What I Learned In Seven Years of Freelancing

Even the brightest lights fall for the easy-money hype.

Felicia C. Sullivan
Jan 12 · 9 min read
Licensed from Adobe Stock // deagreez

There was a moment, not too long ago, when I believed my freelancing career bore an expiration date. I shipped out my resume, flew across the country for interviews, and tried to sell myself on a life of navigating tricky internal politicking, twelve-hour days, and the fear that I would be LIFO’d (last in, first out) should my new company face a dip in earnings. After a slew of interviews back in the bitter cold East coast, I landed in Los Angeles. Catatonic. I couldn’t tell if I was still shivering from the arctic aftershocks or a life I pitched to myself — a life I didn’t want to live.

When I first started freelancing in 2013, I thought it would be temporary. A needed break from an agency job that had given me the gift of PTSD and forty extra pounds of emotional eating weight. But as the years pressed on, I fell in love with the power I had over my days. I didn’t have to bear unhinged clients and their Candy Land-level expectations. I wasn’t tethered to my phone or my desk. And I didn’t have to pretend to make small talk, play the amiable executive when all I wanted to do was lock myself in a room and work.

Freelancing was made for people like me who can only bear people in small, controlled doses.

Over the past seven years, I’ve done the best work of my career even though the years have been the hardest I’ve known. From Sahara seasons when I feasted on ramen and oatmeal for weeks to crippling loneliness, career self-doubt, and friends trying to rip me off, I can see why, in early 2019, I wanted to crawl back to the familiar discomfort of full-time work.

But after I came home from my interviews, I realized that few employers can give me the life I designed for myself — the freedom and flexibility to be curious and agile. To be wrong, make mistakes and learn from them without them being the albatross that’s forever bound around my neck. Two years ago I wrote a similar piece on lessons learned and I feel as if I got an advanced degree in freelancing since then.

Being a consultant forced me to confront and conquer five realities.

1. Even the brightest lights fall for the fast-money hype

I was reared to believe a career resembled a children’s book — made to placate the impatient tyke who’s forever asking, what’s next? Success belies the cult of more, if we’re not projecting our 24/7 highlights reel or showing off our finery, we’re not worth knowing. Once we’ve achieved some level of recognition or achievement, we’re told we have to build that e-course, productize our work, form social media “alliances” to “leverage” someone else’s audiences to build our own.

We become a bombastic mega-brand megaphoning our wares on Instagram and TikTok, shouting our volume-ten hustle on YouTube. Churning out articles humble-bragging our riches on Medium, and you too can make a six-figure income if you buy my $297 eBook, $997 course, or invest in my new line of kitten t-shirts. Neglecting to mention there’s no neat playbook, no template or blueprint one can use to mimic someone else’s magic, luck, or privilege.

But no one wants to hear you have to do the work and make your own way. No one wants to believe that hacks are bullshit and someone else’s success path doesn’t necessarily pave our own, even if we eat, work, write, pray, and fuck as they do. Instead, we’re lulled into slumber by the pack of lies on which we feast.

Please stop buying into the pack of lies. You don’t have to be over-the-top to be successful. You don’t have to focus on ascension. You don’t have to build or make the next thing if it’s something you’re allergic to doing. Just because an echo chamber of hustlers and growth hackers tells you to do something doesn’t mean you should do it. Don’t blindly follow the herd because that’s how the herd makes money; they hope you’ll devour their “knowledge” morsels until you’re reaching for the bottle of Pepto. And sick to your stomach, you still come back for more.

I’ve been a marketer and a traditionally-published author for over two decades. I’ve been a consultant for seven, and it’s only until recently that I’ve considered publishing eBooks and coaching clients because teaching is what I love. I live for making the complex simple. It’s not a tactic I’ve adopted because some huckster told me to. I decided to expand my services when I had a solid framework. When I was almost ready (because you’re never really ready).

What’s worth having is worth fighting for, working hard for. Don’t fall for the fast money and tactics. The real players are invested in the long game. They follow their energy and curiosity — not the roadmaps designed by other people.

2. Follow your curiosity instead of your passion

Passion blinds you, whereas curiosity is a camera lens aperture widening, allowing light to flood the frame. Curiosity is a sampler while passion is a seven-course feast that will knock you out, render you comatose. Clutching your stomach. Make no mistake, passion has its place — it fuels your work and sustains you in the moments when you want to give up or scream into pillows. But curiosity is your cautious, methodical guide. It’s an invitation to try things to see where they lead you. It gives you perspective when passion demands you to be myopic.

Over the past seven years, I’ve indulged my curiosity, which has not only allowed me trespass to new knowledge (and adding new skillsets to my toolkit), different industries, and sectors, but it’s also exposed me to people I would’ve never otherwise partnered with or befriended. Curiosity is dipping your toe into the water to see if this is a place you’d want to swim, while passion is diving in, headfirst.

3. Wisdom is acknowledging what you don’t know, but are willing to learn

One of the reasons I’ve done the best work of my career in the past seven years compared to the previous thirteen boils down to humility. I’m a confident brand builder, marketer, and storyteller and have decades of expertise, experience, and success to prove it, but one learns and grows by being receptive to new tools, methodologies, processes, frameworks, and schools of thought.

If you’re not allowing yourself to question what you know, you’re booking a one-way ticket to the land of irrelevancy. I’m constantly learning from my peers and the verve of kids coming up in the ranks. My framework for building brand platforms hasn’t changed much, but how I deliver them to clients, the shape and form the deliverables take, is unrecognizable from when I started freelancing seven years ago. Over time, I winnowed out the fancy marketing terms and trimmed the fat and focused on helping brands translate data and experience into compelling stories their customers can relate to and understand.

