One of our Self-Made Artist Academy students, Caitlin Wagner - a designer and visual artist based in Chicago - interviewed Chelsie to gain more insight to the art practice and business behind Lettering Works.

What do you like most and least about running your own business?

I love running my own business because of the flexibility that it affords me - both in my schedule as well as the projects that I choose to take on. I am able to work when I feel creative and energized and take breaks and vacations when I need them. I am able to work on projects that I feel most passionate about and truly enjoy, which allows me to produce my best work.

While there are many pros to running your own business, there are some cons such as experiencing is stress related to the sustainability and profitability of your businesses. You don’t always know where your next project or revenue is going to come from. Entrepreneurship isn’t for everyone, but if you are a passionate and motivated self-starter, it can be a very rewarding and enjoyable route to pursue.

What does it take to be successful as a small business owner?

Being successful as a small business owner often means that you are willing to invest in yourself, take risks, and ultimately be proactive in taking your future into your own hands. Maintaining motivation and purpose is key to moving your business forward because unlike a 9-to-5 job, there won’t be anyone in particular telling you what you need to do or what you should be doing next. I’ve personally found that my passion and love for what I do motivates me to learn and progress forward, even when parts of business can be daunting. It’s really key that you are willing and ready to learn everyday as well and do the tasks beyond what you are most skilled at, at least in the beginning when you cannot afford to hire those tasks out.

What was the biggest change you had to make in your life in order to find that success?

Since I bypassed the corporate world and went straight into entrepreneurship out of college, I don’t think I had to make any big changes necessarily. Entrepreneurship is all I’ve known in terms of full-time employment (beyond summer internships that were 40 hours a week). The biggest and most impactful change I’ve made in my five years in business is narrowing my focus to what I really enjoy and leaning into doing what I love, knowing that the money will follow. If you are new to entrepreneurship, an initial realization may be that no matter how hard you work, money isn’t guaranteed. At the same time, you have an infinite earning potential.

How did you conquer the fear of visibility as a small business owner while you were developing your brand?

I think there is a bit of a myth around how much visibility is truly needed for small businesses. It’s easy to compare ourselves to big brands and identify all of the things we don’t have. The reality for many small business owners is that we don’t need as much visibility. The vanity metrics of how many followers you have and how many likes you get are not as important as how many clients you have and the quality of business relationships you are building. All this to say you should be concerned about being visible to the right people, not all people. Visibility takes time and effort to build up.

What was the best investment that you made in your business when you were first starting out?

My favorite answer to this question is always the time I’ve invested in my own personal projects because they are what has led me to doing the most fulfilling work with the best clients. Another investment that I made frequently early on was investing my time into learning new things - this is through free and paid cohorts and online classes and workshops. Professional development leads to growth and improvement that goes beyond your business and can improve your quality of life as well.

From a monetary investment standpoint, one of my best investments relatively early on was a client management software which handles all my contracts, invoices, design proofs, and other client communication in one place. It streamlines my process so much and is definitely worth the money. It’s truly something I wish I would have purchased before anything else.

What has been the most useful resource(s) for establishing and growing your business?

There are so many free and paid resources out there. I think my best advice is to identify what you are struggling with most and find a resource to help you get over that hurdle. At times for me that has been applying for and participating in a free cohort through the WBDC, other times it has been connecting with peers in the industry and having open conversations about what works and doesn’t work for us. If you see someone that you really admire, find a way to learn from them - too often we assume that we cannot afford their services, but more often than not there are many ways to engage with these people and you may be surprised after a little bit of digging.

How do you determine what business growth programs (like the WBDC) to get involved in?

You only have so much time in a day, so choosing how to spend that time wisely is essential. Only enroll in programs that are in alignment with your goals and the questions you are trying to answer. There are entirely too many resources for you to take advantage of, so only go with the ones that really feel right for you and where you’re at. There are lots of really specific programs as well - I was able to join a cohort related to doing business with airports, as one of my goals is to sell my art products to airport gift shops. I always follow my greatest curiosities when seeking out these learning opportunities.

