Silicon Valley and standup comedy - Copywriter Sara DeForest
Sara started freelancing in 2018 after she was laid off from a VP of Marketing role in Silicon Valley. Since then, she’s relied on her network and word of mouth referrals to keep the work coming in.
When she’s not working for clients, Sara spends her time doing standup comedy. As well as gigging regularly, she’s spoken at the SXSW conference about the links between standup and marketing and how practising standup comedy can make you a better marketer.
She chats to Steve about finding balance, working from home, managing her time, and how she combines both of her ventures - comedy and marketing - on just one website.
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Transcript of the Being Freelance podcast with copywriter Sara DeForest and Steve Folland
Steve Folland: As ever, let's get started hearing how you got started being freelance.
Sara DeForest: So I've been freelancing for about a year and a half now and I started after I got laid off from my job at a startup, which is a pretty common story here in Silicon Valley, but it was a total blessing in disguise because it really pushed me to start freelancing, which is something that I wanted to do but was too afraid to try.
Steve Folland: So what were you doing before that? Were you, other than at the startup, had you been working for years in a certain field or what was it before?
Sara DeForest: So I was the VP of marketing at a startup here in San Francisco. So in that role, I mean I was the first marketing hire, so I did a little of everything as you do in startup. So it was, content and copywriting, like what I do now. But also social and email and events, lead generation, hiring a team, branding. So that was a crazy startup experience. But it was a good experience because I learned a ton because before that I was more focused on, just on content and just on communications.
Sara DeForest: Before the startup, I was at Hewlett Packard for a few years doing some digital content, some email stuff. And then before Hewlett Packard I was at a PR agency in New York.
Steve Folland: So you were quite niched and then you went into the VP of marketing and you learned lots of things at once.
Sara DeForest: I think it was ... I think my experience and my interest has always been writing, whether it's at the PR firm, writing op-eds or ghost writing articles on behalf of clients or at HP we did a lot of just kind of traditional communications press releases and things that. So I think writing has always been the common thread, so it makes sense that, that's what I'm focused on in freelancing now. But within the field of marketing and communications, I've been able to kind of touch on a lot of different areas.
Steve Folland: So when you decided to go freelance, how did you get those first freelance clients?
Sara DeForest: I basically reached out to everyone I had ever worked with in my entire career until ... just to put a bunch of feelers out there and see if anyone was interested or needed some help. My first client was this tech company here in the Bay area that I initially was interviewing for them for a full time role. And then I didn't end up getting that one. But then they said, actually we have this contract role if you're interested.
Sara DeForest: And I was like, oh, yeah. I'm more interested in that role. So I took that on and that was a great first client. It was part-time, a couple of days a week. And then around the same time, a friend of a friend who owns his own business posted on LinkedIn about needing a part time marketing consultant. And so I jumped on that. And so those were my two first clients. And that was when I was just starting out, just kind of seeing if this was a thing that I could sustain. And then by the end of the year, I really liked the lifestyle. I liked the flexibility and so I wanted to kind of go all in.
Steve Folland: When you said you were doing a couple of days for a particular company, was that in house or did you get to or have you always been working from home or where do you ... what's it like for you?
Sara DeForest: That so that first company was in the office just a couple of days a week, but it quickly became clear that I preferred working from home. I just, it's not for everyone. I think some people prefer to have a separate space for their work and when they're home they get distracted by things. But I actually, I just find I'm most productive and most comfortable there.
Sara DeForest: And so after an initial few months working very consistently with this client, then we sort of worked it out. So I would just work remotely and fewer hours so I could pursue other clients too. But so I worked pretty much from home. I have some meetings with clients once in awhile, but I would say 90% of the time I'm home.
Steve Folland: How do you manage to sort of stay focused? What technique have you settled on?
Sara DeForest: I'm very tied to my calendar. So I will block off chunks of time on my calendar each day dedicated to like, this is when I am going to work on this assignment. I know that this needs to be done by the end of the week, so here's how I'm going to lay out the rest of my week in order to get everything done. With cell phone distractions. I've learned to literally just put it in the other room, where it's just out of sight, out of mind.
Sara DeForest: Because I know even if I can just see my phone, you're ... we're so addicted to these things that your brain just starts to poke at you like, hey, why don't you see if you've got any notifications, why don't you take a look at it? And so I've learned that I have to not only put it on do not disturb, but actually put it in a different room where I can't even see it.
Steve Folland: Bury it in the backyard.