The mark of expertise is being able to distill complexity, to transform fifty-cent words, frameworks, and methodologies into that which is clear and simple. If I hadn’t learned from my peers and absorbed how they constructed brands, I would’ve held on to my way for dear life. I would’ve been rigid when the world demands flexibility.

I’m an expert and devoted student. I’m committed to teaching and careful study. It’s the balance of the two, the willingness to question your ideas, learn and adapt, that sets you apart from the peanut-crunching pack.

Sometimes, the best answer to a question is: I don’t know, but let me look into that and get back to you. Being an expert doesn’t mean you know everything, rather, it’s how you’re receptive to learning everything.

4. Just because you’re good at something doesn’t mean you ought to be doing that something

I’m an end-to-end marketer, which is a fancy way of saying that I can build your brand and market your products. However, I’d rather gouge out my eyes with an acetylene torch than implement an influencer marketing strategy. I’d rather collapse on a cactus in Joshua Tree National Park (this happened last Sunday, FYI) than run Facebook ads.

Being good at something doesn’t mean you need to be doing that something for a living.

Seven years ago, I started my consulting practice offering all the things. You want me to build your social media strategy? YOU GOT IT. You want me to define and build your brand architecture or conduct a customer segmentation study? BRING IT. You want me to pet your head for $5,000 a month? HERE ARE WIRE INSTRUCTIONS.

I learned quickly that offering a full-service buffet gave me heartburn. It became clear that I loved certain projects more than others and some types of work were more labor-intensive and not as profitable as other types of work. Now, this isn’t an argument about niching because I believe binaries are bullshit. I’ve worked with many successful agencies and consultants that offer a myriad of services, as well as consultants killing it with a single-service offering. One is no better than the other — again, it’s about what works best for you.

It took me six years to realize that I love being at the beginning of things. Building a brand lights me up. I go stark-raving mad if you ask me to become a CIA operative when it comes to understanding your customers. And I’m kicking and screaming with joy if you ask me to architect your story strategy. Everything else I refer to other capable consultants. Because when I said no to the projects that drained me, it gave me space to not only pursue the projects that challenged me, but it also gave me time to refine my process, methodology, and work product. Every six months, I’m evaluating my work product and making improvements.

It’s hard to turn down work, but I’m playing the long game. I want to be known as the woman who tells stories that knock your socks off.

5. You will make rookie mistakes

Sometimes, you’ll take shortcuts. You might forget to send a contract to a friend because of course, my friend wouldn’t steal the money right out of my pocket. You might ignore the five-alarm fires during the pitch and proposal process and take on the nightmare client. You might let them steamroll all over you. You’ll take on projects for the money and feel as if you’re burning from the inside out.

You are human. You are fallible. You will make mistakes — sometimes a fuckton of them — and that’s okay. The mistakes remind you that you’re human. How you rebound and learn from them makes you a pro.

Last summer, a dear friend and former colleague stood silent while her business partner tried to deny a $25,000 final payment. Her silence was her complicity. And I’d made the massive rookie move of not getting the contract — even though a part of me knew I should’ve had one in place. Ultimately, I got the money but I lost a friend and after the shock of it all subsided, I made a point of always delivering a contract.

You’re a friend? You’re getting a contract. You’re my lover? Sign here. You’re my fluffy tabby cat? Send me your Venmo details, motherfucker.


Over the past seven years, I’ve seen it all. From the I can get a kid on Fiverr to build me a brand strategy to the clients who worship at the altar of the Facebook ad fairy, a mythical being that delivers passive income while they sleep. Straight face: I have a budget of $500. Can you build me a million-dollar business by next month? I’ve witnessed freelancers pitching their brand strategy expertise after skimming free eBooks and binging on Gary V videos, which is akin to performing open-heart surgery after having watched The Discovery Channel.

Regardless of how many millionaires in yoga pants tell you to quit your day job and uproot your life, freelancing isn’t for the faint of heart. It’s perfectly fine to crave the structure and rhythms of a traditional work environment. For years, I cried on Sundays, swiped key cards, and sat in offices and cubicles, and I was content with my life. Sometimes I miss comprehensive dental coverage. You try getting a root canal without insurance.

But what I love about being a consultant is that there’s zero room for complacency. When you think you’ve got something figured out, it changes shape and form, and you’re forced to adapt. You have to keep your skills, technology, and perspective fresh. You have to nurture your relationships in a real way beyond the exchange of virtual business cards and blog post links. You have to cultivate a community of peers, clients, readers, and friends that gravitate to your work and vibe — a community where the student and teacher relationship is symbiotic.

And you have to design a roadmap that is wholly your own. No easy template exists. There are no viable shortcuts. You have to show up and do the work. Every day, all day. On your terms.


Sign up for my newsletter where I tell stories — sometimes long ones — each week. If you’re looking for fast hacks and get-rich-quick schemes, this ain’t it. Also, if you steal my work I will find you and ruin you. Namaste.

Falling Into Freelancing

All the tips, tools, and resources you need to thrive after your 9 to 5.

Felicia C. Sullivan

Written by

Published Novelist & Marketing Exec. I build brands & tell stories. Newsletter: https://urlzs.com/8CLu Hire me: https://is.gd/uqGWX5; Buy my brain: t.ly/OrgbJ

Falling Into Freelancing

All the tips, tools, and resources you need to thrive after your 9 to 5.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade