How to Take on Your First Art Commission with Confidence

Congratulations! Someone out there thinks your art is amazing enough to pay you for it. That’s huge—like, do-a-happy-dance-in-your-living-room huge. Breathe that in for a second. Seriously, take a moment to soak up the fact that your creativity has reached a point where someone wants to invest in it.

Okay, now exhale, because you’re probably panicking about what to do next. You might be asking yourself, What if I mess this up? What if I undercharge? What if they hate it? Relax—you’ve got this, and I’m here to help. Taking on your first commission is a big step, but it doesn’t have to be overwhelming. With a little preparation, clear communication, and a solid process, you’ll not only survive this experience but come out on the other side feeling like a total pro.

This guide is here to turn that "OMG I’m not ready" feeling into "Look at me, thriving!" We’ll cover everything you need to know—from deciding if you’re ready to take on the project to setting fair pricing, managing client expectations, and delivering a final product that you’re proud of. Whether you’re brand new to commissions or just need a roadmap to follow, consider this your step-by-step survival guide to crushing it.

So grab a notebook, a cup of coffee, or whatever helps you focus, and let’s get started. Your first commission isn’t just a job—it’s an opportunity to grow, learn, and maybe even have a little fun along the way. You’ve got this!

Step 1: Are You Ready to Take This On?

Let’s start with the big question: Should you even say yes to this commission right now? I know, it’s tempting to dive in headfirst—especially when someone’s asking to pay you for your art—but let’s take a beat. You might have a lot on your plate already, and that’s okay. It’s not just about whether you can technically do the work; it’s about whether now is the right moment for you to take this on without sacrificing your sanity.

If it’s not the right time, no worries! Saying “no” doesn’t mean you’ll never take on commissions—it just means you’re prioritizing what’s best for you at this moment. But if you think you’re ready, let’s ask a few important questions to make sure:

Do I have the time?

Sit down, grab a calculator (or your fingers), and do some math. Think about how long you think this will take—then double it, because life loves throwing curveballs, and you’re going to need some wiggle room. If this project clashes with your long-awaited Netflix binge or that vacation everyone keeps reminding you to take, it’s okay to say no. Ask yourself:

  1. How many hours will this project realistically take, and do I have that time available?

  2. What other commitments—work, family, or personal—might this project interfere with?

  3. Am I willing to sacrifice some downtime or reschedule other plans to make room for this project?

  4. Do I have any upcoming deadlines, events, or responsibilities that could cause a time crunch?

  5. If this takes twice as long as I think it will, can I still deliver it on time?

Is this project in my budget?

Some commissions require tools, memberships, or subscriptions you might not have (looking at you, Adobe Illustrator). If you’re someone who likes to do things right, make sure you’re not about to empty your wallet just to deliver. That said, having the right tools can save you time, effort, and a whole lot of stress. Here are a few essentials to consider:

  • Typeform: Create interactive inquiry forms to gather all the client info you need upfront. Bonus: The premium version lets you accept payments directly through the form.

  • PayPal or Stripe: Free to set up, though transaction fees apply. Both platforms offer a professional and reliable way for clients to pay you with ease.

  • Fiverr Workspace: Manage proposals and invoices effortlessly. You can send polished proposals for e-signing, and it auto-generates invoices for seamless payment collection.

  • Google Drive: Free with a standard Gmail account, but keep in mind that if you’re using a custom domain (like name@website.com), you’ll need a paid Google Workspace subscription. Either way, it’s a fantastic tool to organize your files, store drafts, share updates, and deliver final products efficiently to clients.

These tools can help you stay organized and handle commissions like a seasoned professional.

Step 2: Start the Conversation with the Client

Taking on your first commission can feel overwhelming, but good communication is the key to a smooth and successful experience—for both you and the client. Whether you're chatting via email, DMs, or even a form they filled out on your website, this is your chance to get clarity, set expectations, and make sure you're both on the same page.

Remember, clients don’t always know exactly what they want or how to explain it. That’s okay! It’s your job to guide the conversation and ask the right questions to understand their vision. Being clear and professional will also help build trust, making you look like a pro even if this is your first rodeo.

Here’s what to ask them:

  1. What’s the scope of the project?

    • What size do they want (e.g., 8x10, full mural, billboard for their cat café)?

    • Will it be digital, physical, or both?

    • Is it for personal or commercial use? The simplified version of what that means, “Personal use = it hangs in their living room. Commercial use = they slap it on merch and make money.”

  2. What’s the vibe?
    Ask for examples. Whether it’s a Pinterest board or screenshots from your own portfolio, make sure you’re vibing with their vision.

