How to Freelance (Q&A) Part Uno

Hi. This is my first blogpost on my very own website. ((faint celebratory applause))

I’ve been wanting to talk about a topic much of my personal network is interested in learning more about: freelancing. Over the years, I’ve answered many very good and valid questions (in private) about how to get going with side work and full time freelancing, and I wanted to begin compiling all the great inquiries in a more accessible space for people to reference back to. Below, you’ll find a list of questions from my friends and colleagues, and my answers. Hopefully the following will be of value to you, and the conversation will continue here and elsewhere. Please feel free to ask further questions in the comments.

The following questions were asked in first-come-first-serve Facebook status order.

“Girl how can I make money by doing very little, while wearing pajamas, and on my own schedule. DM me.” - Chrys A.

Heh. Chrys has a way of being a bit tongue-in-cheek, but I think this is a valid question. Many of us want to make money without putting in a lot of work, time, or energy. We also want freedom, like the option to wear pajamas (because who cares what you’re wearing as long as you’re getting shit done?) In before I’ve been writing all my emails naked (joking, but not judging if that’s your thing). We also want to be in control of deciding when we work and how. These are all desires that are shared from what I will guess is millions of people on the planet.

So, a few things to ponder here:

  • How much money do you need to make vs want to make?

  • Why do you want to do very little? What does a very little look like, and why is this important to you?

  • What does choosing what you wear to work do for you?

  • How is creating your own schedule beneficial to your work experience? Such as your personal process, how it feels while you work, or the end result for your clients?

Once you can define why these things are important to you and how you and your clients do/will benefit, you can better understand your values around work and what you want and need to be successful or feel good—whatever is significant and works for you.

“I’m familiar with freelancing and the road getting there. What do you think the hardest part of “the separation” is?” - Major Asselin

I think the hardest part of the separation between freelancing and the average office job surrounds the concept of responsibility. Plenty of people go into an office job fully aware that they are getting compensated for executing upon a list of job duties or responsibilities (hopefully outlined for them during the interview process). When you’re a freelancer, sometimes you get lucky and a similar list is handed to you. Other times, you create that list. You’re telling someone what the job is, what you’ll do, and how much it will cost. With a job, there is often an opportunity already available telling you what the job is, what you’ll do, and how much it will cost. You’ll have to be responsible for managing responsibilities, expectations, and processes. It’s like running your own business, being the President of a club, being the Director of the school play, or being a Mom to a kid. You’re in charge, you create and communicate the rules. This level of responsibility requires just that—the ability to be responsible. You own this, you’re setting the stage. That means a lot of how things are going to start, stop, and go is up to you. You manage the job and the relationship. Congratulations, you are both the Captain of the ship and the boat. But don’t worry, it can be a very rewarding ride.

Cutting free of a 9-5 is not easy after all. I’m asking because I went back to the career life after half a year and would like to know how other people dealt with that.” - Major Asselin

I would ask yourself why leaving a 9-5 is hard to you. I assume it’s the sense of sustainability and certainty that you get with a full time job. I was lucky enough to have some of the worst jobs that either couldn’t keep providing me with paychecks, clients, or general satisfaction. When I jumped ship from the 9-5 to freelancing, I didn’t have a fear of losing a paycheck or health insurance because I already didn’t have those things—and if I did it always ended quickly, anyway. I decided I needed to take control of my career and finances and things haven’t been more stable (knock on wood, for anxiety’s sake). I dealt with it by knowing I had nothing to lose and that if things didn’t work out and got really bad, I would get a “regular job” again or just do something like Rover (a dog-walking app—which I did do, by the way, for extra income, peace of mind, and doggie cuddles :-)

“When you decided to go to freelancing as opposed to working for a company, what was the transition like for you? Thoughts, fears, etc, did you consider going back, regrets.

Example: When freelancing I didn’t have health insurance and I had to go get a career again because of it.... and other reasons.” - Major Asselin

