Design Domination Podcast Episode #107: 5 Business Lessons I Learned the Hard Way

Many graphic designers suffer from business issues that are actually symptoms of a bigger issue. Once you realize this, you can transform your business. Find out 5 business lessons for designers that I learned the hard way, so you hopefully don’t have to.

Show Notes

Design Mentoring

In this episode, I am digging into 5 business lessons for designers that I learned the hard way. Stick around to learn some business lessons from my embarrassing stories.

Creative Business Tips for Designers

This will be a bit cathartic for me to reveal a lot of this. Or I might end up stressed while reliving some drama. I am not sure which.

A lot of these things are straight up embarrassing for me to talk about, and I’ve slightly touched on a few of these things in other episodes. I need to talk about these things.

This is part of my journey. But I am also bringing all this stuff up to hopefully help you and keep you from making these mistakes—ever or from now on. Of course, sometimes we have to learn things on our own—the hard way—for them to really make an impact.

I also want to show you how you can totally change your mindset and your business, because once I had all these revelations about my mindset, it was like I woke up. I snapped out of it, and my business completely changed too.

Most, if not all, of my business issues were actually symptoms of a much larger, deeper problem.

A lot of the mentoring sessions I do with designers revolve around mindset issues. It’s so rewarding to see them come out the other side of these issues because I know just what it’s like on both ends of the spectrum—the before and after.  So many talented designers are doubting themselves and undercharging and putting up with things they shouldn’t.

This is what drives me to do what I do every single day.

I don’t want other designers to feel how I used to feel and to put up with what I used to put up with.

So let’s dig into 5 business lessons I learned the hard way.

Lesson #1: Don’t be everything to everyone.

Saying yes to any work that comes your way is exhausting! It really is. It’s mentally and physically draining.

For years, I did all kinds of design work—logo design, print design, publication layout, proofreading and editing, email design, email coding, web design, custom web development, brochures, flyers, ads, conference signage, book design and layout, presentation slides…

I think there are other things, but I can’t remember them right now. There were a lot!

Some of these types of work I did quite often. Others I did them here and there. The things I did all the time I could do in my sleep—and very quickly. The other stuff took me a lot longer than it would take someone who does that kind of work all the time.

Symptom: Lower profitability

That meant that those particular jobs weren’t as profitable for me.

For some types of work, like email coding—blech!—there were too many things to keep up with. I wasn’t doing that work all the time, so it didn’t make sense to invest in subscriptions for email testing, for example. I also wasn’t interested in keeping up with all the nuances with all the email and web browsers out there, the combinations of them and the browser-specific code to add into the email code. I didn’t want any part of that!

I didn’t want to expend all this effort on something I rarely did.

It made more sense to hire out that work if even I got it. That actually was not only profitable for me, but the client ended up with a better product as a result—and I saved time.

I was busy all the time and had lots of work. But I felt frenzied from all this different work. I was always switching gears, from, say, logo design to publication layout to web development. These all use different skill sets.

Symptom: Lack of processes

Taking on all work also made it hard for me to develop processes. For certain types of work that I didn’t do all the time, I wouldn’t remember everything I needed to include as part of the process.

Symptom: Poor perception

I think that taking on any and all work led some clients to think of me as the jack of all trades/master of none. Most clients are willing to pay a specialist more money than they are someone who is more of a generalist.

Symptom: Unclear messaging

I think it also made my marketing harder too. My messaging wasn’t clear. Who was I helping and what was I helping them do? Nonprofits and small businesses. They all use different terms when you’re speaking to them.

Up to a certain point, I hadn’t entirely figured that out, although I thought I had. My confusion in my head led to clients having confusion. When there is confusion, there are few new sales.

Symptom: Not niching

When I got into accessibility in 2016, I didn’t think it would be something I even did that often. Maybe I would do it here and there if someone needed it.

But I started talking about that one thing. I got noticed for it, and I started getting more and more of that work and less and less of the work I did not want.

Obviously accessibility is a more niched area of design, but the fact that I was talking about one thing and how I could help them made a huge difference. I wasn’t like, “Hey, I do this, and, oh, I do this too. Did you know I also do this?”

I became known for one thing, and not just by prospects and clients but by colleagues. Even though I was always busy and made good money, I was much less memorable and profitable as a generalist designer.

