How to Quit Your Day Job (10 Strategies for going full-time freelance as a creative!)

When you're a creative person, Corporate America and conventional jobs can leave you feeling like a plant without water or sunlight.

I feel you. I've been there.

I'm going to get you to a window!

Here are the 10 STRATEGIES I used in order to become a

full-time freelance artist...

Be sure to scroll down to find out what actionable steps you can take to apply them.

Say yes. Learn later.
Training Wheels - Phasing into Freelance.
Document and share everything.
Seek mentors.
Make friends with uncertainty.
Work ON your business, not just FOR your business.
Be intentional with projects.
Multiply & Diversify.
SERVICE not Sales.
Permission to Change.

1. Say YES (Learn Later)

When I look back so far at my freelance career, it can be summed up as a series of YES-es instead of NOs. Before I became a professional artist I was studying at Berklee College of Music, and working as an RA in the dorms. I needed a creative way to attract students to our residence life events, so I painted a goofy banner and hung it in the cafeteria… The staff noticed, and asked if I could paint a mural. (I had no mural or painting training, so of course I said yes!)

Immediately, after hearing the word YES come out of my mouth, I thought: how do I do that?! I hunted for inspo painting styles on google, bought WAY too much paint (a gallon in every color, because I was afraid I would run out), and then proceeded to just do it.

I was certain they’d find out I was an imposter, but somehow I figured it out and they hired me for 3 more murals, an interior design project, and countless other signage jobs.

Every new opportunity was foreign to me, but I kept simply saying YES and figuring it out later.

When you’re creative, people assume you can do everything. The secret is to say yes to everything and then you’ll realize that they're right!

Over a decade later I’m working full-time as a professional illustrator, but I’ve tried on every art hat imaginable - I’ve designed logos, websites, merchandise, taught paint classes, and painted countless custom portraits— to name a few. Every single one of those opportunities happened when I said YES and learned later.

Above: My first mural and first pro art job at Berklee College of Music. I would do it SO differently now, but I learned a ton on the job and it launched me into an art career!

2. Training Wheels - Phasing into Freelance

This might seem like an obvious idea, but a great way to go full-time as a freelancer is in phases. I started doing commissions here and there during my free time, while remaining employed. Finally, when I had enough jobs coming in, I went part-time at my day job.

Then I gave myself a year and promised I would leave the day job once those 365 days were up. It was scary, but lighting the fire under your own butt can produce results!

Looking back, I can't believe I was that bold, but I think there is power in naiveity. I didn't wait until I knew all the answers. I just took the leap after a buffer period and then figured it out as I went along, keeping open minded about how the money was going to come in. (See #1 about saying YES!)

3. Document & Share Everything:

Why? Because everything you do can live multiple lives—your commissioned painting can be your next portfolio piece; studio photos can be social media behind-the-scenes posts; time-lapses could be content for your client who wants to promote prior to their launch.

When you finish the project, take pictures and videos. Keep these to share with prospective clients as samples. The trick is to NOT be precious about anything- share things despite that voice in your head saying its not good enough and be open about the process, not just the outcome.

Maybe you can offer a promo bundle to your client upfront: for an additional fee, they get a content bundle. If you're doing the work anyway, you might as well turn it into interesting content that can help your client.

Portfolio Management:

Every year, or even 6 months, you should be swapping out your portfolio for a better batch of pieces. Limit your portfolio to under 20 pieces per type of offering if possible.

Organize your portfolio in separate pages on your website for each offering. …For example I have a tab for illustration, graphic design, painting, etc.

I highly recommend getting some outside critique to narrow down your portfolio to the best stuff you have.

4. Seek Mentors:

Find people in your desired field who you admire that are a few steps ahead of you. I say a few, because if they are too famous, they will be difficult to access because of all the gate keepers. But if there is someone who you can learn from, treat them to coffee or lunch and be prepared with meaningful questions. Do your homework on their current work.

People enjoy sharing about themselves and their passions and you can gain a lot of new knowledge and inspiration from them. You might even be able to develop a relationship and receive direct feedback.

Maybe you can exchange help with them, by figuring out what their needs are.

5. Make Friends with Uncertainty:

This is advice I still have to work on constantly. I am a type-A person in a totally unpredictable career, so it’s a constant struggle to embrace the ebb and flow of a creative career.

My secret? When I was chasing “security” in conventional jobs, I was struggling to feel valued or like I was growing. Even though I was quickly promoted, I was terribly unhappy and I began to physically feel the effects of my misery in the form of extreme stress and anxiety.

I finally realized that I had 2 choices: I could struggle for someone else’s dream or I could struggle for myself. It dawned on me that if I put that SAME intense effort toward my own goals I could actually handle the freelance life.

What I discovered was that the tough days working for myself were never as tough as the ones working at a company where I had no support or feeling of meaning.

I did take an interim step to become a nanny, because I love children, and it not only made me lifetime friends, but also renewed my sense of meaning and purpose in my work life. Once I got better with myself, I was ready to jump into freelance life. I will be forever grateful to that family for supporting my decision to go part time and then to move on when I was ready.

TIP: You can't get rid of all uncertainty, but you can mitigate the uncertainty with the structure that you create. Once you create structure you have to stick to it and give it the same importance as you did your previous job. Maybe it's checking social media ONLY during your lunch break, or having rituals like starting the day with exercise, then coffee and emails. Make time for project work, like a couple hours before and after lunch, and then reserve time to work on admin and other business activities. (See next strategy about working ON your business!)

