TCC Podcast #323: Unflubbify Your Writing with Sara Rosinsky

The people and stuff we mentioned on the show:

Join The Copywriter Accelerator
The Copywriter Think Tank
Kira’s website
Rob’s website
Sara’s website
The Copywriter Club Facebook Group
The Copywriter Underground
Free month of Brain.FM
Episode 4
Episode 6
Episode 282
Gin’s website 

Full Transcript:

Rob Marsh:   A few weeks ago, I wrote an email to all of the people on The Copywriter Club list that included some crazy math about skill compounding. Because I know a lot of copywriters say they don’t like math, I added the phrase, “Bear with me,” to my email as I explained how it worked. Only I wrote B-A-R-E instead of the correct form of the word, B-E-A-R.

What’s worse is that I realized my mistake and I meant to correct it, but before I could, I had to run out, pick up my daughter from school. By the time I got back, I forgot. I hit send with my mistake in place. Fortunately, dozens of you caught my mistake and wrote back to point it out, which I really do appreciate, by the way.

One of those kind correctors was our guest for this episode of The Copywriter Club podcast, copywriter and etymologist, Sara Rosinsky. When she responded to my mistake, she offered to come on the podcast and clarify this beastly language that we all speak and make it fun and memorable. We’re thrilled to have Sara on the show today to talk about her business and some of the stickiest language problems that we all deal with as copywriters.

But before we get to our interview, let me introduce my co-host for the week, copywriter Gin Walker, who writes for educators and online experts. She helps them connect with their audiences. Welcome back to the podcast, Gin.

Gin Walker:   Hey, Rob, thank you so much. It’s so awesome to be here. I’m especially pleased to be here for this episode actually thinking about Sara’s fascination with grammar and punctuation and so on, because I spent a good two decades of my life as an editor. And so this is kind of my bag as well. I’m particularly pleased to be here.

Rob Marsh:   Yeah, that’s partly why I thought of you-

Gin Walker:   Oh, really?

Rob Marsh:   … thinking, “Hey, who should we have come on and help?” And I thought Gin would be perfect because she’s kind of into this stuff too.

Gin Walker:   Totally, totally.

Rob Marsh:   This is going to be a great conversation. Also at this point, I need to make sure that everybody knows this podcast episode is sponsored by the Copywriter Think Tank. If you’re looking for a mastermind/coaching program to help you scale your business, check out copywriterthinktank.com for more information. You get one-on-one coaching, not just from Kira and myself, but we have coaches for mindset and for systems and processes and for visibility.

There’s still time to get in and join us for our next in-person retreat in New Orleans in January. Go to copywriterthinktank.com for more information about that.

Gin Walker:   Yes, absolutely. Please, may I say, I am an alumni of the Think Tank and I cannot sing its praises highly enough. Get in there. You will learn so much. It’s just a hugely uplifting experience in every sense. Let’s get to this interview with Sara.

Sara Rosinsky:   I graduated from college and had an abundance of self-confidence. I thought employers would be beating my door down. That was not the case. And so I did what any advertiser should do, which is I put up posters that said I was available for hire. I put up just 8-1/2×11 posters all over Boston’s Back Bay, which is where I was living in Boston, had the little tear off phone numbers at the bottom.

It so happens that I thought I might be interested in advertising and had contemplated taking an ad club class. But when an ad agency called me, I was over the moon. They initially wanted me to hand-deliver some baseballs. They were invitations for American Express, and they were kind of a cumbersome-sized and shaped box, and they wondered if I could hand-deliver these invitations.

That gig did not happen, but the head of the agency kept my little phone number, and when they needed somebody to fill in for the, I’m going to say, girl who was answering their phone, very young woman, I was available. Absolutely, I’d love to answer your phones and type up your media buys and all the things that you need.

That was how I got my foot in the door at a Boston ad agency where I stayed for a decade. That was the beginning of my career. There’s more to it, but I don’t want to go on too long.

