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How to Launch a Freelancing Career, with Rebecca Shapiro

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53 million Americans–one out of three workers–can be classified as freelance entrepreneurs.

A career as a freelancer offers lots of advantages. You work when and where you want. You set your own prices and keep the profits. You choose your clients and your coworkers. (And yes, you can work at home in your pajamas!)

A career as a freelancer has its challenges, too. You have sole responsibility for finding clients, project management, business operations, contracts, taxes, marketing, scheduling, and everything else in what is, essentially, your own small business.

This week’s guest is Rebecca Shapiro, an artist, illustrator, and career freelancer. She shares her experience in the gig economy and offers advice for starting and maintaining a successful career as a freelancer.

This Week’s Guest

Rebecca Shapiro is the author of,Work Independently & Live Connectedly: 52 Steps to Freelancing Freedom.  She’s also a former regional organizer for the Freelancers Union and a fine artist, illustrator and community manager. Rebecca offers experiential art in public spaces and for events and she also makes custom illustrations for medical textbooks, e-books, murals and cards.

Resources from this Episode

Transcript

Mac Prichard:   

This is find your dream job, the podcast that helps you get hired, have the career you want and make a difference in life. I’m Mac Prichard, your host and publisher of Mac’s List.

Our show is brought to you by Mac’s List. Your best online source for rewarding, creative and meaningful work. Visit macslist.org to learn more. You’ll find hundreds of great jobs, a blog with practical career advice and our new book, “Land Your Dream Job in Portland and Beyond”.

Thanks for joining us today. This week on Find Your Dream Job we’re talking about freelance work. If you see three random people walking down a street in the United States, one of them likely does freelance work. Thirty-four percent of Americans, 53 million people in all, are freelancers according to a 2014 survey. Now, a career as a freelance worker offers lots of advantages. You work where and when you want. You set your own prices and you keep the profits. You choose your clients and your coworkers and, yes, you can work at home in your pajamas.

A career as a freelancers has its challenges too. You do all the administration and marketing for your business and this could take up to 25% or more of your time. You can’t bill those hours to your clients. You also have to produce more revenue. Charging an hourly rate that equals your old annual salary won’t cut it because now you have to cover your own sick leave, vacation, benefits, and payroll taxes. This may mean that you have to earn two to two and a half times the amount of your former salary.

In the next thirty minutes we’ll address these and other important issues for freelance workers. Whether you’re about to strike out on your own or you’ve been working for yourself since the Carter administration, Ben Forstag has found a website with ideas you can use to make any freelance business more efficient and profitable. If you’re a freelance worker who is an artist, designer or film maker I don’t have to tell you the difference a portfolio can make in landing your next gig. One reader asked us however, “Can I just present my work online or do I need a printed portfolio?” Cecilia Bianco has the answer.

Let’s start as we do every week by checking with Mac’s List team; Ben Forstag and Cecilia Bianco. Cecilia, Ben how are you two doing this week?

Ben Forstag:  

I’m doing awesome.

Cecilia Bianco: 

Doing good Mac.

Mac Prichard:   

Good. Well, it’s a pleasure to see you here in the studio. This week we’re talking about freelancing and I have to ask you both, have either one of you worked as a freelancer? Cecilia?

Cecilia Bianco:

No, I haven’t but I’ve definitely considered it and I know a lot of people who have.

Mac Prichard:   

There are no freelance babysitting jobs in your past?

Cecilia Bianco: 

No.

Mac Prichard:   

Okay. I haven’t worked as a freelancer myself. I have taken the odd contract job while I look for a permanent position. Like you, I haven’t worked as a freelancer. How about you Ben?

Ben Forstag:  

I’ve taken odd contract jobs between permanent positions, but when I think of freelancing I think of the folks who are doing this as an ongoing career. I’ve never done that. Actually, my wife is a freelancer and she has a rule in our house that one of us has to have a full-time, permanent stable job. Since she’s already got the freelancing gig that leaves me to come into work everyday.

Mac Prichard:  

Yeah. Well, we’re glad to have you. My wife, too, is a freelancer and we have the same arrangement. I imagine when we talk to our guest expert this week we’ll hear more about how that can help a couple because often when one member of the couple has a permanent job they bring benefits, health insurance and other advantages to the table that help freelancers get going. Let’s turn to our regular feature with Ben, who every week is exploring the internet looking for podcasts, books and other tools you can use in your job search.

