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The Business of Successful Freelance Careers

Onward Search Career Cast, Episode #22

Career Cast Podcast

This episode of Onward Search's Career Cast Podcast takes a look at the business side of a successful career in freelancing, whether it's freelance writing, designing, developing or marketing.

Career Cast guest Kristen Fischer, freelance copywriter, journalist, and author of the new book, "Creatively Self-Employed: How Writers and Artists Deal with Career Ups and Downs", shares valuable insight about what it's like to transition into a freelance career and take on the new requirements that not all creative professionals are familiar with. Kristen discusses how important it is to treat a new freelance career as a business and how to handle the less appealing aspects of a freelance career, like taxes and legal preparations.

If you are considering becoming a freelance designer, writer, etc., this podcast will prepare you to better understand and approach the business side of self-employment.


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Episode #22 Transcript

PUBLISHED ON MAY 31, 2011

Welcome to Onward Search Career Cast, the podcast that brings you the latest insight and career advice from experts within the Internet marketing and creative space.  Onward Search is a leading nationwide provider of web-based talent and offers a full range of recruitment and staffing solutions. If you’re looking for a career in search engine optimization, interactive design, or emerging technologies, you should apply online at onwardsearch.com or call 1-800-829-0072 and speak with an experienced recruiter today.

Peter ClaytonPeter Clayton: Welcome to an all new Onward Search Career Cast.  This is Peter Clayton with your host, Hillary O’Keefe, Onward Search’s Online Marketing Manager.  Listen up because Hillary will be talking with a very special guest today about a hot topic for all designers and developers, freelancing. 

How’s it going, Hillary?


Hillary O'KeefeHillary O'Keefe: Hey Peter, it’s going great actually and yes, we are going to be talking about freelancing today because there are so many designers and developers and marketers and copywriters out there who are thinking about breaking out on their own and starting their own freelancing business.  By the way, it’s a totally viable option these days, especially when companies aren’t hiring; you might as well take those dreams about working in your pajamas and actually make them happen, but the only trick is that, you know what, you need to know a lot more than just sort of the skills of your trade and being successful at that to really make it as a freelancer.

In fact, there’s this entire other business side to running a successful freelancing business that not everybody is really aware about.  So if you’re considering starting a freelance career, you have come to the right podcast, because my guest today is an expert on how to successfully take the plunge into creative self-employment. 

Her name is Kristen Fischer and she is the author of Creatively Self-Employed:  How Writers and Artists Deal with Career Ups and Downs.  She’s also a freelance copywriter and journalist herself who hails from the Jersey Shore, and you can learn a whole lot more about her at her website which is KristenFischer.com. 

Hi Kristen, thank you for joining me today.


Kristen FischerKristen Fischer: Hey Hillary, it’s awesome to be here.


Hillary O'KeefeHillary O'Keefe: It’s great to have you.  I understand you learned a whole lot about freelancing firsthand throughout the course of your career as a freelance copywriter and journalist.  Did you start out knowing anything about the business side of freelancing or was that something that you got some guidance on?


Kristen FischerKristen Fischer: Absolutely not.  When I started, writing was always something I was good at and I majored in science in college, which now it’s a good conversation starter when you’re meeting with a client, you need something to talk about.  I kind of fell into copywriting.  I never knew what it was and I kind of wanted a bit of a career change or just to do something creative on the side.  After college, I was a reporter for a while and then I went back into science and I was like the science is just not where my heart is.  I was really, for the most part, miserable in that, which is always a good indicator that that’s not what you should be doing or that you need to switch something up and make it work for you.  The writing was kind of always there, so I came in touch with a marketing company and they gave me a shot and everything and then I worked part-time and built up my business on the side for a year and that was crazy and fun at the same time, because I work nights until like 1 o’clock in the morning.  Which, if you’ve been in the newsroom like 1 in the morning, it’s pretty creepy.


Hillary O'KeefeHillary O'Keefe: Oh yeah, I can imagine, but you were following your heart which is what a lot of freelancers are doing, right?


Kristen FischerKristen Fischer: Yeah.


Hillary O'KeefeHillary O'Keefe: Okay, so let’s pretend that I know absolutely nothing about this business element of freelancing, which is actually not that far from the truth, because looking into what you’ve written about, there is a whole lot more.  I mean it’s almost like setting up your own business and one of the first things that businesses have to do, they have to market themselves, right?  This is really, becoming a freelancer you have to start with learning how to build your own business, right?


Kristen FischerKristen Fischer: Absolutely.  A lot of people – you have your creative talent.  In my case that was writing, but you might not know much else.  The good news is it’s easy to learn and you might find that some of your existing skill sets kind of fit in with that.