Rob Marsh:   But let’s stop there because this is amazing. I started my career very early in an agency as well, and there are so many stories of people who in order to get the foot in the door, join the mail room and deliver letters for a year or two until they can catch the attention or whatever. The poster, they literally found the poster and that’s how they found your name.

Then you worked as a receptionist. Then what was the next step? How did you get the attention of the person to say, “Hey, we need you to help on a project and not just answer the phones”?

Sara Rosinsky:   I was fortunate that this agency was very small, so I was not overlooked at all. I also was doing standup comedy at that time, and the man who hired me, Stan Bornstein, was intrigued by that. He had a concept where he thought it’d be great if we had a standup comedian delivering jokes about our client, Store 24, which was a convenience store.

He almost immediately was engaging me to think of writing and ideas. When he learned that I wanted to take an ad club class, that was when he really said, “Oh, you want to be a writer? You want to write advertising? Don’t pay them. I’ll give you stuff to work on.” He did, and he gave me assignments. I would very shyly put what I wrote on his chair when he wasn’t there because I was too self-conscious to present anything.

Anyway, he mentored me. He really did. I can remember him telling me what was terrible and when I missed the point. I got an on-the-job teaching opportunity.

Kira Hug:   How long did it take you to go from answering the phones to getting that opportunity and moving over to a writing role?

Sara Rosinsky:   I was doing both at the same time for a while. I can’t tell you exactly how long it took before I found myself in an office. It was probably honestly, it may have been a couple of years even. I’m not sure, maybe 18 months. It really was such a small agency that I was their IT department. Can you imagine?

When they got … I am not qualified, but I was the most qualified. Anyway, there was a lot of wearing of different hats and things. It was not strange that someone writing some copy might be sitting at the front desk.

Kira Hug:   Then just to give some context, can you talk about how the roles progressed over that decade, especially for people who haven’t had that agency experience?

Sara Rosinsky:   Let me think about how that unfolded. When they hired someone else to sit at the front desk, that was clearly an inflection point of you are now a writer. I shared an office, and I think I was the only writer besides Stan. I do also remember, probably three quarters of my way into that decade, I remember through my husband’s coaching telling Stan that I wanted to be a senior copywriter because I think there was maybe another copywriter there.

I laughed just because it was such a small shop that that didn’t fundamentally matter, but I supposed it did because the next job I ended up getting at Publix Super Markets in their in-house department. They hired me as a senior copywriter. As I say this out loud and I giggle about titles, they may actually matter. It may be worth pushing for that.

Rob Marsh:   It doesn’t really matter in maybe the work that you do, but it totally matters in the way that people perceive you. I agree. I think within reason, somebody with three months of experience shouldn’t be pushing for a senior copywriter title, but if you’ve been doing it for a couple of years, for sure. That seems smart.

Will you talk a little bit about the creative process at the agency? How did assignments work? I know we’re going back a little bit but working with designers or working with other members of the team, what was that back and forth like?

Sara Rosinsky:   I remember learning it and being intimidated by it. I don’t think I really understood. It was not intuitive to me. Again, because it was such a small agency, you had the opportunity to go and literally sit on the desk of somebody and say, “What might this thing look like?” Really work with a designer, which is of course the ideal. I can’t stress that enough.

I’ve been in other situations where you’re completely divorced from a designer. You’re not going to get as good of a product. I do specifically remember a campaign that we worked on. Stan came up with the concept. It ran in the Wall Street Journal. We did a lot of financial services advertising, and it included a Wall Street Journal type of illustration of a fund manager. Do you remember the little-

Rob Marsh:   Yeah. One of my goals in life is to have a stipple drawing of me done in the Wall Street Journal. That’s one of-

Sara Rosinsky:   There you go.

Rob Marsh:   I don’t have a lot of big goals, but that’s one of them. I want a stipple drawing.

Sara Rosinsky:   You could just pay that illustrator.

Rob Marsh:   I know, I know. Yeah, I thought about it.

