This is episode 86 of the Advanced Freelancing podcast. I’m doing a separate introduction here because this is the first time that I’ve interviewed a guest in this new format and reboot of my podcast.  I was super excited to talk to her because of her expertise.

Today’s podcast guest is fellow freelance superstar Hilary Sutton.

She is a writer, speaker, and consultant that is passionate about helping people spend their days in work that is wildly fulfilling. She is the host of the podcast Hustle and Grace, which you should totally go check out right now.  Binge some of that after you’re done with this episode.

She’s also the author of several ebooks and courses including “More in Less: 21 Productivity Hacks for Creatives”.  She has also served as a Professor of Communications, Social Media and Journalism, at Southern New Hampshire for five years.  And she’s also a freelance writer for hire with expertise in direct response, copywriting, and content marketing.

As a freelancer, she has served clients ranging from Broadway shows to non profits large and small, creatives of all stripes, and consumer brands.  And she has written hundreds of articles in dozens of publications, including USA Today and The Washington Post. She and her family live in the DC metro area.  We will post all of her contact information at the bottom of the show notes.

This episode is for you if you’ve been thinking that perhaps full time freelancing or full time remote work might not be for you.

And how could you create a hybrid blend, where you’ve got essentially an employee-employer relationship as part of the mix, but not as your full time gig. I hear from more and more freelancers these days who are looking to build an intentional freelance business. They don’t want to be working 40 or 60 hours a week as a freelancer.

For some of them freelancing was their ticket out of working in a dead-end job, but they’re now realizing that freelancing full time isn’t quite the right fit either. The cool thing about these side hustlers is that we can rearrange our business and client load whenever we want to reflect the new dreams and goals that we have.  Hilary is the perfect example of that. So stay tuned in this episode to hear more about the different transition she’s made and how she recommends you do things like how to pick which industry or type of skill to focus on how to keep clients thrilled about coming back to work with you on retainer.

With that, let’s get into Hilary’s story.

Hilary shared that she has been a person from the beginning who liked a lot of different things. She’s always been a person who loved writing.  She’s always loved theater. And she loved connecting with people in college.  She could not decide on a major for the longest time and actually ended up with three or four minors as a consolation prize.

She started freelancing around 2007-2008.  Which, if you’ll remember, that was around the time that the great recession hit. So freelancing was something that she wanted to do, but it was also something she was kind of forced to do.  Because at that time, companies were on hiring freezes. People weren’t hiring full time. So Hilary said that it was sort of like a happy accident that she got into freelancing at that time when people were actually sort of looking for some freelancers.

So she started freelance writing, then she was also balancing it with a career as an actress in theater, especially musical theatre.  It got to a point were in between performing, she was doing some writing here and there. But it wasn’t really enough to pay the bills. And so she was also working retail and doing some different things.

Back to School

And so she thought she would go back to school and get a masters degree so she could at least possibly get into the online education boom that was happening at that time. She thought, if she could maybe teach online, she could still have this autonomous lifestyle that she loved.  She could work from anywhere. And she could go audition in the middle of the day.  There was something about a full time job that felt very limiting to her.  It felt very stifling to her and her personality, because in the beginning she had three or four different minors and a love for lots of different things. So she always really liked variety.

So back to school she went.  She studied media and communications with a focus on media.  She really dove into the social media space.  That was also really interesting timing because that’s when companies started realizing, “Hey, we should hire someone or we should hire a freelancer or a consultant to help with our social media.”  And so that’s sort of how she really got started as a full time freelancer.

She did social media. And she did a ton of blog writing. She still did article writing for magazines. That sort of grew into a career as a content marketer and a direct response copywriter that she has today.

Her Life Now

Now she lives in the DC metro area right outside of DC.  She works as a full time freelancer. There was a time just a couple of years ago that she thought that maybe what she really wanted was to work remotely.  She thought that it would give her the flexibility and autonomy that she wanted.

Well, it turns out she really likes working for herself. So she works as a part time consultant with an agency.  That’s sort of her anchor client. She’s technically a W2 there, but she’s part time.  She works remotely. She feels like they’re her client to be honest. But she is part of a team.