6. Work ON your business, not just FOR your business.

Working FOR your business can be a lot of fun - you are doing the creative parts, after all! But you need to make time every week for working ON your business. That means book keeping, setting goals, building your website, client acquisition, advertising, opening up that business bank account, getting a DBA, etc. etc.

You gotta eat your vegetables, folks!

If you always work FOR your business you will have trouble leveling up, like you are wearing blinders and only focusing on the present task. Charting your path with intention and improving your long-term outcomes requires doing some of the less enjoyable parts of running a business.

TIP: do the hardest things that scare you first. Putting off talking to a CPA about your taxes will only make it scarier. Trust me - I used to be like that.

7. Be Intentional with Projects

Treat every project you do with care and passion. When you give it your all and go above and beyond for your clients they will come back to you for more and be a loudspeaker for your business.

Word of mouth is everything, and you are building your portfolio.

Oh, speaking of portfolios - try to only do projects that can further your portfolio and fill the gaps. If you hate logo design, maybe don’t advertise all the logos you did and stop taking on logo jobs, because you will only attract MORE of what you don’t want.

I know it’s hard to face down the scarcity mindset, and trust that the work will come, but you have to go after the stuff that fuels you… why? Because you will do better work when you care, and that will advertise itself.

TIP: One more thing. Try to challenge yourself with every new project to LEVEL UP! Every time I’ve illustrated a new picture book, I’ve tried to explore with my style, and elevate my skill. When you resist the easiest solutions and lean into the harder stuff, you are being paid to “go to school,” for your craft.

8. Multiply & Diversify:

Here’s an idea to multiply your output without working harder: when you negotiate your next projects, make sure to get permission to use them for other purposes, if possible - like the commissioned painting that you could sell prints of, or upload to print-on-demand sites. You might have to think even further ahead and choose projects that will have multiple selling possibilities.

Clearly, you cant sell someone’s logo you designed, so think about what projects you could be paid to do, that could have other “lives.” Maybe you can make an art book with all of your best material, and sell it once you’ve accumulated enough!

Diversify your streams - this is the key to survival as a freelancer. When Covid reared its ugly face, I stopped doing things like murals and paint classes, but I kept illustrating books from home. Thankfully since I had these multiple revenue streams, I was able to simply shift gears from the many sources, and focus on only the ones that were possible. This helped me stay in business, and the intentional focus on illustrating actually helped me progress further.

TIP: Implement passive income streams. I could do a whole separate blog about passive income streams, but it would be a great goal to carve out some more passive streams so that you are always generating income. Print on demand has been a great way to do this, but more on that in another post! Long story short, your passive income sources can help when there’s a slow month, or they can offer flexibility for life balance. Admittedly I am only just scratching the surface with this idea myself, but hey, why don’t we all work on it together?! :)

9. Service, not sales:

Looking for more work? Hate the icky feeling of selling your work? Then be of service, instead of focusing on sales… Don't just complete the task you were hired for--keep your eyes open for other ways you can be of service to your client.

Ask yourself, what are my client’s needs or struggles and how can I help make their lives easier? Instead of waiting to be asked, locate the need and offer your service. Does their website need help? Are they posting compelling content on their socials regularly? Do they need help creating merch? Your creative skills are the solution your client needs, but they might not be aware of it yet.

"But what if I offer, and they say no?"

Then you’ve lost nothing but only gained more respect from them for caring about their needs. Most of the time, if you’re putting sincere care into understanding their goals and charting the path to help them get there, they will gladly accept your help.

TIP: Be one step ahead of them and be ready with reasonable quote!

10. Permission to Change

A lot of us creatives forget to apply our creativity and imagination to the way we see ourselves and the narratives we tell about our abilities. [<-- READ THAT AGAIN!]

Begin a new mantra: it’s ok to decide something isn’t working, or maybe it’s not as exciting as it once was.

You aren’t FAILING, you are EVOLVING!

I’ve written a whole blog post on this before, so I wont be redundant here, but I’ve changed career focus lots of times, and sometimes I put myself through way too much guilt, shame, and worry. I was unfair and harsh towards myself. I didn't allow myself space to become more expansive as a creative.

Evidence: I used to be a full-time musician. I still have my degree, but I am pursuing illustration now as my main job, and music is my side-hustle.

Another thing that helped me was semantics. I didn’t want to make music my “hobby” because it was more serious than that -- I still wanted to make money from it once in a while, so I named it my “passion project,” “part-time career” and “side-hustle”.

Choose the narrative that feels good to YOU and leave that guilt behind.

People may be confused by your choices but you will have to learn to shut that out and listen to your inner voice. They don’t know you. Only YOU know you. People like to put others in an easy box--but you can be a label breaker!

Conclusion:

Becoming a freelancer isn't easy, but I hope these strategies helped demystify the creative career path and provided actionable steps for you.

I am still figuring all of this out, but so far I've learned some big lessons:

Become in love with the process, not the outcome. Celebrate the little wins along the way and never compare yourself to someone else's highlight reel.

Was this helpful? Do you have any other ideas to add? Feel free to comment with your feedback, and/or repost this with your own input on the topic!

Thanks for reading, and stay tunes for my next post about how being a tandem illustrator-designer can turbo-boost your career and add value for your clients.