Last fall, I had this burning desire to send a message to my younger self and any other burnt-out art directors who might be crying on the phone to their best friends about how shitty their “dream jobs” at big agencies were turning out.
So I wrote “Dear Burnt Out Art Director” and the response was beyond anything I expected.
When I posted a summary about the article on Instagram, the comments blew up. They were fiiiiiiilllled with people who were in a similar “rock bottom” spot I had described (for me, it was sitting on the floor of an empty apartment at 3am eating raw ravioli).
“I feel like the universe made you post this for me today… 😭”
“Oh my god I can’t love this post enough ♥️♥️♥️ literally how I’m feeling rn. Need to shake things up... thank you!! 🙌🏻”
“I could cry because of how close this hit home. 😭 Thank you for sharing: currently in a uncooked ravioli on the floor situation rn. This gives me hope! 💛”
“🙌 Can this be required reading for graduating designers?? “
I noticed there were also a ton of comments about The Giant Fucking Leap That Changes Lives: the shift from full-time agency work to freelance creative. So many people wanted to make the jump, but a lot of them weren’t sure how to do it.
“Wow that’s so me 😔 I’m looking for an escape but I can’t help but think that I’m not enough yet.”
“I'm start to make moves to transition to freelance and it's terrifying 😖”
“I guess what worries me is that it is not a longterm career, eventually I’ll HAVE to change what I do and I don’t know what that is yet.”
“It’s so brave to strike out on one’s own as a first step. But what next? Especially on the financial side/healthcare side.”
The truth is that the shift from agency job to freelance can be intimidating, but it can be a lot less scary if you have a plan for how to make that transition and actionable steps to take you from here to there. For me, I knew I wanted to pursue lettering. I figured out what kind of work I wanted to do once I left the agency, how much financial cushion I needed to feel comfortable before quitting my job, and started working towards making those things a reality!
I truly believe that this is a transition almost anyone can make. So, I spent a while thinking hard about the things that took me from miserable-at-an-agency to my-own-boss-and-loving-it. And from that I came up with 5 actionable steps YOU can take to start positioning yourself to go freelance while you’re still at your full-time job.
1. Figure out what you want to do.
Some people want to do the exact same work they’re doing for an agency, but without the incredible pressure and soul-crushing workload. Some will want to transition to a different creative field. Before you make any big changes, you need to reflect on what you want + where you want to go.
You don’t need to have a 10-year plan - what you need is to have a direction. Don’t feel locked in; this can change! I started with digital lettering, and now I do murals, 3D installations and food-based creative photography and a bunch of other stuff. You can simply start by asking yourself, “What would I enjoy creating this year? What kind of work would I love to get paid for?”
2. Get that portfolio lookin’ FRESH.
Revamp your portfolio so it reflects the kind of work you WANT to do. This can be tough because we poured so much blood, sweat, and tears into those damn things for school! I know how emotional it can be to eliminate a favorite project (or three).
But listen. The point of the portfolio is to get you the job! And if you know what kind of work you want to be doing (see why that first step is so important?!) then you know that your portfolio should reflect that work. So be a little ruthless if you have to - the end result will be a portfolio that is a reflection of what you would LOVE to be doing.
You should also share the dream-job work you’re doing! Freelancing is waaaaaay better when potential clients can actually find you online and browse your work. So get your butt on social media and show the world what you’re creating.
If you don’t already have this kind of work, then I *humbly* suggest passion projects as a way to get that portfolio / Instagram feed looking good. The wonderful added bonus of using passion projects to build your dream-job portfolio is they help keep you focused and motivated because you are working on big, cohesive ideas instead of random one-off pieces.
3. Side-hustle like it’s your job.
Dive into the work you want to be doing. Spend your free time (however much you have - even 30 minutes a week counts!) doing the work you want to do. Reach out to family and friends, tell them what kind of work you’re looking for, and let them know to send projects your way. And if your company is okay with it, you can widen the side-hustle work search with social media!
If you’re concerned about your current job finding out about you freelancing, then start a new Instagram or new website where you’re sharing your work. But ultimately, your company does not own you (unless you signed a contract that you wouldn’t do any other work). You can build your own thing outside of your job.
I took on pretty much everything that looked halfway legit when I first dipped my toes into freelance work. Craigslist was my best friend for a while and I said “yes” to whatever came my way. For a while, it wasn’t the bright, shiny career I had envisioned for myself in school…but guess what?! Neither was that art director gig!
Turns out I was waaaaaay happier working for myself, creating my own projects, and learning as I went - even though I was working harder than ever. And because I was continuing to build and refine my portfolio over time, I kept getting better and better jobs that allowed me to start saying “no thank you” to the ones that weren’t ideal.
Learning from a bunch of so-so jobs is way more valuable than talking about your hypothetical freelance dream-jobs.
4. Build yourself a nest-egg.
Alrighty - time for some advice that’s less fun but necessary to say: SAVE MORE $$$.
Everyone has a different financial comfort zone so whatever number works will be personal to you. I’ve heard that it’s good to have 6 months of living expenses saved up to give yourself a comfortable cushion before you leave your full-time job. Figure out an amount you can live with (and on!) and start stashing those dollars.
Having a financial buffer will keep you from making decisions out of fear and scarcity. You’ll be less likely to take on red flag projects because you won’t have to make ends meet. Savings will allow you to take on select client work that you want to do while continuing personal work to build up your portfolio.
Once I knew I wanted to make the leap to freelance, I doubled down on padding my savings account. By the time I quit my full-time job, I had money from side jobs and from the Daily Dishonesty book deal and it made me feel A LOT more comfortable.
Hot tip: another option is to get a part-time job to have some consistent income while you figure out your freelance biz! When I went freelance in 2014, I wasn’t 100% confident that I could support myself from lettering alone just yet, so I got a part-time job as a dog walker for a few months.
5. But also make sure to invest in your freelance future.
Yes, you should save more, but also use the security and resources of your full-time job to get really prepared for the switch. Read a bunch of books on business, freelancing, creative entrepreneurship, and whatever else applies to your dream-job (check out this list of my favorite books here). Invest in classes or workshops to hone your skills. Use that full-time income while you’ve got it!
When it comes to building a business, it’s important to know the difference between a “cost” and an “investment.” A cost is something that you pay for (like a latte, your rent, that late night Indian food delivery, etc.). An investment, on the other hand, is something that PAYS YOU BACK over time.
You don’t necessarily have to invest money if you don’t want to either; investing time is just as important. Follow artists who are running the kinds of businesses you aspire to run, scour the internet for free blog posts and videos (like the Q&A videos I do on my IGTV), and seek out likeminded creative people in your community/online. Psst…our Passion to Paid community has over 1,200 creative students who have been sharing ideas, giving each other feedback, and cheering each other on for the past two years!
I hope this answers the questions so many of you asked after I published the first article! There’s so much opportunity out there for freelance artists, and you can totally be a part of it. It IS possible to make the jump, and it’s actually not that scary at all when you have a direction and some solid steps to take. It might take some time, but remember: small steps are better than no steps.
P.S. Which of these tips resonated with you the most, and which one are you going to start with (or perhaps you thought of another one you could take while reading this post)? Let me know in the comments below.