Sara DeForest: Yes, bury it in the backyard. And I, what else do I do? I mean, I've also been pretty good about keeping regular hours. I think work life balance is really important to me and always has been. So I think maybe that sort of drives me to not procrastinate too much because I know that I don't like working in the late evenings, I'm kind of brain dead and that. I'm definitely more of a morning person. So if I put it off and have to work late, then I'm just not going to produce as good a work. And so I think maybe that sort of drives me too.
Steve Folland: So you'd obviously worked a lot in marketing. How have you found marketing yourself?
Sara DeForest: So most of my clients are still through referrals and word of mouth and, or people I've worked with in the past so I haven't really had to market myself yet. Most of my clients have been through my network. Whether it's people I've worked with who have moved on to other jobs or get referrals through them. I've had a few clients through LinkedIn, if they ... if it's recruiters looking for a freelancer, a contractor.
Sara DeForest: And so I really haven't done too much marketing myself except for making sure to stay in touch with my network. And if there's a client I've worked with in the past or a prospect I had talked to at one point, but nothing came of it, then I try to make a regular habit to reach out to them every so often. And then actually lately I've been trying to do more speaking engagements too.
Sara DeForest: I actually got to speak on a panel at South by Southwest last year, which is a huge tech conference here in the States. Still trying to do a bit more of that and we'll see if in the future, I mean I'd be interested to try doing advertisements or maybe an email newsletter or something to market my own work.
Steve Folland: But it just goes to show that marketing can also just be kind of showing up online and in person and being nice to people and reminding people you exist I guess.
Sara DeForest: Totally. That's what I've really learned through freelancing. It's really important to just never burn any bridges. Even just try to be a person that people want to work with. Even when I was working full time, in house at companies, I didn't know that I was eventually going to be freelancing, but I just ... it's just so important to maintain those relationships or at least be someone that people enjoyed working with so that ... I've had to reach out to people who I hadn't spoken to in maybe five or 10 years and it was good that they could see my name and it would be someone that they were like, oh, yeah, I remember her.
Sara DeForest: She was great, would love to work with her again versus like, remember that time we didn't get along on that really stressful project and now I need something from you. That just doesn't work as well.
Steve Folland: Now, I like how on your website it says at the top a serious marketer brackets who also does comedy close brackets.
Sara DeForest: Yes, I do. I do standup comedy here in San Francisco. So that was yet another reason why I decided to freelance is so I can have a more flexible schedule. I could do shows at night during the week or travel and just not really have to worry about being in the office the next day. So I've been doing standup for about probably five years now. Since I've started freelancing I've really been able to focus on it a lot more, which has been really fun.
Steve Folland: That's cool. When you went freelance, because I loved the fact that it says a serious marketer who also does comedy. The fact that you haven't hidden one from the other or whatever. It's ... Did you at first or have you just gone this is me?
Sara DeForest: It was mainly just, I just wanted to create one website and I had, I had the domain, I had saradeforest.com and I don't know, I would ... but I seriously need to update my website. It's kind of the saying, the cobbler's kids have no shoes. I really need to spend time and update it because I have thought about would it make more sense to use this as just my professional website?
Sara DeForest: And then maybe the headline shouldn't be also comedy and then if people wanted to see comedy, I could have a little page for it if you're looking for it. But I ... it is something I think about a lot. I think overall it's a positive response because it's different and people ... it's a great conversation starter. I have it on my LinkedIn actually that I do standup comedy. I have that as a role I'm in on my profile.
Sara DeForest: So I think it's just helpful to have something a little unique, have something that people can start a conversation with you. And then as a copywriter, I think it's intriguing to clients and potential clients because maybe they've wanted to try to incorporate humor in their marketing and didn't really know how to go about that. And so that's something that I could offer to do for them.
Steve Folland: I like it. There can't be that many generally. It feels different and I can see that it would be a talking point, but when you say that you want to redo your website and I'm the same by the way, I always think this about my own, but what is it that you would change? Everybody, you're going to have to go and look at it really quickly before she changes it or maybe not. Maybe it will still be the same in five years...
Sara DeForest: I'm sure I'll find ways to procrastinate this, then maybe I think your positive feedback will make me procrastinate even more.
Steve Folland: I'm sorry.
Sara DeForest: So maybe it's good as is. I mean just basic things, like I have more recent work that I want to showcase. I also, I'm starting to do a little more social media strategy for some clients. I think I've had a few clients that started out as like, hey we just want to produce a bunch of content and then it sort of evolves into, okay now we want to distribute it. And so I have some more social media management experience that I want to highlight there that's currently not on my website.
