10 Lessons Learned from My First Year as a Freelance Creative.

 In Business

I’m a big fan of using milestones as a chance to reflect. A couple months ago marked one year since I took the plunge into full-time freelancing, and amid many ups and downs, I feel like I’ve learned a heck of a lot. Everyone’s journey differs — so of course your mileage may vary — but I wanted to share the major standout lessons I’ve learned in hopes that they might help others.


Accounting and record-keeping are critical

As a pretty organized person, I started keeping comprehensive records of all income, expenses, and contract details on day one of freelancing. I’m extremely thankful I did, because it made things easier on all fronts when it came time to file taxes. There have also been times I lost track of milestone payments on longer-term jobs, and having records and an invoice history to reference saved me from making a fool of myself.

The low-tech, zero-cost approach is to simply keep a running spreadsheet of all earnings, expenses, and project notes, but follow your own preferences to work out a solution that’s best for your practice.


Good customer service pays dividends

I’ve already written an entire blog post covering my philosophies on customer service, so needless to say it’s a major component of my business model. I’ve lost track of how many times my customer service alone has been cited as the reason for referrals or repeat client work. It’s a simple way to enhance your reputation with clients, so why not go that extra mile to make sure they’re taken care of?


Collaboration is a game-changer

I could prattle on endlessly about how much the founding of Pretty Picture Club changed my creative life and career, but at its core, it has to do with collaboration. Find yourself a group of fellow creatives so you can bounce ideas around, critique each other’s work, and make projects together. Sometimes being able to pop into a group text or Slack channel to vent a frustration or ask a question can bring clarity to a day that would otherwise be derailed by isolated frustration.


The feast or famine cycle is very, very real

I’m not yet at a point where I have any sage advice to give on this front, but I do want to say that feast and famine periods were a huge struggle for me. Either so many inquiries and new work flooded in that I could barely manage it, or there was so little that I started to panic about my business. Rinse and repeat.

The silver lining here is that the more I improved my portfolio, networked, and built up a pool of referrals, the less of a problem this has become, but it’s still something I grapple with to this day.


New work can come from surprising places

Diversify your potential referral sources and the places you look for work as much as you can. Without having irons in the fire on Instagram, Twitter, Behance, and local networks where I live, I would’ve missed out on easily half the paid work I’ve done.

To provide an example: my largest recurring contract with a household name came to fruition from a hiring manager stumbling upon some projects I posted on Behance. They reached out to me! All I did was make sure my work was up-to-date and that amazing relationship happened without any further work on my part. I’ve also made a habit of scouring Twitter for agencies and art directors who tweet calls for work — as silly as it sounds, I’ve gotten numerous jobs just by replying with a, “Hey! I’m interested in working together!”


Share all you can with other creatives

Try to help other artists and freelancers just as much as you solicit advice for your own benefit. There’s more than enough work for everyone out there, so I’m a strong advocate for helping to elevate others. Hoarding knowledge and resources will only ensure others avoid interacting with you altogether.


Seize every learning opportunity

This goes against conventional wisdom regarding specializing in a niche, but I’m a proponent of broadening your artistic skill sets. I’ve dabbled in web design, branding, and print design in addition to just illustration. I still advertise myself as an illustrator, as that’s the type of work that ideally I want to fill my schedule with, but there have been many times when a job started with illustration, then broadened into far more when the client learned about my other skills.

If you work with a client who wants you to do additional work in one of your “gray areas” — those things you can kind of do, but aren’t an expert in — go for it. You bring more value to your client, and you have a chance to practice new things. Just be transparent with them about your level of expertise.


Don’t be afraid to ask for leads

I hate talking about myself, my interests, and especially my artwork to others. It’s a skill I’ve had to work at pretty actively in order to sustain a freelance practice, though. A couple times a year I’ll drop a work solicitation tweet: 3-4 images of work I’ve made that represent the type of projects I want, along with a brief explanation of who I am and what I do. The creative community online is so amazingly supportive, I always get lots of retweets and likes. Try doing this similarly on other sites, too! You’d be surprised at how many people already follow you but have no idea they can hire you to do projects. Dropping an occasional friendly reminder can have a big effect.


Don’t let work consume your life

This is another one I haven’t yet mastered but am trying to be more cognizant about. When your income and livelihood directly depend upon how much you work, it’s no wonder that many freelancers work long days and don’t take time off to relax. The problem is, when your entire life becomes your work, the inspiration to make said work slowly fades away. Take a half or even a full day off. Go on a walk. Take a quick day trip to some different scenery. Recharge that creative battery so you’re inspired to keep making cool stuff.


Take time to reflect on your progress

When I feel down about my art or my business, I look back at where I was six to twelve months ago. I am consistently impressed to see the improvements I’ve made in my craft, the caliber of clients I attract, and the scale of projects I take on. When you’re on the journey, each step forward seems so tiny. But stop and look back and you will be impressed by how big a distance you’ve traveled.


In closing

My first year of freelancing taught me many lessons about managing my finances, managing my time, and how to network while working from home in an isolated environment. I hope to continue improving my work-life balance and find a happy medium between feast and famine. If you’re struggling with going freelance or starting your own business, reach out! I’d love to talk.

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