Sara Rosinsky:   That was one component of the ad, but the rest of the ad was that it began with very large typography at the top that then tapered to become smaller. Therefore, it required a real hand-in-hand collaboration on what is the first line of this copy going to be? Where is the line break going to happen? What is going to… You do understand what I’m saying like it…

I remember being just jazzed about running back and forth with the designer and kind of sweating it out. It was difficult, but it was very gratifying.

Rob Marsh:   I look back at my experience too and sitting there with a designer in the office and bouncing the ideas back and forth is a very different existence than what most of us have as freelancers. We can work with designers of course and have something similar, but just that immediacy, and how fun it was and how you could be laughing about silly concepts and the next minute you’ve got something that’s just an amazing idea. Or it might take days or weeks to come up with things. But yeah, again, just curious about your experience in a similar environment.

Kira Hug:   I want to hear about some writing lessons from Stan. I mean, I guess it doesn’t necessarily have to be from Stan, but lessons one or two that maybe you’ve pulled into your book or you’ve pulled into your business today?

Sara Rosinsky:   I will tell you one lesson that really isn’t about writing, but it is about being a copywriter. It is a lesson I will never forget. As I mentioned, I was very self-conscious about presenting my work, and Stan kind of gave me a hard time about it. He said, “You’re going to have to learn how to sell your ideas.” I can’t even relate to the young woman who was so scared about it. Now, it’s a walk in the park, but golly, it scared me.

Well, so imagine my surprise when this happened. Stan had let me completely handle writing a media kit for Harvard Magazine. In case anyone doesn’t know what a media kit is, it is basically demonstrating to advertisers why they should place their advertising in Harvard Magazine, talking about the demographic that the magazine reaches and so on. I did what was asked of me. I worked with a designer, fine.

The day came that Stan was presenting my creative, and my phone rang. It was Stan, and he was in the conference room with the client. He said, “Sara, I’d like you to come in here and present your work.” When I tell you that my heart was beating so hard, I quite literally thought that people could either see it or hear it. I am not exaggerating. It was the scariest thing.

But he knew that that would get me over the hump. Yeah, that was a real lesson. I’m not sure I’d recommend it, but maybe it had to happen, pull that band-aid off or whatever.

Kira Hug:   Well, and maybe as a follow up, what advice would you give to a writer that is in the early stages and does not have that confidence and really needs to present to their clients, but is just terrified? What would help them?

Sara Rosinsky:   Something that I have really developed in my writing is this, every single word and letter and punctuation mark that I put down, I have a reason for it. I’m sure we’ll get into this later, but I will break rules on purpose. I will choose redundancy sometimes, if I think it lends something to the effect.

I would just recommend that everyone, when you write, feel good about what you’ve written and justify it to yourself. Then when it comes time to present it, you should be able in theory to confidently say, “This is why I did it. I believe that your reader will be grabbed by these first three words because they’re unconventional,” or whatever your reasons are. Just understand why you’ve done it and then you get to share it.

You’re sort of excited about what you did. I think a really good piece of advice is to always lean into your enthusiasm, anything that you’re jazzed about. I remember one time telling an internal client at Publix about an idea I had that I thought was so neat. It was putting something in a clear tube for a mailer. I thought it was the cat’s meow. I remember I fell to my knees begging him, “Can we please do this? I just think it would be so great.”

I guess I would just encourage you to have that kind of passion about your ideas. Nobody can fault you and you can hold your head high.

Rob Marsh:   Did the tube mailer go out?

Sara Rosinsky:   No, sir, it did not. It did not. It was still a great idea. Oh, I know what it was, Rob. I got to tell you, it was such a great idea. It was for single serve milk and they bottled this at their … They have their own dairy. I said, “Why not put the message in the milk bottle and we have that capacity. Why don’t we do that?”

I maintain it was an outstanding concept, but there are sometimes disappointing logistical realities that we have to just accept.