But focusing on one type of work also gave me clarity, and that really gave me confidence. I had had confidence about my abilities in the past, but I don’t think it came through to clients. With this, I was able to focus on one thing and continue to deepen that expertise.

When clients came to me, I could talk about how I could help them, and I was really confident about it. It felt different. I believed what I was saying. I was enthusiastic about it. People appreciated that.

Not only that, but it put me in a different position in the marketplace.

I eliminated 99% of my competitors! I started getting almost every single job I was contacted about and I was also charging more. No one was balking at my pricing.

That was a game changer for not just my business but my self-esteem! I was also doing good in the process. Win win! Or maybe that’s a win win win!

Lesson #2: Choose who you work with.

Another thing I did for years was thinking I should work with any new client who came my way.

I had started my career in the nonprofit sector, and I would continue to get referrals from nonprofits I did freelance work for. It was a snowball effect. I didn’t really choose them. They chose me.

But small businesses would still come across my website and want to work with me, and so I would talk to them and put together an estimate instead of saying no. I rarely got high-value projects from these folks. It was usually more piddly stuff.

When I think back on it, I am sure that’s because some clients didn’t take me as seriously as someone more specialized in their industry. They probably saw me as a jack of all trades/master of none and that my work was over the place. Definitely not a good thing!

There were also times when someone would contact me and they just had an attitude and I would still go ahead and entertain them and put together an estimate. I was more focused on winning work than what happens if I get the work and they’re difficult and I don’t want to work with them anymore.

Lesson #3: Set boundaries.

Setting boundaries was a really hard lesson for me to learn—excruciating actually. For years, I didn’t realize I had an issue with boundaries. In fact, I just never thought about the word at all.

Symptom: Bad clients

I just thought I had bad clients. It was them, not me.

Why was I always ending up with these clients who seemed nice in the beginning but then were so demanding or paid late, ignored my late fees, acted entitled, like they were my only client?

The ones who were so patronizing were always the worst. I remember one who said how important it was to pay their contractors on time. They paid late all the time.

Dealing with abusive clients

Another client, who knew of me through a former mutual coworker, would even call me at my full-time job to harass me about deadlines for her organization’s publication, even though I had yet to ever miss any of her deadlines without her nagging me! And even though this was the first time in 10 years or so the publication was actually getting done on schedule!

Another client, who lived near me at the time, came to my house and threatened me because I would not give him the native files for a project that never included giving him the native files in the first place. He called me a “little girl” and told me to give him the files.

Dealing with disrespectful clients

Another client, a longtime client in fact, stood me up for an online meeting. He never even bothered to reply to my emails asking if something had come up and he needed to reschedule. I never heard from him again.

A woman—a prospect—once called me and rambled on for what felt like a half hour without letting me speak. She was loud. She was overbearing. She really enjoyed telling me about herself, and she apparently really liked hearing herself talk! I, on the other hand, wanted to get off the phone.

She proceeded to tell me about these amazing things she had done and been recognized for and that she had hired a designer to design a publication for her. But she didn’t like their work, so she found someone else. That designer also did not meet her expectations.

The woman had to tell the designer which typefaces to use and, oh, all these other things.

When she finally shut up enough for me to get a word in, I said I only do work with a payment up front and a signed contract.

She proceeded to scream at me—yes, scream—telling me that I had just wasted her time—yes, her time—because she apparently had expected me to do free work to see if she liked it before paying me. She told me I should have understood that’s what she was looking for after all that she had been through.


OK, deep breath.

My point is that I attracted crazy clients! But this wasn’t any different from my personal life either. I had attracted people who took advantage of or treated me like garbage all my life.

After talking with a coach years ago, I started realizing why.

I had been bullied as a child. I had let people walk all over me, even people close to me. I was a people pleaser.

When I asked for advice from unqualified but well-meaning friends and family members about client issues I was having, I was told to put up with it because they were the client and I was getting paid.

I had put up with too much from others, so it made total sense that I was even a more willing victim to people who gave me money.

When your sense of “normal” is people not treating you very well or not appreciating you, then you set the bar low. You take on bad clients. You put up with things you shouldn’t.

It wasn’t until I had been in business for quite some time that I worked with another coach, who helped me realize being treated this way is just not normal and that I needed to set boundaries and how I needed to go about doing that.

