NOTE: This post is the second in a series covering the history of my business, lessons learned, and mistakes I wish I’d avoided. Click here to go back and read or watch post #1.

Let’s dive into Part 2 of my design business journey...and I’ll bet you can even spot many of my mistakes before I get to the part of this post where I point them out.

In 2005, I went full-time about four years after starting my freelance business. Going full-time was fulfilling in many ways. I felt successful and accomplished like I had figured out this business thing at least enough to make ends meet. I remember waking up every day, excited that I didn’t have to rush off to an office. Then I’d sit down at my little desk in our first house (all 811 square feet of it), hot coffee in hand with overwhelming gratitude that I was getting to do what I’d dreamed of doing for so long. I loved being a designer, and now I was doing it with myself in the driver’s seat. 

Staying busy in my freelance business (thankfully) wasn’t a challenge. Past co-workers, colleagues, and referrals generously kept my work pipeline full. I listed my business in the local phonebook (totally dating myself here), and I would get occasional logo or brochure projects that way. 

I don’t think I ever said no to a project. I was just glad to have the work, and I was often afraid of not having enough work, so I took it all on. Any design project was my cup of tea!

I was doing some freelance exhibit and tradeshow graphic design work for my previous employer. I also really enjoyed designing wedding invitations and was exploring making that my primary focus. 

Even though I felt overwhelmed figuring it all out, I told myself that this is just what building a business looks like. I had thoughts like these (maybe you can relate to some of these yourself.):

• I’m basically at the bottom of the marketing food chain, so I better get used to last-minute deadlines.
• Running a business is not going to be all roses and rainbows. 
• I should be grateful that people want to hire me. 
• This is way better than being in an agency where I’m told what to do all day.

[Sidenote: My blood pressure just went up as I typed this list!]

So, to give you a snapshot of my business at this time, I’m working long hours every day, many evenings and weekends. I’m charging hourly for all of my work. To lighten the workload, I decided to hire some part-time help with design and coordination, which was so helpful.

Now, to be clear, I believe that in the early years of business, when we’re figuring things out, there will likely be a lot of hustle and grind. And this works for a while. Building a business is exciting, and we may not mind the extra work. Or maybe we feel like we have to work super hard to be worthy of the money we’re charging. 

But we might start to realize it’s not sustainable to keep up this pace at some point. And maybe we begin to realize that we want more fulfillment and freedom from our business. I know I did! 

Looking back at this chapter of my business, I see the following mistakes:

Mistakes

1. I let my business happen to me rather than taking control. The idea of “being my own boss” was more of a concept than a reality. By not fully taking charge of my business with clear policies, agreements, systems, and processes, my clients became many mini-bosses. They were dictating my schedule and how I delivered work. I was getting better at insisting on contracts but often still leaving money on the table because I was afraid to discuss it. Why was I doing this? Well, here are a couple of ideas:

First, I was acting like an employee. I had worked in two busy agencies previously, and I was used to others dictating the work process and timing, so I didn’t think much of it when I went out on my own. Clients would tell me they needed something in three days. I would move mountains to make it happen, not thinking much about whether or not that timeframe would work for me or what else I would be giving up to meet that deadline. All I could see was the money I’d lose or the positive reputation I’d be missing out on if I didn’t go for it. And when you work in an agency, for others, this is usually what’s expected!

Secondly, my mindset around money wasn’t the healthiest. I grew up in a home where we didn’t have extra money. There was just enough to put food on the table most of the time. My parents were very hard workers, and highly resourceful which taught me how to be scrappy (and I’m so thankful for that). However, it also embedded in me a belief that money is scarce and must be scrimped and saved. Even discussing money was awkward. This belief caused me to think that my clients viewed money the same way I did, so it was tough for me even to discuss money, let alone charge what I wanted or knew I should charge for my work. 

2. Another mistake was taking on any project that came my way. While I think it’s necessary to experiment to figure out the exact services and types of clients you like working with, it can be so easy to fall for the “I need the money so I’ll say yes to it all.” mentality. This mindset results in taking on jobs that we don’t feel equipped to deliver on or with clients who don’t value what we do. 

For example, I mentioned that I enjoyed designing custom wedding invitations. For a few years, I was getting lots of requests, but I quickly realized that the way I was doing it was not profitable. Invitations took so much time to design. The custom nature led to sourcing unique papers and envelopes, embellishments, and printing methods—also time-consuming to research and price. Often, a wedding invitation project would take me 50 plus hours from start to finish. When I did the math, I was working for pennies per hour. Besides, brides and mothers of brides can be pretty picky clients. 

I knew I needed to find a way to make the process more profitable or give up on the idea. So, I researched creating wedding invitation templates but ultimately decided I wasn’t excited enough about that direction to go all-in. So, I shifted my focus to other design projects that made fiscal sense.

Lessons from the “messy middle”:

My schedule and time are in MY control: 

It’s essential to understand that the deadlines clients give are often arbitrary. It's not their fault, but they don’t have a thorough understanding of the design process, the thinking, and the research required to get them great results. When they say they need something in a week, do they? Or is that just a “Nice to have” date? They also are not your only client. 

I now ask questions around due dates to find out the true urgency. I can then decide if I want to take on the project under a tight timeline or let them know when I CAN deliver it and see if that works. Taking control of project schedules allows me to deliver my best work (aka best results for them) without added stress.

A healthy money mindset is crucial: 

I was squelching my business’ profitability by assuming that others were driven by saving money like I was. In reality, money is simply a beneficial tool. A tool that helps us all get what we need and want in life and business. Assuming that we are all equally motivated by money isn’t our job, nor does it serve us well as business owners. If you could use some practical money mindset help (and a very entertaining read), check out the book by Jen Sincero, You Are a Badass at Making Money. (NOT an affiliate link, I just love to recommend this book.)

Asking for help makes business manageable: 

Hiring help in your business can feel scary and overwhelming. My biggest tip in this area is to realize that any help you need can be very part-time and even temporary. You don’t have to hire a full-time employee out of the gate. I reached out to a few freelancer friends to help me when I had too much work. I also was able to hire a part-time junior designer to come into the office a few hours a week, and it saved my sanity. 

It’s important to continuously evaluate the projects and clients that are a right fit:  

I shared the wedding invitation design example because it’s common for us creative humans to feel pulled in a specific direction. We are then devoting a lot of time and energy to it and feeling stuck in a self-inflicted commitment to something that doesn’t serve us. We tell ourselves we must stay with “that thing” even though it’s not an ideal fit for us. 

What if we change our thinking a bit? What if the focus we choose serves its purpose, and then it’s ok to leave it behind when it no longer works for us? 

In my business, we have outgrown specific clients and certain types of projects many times. And honestly, I’m not always quick to change when I know I need to because it can be scary. Still, I’m working to spot those opportunities and pay attention to them. 

Like life, business is ever-evolving, and so are you. Don’t be afraid to part ways with offerings or clients that no longer fit the direction and needs of your business. Instead, be open to seeing new opportunities to help you and your business grow!

These early years of my full-time business were packed with projects and lessons. I began to learn what I loved and didn’t love about running a business. In the next chapter, life gets more wonderfully complicated, and it’s time to make some changes!

In the meantime, please share this post with anyone you think could use some practical lessons AND I'd be so grateful if you would please add your own business lessons in the comments.