Rob Marsh:   Yeah, that’s the reality of having ideas, lots and lots of ideas. You mentioned you went from the advertising agency experience to an in-house experience at Publix. Tell us a little bit about the differences between those two groups, the kinds of assignments that you were taking and what that work looked like.

Sara Rosinsky:   I will mention there was an interstitial freelancing period when we had our daughter, but I transitioned from that to getting this job offer at Publix in Florida. Here’s why it was great. I will tell you my fears and I will tell you why I was wrong.

I was afraid that I’d be doing nothing but writing price and item ads, chicken 49 cents a pound or whatever. I was afraid that I would only be doing one thing all the time and that I would get sick of it. I was afraid that it would be corporate and there would be a dearth of creativity. None of those things turned out to be true. This is because, A, Publix has a dynamite stable of talent like their in-house agency I would put up against ad agencies. It’s really, really good.

I would say in any job, you want to work with good people. I was working with dynamite designers and to me, that’s what it takes. I want good designers. Nothing is more of a bummer than bad designers. You want them to elevate your work, and I had that opportunity.

My concern about variety was quashed immediately because there’s a difference between advertising baked goods and ice cream, and they have pharmacies. I was doing pharmacy messaging. They had gas stations, convenience stores. I worked on that. They owned restaurants. I got to work on that. Anyway, there was a lot of variety.

What other anxieties did I share with you that turned out not to be true? Oh, just the corporate vibe. It is a corporation and there are some considerations there. I was not playing a lot of ping pong and skateboarding down the hall, but just good people. Man, it just comes down to the people you work with. And they really hired carefully. They still hire carefully in that … So I was there for 13 years.

Kira Hug:   How did you make that decision to go from freelance into Publix? What did that look like?

Sara Rosinsky:   That was a daughter approaching kindergarten age and the number of questions, where do we send her? Do we have to go a zillion miles into an exurb to find a school that we feel good. That whole … Anyway, it was time where I could go, I could start working again instead of freelancing with a babysitter. That was the situation I had until she got to that age.

And so I basically put myself out on the internet and said I was available for hire and a head hunter from Florida contacted me. That’s why I ended up, we moved down from Boston. The other anxiety I had about that job was I was really scared of the bugs in Florida. But anyway, I overcame my fear of cockroaches and we moved down to Florida.

Kira Hug:   Are the cockroaches that bad?

Sara Rosinsky:   Well, they fly for one thing. It wasn’t as bad as I thought, but I was genuinely … I will tell you this too, just quick side note, my first day at Publix, I was given an Outlook account and there were some corporate emails and one of the first emails I read was about the fact that the alligators on the corporate campus, it was mating season and that we needed to be careful and not get too close to them because they might be aggressive. And I just thought, “Where have I moved?”

Rob Marsh:   That’s amazing. I love that. That should be everybody’s welcome email. It’s like, “Hey, thanks for being here. Don’t pet the alligators.” You were at Publix for a while. You’re not at Publix now though. Tell us how has your career evolved since then.

Sara Rosinsky:   In 2016, I was living 80 miles away from the Publix corporate headquarters. Long series of events led that to happen. But I was working for a manager who was enabling that to happen. I was working remotely quite a bit and that was really not corporate policy. A day came when there was a level set and it became clear that I was going to have to commute 80 miles each way almost every day. I said, that’s really unfortunate because I’m not going to do that. I’m just not.

On very good terms, we had to part ways. I started freelancing again in 2016. What was the rest of your question? I can tell you about my freelancing trajectory, but I don’t want to assume.

Rob Marsh:   That’s basically it is like how did you go from Publix to where you are today?

Sara Rosinsky:   Yes. That’s when my latest stint as a freelancer began and that is the career I want for the rest of my life. I absolutely love it.

Kira Hug:   Why is that? I mean, I know because we’re also in that camp, but it sounds like you had such positive, wonderful experiences at both the agency and in-house. What brought you to the point today where you’re like, “This is it For me”?