Sara DeForest: So just kind of refocusing the skill areas and updating more recent work. But I would say the biggest blocker for me, and your listeners who use Squarespace will understand that the template I chose for Squarespace has, it's ... I really like the homepage but the kind of separate pages for each skill area are pretty awful for ... from a design perspective. The images are huge and they take over and then the caption for what the actual work is, is super small and sort of hidden and it's just not a great layout.
Sara DeForest: And so what I need to do is just go through Squarespace templates and pick one that works better for what I want. And, but then that means I kind of have to redo the website and that's why I've been putting it off. If it were just I need to add a new link, that'd be fine. But it's kind of a restructure.
Steve Folland: Did other freelances when you went alone?
Sara DeForest: Yeah. I definitely ... I mean I feel in marketing, it's becoming more and more common to freelance. I think that's sort of where the trends are going. Companies are outsourcing more and then workers themselves are ... they prefer this flexible schedule. So I knew a handful of freelancers, whether copywriters like me or I knew a few people in video production. And I talked to a lot of people just on the nitty gritty of how you pay your taxes and how, whether I should set up an LLC and then to the more general things like how do you get clients? So, I definitely talked to a lot of people and got a lot of advice before I really jumped into it.
Steve Folland: And do you get to hang out with other freelancers now or do you just prefer to kind of go it alone?
Sara DeForest: I don't do any meetups. One friend in particular who is a freelancer, she's ... she and I will kind of get together every few months and talk shop and sometimes we've ... I've even brought her on projects that I'm working on where I need an extra help. So we have a good relationship there. And then I ... she's been freelancing longer than I have so I can ask her questions about the administrative side and taxes and things like that.
Sara DeForest: But let's see, I mean I don't do a ton of like I said, meetups for freelancers, but I do feel like I often get connected to people who are thinking about freelancing or people reach out to me directly because they want to get started. But also that's why I enjoy listening to the Being Freelance podcast because it's nice to hear other people's stories and so it's been nice to have sort of an online network as well.
Steve Folland: You said you've been doing standup for five years, I guess that's freelance in itself. Are there skills that kind of go across from being a stand up to being own business?
Sara DeForest: So, that's what we talked about at South by Southwest. That was our panel topic was how stand up comedy can make you a better marketer. So we talk a lot about the importance of listening to your audience, the importance of testing your material before you launch it widely. So in comedy that means going to an open mic and trying out a new joke there instead of trying out a new joke at Madison Square Garden or a huge arena and also the importance of being authentic and knowing what your brand identity is either as a comic or as a company.
Sara DeForest: So, there's actually a ton of overlap except in standup you don't, at least at my level, you don't really get paid. So that's the big difference in freelancing.
Steve Folland: Maybe as you freelance more you'll get even better at negotiating and then suddenly you'll start getting paid more for your standup.
Sara DeForest: I know. Well I think the hope is that as I freelance and can focus more on standup and can put more time into my standup side hustle, then maybe I would get the kinds of opportunities that do pay, the kinds of comedy shows that book comics and actually pay you money to perform instead of just for the privilege of getting on stage, which is great too.
Steve Folland: I love the fact that some people go freelance so that they can be with their kids or to go surfing every day and actually a big chunk of yours is to be able to do that, I don't know, not side, I don't want to say side hustle. That side passion that you were already doing, that actually work was holding you back.
Sara DeForest: I think a lot of people do ... become freelancers so that they can pursue these creative passions. I know a friend of a friend is ... she's a lawyer, but she's also a writer and is working on a novel and she's not freelancing, but she's negotiated a set up with her work where she only works 80% of the week, so she takes one day off from the week just to work on her writing. And then the other four days she's in the office working at the job.
Sara DeForest: But I ... So I think a lot of people find ways to figure out having a more flexible schedule in order to pursue their creative dreams too.
Steve Folland: What have you found most challenging about being freelance?
Sara DeForest: Let's see. I would say overall, I really love it and I feel lucky that I love it and I'm glad that I started this journey, but I think in the early days a challenge was not knowing how to sniff out a bad client. One of my first projects when I was first starting freelancing and sort of just taking any job that I could get was writing a blog post for a tech company and we agreed on the fee, but I didn't put a contract in place because it was just a small one off project.
Sara DeForest: And so I wrote the blog post and sent it to the editor and then just never heard from him. And I followed up and he would just say, we'll get back to you. And I just never heard anything else until about a month later I checked their blog just to see like, oh maybe they published it and they just didn't tell me. But they had published basically a carbon copy of my blog post, but under a different writer's name, under one of their in house writers. So I emailed the editor about it. Still got no response. Luckily I knew his boss, that's how I got the job originally.
