In this episode with Anthony Sills of ProfessionalPen, we talk about his transition from a 9-5 in mortgage banking to freelancing, moving from copywriting to running a content marketing agency for software/SaaS companies, and a generally healthier life as a freelancer — partly because of increased control over his income and exposure to racism.
“I think in freelancing, if you approach it with a business mentality —and that doesn’t mean to work yourself ragged and hustle — if you set your life and your business up right, there’s tons of options.”
Anthony touches on some really interesting points including demand-based pivoting, working with a VA, why he doesn’t need to bill 40 hours a week, and adjusting to life during a pandemic after extrajudicial killings of Black people getting media attention again.
He’s also got some really good perspective on checking in on your business health and useful advice that he would’ve given his former freelance self. If you’re looking for help from Anthony for your own writing projects, swing by his site.
Skyword and Contently.com for working with big brands
Anthony, welcome! How are you doing?
I’m doing excellent. Thanks for having me. How are you doing?
I’m doing okay. Thank you so much for coming on. So we are going to talk about your business, which I’m really excited about because I get to talk to a writer. So we get to talk about The Professional Pen. Tell us a little bit about your business, how long you’ve been doing it, what it looks like work-wise, earning all that good stuff.
My business is, Professional Pen. I run a content marketing agency and I primarily help software, SaaS and technology companies with their marketing. I got started in 2008, primarily just freelance copywriting, I wasn’t so much content marketing then and I guess I just noticed more demand over time. I did a lot of training with Copyblogger and HubSpot and they talk a lot about content marketing and so I saw that companies were spending money in this space and I pivoted to develop more skills around that and then eventually pivoted to an agency model.
Was that a big shift from copywriting to content marketing? I ask because I started straight in the content marketing world, I jumped right into it.
It’s a shift, but I think it helped me to focus. Because copywriting, at least when I started, that’s a broad hat that you’re wearing. You could write a little of this, a little of that and I did that for a few years. Whatever popped up, whether it was product descriptions or sales letters or helping people create courses, which is fun and it helps you learn new skills and everything but, I think you can earn more and also skill up faster if you’re limited to what you’re trying to master. And so, when I pivoted towards more of the content marketing, it was clear what I had to learn or what you were going to sell because it’s a smaller discipline. You’re not trying to do all the copywriting projects.
Right. What does your average work week look like? Have you set that up?
I don’t know that there’s an average week. I try to work off my calendar. So there’s time scheduled for client work, time scheduled for prospecting or marketing and such, admin, but things pop up and so that’s why I laughed. It doesn’t really work out where it’s average. I probably do maybe 20 to 30 hours of client work. I spend a few hours at least on answering emails and invoicing and all that kind of jazz but, I try to split it up. There are days where I don’t really do meetings or calls where I’m trying to buckle down and get work done. And there might be lighter days where I’m doing admin and emailing and different things like that.
It seems like that’s where most people fall, because, if I had to describe my average week, that’s probably it too. That 20 to 30 hour of production and then a little bit additional for like marketing and admin.
Yeah. You can’t forget the marketing because then you won’t have work.
You won’t have that production to worry about scheduling. So how does that compare to your employment history? I know you’ve been doing this for a while, but as far as like time worked.
04:00 You can be more productive with less hours. People are surprised if you say you work 20 hours. But, I’m charging $150 an hour, so I don’t need to bill 40 hours. If I actually did 40 hours worth of client work and then you still have to market your business, you have all this administrative tasks, that would bring me back to the hours I used to work, when I was in mortgage banking, which is like 60 hour weeks and such. I don’t have an interest in doing that anymore.
Same. How did you get started in content marketing? Well, we talk about you moving from copywriting, but how did you get started in paid writing? I should say.
