Undoing loneliness as a freelancer

Nearly two-thirds of freelancers say their job makes them feel lonely on a daily basis.

Most of us are working solo, just singing songs to our pets all day. But human interaction is important as a freelancer.

This episode is an open and honest discussion on how to stay connected and beat loneliness as a freelancer.

+ “When you feel like nobody understands who you are and what you do on a day-to-day basis? That in and of itself can be really really lonely and compound that feeling.”—KM

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When you’re working remotely and alone. Without any co-workers or face-to-face working opportunities, it’s common to feel alone. Kaleigh Moore and Michael Keenan discuss their own experiences with loneliness as digital freelancers and how they combat it.

Why are freelancers prone to loneliness?

+ “I don’t think it’s fair to put all of your emotions and thoughts and everything on just one person.”—MK

Kaleigh: Today we are talking about loneliness and how you stay connected when you work from home and there’s nobody around all day except maybe your pets—who don’t talk back, and even though you sing them songs all day long, they’re just pets. So they can’t help you when it comes to human interaction. That’s just not something they bring to the table. 

I’m curious, Michael, you live in Mexico, tell us about how you stay connected as an expat. What do you do? Let’s start there. Tell us what it’s like being a freelancer, living in a different country.

Michael: It feels lonely… I’m so lonely. No, I’m not actually…Sometimes I feel lonely. Okay, where do I even start? 

I’ve been living in Mexico now in Guadalajara for almost four—a little over four years. In the beginning, it was definitely lonely. I worked from home (obviously), and I didn’t know the language.

Fortunately, I moved here with someone who does speak Spanish, so I, at least, had that one person, but I don’t think it’s fair to put all of your emotions and thoughts and everything on just one person. So I tried to chill with the feelings and [trying to] put everything on him. Cuz it’s not his fault I don’t speak Spanish.

So, in the beginning, I didn’t have an office (I know that sounds so silly), [but I didn’t have] an office to go to, to meet new people. I was in my late twenties, I didn’t know anyone around me [and] the people [who lived] in my building were college kids. 

So in the beginning it was tiring and I had to relearn how to get myself out there and make friends. Because in the past I used to just kind of like quit my jobs and go travel, and it was easy. I used to live in a van, so I was meeting people all the time, but it was out doing van things, not like walking around a city, you know?

I don’t chat with people in bars and stuff, mostly cuz I don’t go to bars cuz I’m boring. So in the beginning, it was really lonely and then after a while we started going to—Jose started bringing me to things like Creative Mornings cuz they had Creative Mornings here. And [to] dance classes, (which are funny because I don’t dance very well), but you know, it’s a place where you have to feel vulnerable. So you start making friends. And slowly but surely, we started picking up friends. 

How to combat freelance loneliness

+ “I need to continue to look for ways to, you know, if there’s nothing around me, maybe build those moments where people can come together and I can have that community that I need so much.”—KM

Michael: We went to one restaurant a lot and we became friends with the owner and we started hanging out with him and his partner and then [we] started going to their house and meeting other people. So it was a slow step-by-step friendship-making process, but I really had to relearn how to make friends. Because you’re in a different country, you don’t speak the language, you work from home all the time and no one else that you’re around is—I mean, there are freelancers here, but the people we were meeting weren’t digital freelancers. 

They were like ceramics entrepreneurs and restaurant owners. So there were some areas to connect on, but [there weren’t] a lot of people that I felt understood my day-to-day life. And that’s even living in a [fairly big] city. 

For you, Kaleigh, you live rural, or in a more rural area. I think you’re considered rural. So what’s it like for you, being a digital worker for so long? 

Kaleigh: I would say number one, I live in central Illinois. It’s a very rural area. I think there are probably about 15,000 people in the town that I live in. It’s the town grew up in.

It can be isolating for sure, especially when the weather’s not great cause I just spend a lot of time inside. So being nine years in, I feel like coming from a nine to five where I was in an office five days a week and I had coworkers and there was so much [of] like people popping into your office, [so many] people to go to lunch with, people to celebrate when it was your birthday. Just those human connections [that] I really, really missed. 

I really struggled the first couple years. I loved that I didn’t have a 45 minute commute each way anymore, but I really missed—I can be a very extroverted person, so I really need that human connection. Actually, I think everybody needs human connection. We’re just kind of wired that way, so I tried for a long time to find outlets for that, which was really difficult where I lived.