Ben Forstag:   

Let me say up front that I don’t know a whole lot about freelancing as a permanent career. In preparing for today’s show, I reach out to some of my friends who are freelancers and asked them for suggestions about what blogs they read, what podcasts they listen to and so forth.

Today, I want to recommend a blog and an accompanying podcast that are designed to help people address some of the challenges that are inherent when they’re running a freelancing business. The blog is called doubleyourfreelancing.com and it’s written by Brennan Dunn, a long-time freelance software designer. The blog tackles questions like how to find clients, how to market yourself, how to price your services, how to manage projects and workflow, how to do your estimated quarterly taxes which I know is a challenge for my wife, and other basic tips on how to improve the efficiency of your freelancing business. Brennan only posts a handful of times each month, but each entry is really nicely written, well thought out and comprehensive. Some of the posts are almost long form in their length. You could spend fifteen, twenty minutes going through some of these posts. I particularly like the post entitled, “The best networking hack I’ve ever used.” I’m not going to share with you what that hack is. You’ll have to go and read the blog, but I thought it was a really interesting approach in how to make lasting connections with professional contacts. In his case, this is how to make connections that will turn into future business.

Brennan’s blog has an affiliated podcast called, “The Business of Freelancing” which is available on iTunes. The focus here is on interviews with fellow freelancers and the discussions surround how to improve clients relations and business practices. It’s a well produced podcast and they release episodes every two weeks or so. I suggest you check out these two resources. The blog is doubleyourfreelancing.com and the podcast, available on iTunes, is “The Business of Freelancing”.

Mac Prichard:   

Thanks Ben. I had a chance to look at that website this week when you flagged it for us. I was impressed by the quality of the information and the large number of articles. I know people like to get content in different ways, so not only are there articles but there’s a podcast. For those who like structure, there’s also a course with a curriculum that looked very useful as well. Now it’s time to hear from you, our listeners. Let’s turn to Cecilia Bianco our community manager. It’s time for her to answer one of your questions. Cecilia, what do you have for us this week?

Cecilia Bianco: 

Our question this week is, “Do I actually need an e-portfolio and a printed portfolio?” Personally, I think everyone should have an online portfolio. It’s a more in depth and visual version of LinkedIn where you can expand on your skills, your past work and your personality. It’s a great tool to show a potential employer why they want to interview you before they actually meet you. It’s a brief look into who you are as a professional and it can be really important in securing an interview.

Ben Forstag:  

Cecilia, let me interrupt here. I know LinkedIn has a projects section, can you do most of what you’re talking about on that tool?

Cecilia Bianco: 

Yeah, you definitely can do most of this on LinkedIn but an online portfolio is more of a personal website where you can showcase your brand and your personality in a more creative way. There’s easy ways to do this using WordPress or Squarespace. Both platforms are super easy and low-cost. I think I pay $30 a year for my customized site. I think that being able to create a well put together personal website shows your skills as far as creativity and visual storytelling, which is another bonus to it. It’s another thing for when employers Google you, because we know they all do, it adds something to Google when your name’s searched and it’s a great tactic to control your online reputation.

Mac Prichard:   

What about printed portfolios, Cecilia? I know most employers are going to Google people and look at their LinkedIn profile, but when you have a meeting with an employer do you think it makes sense to bring one in?

Cecilia Bianco: 

I think it depends on what field your in. Printed portfolios are really only necessary, in my opinion, for people in a visual field like photography or graphic design. Otherwise, it’s really challenging to make it appealing to an employer. To bring in a portfolio full of written content is not that fun to look through and it’s not that fun to create. In my senior year, we were required to make one and I majored in public relations, so a lot of my work was news releases and written content. Printing that out and arranging it nicely in a portfolio was pretty difficult and it just doesn’t seem necessary in a written field when you can display that information online in a more appealing way. I think printed portfolios are necessary for some fields and not for others. Well, what do you think about that actually Mac because you run Prichard. Are you impressed when someone brings in a printed portfolio?