04:50 Prior to this and I mentioned briefly, I worked in mortgage banking and so for one of the companies I worked for, I actually did the employee or internal newsletter. I’d been doing paid writing here and there. When I shifted from copywriting to content marketing, I just jumped in with two feet and went after people that were already… It’s not hard to tell. If you go on their website and they have a blog or they’re publishing case studies, then you know that, that is a potential client for you, that they’re spending money. It’s a matter of getting in front of the people that can make the decision and saying, “Hey, can I help or could I be helpful?” I just went after whoever I could find. Problogger job board, LinkedIn. At first, it’s very much outbound, nobody knows who you are so you can’t just wait for the phone to ring or the emails to roll in. I did a lot of cold email or reaching out to people. Back then, I guess it was a bigger thing with joining certain LinkedIn groups. I don’t know if people even do LinkedIn groups anymore.
I feel like they’re trying to get it going again, but really, it’s not working.
Yeah. Back then, I would be in certain LinkedIn groups where people might share freelance leads or…and so now sometimes I have more clients come through referrals and different things like that, but I still do a fair amount of prospecting or outbound degeneration.
You’ve worked with some pretty big brands. Can you talk a little bit about who you’ve worked with and how you got hooked up with them?
06:34 Networking is a big thing. I know you deal with, I believe Skyward, I work with Contently, so some of the clients came through them and I was with them in the early days. I think at one point they may have had more companies that they were working with than they actually had freelance talent. I’m sure that pendulum has shifted, but they’re like, “Hey, can you do this for this brand?” I worked with IBM, I worked with eBay off of Upwork…
Back when it was… What was the other name that used to be?
oDesk or Elance.
Elance! I was a member of. eBay was on there looking for people. People don’t know, but on Upwork, there’s really good companies that are looking for freelancers. And then there’s people, I won’t say they’re horrible companies or people, but they maybe have no idea what they want or they haven’t worked with freelancers so that’s a whole different story, but there are good companies out there. I wouldn’t say, rely totally on any job board or site, but if you’re just getting started, you can definitely find some potential clients that way.
Yeah. Upwork is a mixed bag and it’s something I’ve talked about on blackfreelance.com. But, I still use it. I’m six, seven years into the game and I still use it. You just have to be really selective and know who you’re working with or you can burn tons of time on people who are like you said, new to freelancers and you basically have to teach them how to work with you or they’re just trying to get the cheapest word they can possibly find.
Yeah, I don’t want to do either one. I can’t do 87 Skype calls and then there’s no project and I can’t teach you your job, not on this project.
One of biggest things for me, as far as shifting from employment to freelancing has been the impact on my mental health and like lifestyle design. What has that been like for you transition wise? I know you talked about your 60 hour work week before and you moved to a less intense workweek, but overall, what’s that been like?
The short answer is, it’s wonderful. It’s a lot better. I feel like I’m a lot healthier and it wasn’t something I don’t think at first, I consciously set out that, “Oh, I’m freelance freelancing because I want to be healthy”. Right. And then the commute, you take that out of the picture right off the bat. I’m preparing meals at home as opposed to eating out at the place that’s closest to my job. I eat healthier, I have more time to exercise, more time for hobbies. Depending on where you live, but, I’m in the Philadelphia area so you can have an hour commute easily depending on where you’re going, if you drive to work. And so, that’s two extra hours back in my day that I can do something better with. I haven’t used an alarm clock in a lot of years.
I sleep until I’m rested and then I get up and I work and it all fits. I have a schedule, but it’s not a forced schedule where I have to take the cold shower to wake up and drag myself out of bed. And I mean, the work is exciting, there’s always something different going on. You can find that in employment, but I think there’s a freedom and a control aspect that freelancing delivers that is not there in an employer employee scenario.
I’m still living the alarm clock life and I’m really curious how to get off of it. I still have that 6, 6:30 alarm block and that’s the last thing that I need to get rid of. Did you just stop using one after you went freelance? Or…
It wasn’t immediate, at one point I turned myself into an early bird and I totally was a night owl before. But I just started going to bed at a certain time and then when I’m done sleeping, I would wake up and then after a couple of years I would just wake up around the same time every day without an alarm clock.
Alright I’m taking notes. The next level up I have to make.
It helps that you don’t panic, right? If you wake up 5 minutes later, you roll into the other room. So you still can get back on schedule. There’s no fear that I’m going to get caught in traffic and now be two hours late to work. So that’s part of it, I guess.