So she does that part time. And then she sprinkles in whatever she has time for around that. So she does direct response copy.  She does freelance career coaching.  And she has some online courses and intellectual property. She does public speaking.  Basically, she does lots of different things. She likes to keep the variety going. But she does have this dependable anchor client in the staffing agency.

I think it reflects a lot of what we freelancers like.

A lot of us get that feeling of being stifled in a traditional job where you’re doing the same thing all day every day. Even though sometimes the variety can be a little bit crazy, it’s often a welcome part of the freelancer’s life.  Why? Because you do get to decide who you work with and who you don’t.

It’s interesting that Hilary brought up that she has this anchor client.  To her, they’re kind of a client, but not really because it’s also like an employee employer situation, but it’s super flexible. So you view it like a client.

It’s very interesting because a lot of times for people that are looking to do full time freelancing, I tell them to never just have one client,  That’s super dangerous, right?  You should never put all your eggs in one basket. And obviously, Hilary done that. But what advice does Hilary have for freelancers who maybe get an offer like that?

I see a lot of people who are like, “Oh, a recruiter contacted me about a remote opportunity or a part time opportunity. They want to pay me W2.  How do you set that up for success in the rest of your business being in the context of freelance?” It sounds like they’re very much like a client for Hilary.

How can freelancers tell the difference between an employer that really wants to treat you like an employee and someone who’s more like a willing to be flexible with the remote work?

Hilary shared that she thinks some of it is that you just have to feel out in the interview process. But she thinks you also have to be honest from the beginning about what your values are and what you care about.  Be honest with them that they’re going to get your 110% effort. But you’re not going to have that same approach to the company that other people might go in there from 9 to 5.

Hilary shared that in her situation, she doesn’t view them as an employer. And she also feels like they put her in my own special category as well. So you know, there are times when it’s so beneficial because she’s outside of the office politics.  She’s outside of the water cooler chatter.  Those parts of working in an office that she frankly, doesn’t feel comfortable with and doesn’t really like.

So she thinks it’s important to be honest from the get go. She thinks it’s important to ask the tough questions in that process in the beginning.  You have to yourself, “Self, what is important to me?”  You have to ask how much anxiety does it bring me to have five different clients that all get 20% of my time or, 10 different clients still get 10% of my time?  Is it less for you to worry about? Is it less for you to think about? Does it bring you some peace of mind to have a client that’s 40%?

Hilary said that to her, it’s all about a happy medium.

Because a lot of times she thinks a freelance line item on a budget feels unemotional to cut at the end of the year. Whereas, if you are a W2, she thinks that employers and companies don’t feel as comfortable just being like, “Oh, we’ll just reallocate that money.”

She has had that experience herself. She had a client that was about 20%- 25% of her income recently. And at the end of the year, they just said, “Oh, we’re just going to rearrange some things. And we’re going to hire someone in house.”  It was over an email and was so impersonal. And all year, they had been a huge piece of her pie. But, she was just a line item for them.

So Hilary thinks there is something beneficial about having that relationship where you’re not full time, you don’t do the commute every day, and you’re not there every day, but they rely on you. You rely on them almost like a retainer. Hilary thinks it’s a good thing. It’s a good situation, depending on what you want and what your goals are.

So Hilary is talking about a setup that’s a little bit different than your traditional freelance setup.

Most freelancers have defined channels for marketing.  They know how they’re going to find their clients.  I asked Hilary what she suggests that freelancers interested in a client like hers go and do to fine someone like that. Do you use different terminology or pitching techniques or networking to find a client like that and to kind of convince them that you’re the right one for the role? Because like Hilary mentioned, a lot of times, we are seen as outsiders.  Freelancers are brought in to work on specific projects.  Or as a writer, they might do some of the content marketing.

How do you kind of bridge that gap between being a freelancer and working as a part time employee or W2?

Hilary thinks it depends on where you’re coming from and what you’re doing just prior to that.   For me and her situation, she had been working full time for a company remotely. And she just put the flag on her LinkedIn saying that she was open to conversations with recruiters. She moved my location to the DC metro area because she was moving to DC and almost immediately when she got there, a local company reached out to me.

It was a marketing staffing agency So they didn’t take long for them to find someone who was the right fit.  Hilary shared that she was a great fit for them not only because she was looking and open to freelance and part time and remote opportunities, but also in her previous job, she was doing the marketing writing.  Which is the kind of writing that I liked, but the topic wasn’t something that I was passionate about.