Sara Rosinsky:   What I am really enjoying as a freelancer is my just absolute autonomy, and I just love making it up. It’s like jazz. It’s like I get to do whatever I want and it’s so thrilling to me to see what works. I love writing for myself, as you can probably tell if you’ve ever seen anything I write for myself. I delight in, I don’t know, being irreverent, using the words I want to, just trying new things.

I have traveled, set up meetings with people in new cities because I can. I’ve gotten to speak. I’m going to Florida on Saturday for a client there. I’m just having so much fun. I love freelancing, and maybe it’s because I have so much experience, and I have so many contacts that it’s been a real delight for me. I imagine it’s a little different when you’re first starting out, but I just love it.

Rob Marsh:   That’s interesting that you mentioned that because you had a previous freelancing period and now you’re doing it again. Are there differences between when you did it the first time and when you’re doing it now that you maybe make it more profitable or more enjoyable? What are you doing differently?

Sara Rosinsky:   I am operating at a much higher level of confidence than I was then. I was charging an hourly rate, absolutely back then. It was not super high. Work was more sporadic. I probably had to beat the bushes to find work a little bit more. At this point, I have just such a strong network. I have worked with literally hundreds of people. The work is kind of just coming in. So I enjoyed it back then as well, but I just think I have a wider array of tools and contacts and I’m just moving through the experience with more confidence I think than I was.

Kira Hug:   What does the work look like today? Where are you focusing your time and energy?

Sara Rosinsky:   Interesting question because every time someone asks me that, I find myself going, what am I working on now? Because it changes a lot and I thrive on that, to be honest. I am someone who much prefers to write shorter pieces. I don’t want to write papers. That is, I think recently, your last guest I think likes to write content and longer things. I will give her my work. That is not my bag.

Although I will say, I have written some long form pieces lately on a topic that I love, which is typography. I’ve been getting to do some writing for Monotype, which is just the company that probably any typography you’ve ever purchased or experienced has come through them. So that, I like. I like writing about topics that I am interested in.

I’m working on positioning. This company that’s flying me to Florida, I’m helping them with positioning, figuring out branding, your space in the market, why do you exist, all of that. I’m sure your listeners are familiar with that kind of thing. I’m getting to do some conceptual work, which is really fun. When I get off of this call, I’m talking to a very B2B company, has to do with agriculture and baby formula, and I’ll find out about it. I will write for any vertical that I don’t find morally reprehensible pretty much, honestly. It’s all interesting.

I probably am not your choice for race cars, football. There’s some things that I am so not interested in that I would turn away, but usually I like to tackle just about anything.

Rob Marsh:   I’ll take your football clients, Sara, just send them my way because that would be fun one to write about. It feels like you don’t have a niche?

Sara Rosinsky:   Correct, I don’t.

Rob Marsh:   Really write for almost anybody. You said clients are kind of coming to you. I was going to say, how are you finding clients, but it sounds like they’re coming to you. How is that happening? How do you make sure that you’ve got work coming in all the time?

Sara Rosinsky:   I will tell you, and this is something else I find so much more fun than approaching someone and saying, “Hey, hey, do you need any work? Do you need me to do any work?” That’s a one-on-one communication. It’s a sales situation, not my favorite. It’s all, I could if I had to, but here’s what I’m doing instead.

In 2016 when I went on my own, I thought LinkedIn is a community of business people almost to a one. These are people who could benefit from a good writer. I want them to know about me. What on earth can I say to all of them? That is when I thought a lot of people struggle with writing and certain pitfalls and problems, and why don’t I share? Why don’t I kind of teach them? I had done a little bit of this at Publix, telling people why they use a serial comma or whatever.

And so I thought, I think I used Canva initially and I made a little lesson about maybe telling the difference between the three spellings of to, T-W-O, T-O, T-O-O and put that out on LinkedIn. That was the beginning. Cut to now, I am putting out writing messages daily and I have a large audience of people who respond to these things, who know about me, who know other people. Do you know what I’m saying? I’m advertising myself.

There is just a large group of people out there who know about me. Many of them are in the ad industry, some of them are in agencies, some of them aren’t. I’m not saying that I’m getting a call every day from a total stranger. I’m just saying that planting seeds regularly, making a habit of it can just ensure that more people know about you, you’re top of mind.

Another thing that I do that I think is helpful, I put this out last night actually. I create an events compilation. I started this for just the Boulder, Denver area near where I live of local events. I like to partner with designers. As I’ve mentioned, I really like good designers. I’ve wanted to really connect with those people. I realized that there are events that appeal to both me and these designers.

And so initially, I would just write these friendly emails, “Hey, did you know about this creative mornings thing that’s happening a week from Friday? Just thought you’d like to know.” Then I would send that same email to multiple people. Then I thought, why don’t I get in a MailChimp account and really do this thing? Now about every three or four weeks, I scour the interwebs. I find events that interest me and I also think would interest people I’d want to partner with. I put this thing together and sure enough, a lot of designers know who I am and they remember me, and it has turned into business for me.

That’s a piece of advice. Think about people who might want to partner with you. Think about if you’re not a strategist, get to know strategists. If you’re not a designer, partner with designers. Maybe there’s somebody who specializes in social media but can’t do, you know what I’m saying? You want to make alliances. I think that ends up you’re getting a sales force essentially.

Rob Marsh:   Gin, let’s break in here. I’m curious what, if there’s anything that stood out to you in the first half of this interview?

Gin Walker:   Oh, so much, Rob, so much. First of all, I was absolutely fascinated and so impressed by Sara’s very first … When she first graduated and to get clients, to get work, to get herself out there. She literally made flyers, made posters, and posted them around her neighborhood to drum up interest, to get people to know who she was. It worked. It worked. What I found really interesting especially was that it worked in a way that wasn’t necessarily what she expected.

For instance, she was picked up by an ad agency who wanted her potentially to deliver some stuff. That gig didn’t quite pan out, that didn’t happen in that way, but the person kept her name, kept her contact details, and then got in contact with her later. That blossomed into this whole other opportunity that she couldn’t necessarily have anticipated.

I think this is just such a lesson in that for all of us in taking risks and putting yourself out there in ways that maybe aren’t over bold. Who knows? I don’t think that was over bold, but ways that you cannot necessarily predict how they’re going to pan out for you and just trust that stuff will come back.

Rob Marsh:   Yeah, it is really interesting to me too. Same thing. We have, I think there’s a handful of go-to ideas of how do you find clients in the world? You cold pitch, you reach out, direct message maybe in a Facebook Group or on LinkedIn. I just like the originality. Now I know it was a while ago and maybe the flyer thing was more common before the internet, I don’t know. But there are so many ways to get our names out there in front of people.

This was a little quirky and it happened to work in maybe a way that wasn’t exactly what Sara was expecting. But I think it’s an invitation for all of us to be thinking a little bit differently. How do we get our name out there? How do we show up in places where the people we want to work with can find us? It might not be the regular email pitch. Although it probably will be, those things do work. There’s a reason they’re the standard go-tos, but there are other ways too and it’s worth considering being a little bit creative in our approach.

Gin Walker:   Absolutely, absolutely.

Rob Marsh:   Tied along with that, the result of that flyer and the connection that she made at the agency is that Sara got to work with a mentor. I know this is something that we’ve talked quite a bit about on the podcast, but it’s worth repeating over and over and over because the very best way to get good at what we do is not just to do the work, but to get good feedback, coaching, and have these opportunities to be able to grow.

It is so much easier to do that with a mentor who you’re working with. It doesn’t necessarily have to be somebody who is there over your shoulder all of the time. We can have these unofficial mentorships where we get on people’s lists and we learn from them or we watch their presentations or we see them speak in person or we read their books, their emails, whatever. But taking it the next step and actually creating that one-on-one relationship, joining their programs, that kind of thing can be a total game changer.