Well, as I mentioned earlier, I really didn’t have anything to lose. I was working for a tyrant who made me rethink leadership. Most of my jobs did not have bosses or CEOs that I respected. They were very emotionally unstable, uninspiring, and/or fake people. We didn’t have the same values and I didn’t look up to them. I have always felt deep inside that I was a self-starter and a leader. I’ve never really followed any common path in life (in my opinion). I’ve read literature obsessively as a child which helped me understand people and independent thinking. I was never in popular crowds, I rebelled against my parents and teachers, I didn’t date in high school or college, and I just generally have always done my own thing. I think developing my sense of self and the confidence to be who I am and do it my own way helped me make this decision. I always knew deep down I didn’t want an office job, but during those years of work it was what you just did, and I wasn’t aware of the concept of anything else. With that said, I’ve always done projects on the side since high school. It started off with developing a passion for an art (which we now call a skill, thanks capitalism), which in my case was specifically reading, writing, and photography. I’ve done this since I was little so when I was a teenager I was already “good enough” to be asked to volunteer in the yearbook or to help someone with a family portrait. It started off very organic. Then I learned there was a word for helping out friends, strangers, and institutions: freelancing. I did side gigs because I was already doing it for free, why not do it for someone for realsies? And I just kept doing that on the side throughout high school and college: taking on little projects and just doing it. Even if it wasn’t good. So that level of background and experience hopefully explains why this feels comfortable for me.

To answer your other questions: I don’t necessarily have any regrets, but I certainly made mistakes. I really messed up the ISO on those yearbook photos. They look terrible and I’m angry, because it’s just there, in my yearbook to this day. I’ve gotten so much paralysis-by-analysis-anxiety over editing photos that sometimes I would never send them to people I said I would, which is not cool at all (I was sent to All Points West, an amazing music festival out of Brooklyn, NY, that is sadly no longer, for one of my college magazines). They took a chance on me and sent me there for free. The pictures were awesome, I still have them somewhere on a hard-drive. I had a blast shooting and enjoying the show. I got caught up on seeing tons of the photographers with better, longer lenses than me who were editing photos on their Macbooks between sets (which I wasn’t doing). So, I never sent the photos, I never got published, and I fucked up. Basically, I was terrified of my work and extremely irresponsible. Another one: I took a two hour train ride from South Jersey to NYC to shoot an event. The client loved my first gig with her so I figured, “I can do this.” I arrived just as the event was getting started, which in her eyes was late. I was really disappointed in myself because me timing it way too closely created a lot of anxiety and disappointment for myself and them. Also, this client didn’t end up liking my photos either. I ended up eating the cost because I felt so bad about myself. The client felt bad and offered to pay me anyway, but I felt I needed to remember this forever, and I was just in college at the time so the money wasn’t a big deal (lol I told myself that then, but looking at my student debt now…)

I did consider going back to office life many times. However, every time I tried, I hated it. I felt I was forced to be in environments that weren’t conducive to productivity (like cramped spaces, computer-against-the-wall-so-my-boss-can-spy-on-me-and-make-me-feel-uncomfortable-and-like-a-child). I was “forced” to have conversations about things that I didn’t care about for the sake of culture and being nice and on good behavior. I just wanted (and still want to) get shit done and not be fake. I genuinely feel like I can do that with the relationships I have with my clients. I am not sure why I always felt I couldn’t be that in an office, but now that I’m thinking about it, a lot of the times I felt I was myself, I felt shame. I just never felt really appreciated and into the whole office culture life, it felt like a forced relationship for the sake of wanting to make money and have a career. This probably means I was the wrong fit for these places or jobs/some people just suck, I dunno. I believe there are amazing 9-to-5’s out there that are perfect for some people, but I haven’t found it and I’m not interested in looking because I’m the happiest I’ve been where I am right now.

Your health insurance question was asked by someone else as well, so I’ll tackle that below (last question, scroll all the way down to jump to it).

“One more question: paying taxes, how do you pay them?” - Major Asselin

Good question. Taxes suck! I take out 25% of each paycheck and put it in my savings. Some take out 30%. I just hired a bookkeeper to go through all of my bank statements and prepare my profit and loss statement for a CPA. Adulting is scary and these simple steps were and are scary to implement, because being responsible is hard and sometimes you don’t have the privilege, space, resources, or courage to do the above. I have messed up here before, but that’s okay. We all do. You learn as you go. Ending this with another, “taxes suck.”

“I need newer ideas. I've been doing it so long, nothing I have in my marketing repertoire is new, and that's crushing my usability. Can't wait to read your post.” - Terra Walker

I indulged Terra a bit more to understand what she was asking here, and she said that she is assuming that she’s offering older solutions to her clients. Again, I would break this down and try to answer your own questions. Why do you feel you need newer ideas? Is it because you’re bored or you feel like you’re not learning anything new anymore? Do you have a desire to serve your clients the latest, fancy, shining marketing tool? Why is that necessary or important to you? I encourage you to explore these feelings and what I will assume are fears. I know that in my experience, I’ve felt that Groundhog Day feeling where you feel like you’re doing the same thing day in and day out, and not growing. When I’ve felt this way at jobs, I’ve tried to collaborate with others, ask for direction, or watch a Lynda course. However, most of the time that didn’t satisfy me. I always got a rush from completing a project I was proud of. Do you need a new client or a passion project to feel like you’re kicking ass? Do something you’re truly interested in and empowered by, even if it’s something small. You might also want to explore doing something pro-bono, volunteer-esque, or even just for yourself, like making an Instagram for a niche personal interest or a YouTube video just because. Do this to experience something creative and new, all while proving to yourself that you are indeed awesome and marketable, or as you say “useable” for future clients. For the record though, lots of clients still need the things you’re doing. Otherwise you wouldn’t be doing them, right? So just ask yourself why it feels like it sucks. And then fix it or change it up a little.