So in her off times from when she wasn’t working on the projects for her job, she was contributing to newspapers like the USA Today writing about careers.  She was writing about how to nail your internship.  Those kinds of topics that actually aligned really beautifully with this client and part time gig that she has now.

Hilary thinks it’s important before you find that perfect sweet spot that you’re really putting it out there and cultivating your own personal brand around the topics and the things that you love to write about or the projects that you just love to do. Don’t just get bogged down in whatever it is that your current job and the projects assigned to you.  Create your own work. Hilary thinks that really attracts those special opportunities. And it will also show that you’re more than just a writer.  You’re more than just a designer.

Whatever it is that you do, you also have a passion for this specific niche. Because when you have a passion for a specific niche and someone needs someone like you, they’re more willing to be flexible.  They’re more willing to be like, “Okay, well we really want somebody in the office.  We really want to pay this.  But maybe we can rework some things because who’s gonna be more perfect for this job that you? Probably no one. So we’ll do what you want to do. We’ll make it work.”

I love that youHilary brought up a couple of things there that I think are so important for any business owner or even someone who’s looking to be a professional and work as an employee.

That is making yourself visible to recruiters on LinkedIn. I probably post about this several times a month in my Facebook Group.  Why?  Because it’s just takes three minutes.  Go turn the button on and tell the recruiters exactly what you’re available for. Because that is always the most searched person. Every time I go into who’s viewed my profile on LinkedIn, recruiters are always number one.  Those are great relationships to cultivate. It’s free and easy.  If your profile is optimized, that’s perfect.

And then Hilary also talked about building your own brand.  I think this is so important.  People get bogged down in that too. If you don’t have a lead at USA Today or Business Insider where you can post, then use your LinkedIn and your website to build your brand.  You need to be posting articles and content that are relevant to your industry.  People also find you that way through the hashtags, through the words that you use, and how frequently you post.

I think Hilary has a really great perspective because she’s worked in these different industries. And one thing I’d love for her to break down is the difference between working remotely and working as a freelancer.

The reason I bring this up is because I’m in a lot of communities with other military spouses and a lot of them are looking for remote opportunities.  Because, obviously, they move a lot. They want a job that’s going to travel with them. And there’s sometimes this confusion between, What’s the difference between working remotely and something like starting my own business as a virtual assistant or something like that you’ve actually done it.  I asked Hilary to share from her perspective, what would you say those primary differences are? And how do you know which one might be right for you?

Hilary said when it comes to what are the differences, it’s pretty cut and dry to start with.

A remote job is a job where you might as well be in an office because you have like one client.  You have one job.  And you have one supervisor.  You’re probably benefited and get things like  401k and insurance.  You’re an employee just like anyone else, except that you don’t have that commitment to the office.

Whereas a freelancer, you can kind of like cultivate it and make it whatever you want it to be. It’s where you are the business.  You don’t work for another business.   But you are the business. So you not only do the work, but you also do the business development.  You go and find the clients.  And you take care of billing and invoices.  So if you’re thinking about if a business is like the office, then you are everybody in the office.

Hilary was referring to The Office TV show because she’s finally catching up on it. It’s like 10 years too late, but she’s in the final season. When you are the business, you are fearless. You are Michael. You are Angela.  You’re everyone if you’re a freelancer.  But if you work as a remote employee, then you are just one of those guys and you work from home.

I think that’s a great way to explain it.

And I think some of it also comes down to the level of risk you’re willing to absorb at the outset.  Because honestly, I know a lot of people are like, “Oh, a full time job, whether it’s remote or an office, it’s so much more stable.” There’s a lot of arguments to make that your job could be eliminated or like the company that I used to work for before freelancing completely closed. So stability and risk is a questionable thing at that.

But when you’re starting out, like you said, as a freelancer, you have to go create your own paycheck.  At a job you’re showing up and they’re telling you these are the things we need you to do. You’re going to get the benefits. This is going to be your paycheck,  It’s going to drop in your account every two weeks. A freelancer is taking on more of that upfront risk of saying, “Okay, I have to go chase the clients. I’m going to take on the responsibility of paying the taxes as a self employed person.  I’m going to figure out what to do with my benefits, etc.”