  3. What’s the deadline?
    Pro tip: Add some buffer time because “shit happens” should really be on everyone’s calendar.

  4. DON’T ask about their budget?
    When it comes to pricing, don’t ask what the client’s budget is—you set the standard for what your work is worth. Letting them dictate the budget puts you in a position where you may undervalue your time, effort, and expertise. Instead, confidently present your pricing (don’t worry, we’ll cover how to calculate it in the next section).

Step 3: The Scary World of Pricing

Let’s talk about pricing—one of the most daunting parts of taking on your first commission. It’s totally normal to feel like you’re throwing numbers into the void and hoping they stick. Pricing can feel especially tricky when you’re just starting out, but here’s the thing: your time, skills, and creativity have value. The key is to approach pricing with a mix of confidence, strategy, and flexibility.

The goal is to ensure you’re fairly compensated for your work while giving clients clear options that align with their needs. It’s not about guessing; it’s about building a structure that works for you. Whether you’re brand new or looking to refine your rates, here’s a simple strategy to get started:

  • Start with your hourly rate.
    If you’re new, $20/hour is a solid baseline. As you gain experience and confidence, this number will grow. For example, I now charge about $150–$200 per hour after a decade in the business (and honestly, I should raise my rates because I get faster every year).

  • Add usage fees for commercial work.
    For businesses, tack on 25% of the project price for limited usage (e.g., two years) or 50% for perpetual use. This ensures they’re paying for the long-term value of your art. These numbers are a starting point—adjust them to what feels fair for you.

  • Offer packages.
    Think of a bronze, silver, and gold structure:

    • Bronze: One-color black-on-white bust, one round of revisions.

    • Silver: Full-color digital portrait with background, two sketch concepts, one rounds of revisions.

    • Gold: Full-color framed print and digital file portrait of you and your pet with a full background, two sketch versions, and two rounds of revisions.

Packages give clients clear options and help you upsell—most people pick something in the middle. Plus, it makes pricing less intimidating for both you and your client.

Step 4: Create an Agreement

Contracts and proposals don’t have to feel overwhelming, full of complicated legal jargon, or impossible to understand. In fact, the whole point of these documents is to make everything clear and easy to follow for both you and your client.

If you’re not into full contracts just yet, a basic agreement via email can still save your sanity. Here are the essentials to include:

  • Deposit: Require 50% upfront to secure the project. This ensures both parties are committed before you start.

  • Timeline: Break down the project into milestones (e.g., sketch approval, final delivery). This keeps everyone on the same page.

  • Revisions: Be clear about how many rounds of revisions are included in your price and how much extra you’ll charge for additional edits.

  • Deliverables: Specify what the client will receive (e.g., high-res PNG, vector file, physical print).

  • Liabilities: Protect yourself by clarifying that you’re not responsible for things outside your control, like files getting lost in their inbox apocalypse.

If you want to skip the guesswork for $5, check out my sample proposal that I send to clients. It’s clean, straightforward, and perfect for helping you present yourself as a pro—even if this is your first commission.

Step 5: Deliver Like a Pro

Let’s be real—taking on commissions can feel like a chaotic swirl of excitement and "OMG, what if I mess this up?" That’s why I created a production process that makes my life (and my clients’ lives) way easier. It’s not perfect, but it’s saved me from countless miscommunications and awkward “I thought you meant…” conversations. Here’s what I do—feel free to steal, tweak, or roll your eyes at it.


Moodboard Magic

First things first, I make a moodboard. This isn’t just an excuse to play on Pinterest (okay, maybe a little). It’s where I gather references the client gives me or pull examples from my portfolio that match their vibe. I’ll toss in some colors, textures, or even weird things like “the mood of a stormy forest but make it cozy.” Then, I send it to the client and ask, “Are we feeling this?” If yes, I move forward. If no, we tweak until it’s a vibe we both love and I make sure that I get that approval in writing via email. :)



Sketch It Out: From Scribbles to Polished Perfection

I start by whipping up 1–2 rough sketches—think less “perfect masterpiece” and more “concept scribbles that still look intentional.” The goal here is to communicate the layout and general idea, not the final details. I always tell clients, “This is your chance to change stuff—speak now or forever hold your peace.” This stage usually includes one round of revisions, which is enough to nail things down and make sure we’re on the same page.

If the client requests edits (and let’s face it, they usually do), I’ll refine the sketch into something more polished. This step feels like extra work, but trust me, it’s worth it. Getting final approval on a clean, polished sketch before moving forward saves you from those “Can you just move that hand slightly to the left?” disasters later. This way, when it’s time to dive into the final draft, there are no surprises—just a clear, approved foundation to build on.