Again, the way Sara did it in joining an agency, something that I did myself and got great feedback on my work, a little different from what most freelancers do in joining programs, masterminds, that kind of a thing. But there are ways to connect with people who can help us grow. It’s worth finding that person. If you’re listening to this and you don’t have a mentor now in your business, that should be one of the things you look for in 2023.

Gin Walker:   Yes, absolutely. I totally vouch for that in terms of the Copywriter Club Think Tank as well. But one of the things that stuck out for me with Sara and her mentoring relationship with her boss Stan, was how he not only inspired her and taught her, literally taught her the skills of copywriting, but also challenged her. Because one thing that she struggled with, Sara said, was presenting her work and finding that confidence, overcoming that self-consciousness about her work enough to actually put it out there.

Obviously she was doing fantastic work, but nevertheless she was holding herself back in that way. Stan almost kind of not exactly threw her under the bus, but made it, so put her in a situation where she literally couldn’t refuse. She had to step up and step into that room and present her own work to the people that needed it. It worked, and they were impressed by it.

But I loved also that she said, coming out of that, the idea of finding that confidence in your work and being able to present it. One of the things that she said, which was so powerful for me was having the way to gain that confidence in your writing work in particular is to make sure that you can justify every single aspect of it so that if you are challenged, why have you chosen this word or why this part here and why that headline there and so on. You can come straight back with your answer. You know why you’ve made those choices and can justify it.

That not only gives you the confidence to be able to present it, but obviously gives your client, your potential client the confidence that what you’re doing. None of this is just by chance and just slapped onto the page. It’s all very, very creative and very intentional.

Rob Marsh:   Well thought out. Intentional is the exact right word. I think that’s one thing that a great mentor does is pushes you out of your comfort zone and helps you develop those skills that you need. Like were saying, what Stan did for Sara in forcing her into this and presenting.

Presenting is a really important skill for all of us. I’m not just talking about standing on stage and talking about the things we do, but presenting our work to our clients and being able to step through, like you were saying, and explain why every single word is there and each one has a job, and this is exactly why I chose this. I used this particular word instead of that one because maybe it generates better interest or it’s unique or it catches your attention or holds your attention. There are so many different ways to do it. That skill of presenting is critical, something that all of us need to develop more of.

Gin Walker:   Absolutely. The other thing that came out of that actually for me was something that Sara said about leaning into your enthusiasm. I think that comes out of having that confidence that you know what you’re doing. You know you’ve crafted this copy in this particular way, and then you can get really enthusiastic and passionate about it. That just comes across so well to your audience.

Whether it is in a presentation room at an ad agency or whether it’s on a stage, people will pick up on your passion for what it is that you do and your confidence in the choices you’ve made. It makes such a difference.

Rob Marsh:   We’ll talk a little bit more about enthusiasm in the second half of this interview when we talk about what Sara’s doing on LinkedIn, because that’s a big part of what she’s doing. I also want to touch, before we go back to the interview on just Sara’s experience working in-house. This is something that’s not all that common in the freelancing world, but it comes up a bit in discussions where people who have been freelancing for a while have an opportunity to work in-house like Sara did with Publix.

Sometimes there’s maybe an argument that we have with ourselves where we’re thinking, “Well, if I am not freelancing, I failed in some way and to move in-house is kind of giving up on my dream.” I mean, Sara did this for a decade. This is something … I’ve worked in-house as well and a couple of different places and probably close to a decade of my experience. I’ll say working in-house can be a phenomenal accelerator for your business because you have a constant flow of work. You don’t have to worry about finding clients and invoicing, all those kinds of things. You can actually focus on doing the work, you can focus on copywriting and getting better at it.

If you’ve got somebody on your team, whether they’re a peer or a mentor, a boss, that can actually help give you that feedback we were talking about earlier, it can like I said, accelerate your career in ways that working alone without those kinds of things, doing the struggle and trying to figure it out on your own just doesn’t do.