Cause we don’t have Creative Mornings. We don’t have local meetups of like-minded people who do similar work. People here, including my own family, still don’t understand what it is I do. And [that is] partially my fault because I don’t know how to explain it, but it’s just not a common job around here. So when I do try to explain it, people are like, “Okay. Yeah, that, I don’t know what that means, but sure.” 

I tried a couple [of] co-working spaces. Turns out there was nobody there. It was just me working in a new space by myself. So that wasn’t effective. I did find another woman who lives a town over and she and I started meeting up for coffee or for lunch from time to time. We still do that, so that’s been really nice. She does [a] similar type of freelance work, but a little bit different. 

But the other thing I started doing too was virtual coffee chats. That’s been a game-changer for me. It’s just reaching out to people who I think are interesting, who do similar or adjacent type work, and checking in with them and saying like, “Hey, what, what are you up to right now?” And just building friendships that way. Again, no ulterior motive there, just kind of wanting to make friends and feel connected to people. 

Sometimes it has fringe benefits of, you know, it’ll lead to referrals or things like that. But for me, those engagements are more just, how do I build connections?

One of the things you and I were talking about yesterday, as I said, I’m really struggling with [is] everything I do, feeling intangible. I work online and I do these virtual coffee chats and investing  [and] you don’t see the money, it’s just numbers moving from account to account. So everything feels so intangible and that’s something I’m still wrestling with. 

My friend Emma and I did a retreat one year where that was a tangible thing. We brought 15 people together down in Austin, Texas. It was just a couple days where we got together and it wasn’t a money maker, but it was such a nice time for us to be together in the same space—real face-to-face interaction. 

So I think I need to lean into that more. I think I need to continue to look for ways to, you know, if there’s nothing around me, maybe build those moments where people can come together and I can have that community that I need so much. But yeah, it’s a work in progress. It’s not perfect, that’s for sure. I’m still quite lonely. 

Michael: Oh, I wanna give you a big hug through my mic right now.

Kaleigh: Internet hugs. 

Why you should combat loneliness

+ “I think the other thing too is you really don’t know what works best for you until you try a lot of different things.” —KM

Michael: I mean, yeah, people do need that social connection and I definitely think especially as digital freelancers, we’re so prone to being alone. And in some ways that’s nice, but there’s a lot of freelancers that I talk to, from a lot of different industries, and they’re all like, “I’m forcing myself to go out of the house today just so I can go chat with a friend or go for a hike or, do whatever—just get out of the house. 

Kaleigh: The other thing I’ll say is being social is definitely a skill. So when you don’t practice it, you get super rusty and awkward. And when you do try to [have] social interactions, you’re like, “uhhh, Hey, how do I do this? I forgot.” And it’s awkward for everyone, but you gotta do it.

Michael: Uh, am I human? 

I think one of the most beautiful things (and I know this can be tough depending on where you live) [is] going to conferences and [to events] beyond the local meetup even. Going out to a conference can have the social connections and benefits, but also the learning benefits.

For example, in February we’re gonna meet in Palm Springs for the eTail or re-eTail conference. 

Kaleigh: Yes. eTail. 

Michael: Yes, eTail. I’m going to learn, but I’m also going because this is a social interaction with the people I talk to every day in the digital realm, and [it’s] bringing us all together. 

Related to your freelance business, it’s combatting the loneliness and everything, but you could [also] write that off on your taxes. (Ding ding.) It is an expense because it’s related to your business. So there are some fringe benefits to going to a conference or even taking the flight, and that’s something that I’ve started doing more [of]—going to meetups out of my town and even meetups in my town. Like I’d said before, Creative Mornings was such a huge part and then the Covid Pandemic shut it down. 

The only fortunate thing about freelancing before [the pandemic] was we were already used to this aloneness. You know, not leaving your house. 

But Kaleigh, I’m curious how you had this long stint of being out, right? You got through the winter—winters in the Midwest can be brutal and very lonely especially cuz it’s freezing. You can’t leave your house. Then you had this long stint once the weather broke of being at all the conferences and hanging out with everyone and then it totally fried you again. So what advice would you give to someone who is lonely? But you need to find the balance of your social relationships also? Because you don’t wanna go all the way out and then burn yourself out, and then you end up retreating back to the place that you came from. 