Sara DeForest: And so I had to reach out to her and luckily she got it resolved and they paid me and it was ultimately fine, but they didn't change the name on the blog post and he never fessed up to ... he kind of tried to explain like, oh that was just an error. But I was like, this is exactly what my article said and you ... I don't know. So just things that where it just showed me how important it is to get a contract in place and just be very clear and have things in writing about what the expectations are before just saying yes and accepting any project you can get.
Steve Folland: And did you put those things into place shortly afterwards?
Sara DeForest: So then after that I knew I'm not going to take a client if they don't sign a contract. There was a few months later I had another potential client where I did one blog post as sort of a trial and hey paid me for that, which was great. And then they asked me to do another one and I was like, great, but, and here's my contract, I really prefer to have a contract in place before we get started.
Sara DeForest: I've kind of learned the hard way and then they just never responded and I followed up a few times and they just ... I don't know. It was something about, for some reason they just were not interested in having a contract. Maybe they got busy and they lost interest, but I was just glad to avoid another. I'm glad I felt comfortable enough to just move on. It's probably a red flag if they don't want to sign a contract.
Steve Folland: Well, one thing I was going to ask is that, so before we started recording I was like, how do you describe yourself a freelance what? And I said, I thought it was going to be marketer because on your website it says a serious marketer who also does comedy. Whereas, obviously I introduced you as a freelance copywriter, was what you call yourself something you've wrestled with at all? Or ...
Sara DeForest: Yeah. It's something I still wrestle with I think. I ... Sometimes I say I'm a freelance marketer who focuses on content and copywriting if I have enough room to play with. But I think when I first started, because I was just coming off of this very generalist role at the startup, I felt I had strong skills across a wide range of marketing areas. And so when I would pitch to clients or when I would get connected to potential clients, they would say like, what can you do?
Sara DeForest: And I would say everything and I would list out every angle of marketing and that, I think that just sort of confused people or they didn't, maybe they didn't really believe that I could really do all those things. And so I've found that it's, for me, it's been better to go in pitching myself as more of a narrow focus. Like say, I do content and copywriting and then once you get the client and you've been working with them, often the projects sort of evolve or expand into other areas.
Sara DeForest: So like I said, I have a few clients who maybe the project started out with just some content but then they realized that they need some help distributing the content and so then I can help with an email strategy or a social strategy. So it's, I think for me it's been helpful to sort of pitch more of a narrow focus. And then once I have the client, then it's a little easier to expand into other projects.
Steve Folland: I meant to ask earlier on when you were talking about your day and you said, oh, I might try and leave the house. Is that a structure part of your day, like getting out of your space?
Sara DeForest: Yeah. That's ... So, when I was working in house I was always ... I always had that attitude of just being in an office and just putting your head down and getting work done and don't take breaks and don't ... I had coworkers who would go and go for coffee or go take a walk and I don't know, I always had this attitude of like, I'd rather just get done earlier so I can leave the office earlier.
Sara DeForest: But then that always ... that doesn't always work out that way. Sometimes you still stay late. But since I've started freelancing, because I'm just alone in my apartment all day, you really do get cabin fever if you or at least I do, I get cabin fever if I don't like ... And also even your legs start to cramp up if you realize you've been at your desk for hours.
Sara DeForest: And so I really try to make a habit of getting out once a day. Usually in the afternoon I'll just go a long walk or I'll do an errand or maybe I'll have plans to get lunch with someone. Just something that takes me out of my apartment and out from behind my desk so that I can interact with the world a bit. Because I've learned that, that's something that's important that maybe I didn't feel it so acutely when I was working in an office with a bunch of people around. But since I've started freelancing, it's something I try to make time to do.
Steve Folland: If you could tell your younger self one thing about being freelance, what would that be?
Sara DeForest: Oh, well we talked about before, always get a contract in place before starting a project. But also I think one thing that I learned early on too, pricing is always difficult. I usually charge hourly and so figuring out my hourly rate, I think when I was first starting, I definitely low-balled myself. And then, when you happen to get a client that's a longterm ongoing client, that's great.
Sara DeForest: But then if you're locked into a low rate, then that can be frustrating. I think I would tell my younger self to not be afraid to ask high and then you can always negotiate down. Sometimes I would get scared to ask for higher rates, but especially for bigger companies, it's ... it doesn't make that much of a difference to them, but it makes a huge difference to you. So I would say ask for our high rate, let me know if that's what you had in mind or happy to discuss if you had another budget in mind.
Sara DeForest: So something that that says what you want, but then leaves it open for discussion if that doesn't work for them.
Steve Folland: Sara it's been really good talking to you. All the best being freelance.
Sara DeForest: Thank you. It's been great. Thanks so much for having me on.