The Biggest Mistakes to Avoid as a Lettering Artist

We all make mistakes as blooming professionals. It’s impossible to avoid and it’s going to happen at some point, but it’s okay. Mistakes are important aspects of our growth.

The key to making mistakes is to only make new ones.

Today, I want to share some mistakes I’ve made in my freelance lettering endeavors. Maybe you can identify with some of these mistakes. Or perhaps they’re mistakes you can identify before making.

Regardless, make sure these are not traps you find yourself in more than once.

Progressing Passively

We want to be the best at what we do. This is a direction we push towards by showing up every day. If you show up, you’ve already done the hard part. But just because you showed up doesn’t necessarily mean you’re using your time to its fullest potential.

I’ve written about active progression before. To me, active progression means progressing on purpose. You can’t expect to grow quickly if you’re not challenging yourself. Put yourself in state of discomfort and unfamiliarity.

You’ll grow faster when you conquer your fears head on.

When I first started, I learned the basic blackletter alphabet. I was able to get the basics down quick and could reproduce letters accurately from memory. The problem was in my mind, I had mastered this style. As a result, I stopped paying attention to small details I could improve upon.

Months later, I was browsing Instagram and came across a blackletter calligraphy artist. This artist’s work blew me away and it made me realize I hadn’t even begun to scratch the surface of blackletter. I was living in my own tiny bubble thinking I had mastered something I was still a novice at. I had delayed my growth by months.

Never do this to yourself. Set goals to continually challenge yourself. Always have a challenge you’re working to overcome and you’ll avoid passive progression.

Feeling Like an Imposter

In a world where the best talent is always front and center of your social media feed, it’s easy to feel hopeless and defeated.

There have been a number of times where I’ve been very close to throwing in the towel. Even just a couple months ago, I had a bad week where nothing I was creating felt good enough. I would sit at my desk putting ink on the page, and every single page I touched ended up in the trash bin.

I thought to myself “Jeez, I blog about this stuff. I teach it. I offer advice to people and some people might even take it. Who am I to be an authority on this when there are people out there whom are actually amazing.”

I felt like a fake because I was comparing myself to other people. This is a poisonous thing to do.

You must remember everyone starts at the beginning. Just because their work is better than yours does not mean they are better than you. They’re just further along in they’re journey. You’re going to get there too if you continue to push towards excellence.

If you can find one person to engage with and help, then it’s all worth it.
You have the right to be publishing work and content. There might be never-ending list of people you look up to. But don’t forget there are also people looking up to you too.

Even if you can’t see them, there are silent admirers somewhere in your audience.

Not Charging Sooner

Feeling like an imposter can also paralyze your ability to work with clients in a professional manner.

Back before I had my own website, I would post my work on Instagram everyday. One day, I got a message from someone who asked me if they could hire me to help with their branding. This person wanted to pay me.
This scared the hell out of me.

“How am I qualified to do charge someone when I’ve never done this before? I don’t even know how to write a contract.”

I lacked confidence to the point where I replied to them and offered to do the project for free. I literally said no to money.

This actually happened a couple of times thereafter. I was desperate for client experiences and was terrified they would walk away if I put a dollar amount on their project. Sure, these made good case studies, but there was really no excuse to not get paid for the value I brought to the table.

Finally, another project came along and I figured I had to charge. Even though I was scared, my work was too good to be giving away. I got a contract together stating my process and a price. I held my breath and sent the email thinking it would never work out.

Ten minutes later, I got an email from Paypal saying telling me my invoice had been paid. Then a second email with a signed contract. The project went great. I over-delivered and my client was thrilled. From then on, I knew I had a right to charge.

Offering Discounts

Don’t discount your prices. Ever. If you really want to hook up a friend, then do the work for free. Otherwise, charge them your full rate.

Picture yourself walking into a high-end clothing store. You find a new pair of shoes that are regularly priced $200, but today there’s an 80% discount. You think “Whoa, what a steal. Only $40.” You walk out of the store with a bargain. Now, when you put on those shoes, do you value them at $200? Are you any less likely to wear them in the rain? Probably not. You’re actually more likely to beat them up and treat them as throw-aways because you got them at a discounted price.

When you discount, the person who gets the discount values your work at the price they pay, not its original worth. You’re simply degrading the perceived value of the work.

I’ve discounted my work for a client and it ended up souring the relationship. The client ended up asking for more than I had originally promised to deliver because they weren’t valuing the work I was delivering in the first place. They were trying to squeeze every drop they could out of a cheaper investment. This is my fault. Not theirs.

Charge premium or pro-bono. Nothing in between.

Saying Yes to the Wrong Projects

It feels good when a potential client approaches you because they want to work with you. They sought you out organically and they want to pay you for your work. Your first inclination would be to take this project on because it might be your only current opportunity. It seems logical to assume one project is better than no project.

The problem here is not every potential client is going to be a good fit for you. A good client is one who respects your process and also understands your process. They’re also also someone who is going to trust you to make the right decisions for them based on the information they provide.

It’s very possible your client has worked with someone who is not professional in the past. They’re trained to work a certain way based on their past experiences. This is something you need to watch out for.

One time, I took on a client who happened to be a bad fit for me. I had several hour long phone conversations during my discovery process in an attempt to uncover what it was they needed. However, their answers to all my questions were vague and gave me little to go off.

I thought it was fine because I was following my process and my client was taking my lead. However, I ended up having to make uneducated assumptions about the nature of the work being done. When I presented the work, it was not what the client was looking for. In fact, they had decided to change some of the initial direction they gave me.

The project continued to fall apart over the next couple of weeks. It was very clear there were frustrations between the client and I. It got to the point where we were doing so many revisions, we ended up with a bastardized design. It wasn’t even the sort of work I would be proud of showing my portfolio. The project eventually ended and we went our separate ways. But I knew from there on, I would never make this mistake again. Taking on bad clients is not a good practice even if its the only current opportunity.

If you’re going to do work for clients, make sure you’re saying not the wrong ones. This is going to allow you to say yes to the right ones.

Only Make New Mistakes

Mistakes are good and you should make them. But avoid making the same mistake more than once because this is when they can become paralyzing.
I hope that you haven’t made these mistakes as a creative professional. But if you have, it’s okay. Just remember:

  • Progressing actively by always having a challenge you’re working to overcome. Force yourself into unfamiliar territory and conquer your fears.
  • You’re not an imposter. There are people out there who look up to you — even if it doesn’t feel like it.
  • Charge for your work. I hereby give you the permission to sell. You’ve earned it.
  • Never discount your work. Unless, you’re willing to do pro-bono work, always charge your full price.
  • Say no to the wrong projects so you can say yes to the right ones.

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