Kaleigh: Yes, exactly. 

So I think a good way to get around this is to do what I’ve heard people call UN-conferencing. What I did is I was all in. I’m gonna go and speak at these conferences, which means I have to be on. I’m gonna be interacting with people on a really kind of strenuous basis, which can be really, really stressful. 

However if you just go to the place where the conference is being held and maybe you go to some sessions, but maybe you also give yourself plenty of time to get lunch with somebody there, go have a coffee with somebody cuz you guys are in the same space for a few days. 

I think that that’s a really smart approach to not overextending, but also putting yourself in an environment where you can have those interactions on a basis that makes sense for you where you’re not like, “Oh my gosh. I’m, I’m obligated to, to be face-to-face at all of these things all the time because I’m being paid to be here.” 

I think it’s much more manageable when you are going, just more as an attendee. And even if you don’t wanna go to the conference at all, maybe just stay at the hotel where the conference is being held and like, “Hey, let’s meet up at the pool later and, and catch up on what you’ve been working on.”

That’s a little bit of what happened this February and it was lovely. It was so nice. It was low pressure, low stakes. Great environment. It was perfect, so I think that makes a lot of sense. I think the other thing too is you really don’t know what works best for you until you try a lot of different things.

So I wouldn’t have known that I overextended and totally overdid it with speaking until I did that. I just thought before doing that, this is what I need. I’ve been waiting for this. I’m gonna do this. It’s gonna be great. This is gonna be the next step in my career where I’m speaking all the time.

What I learned from doing that was, “Oh, that was a little bit more than I thought it was gonna be. It was a bigger bite than I expected.” So yeah, I think you just have to experiment and see what works for you and start slow. 

Start with the lower stakes environment before you go all in on speaking or being on a panel and always making every trip that you do a work [thing]—like you have to be somewhere at a certain time type thing. Give yourself flexibility. 

What about you? What do you think? 

Creating and finding support

Michael: Earlier in my freelance career, (and I’ll never forget this cause it was amazing) one of my clients flew me—I was in, where was I? Boston. I think I was living in Boston. I don’t remember. I’ve lived there and I was, and they flew me to LA to do an onsite for three days. And I was like, “Hell yeah”… Yeah. I was living in Boston. I just remember cause I remember the email and where it was. And it was such an awesome experience.

That guy actually became my mentor. And one of the ways that I think is a really cool way to feel less lonely is by getting a mentor. And not every mentor is gonna fly you across the country to hang out for a few days. But what I like about a mentor is sometimes I feel like my own victim. I’m like, “No one understands me. No one understands where I wanna go in my life or what I wanna do.” And that actually prevents [me] from making connections with people because I’m like, “No one’s gonna get me. No one’s gonna get this. So what’s the point of even talking to people?”

That’s such an easy hole to slip into especially when you are literally sitting by yourself all day working alone. You can just convince yourself that you’re right. But most of the time, in that sense, I’m not right. And having people that you aspire to [be] or just people that inspire you, that are in your realm of connections—I think that’s really important too. It’s not the end all to solve your loneliness, but if you feel like people around you don’t understand you or your work life or your personal life or your feelings, you can find people out there who you want to be like and who understand. 

Like Steve for a while, (that was my mentor) he understood everything and he actually helped me a lot through the earlier times in my freelance career. [I would] hit him up with questions and he [and I] would meet and I was very fortunate to have him cuz even after we stopped working together, he still continued being my friendly mentor and working with me through things.

I just remember how impactful that was on me, as a person, on my happiness, and on my freelance business. Which is why I say, even if it’s not an official mentorship—you don’t have to go to a website [or a] find me a mentor type thing (even though those work)— it could be just connecting with someone that you think would is in a position that you want to be [in].

Maybe they’re a real estate investor or a design agency owner, or an awesome trader that’s not hiding behind an N F T P F P. An actual person and making those connections with them, to one, expand your network and also, meet some inspiring people. 

Kaleigh: Yeah. I would also advocate for going to therapy regularly because you touched on it in another episode. You don’t wanna dump on your partner because they’re the only person that’s around you on a regular basis. 

Michael: It was this one.

Kaleigh: Was it this one? I don’t even know. Oh my God. 

Michael: I love it. Keep going. 

Kaleigh: Sorry people. God. Okay. Yeah. 

You don’t wanna dump everything on your partner because then they’re gonna come to resent you. Like, “Hey, every time I walk in the door, you’re like, ah, you wanna talk to me and I’m your only social interaction. This is too much pressure.” So therapy is really great. Huge advocate for that. 

Mentors are wonderful. Some people prefer the coaching relationship where it is a paid relationship. I feel like sometimes when there is that money associated with—[and it’s the] same thing with therapy, it’s a little bit more reliable, right? There’s skin in the game. As gross as that sounds. 

Other things too, find somebody who does really similar work to you and have them be somebody you can vent to and bounce ideas off of. Emma Samco, who I host the Freelance Writing Coach podcast with, she’s been that person for me for years. And now Michael, you and I text every day. We also have a group chat of the group from our February meetup (which has been super fun), where we can just kind of like pop in and out as needed.

Communities can be really great too. So Peak Freelance is a great one. There are Slack channels where people feel really connected. You can do DMs in there. 

I wanted to ask you, do you know of any groups that you think are really great for freelancers that maybe we should recommend? 

Michael: Yeah, I mean Creative Class has a Slack group that’s part of the course and it’s forever yours along with all the material. That’s a really beautiful place where freelancers come in from all different walks of life and can connect there. There’s also Peak Freelance, which is generally more [focused] towards writing, content, editors, [and] marketers. People who gravitate towards content usually fall into those buckets. Those are the two communities that I’m familiar with. 

So Kaleigh, do you know of any others? I know there are more out there like there are a bunch of ones for different niches.

Kaleigh: Yeah, I know that Superpath is one that’s getting a lot of praise right now. They have a great Slack. So that’s one I’d recommend. 

I think it just kind of depends. You just have to ask around and [ask] people who do similar work, “Where do you spend time? Where do you hang out? Online? Do you have any recommendations? Or like if it’s a closed or private group, can you send me an invite to that? Because I’m looking to become more connected. I’m feeling lonely, whatever it is.”

I think that another piece of this conversation is, you have to be willing to be vulnerable and say to other people, “Hey, I’m kind of struggling right now. I could really benefit from [having] somebody to check in with on a monthly basis. Would you be willing to be that person for me? I’m not asking you for anything. I’m just, I’m lonely. I want somebody to talk to somebody who understands the stuff that I do and really gets the work that I’m doing.” 

That’s a big part of it. When you feel like nobody understands who you are and what you do on a day-to-day basis? That in and of itself can be really really lonely and compound that feeling.

So just ask around. Find people who do similar work and say, “Where should I be going? Where should I be looking for this sense of community that I so desperately need?” 

Social media is not the solution to loneliness

[When] feeling lonely, the last place you should turn to is Instagram or Facebook or whatever. Instead, you have to hold yourself accountable and be like, “All right, I’m gonna actively do this and I have to be vulnerable in order to get myself out there and meet people.”—MK

Michael: Yeah. And the last tip to kind of wrap that up is stay off of social media. Create a healthy balance with that. Because, especially if you are feeling lonely, it is way easier to just go to Instagram and scroll and look at everyone’s so-called amazing life.

I don’t have social media because…I just don’t like that. So that’s why I advocate against it. [When] feeling lonely, the last place you should turn to is Instagram or Facebook or whatever. Instead, you have to hold yourself accountable and be like, “All right, I’m gonna actively do this and I have to be vulnerable in order to get myself out there and meet people.”

Kaleigh: And I think that’s good parting and advice. 

Michael: Yeah, totally. I just love that actually has worked with you, Kaleigh, cuz we became friends and now I send you selfies from restaurant bathrooms when I’m having a couple too many drinks. 

Kaleigh: Yes. I love that, so fun. You gotta have that friend. You gotta have that friend.

Michael: Yeah. Look at my boots. Look at my butt.

Kaleigh: Yes, look at my outfit, don’t I look great? You have to have that friend. 

But I love your advice about, do not confuse social relationships on social media for actual friendships because that’s so passive. There’s no depth to it. It’s all surface level. It’s not real. And if you need real connection, get real connection. Do not confuse social media for friendships because it’s just not the same. 

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