I used to be hardcore, six o’clock I’m getting up, but lately with everything going on between the pandemic and just recently, George Floyd’s murder, I have to give myself some space somewhere so I’ve been more lenient on that and I’m noticing that I’m getting up with the alarm clock and I still have a little bit of that panic but I probably need to try to start letting that go.
My morning routine, I don’t pop up and work though. It’s a couple hours after I’m up, when I actually am sitting down to work. I read a meditation prayer…
A whole routine, get some breakfast in. When I do sit down to work, I’m not tempted to go near the refrigerator because I’m a vet now so that’s a trap. You have to stay away from the TV, the refrigerator, don’t go near your bed and get a couple of hours of work done. But, I definitely don’t pop out of the bed and turn on the computer or check emails because I have to ease into my day.
Yeah. That slow transition has been nice. That’s one thing I absolutely love when I get up, between the time I wake and start working, it’s probably an hour, hour and a half.
Have to get time for your brain to get all the way out on and functioning.
Exactly. With everything going on right now, everybody’s going through something right now. People are working from home because they can’t go into an office anymore. Across the board, freelancers don’t seem to be navigating as much change, but how has your life changed between COVID, between what’s going on after George Floyd being murdered? What have you seen going on differently? Are you doing anything differently?
Speaking first to COVID, obviously I was already working from home, I don’t really do the coworking spaces. If I got bored, I would go work from somewhere else every once in a while. I’m in Southern New Jersey, outside of Philly and, by there being so many people up here they totally locked us down, there were little curfews. And so, when you’re in the house all day and then you can’t go out, I just got antsy and it’s like, “I want to do something”, even if I wouldn’t normally be doing something, but you have to do the safe thing. Luckily, I live on a nice amount of land so I could get outside and I’m still not near anybody. And so I go out, take walks and get some sunshine and get back to it.
My work picked up a little bit because a lot of the clients that I’m working with, they had to either reposition their messaging or they sell something that is needed during the pandemic and so, I saw a spike in projects, which I’m still busy as a result of. Recently, it’s been hard to stay focused with the different murders and the protests that are going on. It’s like you’re keeping one eye on the news and then you don’t want to watch the news and with doing so much networking and work in the online space, I’ve been falling back off Twitter and LinkedIn a little bit the last few days or weeks because there’s a lot of toxic stuff on there and that’s a distraction. I’ve just been trying to watch what’s going on and figure out what the next move is and keep my business going and stay healthy and that sort of thing.
Yeah. You know I’m always preaching marketing, but even LinkedIn, which is usually pretty neutral or at least not neutral because there’s a lot of foolishness on there too, but it’s usually easier to avoid. You just talk to your people and there’s nothing really very controversial going on, but right now, even the top trending topics, it’s a lot. So I probably haven’t done any marketing in a week, week and a half.
I haven’t done anything. I haven’t mailed my email list since this started. I don’t want to add to the noise. I’ve gotten a lot of stuff from brands that were completely tone deaf and I’ve gotten emails where they’re trying, but even okay, you’re in solidarity with the protest and why your brand has no connection so you still didn’t have to send that email. I don’t want to be one of those people. There are people that I was already talking to, I’m still following up with them like, “Hey, do you need help with that?” But I don’t know that I’m just carpet-bombing, everybody with hire me, hire me, it’s tacky.
Just take a step back, it’d be okay if you’re aren’t marketing for the week or so.
Plus my website is up, profiles in different places, so people know how to find me. Not everybody probably, but enough.
We’re talking about marketing, we talked about LinkedIn and referrals, so is that how most of your business is coming in right now? From a network or how does your marketing strategy work?
I get a fair amount of referrals from people in my network. I am trying to be better about building my email list and marketing that way because obviously you’re more in control of that. I still do, when needed, I go poke around on Problogger, AWAI, Direct Response, JobScore, Upwork. I may spend an hour on Upwork and poke around and see if anything looks interesting with clients in my space or sometimes I just email. I have a spreadsheet of SaaS companies and so I’ll just pick a few of them and reach out to whoever is in charge of their content and see if they need help with anything. I just try to stay busy. I don’t think I’ve nailed the perfect mix of; pull these three levers with marketing and this many clients come out, I’m still working on that, but I know to stay busy. You have to contact people. You maybe get rejected a little bit, but let them know that, “I offer this, this is how I can help you” and just stay out there and stay moving.