"How do you hustle and find clients?” - Anna-Marie Walsh

Let me run through some examples of ways I’ve gotten clients, from earlier to later examples.

  • Passion. I practiced my craft (photography, writing) and people saw me doing it and recognized me for it. So when opportunities came up, they thought of me. I did a lot of volunteering and free work because I loved what I did and didn’t care at the time. It wasn’t to make money. But this is what led to later money. So, do stuff and let that be your portfolio, literally and figuratively.

  • School. I did (paid) photography for an event as a freelance photographer, and the speaker for the event liked my work and wanted me to shoot another event for her. I also ended up writing for her business, too. See how things just flow, sometimes?

  • Friends. I socialized intensely in high school and college, this allowed me to meet a lot of people and explore my personal interests (music, photography, writing, art, community, organizing). One thing leads to another and you’re known as “the photographer” or “the blogger” or whatever.

  • Work. You meet people at work (your coworkers) and you meet your clients/partners sometimes, too. In one scenario, an old coworker hit me up after I left the job and asked me to do side work for her. She was one of my first social media clients. In another situation, I did a blogger event for my job at the time and interacted with influencers for the event. These people became a part of my network and some even became my friends, due to shared interests and seeing each other at industry events. This led to more opportunities that came my way.

  • Conferences. You meet so many people at conferences. I volunteered for many, doing photography and social media and whatnot. I also attended some for myself. You meet people, they become a part of your network (and sometimes friends!) and then boom: “Hey, Cat, I have a client who needs this. Can you help?” Yes.

  • The internet. Do you know how many places you can get clients from online? One of my earlier clients found me on LinkedIn (aww yeah, inbound marketing!) We worked together for years. Pretty cool moment. Also, I landed the biggest digital marketing client (so far ;-) in 2018 through a Facebook Group that my previous Rutgers-photography-teacher-turned-friend (see, networking) recommended me to join for clients and general freelance advice. All I did was respond to a post, and by the end of the week, I had the gig. So, be a person on the internet. Join groups, set up your LinkedIn. Put yourself out there. Engage. Be in these spaces, allow opportunities to come to you, and go after them. Boom. In the bag. Also, this will all be scary. Do it anyway.

  • Referral. In one way or another, the above stories show that if you are involved in the community (your city, your office, your school, the internets) then things will happen for you. Just be brave and chat with people.

  • Asking. Who would have thought? Asking for new clients? Whoa. Yeah, it works. I asked for new clients on Facebook once and got too many to handle at the time. Ask and you shall receive, peeps.

How do you sell new clients?” - Hannah Marie Watkins

Similar question to Anna’s but there’s a differentiator. Anna wants to know what actions you have to take to find new clients or have an opportunity come to you. Hannah’s question is more about how to close a deal. The answer is that it really depends on the client and the project at hand. In the beginning, when I was trying to do things “officially” as a full-time freelancer, I remember sending out a crap ton of proposals and never getting the damn thing signed. I always felt like leads were just taking my ideas and implementing themselves, so I started providing less and less information in those proposals. Today, I still have a process where I send a proposal, have the client review it, negotiate, and then put it in a contract. Then we review the contract and sign off on it. I typically do a 3-month contract to start, to make sure it’s a good fit and to get everything set up. But reading in-between the lines here: the unsuccessful leads (as in, those that didn’t sign) really weren’t sure about what they wanted or needed, or it just wasn’t a fit. Some of them didn’t have the money, even though they said they would invest X amount. Some of them didn’t like the way I wrote an email. Honestly, it’s random. So just take what you can from each “failure” and decide what you can improve on versus where the client is at. Sometimes it’s just not a fit, and sometimes they’re not ready. The leads that have been the most successful to me felt super ready, were super on my ass and quick to respond, and were usually sent to me by a trusted source: someone who’s already worked for them or who can vouch for them. Anyone who has sent me someone with some sort of caveat like, “I don’t really know about her, she’s flaky but she needs help…maybe it’ll work for you?” Yeah. That shit never worked out. Just do your thing, kiss a lot of frogs and you’ll get a prince. You’ll gain confidence and a sense of intuition the more that you “sell.” It doesn’t even feel like selling to me at the moment. I just feel like I’m giving something to someone who already knows exactly what they need and what I can offer them. It’s smooth sailing, sometimes. If you have to try super hard to sell to a client, do they even really need or want you? It’s probably a red flag if it’s too hard, so keep that in mind and just experience trying. Read the above on how to hustle for clients and then try selling to those that you approach or that come to you. See what happens with a handful of leads. You can and should do this if you want this. You’re smart.