Hillary O'KeefeHillary O'Keefe: Oh, that’s helpful.


Kristen FischerKristen Fischer: Yeah, it is because you might like – I never felt like sales – I don’t want to be salesperson, but that’s what I do now and that kind of persuasive personality kind of has helped me.  What I tell people always is you can learn about the accounting and the legal stuff and the stuff that makes your skin cringe.  You can learn that but you have to be aware about that in order to have a business.


Hillary O'KeefeHillary O'Keefe: So it’s about sort of figuring out what you don’t know first off.


Kristen FischerKristen Fischer:  Yeah, it’s about figuring out what you don’t know.  I mean obviously, if you approach it from a logical progression, I wanted to write and I needed clients and they weren’t going to come knocking on my door.  So you really have to be your own advocate, your own marketer.  That got me into learning about direct mail and how do I reach my audience and what kind of clients do you want – these are all things to really think about.  To be honest, it’s a lot of trial and error and that’s good, because if we had all the answers when we started, what fun would it be.  You have to make mistakes and fall on your face a little bit.


Hillary O'KeefeHillary O'Keefe: Right, and no one else is going to promote you, right?


Kristen FischerKristen Fischer:  No, absolutely not.  That might be where you’re good at.  Like for me, I was good at writing and telling people about things and kind of bringing people together; I was always good at that growing in college so that was, again, one of my natural skills that kind of helped me with the marketing aspect, definitely.


Hillary O'KeefeHillary O'Keefe: Let’s shift real quick and talk about what you said earlier about the aspects of freelancing that will make you cringe, like accounting.  I could just imagine someone who’s been a designer their whole life sitting down and being told here’s the part where you have to work out an income or a balance sheet or something like that for yourself, so that you keep on top of your expenses throughout the year.  Is that something that is easy to pick up?


Kristen FischerKristen Fischer: I think a lot of when you start this business, you have to kind of think about your processes.  You have to think how am I going to invoice people?  When am I going to invoice people?  What’s the form going to look like?  How am I going to track that? 

Some people track their profit and they have super business plan and stuff, and I think a big part is like do it your own way, do it effectively.  It doesn’t have to be this big model that other companies have used, but it has to work and it has to be effective for you.  

For example, my husband is telling me, “Please just invest in one of these accounting softwares,” and I refuse.  I tell him I’m doing everything in Excel and this is one of the things I joke about but it works for me, it’s accurate and it’s a little antiquated.  A lot of people laugh at me, but that works for me.  At least I’m taking care of my finances, you know what I mean?


Hillary O'KeefeHillary O'Keefe: Ah a good point.


Kristen FischerKristen Fischer: At least I’m writing things down.  So you don’t have to go out there and get like the QuickBooks 20.0 or whatever, not to diss  QuickBooks but there are ways to come up with some of your accounting process that make it less daunting, but you do have to be aware of it.  You can’t ignore that because otherwise, you’re going to be doing all this great designing and you’re going to be poor because you forgot to invoice the client and you’re going to be like, “Where is my money?”  If you don’t have the contract in place and all those ickies that we don’t want to deal with, but they’re important.  They’re important to get things running.  Once you get them in place, I find that you’re okay; now I have to do my accounting.  I’m just going to take a deep breath and get a jug of coffee, and you’re doing it.


Hillary O'KeefeHillary O'Keefe: It sounds like getting creative with it and making it your own,  just like any of your projects, is going to help.


Kristen FischerKristen Fischer: Yeah.  If you can’t understand it, you know what I mean?  Like I’m no tax expert, but at least I know how to do some of my basic financial stuff.  When I started out for the first two years that I was really full-time and really being at home full time, I had an accountant and there’s nothing wrong with outsourcing something.  I got my taxes done really good and I learned what receipts to save and what I could deduct and if you don’t know that, that could be detrimental to your business.


Hillary O'KeefeHillary O'Keefe: Speaking of getting paid, you have to get clients and you have to understand how to put yourself out there basically sell yourself so that people will say, you know what, yes, I have got a problem, it’s a creative issue and I want you to solve it.


Kristen FischerKristen Fischer: You also have to go from job seeker mentality to you’re  running your own business.  You have to say here’s what I can offer, instead of “Please hire me.  I need this job.  Here’s my background.  I can do the job.”  That’s like kind of a little bit of an archaic, “Here’s my background.”  That used to be enough, now it’s not.  Everybody has got a degree and everybody has got some experience and there’s always someone that can do what you can do.