That spreadsheet that you’re talking about, that prospect list, that’s honestly the make or break of your marketing. How do you get companies on there? How do you decide you have enough? Or how do you decide to work them again? What goes on there?
So the funny story about the spreadsheet is, I was working with a VA for a while and she was great. And so I actually did the lazy route of, this is what I’m trying to do, can you do it? And I hate Excel anyway. That’s another thing, Google sheets, whichever one, they freak me out. I like Microsoft word, Google docs, let me do the words. I don’t want to mess with that. But anyways, she made me this spreadsheet and it was the [inaudible 18:08]is a list of SaaS companies so put all 250 of them on there and then I think she went back two or three years. So it’s two or three years of who was on that list.
And then there was this software conference that happens in Philly every year. So, I just had her go on last year’s page and all the sponsors and everybody that presented. It ended up just being this massive spreadsheet of software companies and she would little by little go in and fill in where she could find it, the name of the marketing director or content marketing manager; name, email, social handles, if she could find them and then I would just work through this list. But by the time I get around to some of them, they’ve moved on to other roles. So now you have two leads because they went somewhere to do the same thing and then they were replaced by somebody else. Even when it gets outdated, it still gives me a starting point. You don’t have to say, “what am I going to do this week? How am I going to market my business?” You have some kind of starting point.
So the VA thing worked out for you?
It did because that was something I was never going to get around to. Like I said, I don’t like manipulating spreadsheets. And so that, and doing the research after all day of already trying to market and then doing client work, that was the thing that kept getting put on the back burner. But once it was done, it’s like, okay, I just have to open it and then email these people and so, that’s not hard.
It’s like such a good indication like this is one of those things to like…that’s a reason to outsource something. You see something that you’re just putting off and not doing, that’s probably a good sign that maybe you should consider outsourcing it or automating it somehow.
Sure. And I think how it worked out for me, you have to be very specific what you want. It wasn’t like I said, go find me some companies I can do content marketing for because, how would she know? I had an idea, if I use these lists, they’ll be companies with a certain funding status or of a certain size and they’ll have budgets so she had a clear idea of what to look for.
That’s something I need to get into too. Overall, what would you say is the biggest challenge you’ve faced in your freelance work?
Probably putting all the pieces together. Because, there’s freelance and there’s the thing you do. If it’s in my case, in your case, writing, but then there’s running a successful service business and all the components that come with that. You can be a kickass writer and if you don’t know how to collect on invoices or if you can’t sell yourself, you’re going to struggle to earn what you want. And so, I think my biggest challenge was realizing that you can’t just excel at that freelance part, you have to handle every aspect where like, compared to employment, where you have somebody handling payroll, benefits, scheduling, lead gen, sales and you just do your thing. You could just write, sit in your cubicle and write. When you’re freelancing, you have to wear all those hats. So I think that was the challenging part of maybe developing the systems and learning new skills so that I could run my business.
What did you do to develop that? Because that’s why I think most freelancers struggle because most of us are new to business. Even me, I went to business school, but I was new to being a one-person business. It’s very different.
It’s a completely different thing. I have a MBA and I worked with a lot of small business owners like brokerages and stuff like that and so, I have a sales and marketing background. I have no problem emailing people or jumping on Skype or Zoom to present the case of how I can help their business. But, it’s the rest of it. I don’t want to do paperwork, I don’t want to email back and forth, I want to write and so, it was definitely, ‘how do you stay on top of it?’ Like project management, let’s get some tools in place and I stole ruthlessly from people. If anybody goes on a podcast or blogs about their system and I like part of it, I’m going to incorporate what works into what I have going on. I’ve purchased a [inaudible 22:19] of workflows and different things that have been part of…
Oh wow! Okay.
They’ve been part of training courses or something I did, but it’s like, okay, if that’s what they do and it works for them, let’s try it and then you tweak it to make it work for your specific business.