Some people are a little bit more averse to that. And others might be like, “Oh, yeah, I absolutely want to be my own boss.” So those are the important differences between remote and freelancing. I think it’s helpful for people to know that,  The good thing too, is you could work remotely and still have a freelance side hustle.  There’s lots of different ways that you could set it up.

Hilary talked about doing a lot of different activities and using those to land where she is now.  So I asked, for people who are just getting started with digital marketing and freelancing, how do you figure out what it is you want to specialize in or do and pitch that when there’s so many options?

I know a lot of people who are like,  “I’m kind of into social media and maybe a little bit of writing and some other things.”  I asked Hilary how do you decide to narrow down or do you not recommend doing that?

Hilary thinks it depends on your personality. She thinks it depends on how much time you have on your hands that is available. And how much of a learning curve there is.  If you got a degree in marketing, and you’ve kind of been in that world and you already have specialized interests, pay attention to the things that catch your eye. Pay attention to the pages that you follow on Facebook, the brands that you scroll through on Instagram, and the accounts that you follow on Twitter.  What are the topics that catch your eye that you have a natural interest in?

She thinks that’s a really great place to start. Because she thinks that you’re going to be more invested.  You’re going to have more of a passion for those projects. If you’re still in the stage of  building a portfolio and finding who you are as a marketer then she thinks that it’s good to start small.  Build those personal relationships and personal connections.

Start spreading the word that you’re building a freelance business.  Maybe you don’t want to ask someone directly for them to hire you or for their business.  Maybe you do.  You can minimally start spreading the word in your network by saying, “Hey, like I’m getting into this. I’ve always kind of had a knack for social media. I really think that I could help small like mom and pop restaurants, in particular, really nail their social media. I see so many bad pictures of food on Instagram. I really love taking pictures with this amazing portrait mode that I have on my latest iPhone. I really think that I could help people.”

Just start one email at a time or one Facebook message at a time.  You could do one coffee meet up at a time and build, build, build.  Spread the word about what it is that you like. And she  thinks starting with some that you’re passionate about and pairing that with a skill that you’re confident in is a really, really great place to start. And she thinks that there are lots of different things that you could do. But the more that you narrow down in the beginning, the more success that you can have because you can be confident that this is what you do well and you can really serve your clients well that way.

I love that advice, because I think it helps to be a little bit of a generalist when you get started because you don’t know what you like or don’t yet.

But I feel like when you say, “Alright, I’m going to be a social media marketer. I’m going to do content strategy. I’m going to do SEO and pay per click ads.” When you take on 6 or 7 different specialities, it’s really hard to keep up with the changes and software in six or seven industries. Claim competency in one or two where you’re like, “Yes, these are the blogs I follow. These are the podcasts I listened to. I do it enough within my day that I know what works as a best practice and what things are coming down the pike as trends.”

But I feel like I see a lot of freelancers, especially VAs, post on their website, “These are the 45 different services I can do for you.” That sets you up to be so frazzled and constantly having to go back and be like, “Okay, have there been updates in Facebook ads? I haven’t worked at the Facebook Ads client in four months. So now I have to go back to the drawing board reteach myself that again.”  That can be really stressful.

So I think it’s good, like Hilary mentioned, as soon as you get started, start seeing what you gravitate to.  Start seeing what you like and what converts well with clients.  What are clients asking you to do with them? Are your sales calls easy and they’re like, “Oh, sold! I so don’t want to do this.  You sound like the expert.”? Those are all signals that you can take and apply to your life.

I asked Hilary, what would be one of her best tips for getting clients to work with you consistently?

This big hurdle for a lot of freelancers both new and experienced.  They do a lot of one time projects. Since Hilary seems to develop relationships with her clients where it’s more of a long term situation, how does she suggest that freelancers set themselves up to be open to more of those opportunities?

Firstoff, she thinks this is so important.  A few different things come to mind. The first is to  say yes to projects that you know you can nail.  I think it’s nice to stretch yourself.  It’s nice to try new things.  But in terms of building relationships with clients that you’re going to have for a long time, you really want to build that dependability and that trust. So say yes to things that you feel very confident in.