The Final Stretch: From Chef’s Kiss to Client-Approved

Here’s where I go full turbo and bring the piece to life. This stage is all about refining details, adding colors, and polishing everything to perfection. It’s my favorite part—turning all the planning and sketches into a finished masterpiece. For longer projects, I like to send quick updates along the way, like a “Look, progress!” email or message. Clients love feeling included, and it reassures them that you’re on track (and haven’t ghosted them).

Once the piece is complete, I let clients request small tweaks—things like adjusting colors or fine details—within reason. (Cue me internally screaming when they say, “Can we try 10% less blue?”) If the requested changes are minor, I include them as part of the project. However, if they want major revisions or a total rework, I explain that it’s outside the scope of our original agreement and provide a clear estimate of the additional cost. Typically, if I have to start over, I charge about 50% of the original fee.

This balance ensures the client gets a piece they’re thrilled with while protecting your time and boundaries. Communication is key here—be clear, be professional, and keep it all positive. By the time the final version is approved, both you and the client should feel proud of the work.



The Grand Finale after final payment

When the project is complete, it’s time to deliver the final product—but not before the final invoice is paid. I always make it clear that files are sent only after the client has settled the remaining balance. Once that’s taken care of, I finalize the delivery. Here’s how you can approach it:

  • Final Files: Send high-res PNGs, editable vector files, or whatever format was agreed upon. If it’s a physical product, prepare it for shipping with care.

  • Approval Presentation: After the client approves the final colored version, consider creating a presentation that walks them through the piece. Highlight your design decisions to show the thought and effort behind every detail.

  • Bonus: Blog It! If you’re up for some extra work (and extra visibility), write a blog article about the project. Share your process from start to finish, explain your creative choices, and turn the project into a case study for your portfolio. It’s a great way to attract future clients while giving this one a little extra spotlight.

For delivery, you can:

  • Send the files via email with a heartfelt thank-you note.

  • Be the person who attaches the final invoice to an email with the completed image included (if that works better for your workflow).

However you choose to deliver, I always wrap it up with a genuine thank-you and a subtle, “Let me know if you need anything else!” nudge. It’s not just about ending this project; it’s about planting the seeds for future collaborations.

The Awkward-but-Helpful Follow-Up

Once the project is wrapped up, don’t just vanish into the ether. A week or two later, I like to check in with clients to make sure everything’s still looking good on their end. My go-to message is something simple like, “Hey! Just wanted to make sure you’re still loving your piece. Anything you’d like to share about working together?” Sometimes, this leads to glowing testimonials that make you feel like a rock star. Other times… crickets. Either way, it’s worth trying.

It’s also a great time to offer a little extra customer support. Sometimes clients have a lingering request or need a small tweak but didn’t want to “bother” you. By proactively asking, “Do you need help with anything else?” you show them that you care and make the whole experience even more positive.

As an added touch, I’ll ask, “Can I add you to my client newsletter?” This quarterly update shows off the cool work I’ve been doing for my shop and other clients. It’s a low-pressure way to stay on their radar while showcasing your growth. Plus, it’s an easy way to keep the door open for future projects without feeling pushy.

This follow-up isn’t just about wrapping up—it’s about planting seeds for future collaborations. Keeping in touch with clients builds trust, and honestly, they might just hire you again when the right project comes along. Win-win!

Dina Rodriguez

Every day I combine my 10 years of design experience to create lettering that entertains, engages and inspires a community near you. The kind of design that’s custom-made to attract your audience through the combination of beautiful letters and handmade illustration.

Over the past five years, hand lettering has been the primary focus of my career. What started as a hobby drawing letters for a few hours every day, quickly turned into a full-time passion doing client work for companies like American Greetings, Wacom, and Penguin Books.

Since 2013, I’ve worked with over 300 carefully selected clients working on everything from apparel design to chalk murals for businesses all over the United States.

Early on I started teaching everything I know on lettering and freelance so I could better understand my craft to help others do the same. I started blogging, writing books, and began to live stream my work on Twitch twice a week so I could build a creative community around my hand lettering.

Fast forward to today, and I’ve named 2017 as the year of art education for my brand. I’ll be traveling the country teaching lettering and the business of illustration at design conferences like Creative South and Design Week Portland. I also recently landed an opportunity at the Pacific College of Fine Arts teaching Illustrated Lettering once a week.

All this teaching means I’ll be devoting my time and skills to just one new client a month. So if you are looking for an artist with a broad range of lettering styles with a proven track record of happy customers, then I invite you to fill out my Project Questionnaire to get started on your next creative idea.

http://lettershoppe.com
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