What are some of your favourite courses or even like coaches or platforms? You mentioned AWAI already, I heard you make a little illusion [inaudible 22:44].
Ed’s great. I learned a lot from Ed and he actually helped me with, I forgot the specific offer it was, but it was basically getting your lead magnet and your email marketing set up. And so that was another one of those things like my spreadsheet of leads, it’s like I know I should do it and I should be email marketing, I should have a lead magnet and it wasn’t until I worked with Ed that I pulled the trigger and did it, and now it’s done and you can add that into your marketing mix. I like courses like that, where it’s something actionable at the end, your business has changed, not just hear some theory. I did a lot of courses with Copyblogger, which I think you did some training with them as well.
23:31 Yup! I’m certified with them.
Yeah. I love their stuff because it’s like real world that they built their brand on content marketing so the stuff that you’re learning is actually what works. I just try to learn people that are really doing it and not people that just blog about it. Copyhackers, they have a lot of great training. I’m trying to think, off the top of my head these are the ones that… HubSpot, obviously they have really in-depth stuff in their trainings and certifications. I like what you have going on with your academy, because going back to, you said the biggest challenge, there is the putting the pieces of your business together or what path towards building your freelance career are you going to take? And so a lot of these resources are just about the one part, like how to write or how to code or how to do graphic design but, I don’t see so many that are helping people put all the pieces together. So I think that’s…
Awesome. That’s good to hear. Thank you very much that is good to hear. So what would you tell Anthony back from 2008 when you got started? What’s the biggest lesson you’ve learned over the last 10+ years?
Don’t make things more complicated than they have to be, maybe.
Oh, that’s a big one!
Things will be humming along and I’ll be like, I’m going to build this or I’m going to contact 10,000 people. Just contact 10 and see how it works. If I had to [inaudible 25:06] and I could go back, I would keep it simple, you’re after a certain goal, so what gets you closer to that goal? And do that.
That is so hard. I’m deliberately trying to keep things simple and I still just veer toward making everything as complicated as possible.
I do a lot of checklists now and putting stuff on my calendar, and so when the notification goes off, do the thing and then it’s done. As long as I have the right pieces in place, I feel like I won’t run everything into the ground. Somebody shared something with me, I’m going to see if I can pull it up really quick. If not, I’ll tell you just what it was. But it’s like, every Friday they were saying, they do this quick check-in, like on your business. And so the questions they shared get you thinking; what did I do this week? And so, I added that as a Google calendar reminder, every Friday to go off in the morning.
I like that.
That way, if I didn’t do what I was supposed to, the week is now over [inaudible 26:14]. So some of the questions were like; Am I focused on where my business is heading? How have I made my business better this week than it was last week? Am I on top of money that I’m owed? What were my sales last week? Am I charging enough? Did I get word of mouth referrals in the last week? Have I spent time researching trends within my industry? How did I invest in my team and myself? How have I contributed to my community? Am I taking care of myself? And so, if you answered those 10 honestly, sometimes I’m finding, and I’ve only been doing it a few weeks, but it’s like, I need to do X, Y, and Z because I didn’t get around to that this week. I think you should take stock of your business every so often. So for me, that’s been working every Friday, I don’t think you should wait until New Years and be like, okay, what do I need to adjust? and it’s been a whole year. Quarterly works for other people I know. They think about stuff quarterly and pivot and readjust. But, I do think you have to take a look at like your whole business and say, what am I good at? What do I need to get better at?
I’m stealing those questions because right now, I have a weekly check in, but I’m checking in on my clients, I honestly need to do it more for myself. I will say that I have it on my calendar, but I have not given myself the right questions to make it actionable like that. Think about your business and it’s like, “I’m doing great, everything’s wonderful”. But having to answer those questions, already has my mind moving.