Also cultivate real relationships. When you hop on a call, don’t just get right down to business.  Ask someone about their family or how their sports team did.  You can ask things like what’s the weather like today or where you are. She knows it sounds silly to always start with the weather, but it’s such a nice icebreaker. And such a reminder of, “Yes, I’m here alone in my home in Northern Virginia, but you might be in your home office in Nashville.” She thinks it’s so important to take the time to build a relationship besides just getting down to business.

I love that!  And especially notice that if you live somewhere unique, that can also really be a great icebreaker.

My husband and I just relocated to Minnesota a few months ago. And every single person who finds that out wants to know how cold it is.  They want to know how bad the winters are and why on earth would we move to Minnesota.   It just it instantly breaks people down from that level of professionalism when you show up to a call.  I used to say when people would ask me where I lived.  I would share that my husband is in the military. So we live wherever the Navy sends us.   And it would always disarm people to make them feel like they’re talking to a person and less salesy and everything. So I totally agree.

And another one of my tips for that is when you are preparing to talk to a client or to start building that relationship, check out what you can about them online. A lot of people will share things on their LinkedIn or on other social media.  And I just openly admit to it like, “Hey, I kind of stalked you a little bit. I saw you run marathons. That’s amazing.”  People are so flattered by that.  They’re like, “Oh, yeah, I started doing it five years ago.”

It starts this whole honest communication thing, where you really are trying to get to know them. And you can ask questions about it or use that as an icebreaker. And you’re right, it really sets people up to want to continue to work with you, because you took that little bit of extra effort to build a relationship and to have communication.

Move from email to the phone as quickly as possible

When I was talking about hopping on the phone and talking about something like that is one reason that Hilary is a big believer in moving some conversations from email to phone as quickly as possible.  When they email her and ask what her rates are or something like that, she wants to move that conversation from like cut and dry email to the phone as quickly as possible because she wants them to know that she’s a human. She wants to know that they’re human. She wants to figure out how she can help them succeed at their job. If she can write the perfect thing for them, then that’s going to help them put food on the table for their family. So as soon as you can, move from email to phone.  She thinks that’s something that is really not done as much these days as it used to be. But she thinks that that can really be a game changer and building that rapport and building that connection with a client.

I am the same way, I always want my clients to get on the phone with me, even if it is for five minutes, because people can present themselves differently on paper than even in like phone or zoom or Skype communication. So I want them to know I am a real person.  I also feel like it’s a much better chance for you to convert the sale.  If you get one of those emails with like, “Oh, send me your rates.”  And then you write back with your rate sheet. It’s so impersonal. There’s no value demonstrated there.

And the whole conversation is revolving around money, which does not put you in a positive negotiation situation at all.  It’s very easy for the person on the other end of that computer to open it and think it’s too expensive. But when they’ve had that conversation with you, they’re like, “Man, she really knew her stuff. She seems pretty organized. I saw her website and clients are raving about her. I just need to get this off my plate.  Why waste further time thinking about it?”  You built up that value there. So I could not agree with Hilary’s advice more.

So many freelancers are like, “Oh, we live in a digital world. Let me just close it over email.”  And not everyone can close over email.   You’re still a stranger to them. So let’s take that off the table a little bit and have even a 5-10 minute phone conversation. You’re in a much better position there. So I love that advice, because I try to do the same thing.

I want to thank Hilary for agreeing to come on the show and sharing so much of her insight. I think that’s going to be really helpful for people who are either new to freelancing or who are thinking about expanding their freelance business.  She shared a lot of really valuable insights.

Thanks for tuning in to 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.

Hilary Sutton is a writer, speaker, and consultant passionate about helping people spend their days in work that is wildly fulfilling. She is the host of the podcast, “Hustle and Grace” and the author of several eBooks and courses including More in Less: 21 Productivity Hacks for Creatives. Hilary served as professor of communications, social media, and journalism at Southern New Hampshire for five years. She is a freelance writer for hire with expertise in direct response copywriting and content marketing. As a freelancer she has served clients ranging from Broadway shows, to nonprofits large and small, creatives of all stripes, and consumer brands. She has written hundreds of articles in dozens of publications including USA Today and The Washington Post. Hilary and her family live in the DC metro area. Connect with Hilary on Facebook and Twitter @hilarysutton, on Instagram @hilary.sutton and on her website at hilarysutton.com.