One of these questions I see coming up all the time for people who are just thinking about making the leap into working from home is whether working remotely and freelancing are the same thing. It can get really confusing because plenty of freelancers do work remotely. But that’s not necessarily the same as someone who’s working on an hourly, part time, or salaried, full time basis as a remote worker.
In this episode, I was so happy to be able to invite my guest Maryellen Stockton to chat about what it means to work remotely, successfully. We talked about a lot of things including how to be successful with a remote job interviews and tips that can help you be successful and effective with potential clients and employers in this digital world we live in today.
About Maryellen Stockton
Maryellen Stockton is the co-founder and CEO of Work Well Wherever. She is a People Operations Consultant who has worked for 15 years encouraging individuals to achieve positive work/life experiences and helping companies create inspired work cultures. Six years ago, she began working remotely for a virtual staffing firm and quickly became an expert in company culture, employee engagement, and building teams outside the traditional office.
She lives in Atlanta with her husband Matt and her two kids, George and Winnie. The things that make her happy usually include coffee, people she loves, and mountains. And to that, I say I feel the same!
I hope you will find this episode helpful for learning more about why remote work has become so popular.
We’re living in an amazing time as freelancers or as remote employees where companies are finally opening up to the idea that they can have very effective, efficient, and great teams with excellent communication in locations all over the country or even the world. So use that to your advantage. Make sure you file away the tips in this episode and avoid some of the pitfalls we discuss that are costing people remote work opportunities.
I was thrilled to be able to chat with Maryellen because I think she has such a unique background with remote work. She is also, in a sense, like a consultant herself running her own business. So she has this really unique blend of both of those backgrounds.
I’d love to kick things off by talking a little bit about the difference between remote work and freelancing.
Sometimes we’re talking about the same things. But increasingly, these words are getting their own definition. So I really wanted to hear her perspective on what that difference is.
Maryellen’s thoughts on on freelance work is that you are usually not working full time for one employer. You are usually working full time maybe for multiple employers or maybe you’re working part time for multiple companies or on multiple projects. And you are not necessarily like a part of a team.
With remote work, and especially with the growth of this full time, remote work, the difference is that you’re usually devoted to one company or organization. And it is a company that is either distributed where they have offices all over or they have teams that are. Everyone works from home or maybe it’s a combination of both.
Maryellen shared that you are seeing increasingly more and more companies hiring freelancers to do certain projects and also they have remote teams. That actually worked for the organization. And that’s increasingly more common.
I totally agree with that. I think that the confusion for a lot of people is because most freelancers today are working remotely. Now, that’s not true for everyone. There are definitely some freelancers who still go into the office and things like that. But most of them are working remotely.
So when someone is thinking about getting started working from home, it’s actually quite different working for one company, or maybe two companies that you’re working remotely for part time versus running a freelance business where you may have multiple clients at the same time. And there’s not always that expectation that it’s ongoing. Like if you take a full time, or part time remote work job, unless the person has told you that this is temporary, there’s that expectation that it’s like a traditional form of employment. It’s expected to go on unless there’s a reason for either party to decide to end the relationship. Whereas, freelance work is so much more flexible. It might literally be that someone needs you to do something this week and then never again. I still have some of my clients from years ago. So it’s all over the board.
One of the things that’s cool about the time period that we live in is that remote work is becoming more and more accepted by companies of all sizes. Employees are wanting it. So it’s a great time to be either a remote worker, an aspiring remote employee or a freelance. Because this whole idea of working with people who are not in your office is so much more accepted.
What other trends have you seen in the last couple of years around remote work?
Maryellen shared that there are employers who have a corporate team that is fully remote. And then they also hire freelancers. So they have contractors all over the US. So they are all under one company. The contractors are 1099. These freelancers are 1099. And it’s a lot of part time. Then they also have these corporate team employees that are remote. So it’s interesting to see.