If you’re not healthy, you can’t do the best work for your clients. And then if you’re stressed about money, then negotiating or selling your services becomes tricky because of that mental game thing. I want to stay on top of everything and that way, if I don’t need your money then we work together if it’s a great fit, there’s no pressure from either side. And so, I do think it’s helpful, to obviously check in on your clients. What can I do better? Do you understand why we did this? And where are we and what’s next? But, I think you should take that same level of evaluation to your own business. You can’t stay stagnant, you’re either getting better and growing, and I’m not necessarily saying growing of bringing on employees or…but you want to grow your revenue, you want to grow and get more clients or better clients. So how do you do that unless you evaluate, where am I current clients coming from? It’s cool to have work, but, where does most of it come from? You should know that. And so…
You can end up getting caught. Look at COVID, a lot of freelancers, our strong suit here now, is that we can pivot. But if you’re not paying attention, you don’t know where to go when something like this hits.
Right. Because money is still getting spit. For every retail place that’s closed down or whatever there’s… struggling to pick, but like medical
Yeah. I’m in healthcare, there’s tons of money being [inaudible 29:09] about right now.
And I know a lot of tech companies have solutions that are useful. One of my clients does software that helps with visitor management. And so, with this contactless check-in, they’ve added new features to their stuff and they need blog posts and social media copy to get the word out. And so, if you’ve been writing in an industry that’s slow, I think, yeah, you have to… And so that relates to one of those questions; did you spend at least 30 minutes this week looking at your industry so you can help your clients? So you know what’s going on, the direction the money is flowing? You have to step out of your business. You can’t be doing client work and accounting and you have to just look at the business and say, “okay, what are the trends?” and work that way a little bit.
In that vein, what is the main thing you would want other black freelancers to know about what you do and about freelancing in general?
I guess, that we’re out here.
When I started, I mean obviously there was social media, it was 2008, but it was different a little bit. I mean Slack is more prevalent and stuff like that now. And so, most of the resources and the training and the communities, you didn’t see as many black faces. I don’t know if you existed then…
I did not.
If you did, I didn’t know about you. And I definitely found very, very helpful resources, but you get that feeling of being the only person in the room and all that sort of stuff. I would just want them to know that there are communities out here. I mean, now there’s black stock photos and stuff, that didn’t exist a few years back. And so I think people should know that they’re not alone on their freelance journey. Even though there are unique challenges that you would face being, say a black freelancer, there are resources available, you don’t have to just struggle on your own.
Yeah. And that we’re doing well. There’s a lot of us doing very well out here.
That too! I saw a conversation happening on LinkedIn actually, yesterday or earlier today, I can’t remember which. They were talking about racism within freelancing and all that kind of stuff and pay rates and it exists, I don’t want to say it doesn’t exist, but I think that you have much more control over your income as a freelancer, as far as racism and stuff than you do in an employment model where you’re supposed to work there for a year, but now you’re stressed because of racism. And then you look like you bounce around jobs. And so freelancing, if you don’t want to work with the client, then don’t.
And that’s the point. I can’t say I’ve encountered…I probably encountered the same types of people in freelancing, especially cause I’m in the same industry, but my options are completely different. So like one little microaggression and I can be like, bye. Why am I going to work with you and deal with all this? Versus like you said, being stuck in the situation and figuring out, okay in what basket do I put all my eggs now?
So besides the fact that we’re out here, I think I would say that there’s a little freedom in it. You know if you get your business to the part where you can be location independent, if you have your life set up that way, then a lot of these societal pressures, you have options that are not available to somebody who’s work is tied to a location or to an employer. I don’t know, God forbid, if there’s too much unrest, I might get out of here, take my laptop and go.
I at least plan on taking a break as soon as we’re allowed to leave the country. As soon as people will let us into other countries.
That’s the sad part. We’re Americans and we’re not allowed. We are on the watch list now of everybody’s country.
Yeah, the privilege runs out quickly. We’ll see. The world’s changing fast, but there’s new opportunities popping up.
I think freelancing, if you approach it with a business mentality and that doesn’t mean, work yourself ragged and all that hustle, but if you set your life up right and you set your business up, right, I think it offers tons of options and obviously I’m biased, but I wouldn’t go back to work for somebody else’s company when I could grow my own.
100%, same boat. Alright Anthony, thank you so much for taking the time to talk.
Thank you for having me, Meghan. I really appreciate it.
Talk to you later
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