“I'm interested in freelancing I'm just nervous obtaining clients and question how much they'll pay me.” - Sam Clark

I asked Sam what he’s nervous about, and he said, “Not 100% sure. I'm used to rejection being in sales previously. I think it's mostly self doubt.” Look. Self doubt is a bitch. We can think ourselves out of anything and everything and not get anything done. So, explore that. Why do you doubt yourself and your abilities? Is it because you’ve gotten more losses than wins when you were in sales? Are you afraid you won’t be able to get a client, or keep them? Are you worried that you aren’t worth being paid to do what you are willing to offer at all? Or that you need to charge a low amount in order to get or keep your clients?

I’m not going to lie. You need to have confidence to do this shit. Start there. Offer doing something for someone for free. Say your skillset is building websites. Build your own website. Boom. You did something. Should feel good, right? Second step. Build a website for a friend, a coworker, or a local non-profit in need. Put that on your website. Talk about the process: what you did, how you did it, why, and the results. This is called a case study. Do some shit and then share it, show it. Build your confidence. You are worthy, and someone out there needs someone like you to help them. :-)

“I’ve been out of school for a long time and my last marketing job is not something I want to put on my resume. How the hell do I even get started after a hiatus that I’ve taken? Haha.” -Roxanne Pettit

Heh. Roxanne and I both worked at one of the worst companies I’ve ever worked at in my life, where we experienced actual trauma and had to leave. So her question hits home, considering the shared experience we endured. But that’s a story for another day ;-)

You don’t need to be in school to get a marketing job. I know the world tells you that, but what you really need to do is define what kind of job you want and why. Do you want to get a job to make money? Do you want to get a job for status purposes (look at me, I haz a job!) Do you want to build a career for stability or financial reasons? Are you passionate about a specific industry or type of role? Explore this. Who are you and what kind of job aligns with that? Or does that not matter to you? Knowing you personally, I think you would do well in any type of role that requires good communication and creativity. Start dreaming. Start lurking people with cool jobs on LinkedIn and Facebook. Start interviewing for random jobs just to practice and see what you like. See what’s out there. I know it’s important for you to feel loved and appreciated at a job, for you to be creative, and for you to communicate well. See what you can do with that mixture.

As for the last marketing job you had that you don’t want to put on your resume: same. I personally removed the name of the company from my resume and kept it vague. No one has asked me about it. I also removed it entirely from LinkedIn. Look, recruiters are busy, interviewers rarely know how to interview properly, and no one is even reading a resume these days. And if they are, they have a legit resume-inspecting reason, and you can speak to your experience. You did things at this job. You got paid for doing said things. That is worth something for you and for this company that is thinking of hiring you. So, what can you do with it? Get creative. Talk about it like it was a contract, or a project. Get vague. Find a solution, any solution, but don’t bury your talent and what you learned and contributed. Experience is experience.

And don’t worry about a hiatus. Update your resume and get that next great gig you want. People take gaps, and in your case you really didn’t. You just need to translate the skills that are relevant to marketing to your resume. Plus, we all have different backgrounds. You’ve valuable and have something to offer the next company that is lucky to have you and your positive attitude.

I also asked Roxanne if her goal is to freelance in marketing, freelance in general, or just get a marketing job. She said that she wanted to learn about freelancing in general, and went on to say, “I am really lost when it comes to a career path. Let’s call it my 30 year old crisis haha.”

Everyone is lost. No one has a path. And if they do, it changes quick. Just do something over nothing (which actually, you are doing). You have a great job. There are things you’re doing that translate to both marketing and freelancing. Write a list of all the skills from your current and past jobs, start diving into what you’ve done first. We can worry about organizing it into a resume or a portfolio later. First you just need to acknowledge your accomplishments, skills, and learnings. Secondly, you have a fantastic social media presence. You have more followers than most people I know who call themselves influencers. You don’t even call yourself an influencer. I know you personally and I know you’re very humble when it comes to your skillset. You’re good at what you do because you are passionate—that’s a good thing because it makes you a natural. You need to recognize this and then find the right fit so that you can do this for someone or something in exchange for money (or whatever you want). I would start dreaming… what kind of freelancing do you want to do? And why? Dream big and you can figure out the solution to getting there. First you need to know what you want to do and why.