Maryellen has seen a rise of wanting to incorporate the freelancers more into the company. She has some thoughts and ideas around it. But it’s like that is something that you have to figure out as you go along.
She said that in Atlanta, there are companies that staff assistants, bookkeepers, or marketing team members. And then they also have a remote corporate team. So it’s just interesting trying to bring them into the fold. And especially when they’re thinking about how they want these freelancers to be a part of their culture and have better communication. How do you do that? How does that happen?
That is a really unique challenge.
And the way that I have come across that topic is when I’m coaching freelancers, who are in some of these teams, but they’re being brought in on a short term basis or even on a long term basis. But as independent contractors, there’s a really fine line that employers have to walk between legally with how they treat freelancers.
So it’s this big gray area where sometimes companies don’t even realize that they’re doing it. For example, you want to bring this freelancer into the fold of your company culture. And you want them to feel like they’re part of a team. You want to have great communication channels. But at the same time, the way that you treat an employee, you can’t always necessarily just assume that the freelancer is another employee and that that’s okay.
So I think that’s a challenge that’s really facing both freelancers and companies that are trying to leverage their talent right now is figuring out like, “Okay, we have someone who’s not really part of the team, but we’d like them to feel like they are without crossing the line. How do we get that perfect Goldilocks situation there?”
Maryellen thinks it definitely starts with the communication and how you are tracking things.
How often are you bringing the freelancers into the discussions if they’re working on a certain project? Because sometimes she thinks the common thing with with freelancers and with teams, whether they’re remote or in the office, is that they have a meeting in the office or they have a meeting on video. And since the freelancer is only working on one part of the project, they don’t loop them into that conversation. She sees that happening a lot. And so the freelancer is actually missing out on the valuable information by not being involved.
I didn’t think about that. There’s so many conversations or even feedback loops that are happening, whether it’s in an office or it’s a remote team, with the rest of the team. So it can be a challenge. Something for companies to keep in mind is, when you do these update meetings or progress, how do you fold in a person?
One of the ways that this has come up with a lot of freelancers that I work with is, they’ll have a client who’s new to working with freelancers. And they’ll say, “Oh, hey, can you hop on the phone in an hour?” And that’s not possible for freelancers. Companies should be prepared to work ahead with that sort of thing.
Maryellen thinks one of the ways that you work around that is realizing that now we might have to have a regular update especially if there’s a big project going on. Maybe you have to have the team meeting weekly, based on the particular project, as opposed to when you used to only have to have monthly meetings, You just have to think about different ways of communicating so that everyone’s on the same page and that no one’s left out or is missing information.
I think that’s really great for freelancers and remote workers alike to consider. And that gets into our next topic here. Remote work has definitely gotten more popular with a lot of different companies and in a lot of different industries. But I still feel like, and this is true of freelancing, too, that there’s a lot of misconceptions around remote workers and remote working.
What are those misconceptions and myths that are still out there?
Maryellen shared that she doesn’t know when we’ll get over these misconceptions. But the biggest one is that if people work from home or telecommute or freelancing or any kind of remote work that they are not really working. She admitted she had this misconception too, before she started working remotely six years ago. It’s hard to turn it off.
When she started working remotely, she really had to figure out a way to stop and schedule myself and be organized and set boundaries and establish my working hours and make sure that I was communicating all that Because it really is hard to turn off because you can take it anywhere. That’s the beauty of it. But then it ends up causing issues.
This happened to me with my freelance business. My husband just commented on like, “Okay, some days you’re working from your laptop in the living room. Some days you’re in the bed working. And some days you’re over here.” He said that my workspace had become the entire house. And this is good because it’s so easy to grab for that laptop and go, “Oh, I’ve got 15 minutes. I can knock out that email.”
So I love that idea of, what are your working hours going to be? Either because you’re a remote worker and you need to have that expectation of when you’re going to be online with the rest of the team and available to talk to you. As a freelancer, it went against everything that I wanted in my freelance business. I was so dumb. I don’t want to be nine to five. And so I was like, “Well, I can’t work between nine to five. I just don’t want to make that my office hours.” But finally, when you make some sort of clear schedule, or when you have a home office, where that’s where you go to do your work and your calls, it’s that much easier to prevent it from bleeding over.
Sometimes I feel like remote workers and freelancers feel as though they have to prove that they’re working.
They feel the need to document what they’re doing, take screenshots, or send like a recap of what they have done. And that’s not always necessary or productive or the best use of time. But part of that is because I think we worry about, “Well, does this person believe that I’m really working or not? Do they think that I’m just here billing them for time or essentially on the clock when I’m not doing anything?”
Maryellen thinks that if you’re an owner of a company, and you’re hiring freelancers, or you decided to let people work from home a couple days a week, then you have to trust that you’ve hired the right employee for the position. And you have to be crystal clear about the expectations and goals everyone should have.
These should be expectations and goals that align with their position or project or whatever it is. So that should be communicated well, so that everybody has set expectations that are not limiting someone in their flexibility. It’s actually like leading them well and allowing them to do their best and in the role.
So she thinks that sometimes when people are switching to remote, there is that sense of, “I don’t want to micromanage.” So they don’t put any guidelines or expectations in place. But you actually are not doing anyone a favor. Because then people don’t really know what’s expected and everyone does want to know what’s expected of them. It’s not really rules, per se. It’s just leading leading well. It’s just guiding your team to do the best that they can and also setting the employee or Freelancer up for success.
I think one of the most common breakdowns that I’ve seen is around communication expectations.
Because if you’re bringing someone into your team, they need to know what the communication expectations ares. For example, you may be the type of person who only checks your project management tool once a day and your email twice a day. If you have someone new on your remote team who’s like starting at nine o’clock in the morning, they might be sending you messages over Slack or over email like, “Hey, I’m unclear about something.”
And if they don’t know that the expectation is, “Oh, hey, we always chat during the midday daily meeting or on Fridays. We map out the week ahead. And so you should be prepared to show up to the Friday meeting with all of your concerns and questions and intended priorities.” You’re just making that person feel more and more awkward. And they’re wasting time as well. Because that person is just sitting around not realizing that that’s part of the way that your remote team works.
So I think that’s important to remember, too. That not all remote teams are created equal. And when they have this mix of remote workers and freelancers and sometimes even people in an office in a different location, you’ve got to suss out that culture.
So how do you do that if you’re the intended employee or the freelancer? How do you tell what a company’s culture is when you don’t have that ability to walk into an office and get a vibe that way?
So from the employee’s perspective, or freelancer’s perspective, but I guess mainly when you’re a remote worker where the culture is more important. I mean, you still wantan awesome culture for your freelancer, but it’s more temporary. Maryellen shared that if she’s going to interview for a remote company, she’s going to do her research first. Just as with any company. She’s going to do my research.
One of the things that she thinks is hugely important in remote work is that when you’re applying for these jobs, do you align with them? What is their mission? What is their purpose? Does that speak to you? Is that intriguing to you? And are their values communicated clearly that you understand? And what are their processes? It’s good to ask how often does the team meet?, How do they meet? Are you meeting in person? Do you have the tools in place to know that everything is heading in the right direction so that you will be able to connect? It’s so important to be able to develop a connection with other employees.
I feel like whether you’re working remotely and trying to land a remote traditional job, or you’re a freelancer, we tend to worry about wasting people’s time.
Especially if you’re being paid for it. For example, say you’re an hourly freelancer, and you’re like, “Well, I don’t want to waste three minutes of this phone call asking this person how their kids are doing.” But it’s actually important to do that sort of thing. And as long as it’s not excessive, I think that people don’t even think about that in terms of like, “Oh, this person is trying to draw time or wasted or isn’t sensitive to the fact that I’m a busy person.”
It’s so important for that connection to feel like you are part of the team and to really get to know who you’re working with. And I’m guessing that there are more downsides than this, but I know for myself that isolation is one of the hardest things about being working remote. It’s wonderful to work from home. It’s nice to have your home office, have your pets around, and all of that stuff. But it can also be super hard.
Do you see any other like downsides or things that someone should be aware of with working remotely that they should be prepared for before they start?
Maryellen does think the isolation thing is huge. That takes a little bit to get adjusted too. So some things that she did was just have a set date if I didn’t have video calls to be in a coffee shop, just to be around people. Or she had a workout class two days a week that she liked to go to. And so she would schedule that time. So that goes back to the things that we talked about. That also helps you to turn things off.
The other thing that’s the downside of remote work, is just figuring out a schedule that works for you and works for the company. One that allows for flexibility, but where you’re able to get things done but still have a routine or schedule. She thinks that was super helpful to her to avoid isolation and to avoid over overworking.
Because there are those days for any of us, in office or not, where maybe from 12 to one you go to your kids ballet performance or you have a doctor’s appointment, and you have to get back online after the kids are to bed or your partner goes to sleep or whatever the thing is that happens. But if you can, you don’t have to have this like rigid schedule. But if you can somewhat schedule and know what you’re going to tackle next and have a sense of the things that you need to be more productive during the day, that helps with the with the isolation and the overworking part that that I see people face.
This goes back to that company culture idea that you’re trying to assess when you’re working with someone new.
What is their company culture? Do they expect you to be online all the time or not? Because that’s something to really know up front so you can plan around that. And I love that idea of getting out of your office when you can even if you’re a remote worker. See if there’s someone where you can have lunch with them on one day a week where you leave your home office.
For me, my husband and I just moved to Minnesota a couple of months ago. I knew one person here. So I forced myself to go to Minneapolis a couple times a month. And then every Wednesday night I go to an adult tap dance class and I interact with other people from Minnesota and get to be part of the whole culture here.
So I feel like that’s important to even the schedules that you have during your work day. And even when you’re not working that can help if you don’t have that water cooler gossip. You don’t have that going out with your co workers at lunch type of thing when you’re working remotely, but you can build in that connection in other ways. I found that that helps me too. Because if I have evening events, I can’t work past a certain hour because that’s where I need to go. So it’s a really it’s always a balance but definitely important to keep that
Maryellen asked me if there is something that I hear freelancers or people I work with encounter that they consider a downside.
There’s two things. So one is that people don’t understand what you do. For the longest time, my in laws described what I do as something on the internet. Then I’d say the other one is that people tend towards being a little too reliant on technology. We live in this digital world. But we need to find that fine line between things that can be sent over an email and it’s going to be interpreted the right way by the person receiving it and need to actually have a call.
If I have 20 questions that need answered, then it’s just going to be easier for us to get on the phone and hash out those 20 questions in 30 minutes rather than me work on a project and get all the way to the finish line and have my client or employer say it’s not correct. A phone call or video call could have cleared that up 10 steps earlier in the process. And assuming that all people write emails the same way I do. I would say that’s the other big challenge for working remotely that I see a lot.
One of the things you are looking for when you’re you’re looking for someone to work remotely is great communication skills. It’s somewhat like being a little intuitive or a problem solver. And that’s part of the communication thing is saying like, “Okay, I can’t even explain this in the email. I’m just going to pick up the phone and call them or I’m going to ask if they can jump on a call later.” It’s fine If you call and they don’t answer. Then maybe you go back to the email and figure something else out. But sometimes it’s just quicker to have that conversation than to type in emails. It can hit a point where it’s getting too long or doesn’t make sense or it’s not going to be received. It’s knowing when to do what .
Especially if you are the worker who’s getting an email or a piece of feedback on something that says, “I don’t like this. This does this.” Well, what does that mean? Because I could interpret that as they hate me or they want to fire me. And they could have just literally meant like, “I don’t like the color yellow. And you put yellow on that.” This is a five second fix. But over email, it can be interpreted differently.
So one of the things that I like to do with that is if it seems like there’s going to be confusion, or if this is a little more complex than an email, I will just say that in my message that I want to schedule a call with them. If they have an automated booking where I can go right to their calendar and book a call, I’ll do that. If they’re busy, and I don’t know what their schedule is, I’ll just send a message like, “Hey, I’m really thinking with a 15 minute phone call we could knock out all these questions and clear things up. Are you up for that?” That way it doesn’t seem like I’m intruding. But I don’t think that workers and freelancers should be afraid to bring that up. No one’s going to get mad at you if you feel like you need the video screen by screen walkthrough to learn something new or to get on the phone call and ask those questions. It shows that you’re trying to be mindful of the entire project and the purpose and something that you’re confused about.
Do you think that there are certain people who remote work is the right fit for them? Are there certain traits that people are better suited to work remotely than others?
Maryellen does. And she thinks that you screen for it. For example, people that have had their own business, you can say that they’re probably self motivated. She thinks this is a huge one because there’s not just someone right beside you to ask in the time frame that you need it. So she would say self motivated, organized, excellent communication skills, and proactive are important trains to have.
And she really thinks a natural problem solver is also a good trait. Because there are all these tools and technology that we’re getting used to, but you have to be able to say, “Okay, I may not be able to get the answer right away.” Can you come up with a solution then and figure that out on your own?
Or even that ability to say, “Okay, this project is stalled out because I need an answer from x person and x person isn’t available. So how can I table this? And what is the next project I jump to?” I think that some people just naturally gravitate towards being able to do that. Whereas others need to be told by someone else what step one is and step two is this. And so being able to balance those different priorities and saying, “Alight, I’ve got more time here that I can work on something different, because I’m not able to move forward on this until I get an answer or something that’s important as well.”
Maryellen thinks sometimes sometimes people are easily distracted, which means they want to be in an office. Or they feel like they’re missing out. And some people are easily distracted and they want to work from home because they can be more productive. So there are those things too.
I like to ask freelancers, “In college or grad school, were you the person that actually got the group project done?” Because you probably have what it takes to be a freelancer, if you were not stalled out by everyone else’s lack of communication and ability to work together. But you were able to bring that project to the finish line, because that’s a big part of it.
How do you set yourself up for success working from home?
I found it to be hugely distracting to work in an office when I had a more traditional job. There were always other people talking. Somebody next to me playing really loud music. I just felt like I got less done because of that. So being able to do my work from a quiet home office works for me. But for other people, they would absolutely hate it because they don’t other people around. So it really depends on what works for you.
If you’ve never been a remote worker before, how do you show an employer or a freelance client that you’d be really good working remotely?
Maryellen shared that part of that has to do with with the person interviewing. She thinks that there are some things that you can highlight as a freelancer if you’ve never worked remotely. One of them would be tell me about a time you’ve completed this project, but maybe you’re working on a team and you didn’t have the answers. She thinks being able to highlight any way that you solve problems, communication skills, and organizational skills in your resume.
Another thing that we didn’t talk about, but she thinks professional development and growing your skills and remote work or as a freelancer is a great thing. When you’re interviewing a freelancer and they’re continually like taking classes or reading books or doing different things. She thinks that shows the self motivated, proactive type that is successful when working remotely or freelancing.
I think all too often people who would do really well working remotely or being a freelancer, they write themselves out of the whole topic before they even get a chance to start.
Because they’ll say, “Well, I’ve never worked remotely before. I don’t think anyone’s going to buy into me working from my home or being a freelancer when I’m brand new to this.” The truth is that you probably have things in your background, either your core personality, or even your experience in the workplace, where you’ve had to coordinate. Say that you were an event planner in an office. You coordinated with vendors and other locations. You kept all these details organized to have an event or project come together. And so those skills can transfer over into remote work as well. So don’t be afraid to talk about how those non remote work skills could actually work remotely for you as well.
So my final question here is how do you prepare for an interview for remote job? Are there mistakes that people make in doing this? What should you really be prepared for?
Maryellen thinks so. Because there is a confusion in this freelance or remote work or work from home thing, she thinks sometimes people don’t show up as they would if they were actually interviewing in person. And you should. So if you think about the same ways that you would prepare for an in person interview, because most of these remote teams are going to interview over a video first. So she would say that’s the thing. Think of it as how would you show up to this company? How are you going to show up to an in person interview? And do the same.
Have your background is clear of clutter. You have tested the tools that you’re going to connect with. So if you and I are going to connect over Zoom, then that I have tested Zoom to make sure that it works and I have everything working so that I can easily jump on and limit distractions. So if you got a dog that’s gonna bark or anything, put those things up. You want to show up as a professional. You want to show that you that you can work from home and you do have a space to do that in. It’s really no different than going to an in-office interview. Just treat it the same.
Do you feel that that extends to clothing as well? So should you be fully prepared as if you were showing up to someone’s office for regular interview?
Maryellen doesn’t think so. She’s not expecting to get on a call with people in a suit when she’s interviewing people, or when she’s interviewed people in the past. But just think about the level of professionalism. A plain shirt or anything is fine, but just think about the level of professionalism, You probably do not want to wear a hat or anything like that. But, no, she doesn’t expect to see a suit.
You want people to see you and be able to talk to you about your skills and you don’t want them to be distracted by things that are going on around you. So if your background is like super distracting or cluttered, they might be focusing on that. Present yourself well. And go that extra step to make sure that the area you’re in is relatively quiet. If you’re in New York City, you can’t help it if there’s cars honking their horns are an ambulance going by. But she thinks a lot of people underestimate how loud the TV in the next room is or their spouse cooking dinner in the background.
So just be aware of that. Things will always happen when you work remotely that you can’t exactly anticipate. I would train my husband. I would tell him like four or five times whenever I’m recording a podcast or I’m going on someone else’s podcast. And go that extra mile. Do that if you need to. If you have something that’s uncontrollable where you’re like, “Yeah, the neighbor’s dog has been barking all day or the guy next door just started mowing his lawn five minutes before we start.” Let them know because what you don’t want is to have someone thinking that that’s your everyday working environment. It’s just extremely loud, distracting every minute.
Invest in headphones.
You should be doing that anyways. Because when you are doing video calls, which you’re certainly going to be doing as a remote worker, as a freelancer, when these calls are being recorded, you can create a lot of problems with feedback if you don’t have the headphones plugged in. So it’s important to invest in these little things that will make it easier for you to work and help you appear professional on screen or over the phone when you’re connecting with clients.
Well, this is really this has been so helpful. I think so many people in my audience who are thinking about remote work or freelancing are going to get a lot out of knowing the do’s and don’ts from your expertise.
Where can people go to learn a little bit more about you?
Maryellen is on Instagram and LinkedIn. It’s Work Well Wherever. Her website is workwellwherever.com.
Maryellen Stockton is the co-founder and CEO of Work Well Wherever.
She is a people operations consultant who has worked for 15 years encouraging individuals to achieve positive work-life experiences and helping companies create inspired work cultures. 6 years ago, she began working remotely for a virtual staffing firm and quickly became an expert in company culture, employee engagement, and building teams, outside the traditional office.
Maryellen lives in Atlanta with her husband Matt and her two kids, George and Winnie. The things that make her happy usually include coffee, people she loves, and mountains.
Thanks for tuning in for another episode of the advanced freelancing podcast. For more freelance advice, get a copy of my book Start Your Own Freelance Writing Business—available now! Buy it from Amazon, Barnes & Noble, Apple Books, and more.