Obviously you are (or want to be) a freelance web designer. I know this because you’re hanging out with me on MMMW! Look, it’s a pretty sweet side hustle; making a nice amount of money while serving your own clients on your own terms—all while enjoying a creative outlet your day job might not provide. For many people, that’s enough and I commend you for it. The rest of us, however, see a glimmer of opportunity and our wheels start turning.
Personally, I’ve been looking for a way to get out of working for others since I was 14. It’s simply not in my DNA to get excited about making someone else’s vision possible—being an anonymous cog in the corporate machine. I was always destined to be my own boss, but it wasn’t until recently that I actually went for it. Here are some considerations for my fellow freelancers looking to make the big leap from side hustler to CEO…
Are You Ready?
You can envision yourself being your own full-time freelance boss; no suits, no time cards, no inner-office backstabbing, no screen monitoring, no microwaved fish in the break room… it all sounds so, so great. But are you ALSO ready for no steady paycheck, no 401K matching, no health insurance, no paid vacations, and no warm cocoon of gainful employment?
Make no mistake, going out on my own was one of the best moves of my life but the little perks and securities of a regular day job are not easily replicated in solopreneurship. Have you ever actually priced health insurance as an individual? It’s like a second mortgage. How do I pull it off? My wife is a teacher and our entire family is on her state health plan. Her paycheck each month is pretty much zero as a result (not kidding). I’m endlessly grateful, however, that I can focus on bringing in cash and growing my business without worrying about benefits.
I also want you to ask yourself, “am I ready to not have co-workers?” I myself have never been drawn to the social side of the workplace—but I know many people bask in it. You’re part of a team; you have something significant in common. Maybe you’ve graduated from water cooler smalltalk to drinks after hours. Intramurals softball league anyone? I had some co-workers at my wedding for heck’s sake! Are you prepared to be a lone wolf (in the beginning anyway)? I feel like I’m on calls with clients all the time but within my own business, it can seem lonely on occasion. Will that drive you bonkers or does it sound like heaven? Be honest with yourself and do what’s right for your own personal sanity and professional goals.
The Ramp Up
Let’s assume you are doing creative work on the side right now while employed full-time elsewhere. You’ve decided you want to go for it and take the next step in your freelance journey. You, my friend, are in an ideal position because you can be strategic and intentional about your transition. First thing’s first, you need some bucks in the bank.
A lot of new businesses don’t turn a profit in the first year. You have some clients and a game plan to get more so I doubt you’ll find yourself going that long without income. Still, you need to create some financial runway. How much would you need in savings to live for the next 3-6 months? I do not recommend spreading your wings to fly until your war chest is as full as possible.
I mentioned clients a minute ago. Let me tell you, it’ll be a long first day as CEO of your own company if you spend it staring at your phone, waiting for it to ring. Just like you’re socking away dollars, you must start to collect a solid book of clients who either need frequent ongoing work or are about to kick-off a big project. This way, you’re not twiddling your thumbs and questioning your life decisions by the end of day one.
My Freelance Story
If you’ve been following me, you know a bit about my own freelance trajectory—which I occasionally mention in somewhat vague terms. After college, I worked for a non-profit for nearly a decade in New York. The pay was garbage so I started pursuing supplemental income streams out of pure survival. I left that job to take a high-salary gig doing digital marketing for a commercial real estate firm. If I had any doubt in my mind that I didn’t belong in a 9 to 5 setting, this five months solidified it.
Merely quitting wasn’t enough. No, this class of career misery deserved a far more epic departure. So I packed my bags and moved to South Carolina on a manic whim, without ever visiting beforehand. I got hired to work for a boutique web design company by the beach. I had a private office and it was a decent situation—but I was swiftly fired for working on freelance during office hours (not recommended).
My next position was Creative Director (working remotely) for a creative agency based in D.C. Let me tell you, everything about this job was ideal for me. It was exactly what I thought I was looking for this whole time. Unfortunately, once I had it, I realized I could never be truly happy working for someone else. After almost three years of hustling for this company, I began to hatch my exit plan. I had a Google Doc with steps and milestones and target dates and everything. I woke up with a new sense of joy every day knowing what I was working toward.
The cushy luxury of planning this while collecting a salary at my J-O-B was quickly extinguished, however, as the pandemic tore through my employer’s financial outlook. He bought some time with a hefty PPP loan but started making cuts the day it ran out. I was one of those casualties.
My six-month plan to go full-time freelance became a six-day plan in the course of one afternoon. Luckily, it was the best thing that could have happened for me. I can plan and whiteboard and meditate until I’m blue in the face—but being dropped off in the middle of the ocean was what I really needed.
Today, I have my own office with a plant from Costco that I’ve managed to keep alive for over 6 months now. It’s become one of my favorite places to be. Sure, I love spending time with my wife and kids, but this is my productivity HQ. I go home to BE with my family; I come here to FUND my family. It’s been just about a year since I was let go from my “real” job. I’ll admit, I haven’t taken too much time to stop and appreciate. I should, though, because this ride has been worth it and my 15 years of freelance is paying off in a very meaningful way.