It was super scary to make changes, but I had to do something. I was always frustrated and I cried a lot. I couldn’t take anymore.

I figured some clients would push back, and they did. One client said he’d go elsewhere if I decided to still enforce my late fee after he pushed back. It was only a couple dollars, but I was strong enough to push back on him this time. He was a habitual late payer and a bully. He deserved no favors. No soup for you!

And darn it, I deserved respect!

I put my foot down. I lost a bad client that day over a few bucks. Some people might think that’s completely crazy.

It was a huge victory—both personally and business wise.

Ever since I put policies into place and started enforcing boundaries, I started getting more respect from the good clients, and the bad ones I had been working with gradually weeded themselves out, because I was no longer putting up with their crap!

Whew! I feel like I need an intermission after talking about all that.

Lesson #4: Know your worth.

Symptom: Undercharging

It should come as no surprise to hear that because I was allowing myself to be treated like that, that I was also a chronic undercharger. But 20-some years ago, I was charging a lot more than some designers do today.

For years, I got turned down for work from potential new clients because of my pricing. I tried to justify it, saying I was just one person, so I had lower rates than a design agency. They never cared about that.

They always took it as I didn’t understand all that would be involved with the work, even though I did and even though I said so. I know because they told me this. I would ask why I didn’t get the work.

Symptom: Mismatched marketing

I knew I had a lot of skills a lot of designers don’t typically have, like proofreading and editing.

I was really good at checking my work. Clients didn’t need to babysit me. Some would hire me because of that.

I also have a degree in Spanish and French.

I knew I had a lot to offer, but I didn’t convey it properly—like why these were beneficial to them. I also think some clients just didn’t care about any of these things. I wasn’t necessarily marketing these additional skills to the right people.

Symptom: Convincing

The other thing I did as a result of not knowing my worth was feeling like I needed to convince a client to work with me. Instead of asking about their needs or their problems, I would feel the need to explain why they should work with me or to justify my pricing.

All these things did was scream lack of confidence, and that doesn’t build trust with clients even if you indeed know what you’re doing and are good at it.

They’re not looking to take a risk. They’re looking for someone they think can do the work and do it well and get them results.

Symptom: Setting a bad precedent

Not knowing your worth also sets a bad precedent—being hired for being cheap. Clients will come to expect low pricing from you with future jobs too.

It is really hard, if not impossible, to reset client expectations. I found some clients to be understanding about it, and to others anything I said to show the value fell on deaf ears.

It’s like the saying “New is better than best” or “Different is better than best.” It doesn’t matter how much you try to prove your worth at that point. They will happily pay the next new designer or firm more money.

Lesson #5: Trust your decisions.

Another lesson I learned the hard way was trusting my decisions. I was brought up with the mentality that mistakes were not good. Anything less than perfect was not acceptable. I wasn’t brought up to think about making my own decisions.

Symptom: Fear of failure

I was constantly in fear of doing something that would be considered wrong or not getting things right the first time.

I’ve made mostly good decisions throughout my life, but I always overthink things. I don’t do it as much anymore, but old habits die hard.

As a result, in my business, I would second guess myself about how to handle a situation, and I was afraid to assert myself. I knew it would be really uncomfortable to do and the reaction would probably be unpleasant.

Symptom: Looking for approval

Like I mentioned earlier, I asked well-meaning family and friends their opinions. They weren’t qualified to give business advice, but I still listened to them at the time.

Asking other designers would have been better. But I would have needed to understand that everyone is different and has different business goals. What is OK for one designer’s business isn’t good for another designer’s business.

Just because someone else is willing to put up with something that you don’t think is OK doesn’t mean you should. It doesn’t matter what they think. It matters how you feel.

So instead of making decisions to change the business issues I was facing, I didn’t do anything until I paid a coach who told me how to do that. Some of those were expensive lessons too.


I hope this has been helpful for you. I hope you never have to go through any of these things. But I know most creatives are empathetic, and many of us are people pleasers.

It can be really uncomfortable to do what we need to do to make our businesses better and more enjoyable. Please just don’t be afraid to do it. It’s so much better—and easier—on the other side.

If you need help working through a creative business issue, freelancing issue or a client issue, go to and I will respond right away.



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