Hillary O'KeefeHillary O'Keefe: You’re still beating out competition and it is almost like a job search, except you’re vying and you are competing and putting yourself out there to get that next project and that next client and especially that also ties into referrals and people who are going to tell other people about you and then you get more business and it works from there.  So that side of it – the getting of clients into working with them – that’s another side of this whole business, which also leads me into once you get those clients, what about setting up contracts and being legally protected when you’re doing this kind of creative work.    What do designers and developers have to worry about in that regard?


Kristen FischerKristen Fischer: So important, oh my goodness, so many things.  You want to make sure obviously that you’re getting paid obviously, and especially in the design world, I know so many designers that have had their work just blatantly ripped off.  So you want to have these things in place to protect, because you can come up with a company’s whole branding and then they can say “oh I really don’t like that,” and if you don’t have it in writing that they have to pay you, I know people and I have friends in the creative community that have had to go to court.

It sounds a little overwhelming and I really did not like the legal aspect and I really still don’t, but speaking to a lawyer, kind of going through a contract and just having something written, especially in the beginning as you get going and then it’s good to have somebody to call in case you have questions kind of pop up with different things, but you don’t have to have like a lawyer by your side all day.  It’s not going to be like that, but it is important, especially just to have the contract is a huge start and it’s more than many freelancers have.


Hillary O'KeefeHillary O'Keefe: That makes a lot of sense and I think you said it perfectly in the beginning when you said that there are a lot of icky parts to this process that nobody really likes or wants to think or talk about but in the end, it all makes it worth it because just as you went from your science career into copywriting and really following your passion and doing what you love, it’s worth it for that.


Kristen FischerKristen Fischer: It’s worth it because if you get things set up correctly, you don’t have to worry as much.  I still go through business ups and downs.  I’m hopefully just coming out of what I like to call the tunnel where a little time of a drought, a little time of like ‘what’s going on?  Where are my contacts?  Where are my people?  Why is nothing coming through?’  But if you built it strong and you kind of sow your seeds, it will come back and if you have those processes in place, you’re not kind of going back and forth and screwing up invoices or ‘Oh, did I get that check?’  It all affects how you come off because you’d said before about winning jobs, you’re also trying to win a long-term relationship.  In my case, I don’t want to win a job, I want to win you as my client so every time you need something written, you’re like, “let me call Kristen,” you know what I mean?


Hillary O'KeefeHillary O'Keefe: Absolutely and that’s a long-term brand.


Kristen FischerKristen Fischer: Because that’s less stress for me.


Hillary O'KeefeHillary O'Keefe: Yeah, that’s a long-term brand and it’s making sure that you can do what you love for the rest of your life.  That’s what freelancing is all about, right?


Kristen FischerKristen Fischer: Yeah.


Hillary O'KeefeHillary O'Keefe: Thank you so much Kristen.  This was fantastic advice.  I really appreciate you breaking all this down for me.  This is wonderful.  Do you have anything that you’d like to share with our audience?


Kristen FischerKristen Fischer: I did just get an agent.  I’m going to have a third book out soon.


Hillary O'KeefeHillary O'Keefe: Cool.


Kristen FischerKristen Fischer: It’s tentatively titled It Takes More Than Talent, so you can stay on top of it and check my website back in a little bit for some more information and also check out FreelanceRadio.com.  I podcast there and it’s kind of similar to what you do but we do talk about more of these client conundrums and technology issues and lots of icky stuff but we make it fun.


Hillary O'KeefeHillary O'Keefe: Good.


Kristen FischerKristen Fischer: I love icky.  It’s my new professional term; there’s just no other word that you can use.


Hillary O'KeefeHillary O'Keefe: Making the icky stuff work.


Kristen FischerKristen Fischer: Yeah, exactly.


Hillary O'KeefeHillary O'Keefe: There you go.  Thank you so much for joining me today on the Onward Search Career Cast.  This was fun.


Kristen FischerKristen Fischer: Thanks Hillary.


Hillary O'KeefeHillary O'Keefe: You got it. Anybody out there, if you’re thinking about going freelance yourself, make sure that you pick up Kristen’s book, Creatively Self-Employed:  How Writers and Artists Deal with Career Ups and Downs.  And don’t forget of course to check out all the contract jobs that are perfect for freelancers.  We have bunches of them on OnwardSearch.com.

Until next time, this is Hillary O’Keefe with the Onward Search Career Cast.  Good luck with your job search, and take care everybody.


Thank you for tuning in to Onward Search Career Cast. For more information on the career opportunities available through Onward Search, you should visit us online at onwardsearch.com or call 1-800-829-0072 and speak with an experienced recruiter. And you should also follow Onward Search on Twitter at twitter.com/onwardsearch.