If you are listening and thinking, “Oh, I had this opportunity, but I don’t want to give up on my dream.” Of course, if your dream is to work for yourself, stick to it, you can make it work. But moving in-house or joining an agency temporarily or even for the rest of your career is not a failure. It is a great way to be a good copywriter and to serve a particular client in a way that is really hard to do as a freelancer.

Gin Walker:   Absolutely. As you say, it can be an accelerator. It needn’t be a permanent thing, a permanent move. But to spend a few years or a period of time in that structure can really help you, as you say, to develop your skills in copywriting itself without having to worry about finding those clients or all the other aspects of working as a freelancer or as a business owner.

One of the things that Sara mentioned was she was slightly afraid of going into this corporate context because she felt that maybe that was very narrow. It would restrict her opportunities. The variety wouldn’t be there. She’d be kind of just churning out the same old, same old all the time. As she found, that is not necessarily the case at all.

In her case, it absolutely wasn’t the case. She found that she was able to experience all kinds of different … Writing for all kinds of different products and the variety of that was a context in which she could really thrive. As she mentioned, it really just comes down to, at the end of the day, the people that you work with. She mentioned the Publix, the company she was working with, they hire very carefully. And so the team that she was working with was very well-curated in that way. That structure was one, as I say, in which she could really thrive.

No, absolutely. I worked in-house for some years as well and it was a great grounding, a wonderful place to be able to learn and hone my skills. That was as a book editor actually as it happened. But nevertheless, same principle and no, I wouldn’t give up that time for the world.

Rob Marsh:   There’s a lot to be said about that steady paycheck, the benefits, all the things that come from working in-house. I think sometimes the argument is it’s maybe more steady, the work is more steady. Obviously, that’s not always true because of layoffs and economics that focus on business sometimes. Placing your trust in an employer that is just as risky as running your own business as a freelancer.

But the risks are different. For some people, they’re a better fit or at different times in your career, they may be a better fit if you’ve got certain needs in your family, your lifestyle, whatever that benefits may help out during this three or four-year period. Maybe you can risk some things later on or earlier on, whenever. It’s still a viable path for a great career.

Gin Walker:   Absolutely. I second that for sure. All right, so let’s get back to the interview with Sara and find out how she secured an out-of-state project.

Kira Hug:   I want to go back, just because we skipped over this. You mentioned flying to Florida to focus on this positioning for this client. That seems like a really great project where they’re flying you, they’re paying you to be there. It seems kind of like a dream project for many writers who want to get more into positioning. Can you just talk about how you would package something like that is larger in person, what that looks like, what you do during that session?

Sara Rosinsky:   I would like to tell you that I made this happen. I would like to tell you that I proposed it and it was all because of my … I’ve joked with friends that this is probably the pinnacle of my career and it’s going to be all downhill after this. This is a situation where I am fortunate. The person who hired me really values what I can do. I helped this client win a very big account and they really appreciate my creativity.

I’m just telling you what they’ve told me. I’m still a little just incredulous that this is happening. But this particular client is just, they’re smart about bringing in people who can help them to grow and they’re hiring a firm and they’re hiring me, and we’re going to work out some ideas together.

To answer your question, Kira, about what you might do, you could create a product where you say, we’re going to have a brain tornado, or you can come up with your name. We’re going to sit in a room. You could be really clever. You could say it’s going to be for 97 minutes. You could say that that’s the amount of time it’s going to be constrained, and we are going to come up with at least a dozen ways, whatever you want, whatever your deliverable might be. You could absolutely productize something.

You could, even if you really wanted to travel, you could say, “If you pay for half of my expenses, I will be there. And I promise you that when we are done, you will come away with a touchstone document that you can use for all of your communications moving forward,” whatever. You could absolutely do that. You would have to sell it, but I think that’d be fun.

See, that’s an example of being autonomous, coming up with an idea and then presenting it. And maybe you have a beta test. Maybe you say, “Because you’re the first person signing on, I’ll pay for three quarters of my travel expens