My 1st Year as a Freelancer: 10 Lessons Learned

Alanna Flowers
7 min readJan 1, 2022

On January 1st, 2021 I launched my business, AGF Design Studio. Within my first year I worked with clients like Adobe, American Greetings, LUNA Bar, and Little Brown Young Readers to create lettering and illustrations for a variety of projects. As I celebrate the first anniversary of my business, I wanted to share 10 lessons I’ve learned as a creative freelancer.

My decision to go freelance was ultimately catalyzed by the chaos of the pandemic and not feeling creatively fulfilled in my position as a Graphic Design Manager. I'd been doing lettering as a hobby for about 6 years at that point and wanted to take the chance to bet on myself. No matter where you are in your journey, I hope this article and my reflections help you as you navigate your career.

1. Introduce Yourself

If you’re an introvert like me, the thought of sharing vulnerably online (or at all) can make you feel a bit nervous. However, the reality of being a business owner and freelancer is that no one will know about what you do unless you tell them. For my business launch I created a carousel post on my Instagram profile to make the announcement.

This was a good way to get the word out about my new business. After that, I hit the ground running with e-mails to my inner circle of contacts. This meant my old college professors, former supervisors, and family friends. So don't be shy. Get out there and tell the world that you’ve arrived!

2. Show & Tell

When you start out it's easy to feel like a lot of things are out of your control. One of the most important things you’re in control of is how you present your work to the world. I put together a whole YouTube video on showcasing your work online that you can check out here.

Essentially, you should only show the type of work that you want to get hired for. If you’re starting with zero clients like I did, passion projects are a great way to add to your portfolio until you get paid clients. As long as your work is professionally presented, you’re already headed in the right direction. While creating a website can sound like a big investment (both of time and money) it might surprise you how you can utilize free social media platforms like Instagram or Behance as a portfolio.

3. Reach Out

Like I mentioned, I started my freelance career with zero clients on the books. Definitely a risky move, but what I did have was a plan for outreach. That meant sending a lot of e-mails. After starting with my own immediate circle of contacts, I expanded to every Art Director, Creative Director, and agency lead I could find. In fact, this is how I got all of my art licensing clients this year.

The key to this lesson is to make yourself known to the people you want to work with. I suggest using a spreadsheet with the companies and contact names you’ll be pitching to. This will allow you to easily track your progress and make timely follow-ups. Not sure where to start with finding contacts? I suggest using platforms like LinkedIn, seeing who your peers are working with, and using

4. Expand Your Network

There are a lot of freelance creatives trying to navigate the world of invoice chasing, client onboarding, and all that comes with managing a business. The importance of expanding your network is remembering that you’re not alone. Review who you follow on social media and whose work you regularly engage with. You'd be surprised how quickly relationships can form from exchanging comments and DMs.

But don't think that Instagram is the only place you can find other peers. Twitter has been a huge resource for me this past year. Not only have I connected with a lot of other amazing creatives and artists, you'd be surprised how many freelance opportunities get pitched. Your next big opportunity could be a tweet away.

5. Become Money-Minded

When I was still deciding whether or not to become a freelancer, one of my biggest concerns was money. I wasn't sure about how much to charge and how to handle money talks with clients. Being totally clueless on how to start a business, at the end of 2020 I decided to enroll in the inaugural class of Leap Now, the freelance course by lettering artist, Martina Flor. One of the modules in this course was about money which covered how to calculate what to charge, and what you can expect to make off of certain types of projects. While a course like this can be a significant investment, books and guides are also a great resource.

As a freelance lettering artist, I’ve found these resources and books helpful (some links may include affiliates):

The Dark Art of Pricing by Jessica Hische

Little Lettering Pricing Handbook by Molly Jacques

Price with Purpose by Loomier

Lite Box Wage Transparency

Graphic Artists Guild Handbook Pricing & Ethical Guidelines by the Graphic Artists Guild

When we educate ourselves on how to price our work, we set ourselves up for success early. When in doubt, ask your peers and negotiate!

6. Invest in Yourself

One thing that I did a lot of this year was attend as many workshops, webinars, and conferences as I could. The cool thing about being a business owner is that when you invest in these kinds of activities, you’re developing your skills and increasing your value for your clients.

Don't think you have the funds to invest back into your business? Try setting aside a percentage of what you generate from projects to go towards any future conferences or workshops you'd like to attend. However, you don't always need to invest money. A lot of events I attended were free and virtual! These are some of my favorite organizations to look for free or low-cost art and creative programming: Type Thursday, Ladies Wine & Design, Creative Mornings, and Poster House NYC.

7. Your Time Has Value

One of my main motivations for going freelance was wanting to have complete control over my time. Without the rigid structure of a 9 to 5 it can be easy to work yourself into the ground. I know that it’ll be tempting (especially in your first year) but trust me, this isn't the way. Your work/life balance should get better, not worse. No matter what line of work you’re in, you need to take breaks. Get yourself organized with project managers like Asana or Notion, and be the best boss you’ve ever had.

8. Read Your Contracts

Contracts are a necessary part of freelancing. Not only will you be providing clients with your own contracts, but often times you’ll be signing contracts from other companies. In the beginning, you probably won't understand what certain things mean. If I'm being honest, some things still leave me feeling completely confused.

This is not professional legal advice in any way, but a great resource for decoding standard artist contract language is the AIGA Standard Form of Agreement. Still stumped? Don't be afraid to ask questions before you sign. Asking questions makes you more of a professional, not less. Not understanding your contract terms can mean the difference between owning the rights to your work and losing it, so get contract savvy.

9. No Doesn’t Mean Never

E-mails go unanswered sometimes, and that’s okay. The people who didn’t get back to my well researched and thoughtful e-mail pitches probably just didn’t need me…yet. Or maybe they were busy. The point is that you shouldn’t see those doors as being closed forever. Keep pitching, and keep following-up. As you grow in your craft, the e-mails that land in your inbox might just make you do a double take.

10. Ask For What You Want

This applies to negotiating project fees, seeking new project opportunities, and more. When I'm open and looking for new opportunities, I send out a tweet about the specific types of projects that I'm interested in taking on. The more specific the better! Keeping your networks in the loop puts you at the top of mind for the people who can send those opportunities your way.

While negotiating project fees can be intimidating, like many things, it's a skill you develop over time. If you told me a year ago that I'd successfully negotiate with a major publisher for a higher project fee, I would’ve laughed in disbelief. Being able to negotiate takes repetition, courage, and an understanding of the value that your work provides. In these moments you might feel anxious, unqualified, and insecure, but ask anyway.


I hope that this has provided you with some insight into the wonderful and complex world of freelancing as a creative. I’ve definitely learned more beyond these 10 lessons but these are the ones that I would share with myself if I was starting all over again. Leave me a comment with your thoughts and share the article with a friend! You can also check out my YouTube video here:

If you want to hear more about my career journey and reflections on my first year as a freelancer, check out my latest feature on Episode 431 of the Revision Path podcast.

Alanna Flowers is a freelance lettering artist & illustrator based in New York where she runs AGF Design Studio. Feel free to connect via Instagram, Twitter, YouTube, or her newsletter to keep up with AGF Design Studio, and to help grow our creative community.



Alanna Flowers

Freelance lettering artist & designer | Writing about creativity, community, and freelance |