Also, your 30 year old crisis is something we all face like every day/week/year. Don’t worry, we’re all figuring out what we want to be when we grow up. Just start brainstorming and seeing what’s out there. You’re perfectly capable of doing whatever it is that you want. You don’t really always know exactly what you want until you do something you don’t want. So just test the waters, have fun. Maybe shadow some people and ask if they like what they’re doing. See what appeals to you.

“Excited to read this! I’ll throw in: What do you do for health insurance? and, how do you land contract gigs, like the one at your last agency (was it listed or did you pitch them)?” - Kathleen Garvin

Thanks, Kathleen. Ah, health insurance. What a bitch. So, there have been a few situations in which I dealt with health insurance changes. Here are some of them:

  • At some point when I was under a contract and I didn’t have health insurance, I also had the privilege of living with a boyfriend. This put me in a spot where I could claim a domestic partnership through his work. He had great insurance, and yes, I was lucky to 1) have a partner who had a job that offered health insurance 2) and that job accepted domestic partnerships. Poke into it a bit to see if you apply to this situation, but generally it’s as easy as just sharing rent and bills.

  • Some contracts you land will offer you health insurance! I had the worst health insurance ever through one of my clients. It also made me feel tied to the gig, but hey, health insurance! But it gave me that sense of security we want and need when it comes to our health, and also as much of a pain in the ass it was to get claims paid, it worked out in the end. It was a very odd and not so popular company, but I’m pretty sure it was a brand similar to Obamacare. I realize this doesn’t sound encouraging but I felt great having something over nothing.

  • Sign up independently! I went through, answered some questions, and pay about $300 monthly. It’ll depend on your income, state, etc. Some people pay significantly less (lowest I’ve heard is $100 a month) and some pay significantly more). It’s worth the peace of mind in my opinion to have health insurance. Anything can happen at any time. Truly. I know some very healthy people our age in the hospital right now. Whoops if I’m freaking you out. :-)

  • Don’t have any! Sorry to suggest this, but tons of freelancers choose not to have health insurance. Some can’t afford it, so that isn’t necessarily a choice, and that’s a conversation for another day. But usually in that situation you can qualify for a very low monthly premium. When I didn’t have health insurance I was “okay” AKA LUCKY and just paid out of pocket for doctor’s appointments. Yeah, it’s weird not paying a $30 co-pay and giving your doctor $150, but that’s kind of the trade off for not having health insurance you pay every month. Some people are comfortable with this and just do it this way long-term. My fear, however, is if shit hits the fan and you land in the hospital or get very ill. But some people choose to take that risk and deal with that when it happens. Which, it does.

  • You can check out other sites and resources like the Freelancer’s Union which has some really good options depending on the state and your age and such. There’s also a Facebook Group called Freelancing Females that talks about health insurance alllll the time. You could probably find like 50 threads on this subject in there right now. Like, we’re all trying to figure this shit out, tbh.

As for your other questions, I land contract gigs in all sorts of ways. I would scroll up to Anna’s question about how to hustle, and pop over to Hannah’s as well regarding selling to clients. Specifically for the last few agencies, I joined a freelancer’s network that has opportunities thrown at me frequently. This gives me the opportunity to work with different agencies and clients for short (or long) period of times. Freelance opportunities are not as scarce as people may think. There are companies out there working with tons of freelancers to sustain the business or just TrY to Be EdgY and pRoGresSsivE for MiLLenniaLs. It’s often in the company’s best favor to hire a freelancer over an employee. It can be very cost-effective for some projects/clients. Another agency I work with remotely is a very small team led by a CEO that I’ve known for years. I basically went up to him and whined about needing new clients, not even thinking “duh this one has his own company”. I just looked to him as a mentor and boom, he was like, what if you work for me? Sometimes things just work out. So just talk to your network and tell people you’re looking for a freelance opportunity. Get to know agency owners, mingle at networking events and talk to them on Twitter. That’s “the pitch.”

Hope this helps a little. Please feel free to ask any further questions, clarifications, or hell, your own two cents, in the comments. Also if you read this entire thing, please let me know because I will be genuinely shooketh. Also, to celebrate my first blog here, I’ll be printing out any hate mail and/or screenshots of the lack of social media likes for my home office.