard without alarming the world. Or if our daughter is cruising up and down the hallway between our main living space down the hall to her bedroom, it goes right past Jonathan’s office. And so, he can hear that too. And there are times when that noise and that disruption doesn’t matter, but there are definitely times where it very much does. And so, the knowledge and the adaptability and the grace that is needed as a family, as a whole, not just me as a wife, but it’s also our daughter, in knowing that at any moment, Jonathan may poke his head out of the door and be like, “Guys, I really need it to be quiet right now.” And it really doesn’t matter what we are in the middle of. If Daddy needs it to be quiet, then we need to make it quiet.

Jonathan Yeah. That’s definitely been a challenge. And I don’t think it’s... It’s one that is influenced most, I would say, by the culture of the project that I’m working on. Because when I was working for the enterprise consulting agency that we had, like I said, we had 65 people, which included all the families and kids and everything else, and very often on a call, kids would wander in. And, you know, they wouldn’t always knock on the door. They’d just come on trotting in and saying hi to Dad or Mom. And that was normal, and that was really the culture that we embraced as a company and organization, and it was no big deal. There have been other projects I’ve worked on where that is definitely taboo. You’re expected to keep things as quiet and professional as possible, and you might as well be working in a remote satellite office, and that’s the culture that they want to really broadcast.

Erin And I think, as a family, we can feel that, because you are a little more tense, because you want to make sure that things stay looking and sounding basically like we don’t exist during your work hours. And so, we more or less have to sound and act like we don’t exist. And that can be fine, and sometimes that can be really difficult.

Jonathan Mm-hmm. And that concludes the first half of our interview. The second half will come in the next episode. But what were some of your thoughts, Ari?

Ari Well, it’s always interesting to hear your back-story, not just from your side, but also how your wife saw it with your going through...your timing, for one thing, in deciding to take this adventure and start it out. Just to see her whole perspective on, as you took a lot of different kinds of remote work-type experiences, you did some freelancing, you’ve done contracting, you’ve done working for a company. And so, you’ve kind of had the opportunity to run the gamut of different kinds, and therefore, you’re able to see how the significant other takes the ups and the downs of each of those different experiences.

Jonathan Yeah. And it definitely was interesting for me, hearing her side of the story and looking back, and now even a couple years past some of it, and just seeing how it changes. Because there’s definitely one experience when you’re in that moment, living it out, and another one in retrospective. It’s had its challenges, but overall, I think it’s been a really positive experience.

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