What's the best/worst advice you've gotten about owning your own business?

First off, only take advice from someone who you’d be willing to trade places with. That being said, the worst advice usually comes from people who don’t truly understand my passion and why behind my business. They often provide advice that doesn’t align with what I am trying to do or doesn’t take into account things I know from my own experiences in business. For me, small business ownership and entrepreneurship are about making your own path and acting on advice that resonates with you. The best advice I’ve been given is to invest in myself and trust myself as the expert in my field that I am. This advice gave me permission to lean into my biggest ideas and spend money on personal projects that might not immediately be profitable.

Do you have any tips or tricks to successfully establishing systems/processes (and making them stick) in your business?

Document everything, whether or not you have a process written down, you often still have a process or way you do things naturally. Document it so you can be aware of it and optimize it to be efficient and work for you. When trying to implement new systems and processes in your business, start with one and build on it. Trying to improve everything at once will likely lead to overwhelm and reverting back to old ways out of comfort. The book Atomic Habits helped me to focus in on habit stacking and changing the way I do things personally and for my business.

What does your typical process look like for a custom project?

Custom projects always start with a conversation to help me understand what the client is looking for and best determine how I can help. After we agree on the scope and terms of the project, I send over the necessary paperwork to onboard the client. Because of this, I don’t take on any projects that don’t pay enough to cover the time of this onboarding process. It’s not worth it to skip over having a contract and clear agreement upfront. Once all paperwork is sorted and the initial invoice is paid, I send over a questionnaire or schedule a meeting to gather any ideas and insights the work may require. I use that as a guide to work on the design itself and communicate with the client throughout the process to gather additional feedback at key points. Once we land on the final design, I send a final invoice and once it is paid, release the final files. If the project is something that I would like to do again, I’ll share it across my social media and add it to my portfolio.

What has been the best policy that you have implemented in your business that helps you maintain boundaries with clients?

The best policy I’ve implemented is having a solid contract reviewed by my lawyer and being upfront with anything that I think may be a concern. The further along I’ve gotten in business the more upfront I’ve become on what I can and cannot do. I’ve learned that I am not the right designer for all jobs. When a potential client inquires with me, I have to be diligent about asking questions and “interviewing” them as well to ensure we can be successful working together. I have gotten a better grasp on who I can best help with my skill sets and strengths. I intentionally seek out those types of clients to ensure I don’t have any issues with boundaries. Also important is not being afraid to fire a client or end a project if it’s really not working.

Have there been any beneficial practices that you have adopted for connecting with potential clients or customers as a solopreneur?

My passion projects have been my best generator of quality clients as they serve as conversation starters and help me connect with potential clients on a deeper level. Putting myself into my work has helped me attract potential clients who want to work with me personally, which usually yields a better relationship and better work. Also, don’t underestimate the power of simply reaching out to someone to let them know you are available and would love to work with them.

ABOUT CAITLIN

Caitlin Wagner is a designer and visual artist based in Chicago. Her multidisciplinary practice experiments with variations on form and explores color and texture inspired by the relationship between identity and design. Caitlin's studies in fashion planted the idea of design as a method for extending expression beyond the self and encouraging authentic connections with others. Her journey through design provides an opportunity to further develop self-awareness and improve her ability to communicate passion through a clear vision. She continues to explore these core concepts while working alongside small businesses and startups to help establish visual identities for their growing brands by producing a cohesive design story across channels.

Caitlin participated in the first cohort of Lettering Works’ online course for artists and shares: “Self-Made Artist Academy is a great foundational course for anyone wanting to take their passions to the next level. Chelsie does a great job of laying out the basics while also empowering further individual exploration, especially into the importance of building your business in a way that helps you reach your own goals. Very helpful in making the uncertainty that comes with entrepreneurship a little less intimidating!”