Mac Prichard:  

Generally, it’s someone who is a designer and they will have a book with samples of their work. I do enjoy going through the book with them. The advantage of that is they’re telling a story and they’re sharing examples of their work to make their points about that story. I have seen those portfolios at a university that writers have used and I think there is some advantage in, again telling that story, it’s a way of doing it but it’s not the only way. The short answer to your question, Cecilia ,is I think it’s a must for designers and photographers. There could be some value for writers, but I think there’s so many opportunities to do that online and there’s only so many hours in the day. I agree with you. I would give precedence to an online portfolio.

Cecilia Bianco: 

Yeah. I agree.

Mac Prichard:   

Thank you, Cecilia, and if you have a question for Cecilia you can email her day or night. Her email address is cecilia@macslists.org.

The segments by Ben and Cecilia are sponsored by the Mac’s Lists Guides, publisher of our new book, “Land Your Dream Job in Portland and Beyond”. The Mac’s Lists Guide can be the tools you need to get the job you want. We show you how to crack the hidden job markets, stand out in a competitive field and how you can manage your career. The book has eight chapters and in each one experts share job hunting secrets like how to hear about jobs that are never posted and what you can do to interview and negotiate like a pro. To download the first chapter of the book for free visit macslists.org/macslistsguides.

Now, let’s turn to this week’s expert. Rebecca Shapiro is the author of, “Work Independently and Live Connectedly: 52 Steps to Freelancing Freedom”. She’s also a former regional organizer for the Freelancers Union and a fine artist, illustrator and community manager. Rebecca offers experiential art in public spaces and for events and she also makes custom illustrations for medical textbooks, e-books, murals and cards. Rebecca, thank you for joining us here today.

Rebecca Shapiro:  

Thank you. Thank you for having me.

Mac Prichard:   

Yeah, it a pleasure to and thank you for coming to the Mac’s List studio. Let’s start with freelancers in general. Is there a typical freelance worker out there in America today?

Rebecca Shapiro: 

Well, actually there’s 53 million of us in the United States right now. One out of three workers is an independent worker, so they’re a freelancer whether they’re working part-time or full-time. There is a typical freelancer out there and I think there’s a bunch of us because we are finding ways to create livelihood for ourselves.

Mac Prichard:   

Okay. I think when people hear freelance they think a writer, someone in the creative field. What other kinds of careers might lend themselves to freelance work?

Rebecca Shapiro:

Well, that’s a really good point because when I first started working with Freelancers Union I always considered myself an entrepreneur because I couldn’t find any other word to describe what I was doing. I thought freelancers applied to copywriters and maybe a graphic designer, but really it’s anybody who’s working independently for themselves, like I said full-time or part-time, so it could be taxi drivers, babysitters. It could be somebody who is a copywriter, I’ve worked with a lot of copywriters, illustrators, web programmers. It’s everybody. Anybody who is creating income for themselves is considered a freelancer.

Mac Prichard:   

Now, you’re the author of a book about freelancing and you have practical tips in that book about what freelancers can do, in fact, one for every week of the year. What’s striking about your book is its emphasis on community, relationships and collaboration. Can you tell us more about why you focus on those themes?

Rebecca Shapiro: 

Probably because if you don’t have relationships you basically have yourself and you’re unemployed. You need those relationships to have partnerships with other people so that you can work on projects together, to have clients and healthy robust relationships with those clients so they keep coming back. Then, the other relationship that I think is really important is the relationship with yourself. You really have to know yourself. I joke sometimes that working for yourself is almost like a spiritual path because you have to have so much awareness about who you are, the way that you work and what you like and what you don’t like in order to have a healthy freelancing business.

Mac Prichard:  

Now, every time there’s a recession I think when people lose work they think, “Well, maybe this is the time to strike out on my own.” Is there a particular kind of mindset you need to be successful as a freelancer?

Rebecca Shapiro:   

Absolutely. You and I spoke about this earlier, I really have a soft spot for the people that have been laid off and have either been so discouraged that they can’t find work or just kind of give up and they decide to go into freelancing. I think it’s really important when you find yourself in that position, or if you’re just choosing to go out on your own, that you find a community of freelancers in which to participate because you can have conversation with people and find out what’s working and what isn’t for them and build experience for yourself and figure out like, “Okay, this piece might work well for me. This piece isn’t going to work so hot.” You can put together, cobble together, this business for yourself so that you’re successful.

Mac Prichard:   

Learning how to be a freelancer it’s not only a mindset, but it requires a set of skills. I run two small businesses, Mac’s List as well as a public relations company, and I had worked for large organizations for many years; non-profits and public agencies. I needed to learn how to create and run a business and that was different from the technical skills I had. Do you find that successful freelancers have to go through a similar process?

Rebecca Shapiro:    

Absolutely. In fact, the learning curve is really pretty big. That again is why the relationship building piece is so important that you sort of find your tribe or your educational group or your mentors that are going to help you be successful with your freelance business. Part of that is also finding your support team.

For example, taxes is something I’m not interested in nor am I very good at so I see my relationship with my CPA as a collaboration. It’s a very good one and he makes sure that I don’t get into trouble and that I save a lot of money on my taxes. That’s one example. If you can find … I think it’s really important for you to to be able to realize if you’re going out and becoming a freelancer or starting out look for communities that you can jump into and then definitely look for ways that you educate yourself on as many things as possible.

Some good places to look would be the classes at CreativeLive or on Skillshare. They have a lot of entrepreneurial business freelancing type classes that they teach as well as specific skills that you might need. Let’s say that you wanted to go into graphic design but you were kind of wobbly in one area of it. You could look for some specific classes that would help you build up your skillset.

Mac Prichard: 

Okay. There are resources out there to help you with your technical skills, whatever service you might be offering to clients, but you also need to connect with others in the community to work on your business as well.

Rebecca Shapiro:  

Absolutely. I think the more support that you can get for setting up a healthy structure for your business the better. If you can learn how to do things like time management … At lot of times when people … And this is a key point, a lot of times when people are leaving their desk job they try and recreate that environment working on their own and it’s not a very efficient way to work. Learning how to shift out of the worker mindset into “I actually run my own business mindset”, there’s a difference between those two. When you can go to groups, for example Freelancers Union has I think sixteen cities around the country where freelancers of all different types get together and they communicate and talk about their businesses. Then, you can learn from those people that are doing it well. Also, a lot of them are very honest about the mistakes that they make. I think that’s really valuable. These conversations are part of having a healthy freelance economy in each of our cities so when we can have these honest conversations about what works well, but also what kind of mistakes to avoid and personal stories about what went wrong can really help you figure out how to run your business better.

Mac Prichard: 

As you talk about learning those skills, I’m reminded that old habits die hard. When I was in my early thirties I had the good fortune to go to graduate school full-time and I worked in government for almost ten years. It was a masters in public administration program. It took about a month, there were a group of us who had worked in government, even though classes didn’t start until 9:30 we all showed up at school at 8:00. We just were trained to do that and it took us a while to get into the student mindset. I imagine it’s challenging for people to get into that freelance mindset if they treat it, as you say, just like a job.

Rebecca Shapiro: 

It is. The more that you can read … There’s so many great blogs out there including Freelancers Union. If you just Goggle freelancing resources there’s a lot of great information out there that will help you start to think about running your freelance business differently. It helps you start to shift your mindset so my recommendation is read as much as you can and talk to as many freelancers as you can and it’ll start to get you changing those habits that you talked about.

Mac Prichard:   

You have a book and it has actionable steps, and we’ll be sure to mention it in the show notes, but Rebecca of those fifty-two steps are there two or three that you always recommend that people can use if they are starting out as freelancers or maybe they’re experienced freelancers and they just want to take their business up a notch.

Rebecca Shapiro:  

One that I frequently run into, especially when I was working with freelancers, is to set healthy boundaries. That’s part of taking care of yourself, but also it’s also part of taking care of your business. When you can set healthy boundaries and let your clients know that you are not available 24/7 every single day of the week, you don’t end up resenting them and you end up being able to take care of your time so that you have time away from your clients and doing actual work. It also helps your clients know that you value them and that you also take your business seriously.

Setting up those healthy boundaries is really important and an easy way to do it is just to have a policy where you talk about your payment policy and when you’re available and all that sort of stuff. You can put that on your website. You can put it in your contracts. You can have it in your face to face conversation when you’re talking with a client before you get started because so many freelancers make the mistake of bending over backwards. Especially when they’re starting out, they’ll do everything for their client. What you’ve done is you’ve successfully trained your client to realize that you’re going to go two hundred extra miles for them. You can’t sustain that and then you end up screwing up later on down the road. Everyone gets really frustrated and disappointed so it’s better to just set healthy boundaries right in the beginning.

Mac Prichard: 

I think that’s excellent advice. I work with other public relations agency owners and small business owners and they all tell me that they expect vendors, whether they are freelancers or small businesses to have contracts and scopes of work and to send out invoices at a certain time. I would say to freelancers or people who are thinking about doing this who are listening, this is how business is done. It’s normal. Your customers won’t be surprised when you do set those boundaries or set those expectations.

Rebecca Shapiro: 

One of my boundaries, and I’ve had to turn away work, is I use a contract. I always use a contract. There have been some high profile people that have said, “I don’t want to sign a contract.” I’ve actually stepped away from the work. It’s a hard decision but it’s a policy that I have because I know that the contract … So many things change over time of the project, it’s hard to remember where you started and the contract is a way to protect yourself as well as the relationship with your client. I’m really glad you brought that up.

Mac Prichard:  

I, running my own small business, made the mistake once of not having a contract and we can share horror stories about that after the show.

Rebecca Shapiro: 

Yeah. All it takes is one time.

Mac Prichard:  

Yeah, you learn. I’m conscious of the fact that our time has come to a close and just thinking about our listeners who are thinking about doing this and they may have very practical questions. Why don’t we just go through a short list?

Rebecca Shapiro:  

Okay.

Mac Prichard:   

Your best advice for people who are thinking about getting started, what are one or two things they could do right away or they should address?

Rebecca Shapiro:  

Okay. The first thing that they should do is they should go find a group. Go find their tribe. Whether it’s Freelancers Union or maybe it’s a co-working space, there’s a lot of co-working spaces that have a community component and an educational piece to it. Get online and in person and look for those types of communities. That would be the first thing that I would absolutely do.

Then, the second thing I would do is get really clear on what it is, what is the product or service that you want to provide for somebody? Then, look for other people that are doing something similar in your community that you could actually sit down and just talk to them. Find out how their doing it. You know, it’s funny it’s really hard for us to ask for help, but I’ve found that almost everybody wants to help. It’s kind of a nice way for people to realize that you’re not invincible and that you’re accessible. Ask for help and people … I’ve actually have never found somebody who’s said, “No”.

Mac Prichard: 

That’s been my experience too, but I’m glad you’re bringing that up because I think a lot of people hear that advice and think, “Well, why would a potential competitor give me advice? Why would they be helpful?” What’s been your experience there, Rebecca?

Rebecca Shapiro:   

I’m a big advocate of collaboration versus competition. In the traditional business realm it’s more like you have to be bigger, better, faster, badder than your competitor. When you’re a freelancer you’re both a person and a business and so this can feel contradictory. I find that going to your competitors, even when they’re working in the same field you each have different strengths, and you may find that you can create a relationship where you can work together. I’ve had that happen to me several times and they’ve turned out to be really satisfying working relationships and even a couple of them have turned into personal friendships. Don’t be afraid to go talk to people that are in your field. Conversely, I encourage freelancers, because we like to hang out in our field especially when we are networking, to step out of that comfort zone and look in different fields and pick one person every once in a while that you can work with that’s vastly different that you are. What you can do is look for strengths in that person and strengths in yourself and see where you can meet up.

Mac Prichard:  

That’s how you get started and collaboration is very important. Don’t be afraid to reach out to competitors for advice. What about finding customers? How do people find customers who’ve never done this before?

Rebecca Shapiro: 

Gosh, that is such a good question. There’s a couple ways. One, of course, is to have an online presence. You guys have talked about this actually in some of the past podcasts that you’ve listed that I found was really a great resource. Also, again when you go to these networking events … Don’t let the word networking make you blanch and kind of shy away, just reframe it as an opportunity to make friends and meet interesting people. Most of my work has been through word of mouth and so going to these events, going to conferences, meeting up with people for coffee it gives you a chance to get to know one another. You never know. It’s what I call building a reciprocal network. You never know where that relationship is going to lead. Again, I’ve found most of my clients through word of mouth and through other people, so that relationship piece is one of the key ways that I find my work.

Mac Prichard:   

What about people who have had a traditional job and they want to match their old salary. Is that realistic in the first year? How do you do it? Is it something that you have to invest time in? What do you see out there?

Rebecca Shapiro:  

That’s a really good question. I see both. Every once in a while there’s that unusual person who just, they do fabulously well. When I was at the Ted conference earlier this year, there was a gentleman who was talking about businesses and whether they flew or didn’t fly. It was all about timing. The ones that really took off, it was just perfect timing. It didn’t matter if their brand was spot on or anything, it was just timing. I think sometimes that plays a really huge part in somebody being massively successful. I would encourage, this has been my experience as well, it takes a while. Be patient and definitely plan for unexpected contingencies like new relationships or maybe you have kids or maybe there’s unexpected events that happen, people die, or there’s accidents or things like that that may have an impact on your work. You want to plan ahead for those, but I think it’s really important to look at this as like this is a long term relationship that you’re having with yourself and what kind of things you want to put out in the world and your business. It takes a while to build that up. Especially if you’re just starting out.

Mac Prichard:   

Okay. Well, thank you Rebecca. Anything else you’d like to add?

Rebecca Shapiro: 

Just that I am really pleased that you all are doing this. I think it’s a really great resource. One of my favorite things to do is to look at other business models and ideas and lift them and apply them to my own life, and so even though some of the former podcasts have been about more traditional job finding, there’s been some really terrific suggestions and tips in there that I’ve been able to apply to my freelancing work. I really appreciate the resource that you guys offer.

Mac Prichard:  

Thank you. I appreciate you being here and sharing your wisdom with our listeners. You can learn more about Rebecca at her website, it’s rebeccashapiroart.com. You can find her book on Amazon. The title again is, “Work Independently and Live Connectedly: 52 Steps to Freelancing Freedom”. We’ll also include links to these two resources as well as Rebecca’s LinkedIn, Instagram and Twitter accounts in this week’s show notes.

We’re back with Ben and Cecilia, so what did you two think? What were the most important points you hear Rebecca make?

Cecilia Bianco: 

I really liked her points about networking and having the mindset that you’re just going to a party to make some new friends and not looking at it as an awkward business gathering. I thought her points about that were really great.

Mac Prichard:

I agree Cecilia. When people hear networking I think they break into a cold sweat sometimes. It’s about relationships. We’re all human beings and we all enjoy and get energy from connecting with others and that’s what happens when you network effectively.

Ben Forstag:     

I think the key point was that when you’re freelancing you’re essentially running your own small business. When you’re making the decision of whether you want to go in the freelance direction or not, thinking about all the other pieces that have to be wrapped around that; the accounting, the business practices, the invoicing, the contracts. All of that. It’s kind of the whole small business package so it’s a big task.

Mac Prichard:   

It is. I do find in large organizations there are people who have spent their careers in jobs but they have an entrepreneurial bent. They know how to set goals, build teams, collect resources. I say that because if there are listeners out there who are thinking to themselves, “I don’t have the skills it takes to run a small business.” Take a second look at your experiences and your background and what you’re doing, even if you’re in a large organization. You may surprise yourself. Probably, if you are successful, have many of those entrepreneurial skills.

Ben Forstag:   

Definitely, and I think it has to be said that this is a direction the labor market is going in in general. You hear people talk about the Uberization of the economy, that we’re all turning into essentially gig workers where we kind of do the patchwork, DIY career thing. Having these skills and having the backbone to engage in that “I’m going to do it on my own approach.” I think that’s a real asset you could have.

Mac Prichard:  

Okay. Well, thanks.

Well, thank you all for listening. We’re grateful to the scores of people who’ve left ratings and reviews for our show on iTunes. This helps others discover the show and helps us help other job seekers. If you have a moment, please visit us on iTunes and leave a rating and comment. We’ll be back next Wednesday with more tips and tools you can use to find your dream job. In the meantime, visit us at macslist.org where you can sign up for our free newsletter with more than a hundred new jobs every week. Thanks for listening and we’ll see you next Wednesday.