Episode 011: How to Build Your Team as a Creative Entrepreneur with Jessie Roseberry of Roseberry & Co.
Photo by Crimson Seas Photography
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What began as a fun, unique way to raise money for a mission trip through watercolor artistry became a passion, a way to connect with others, and a successful business.
Jessie Roseberry of Roseberry & Co. is a watercolor artist and educator based in West Lafayette, Indiana. She teaches Wine and Watercolor classes, once a month, at the Fowler House Mansion in Lafayette, Indiana. (I 100% recommend her classes if you’re ever in the Lafayette area!)
While Jessie’s business started small in 2017, she quickly had more work to do and orders to fulfill than she could handle on her own. And, it didn’t take long for her to realize that if she wanted to keep her business stable, have a steady source of income, and maintain joy for her work, she needed to hire.
In this episode of Priority Pursuit, Jessie and I share what hiring has looked like for our small businesses and how you can build your team as a creative entrepreneur!
After the Christmas from ‘hell’, Jessie knew she needed help.
Jessie shares that, “During one Christmas season, I had taken on 80 custom orders, and I kept saying yes to little ones here and there. I was shipping prints out and going to the post office three times a week with stacks of boxes. I just remember standing in the post office line and thinking, ‘This is miserable. I can’t do this anymore. I’m not going to enjoy this work if I have to deal with all of this stuff. It isn’t that I’m above all of it; I just can’t do all of it.’”
Jessie was feeling more than overwhelmed. Then, she happened to listen to a Jenna Kutcher podcast with guest Emily Grey who talked about her experience building her team. This podcast episode actually resulted with Jessie scheduling a coaching call with Emily Grey who asked a thought provoking question about the kind of work Jessie was doing.
Are you doing $10-an-hour work, $100-an-hour-work, or $1000-an-hour work?
Jessie says, “I realized I was doing $5-an-hour work, because I was run so ragged. I wasn’t even making minimum wage because I wasn’t managing my time well. I [was] saying yes to too many things.”
Let’s be honest; it can be hard to say no when someone likes what you do and wants your product. And, saying yes is easy at first because it’s only for a “few things” or a “few friends,” but before you know it, you’re saying yes to everything and every friend (and friend of a friend). And, you just can’t do it all.
Start building your team by simply hiring one person to help you a few hours a week.
As a creative entrepreneur, the thought of building a team might seem scary. It was for me anyway. But, you can absolutely start small, which is exactly what Jessie did.
Jessie started by hiring a girl in her church at $12 an hour to help with shipping, packaging, and some administrative work. Having someone who can help out with even a few things on your full plate can make a huge difference in managing your workload while simultaneously encouraging joy and excitement about the work you do.
Jessie’s initial assistant helped just for a season. But, when Jessie was ready to hire a more permanent assistant, she knew she wanted to hire someone who could help her fill in the gaps of her own skills.
Surround yourself with people who can do the things you can’t do and do them well.
Today, Jessie has one assistant, Hope. Hope is a photographer and a hairdresser with a great deal of creativity and a type A personality, which meshes well with Jessie’s type B personality. Between her great ideas and courage to take initiative, Hope has been a great addition to the Roseberry & Co. team.
Jessie shares that, “Hope packages prints when they come in, organizes my studio for me, helps me order things I need, updates my website (uploads new products), does some graphic design, and does some photo ops of products and business branding.” (Jessie does pay Hope’s photography rate when she shoots for Roseberry & Co..)
It might seem like an impossible task to find someone who is willing to help you just a few hours a week, but chances are, there’s someone out there who would be truly blessed by this opportunity. Rather than getting self-conscious about asking, consider how a college student, stay-at-home mom, or someone who is simply passionate about the tasks you need help with could be blessed through the opportunity to work alongside you, earn additional income, and share their own abilities and skills.
If you’re looking to hire, sharing the job description on social media is a great place to start.
If more work than you can handle on your own is coming in, chances are, you’re ready and can afford to bring on help. (Plus, with help, you’ll be able to spend more time focusing on what actually brings in money for your business!)
If you’re ready to add your first team member, think about the kind of help you need, and decide whether you need assistance short term or long term.
Then, make a list of all the tasks and responsibilities you really don’t enjoy doing, things that you wouldn’t miss if someone else did them, and things that you don’t HAVE to do yourself. (Example: Jessie has to create her artwork, but she doesn’t have to package her pieces and take them to the post office.) Then, use this list to create a job description, which can be as simple as a bulleted list of responsibilities.
While you might not enjoy the tasks on this list, chances are, somebody out there would thrive in these areas and would love to take on these responsibilities. Just be sure to be clear about what you need that person to do and what is expected of their role to ensure (1) they can meet your needs and (2) the position can meet their needs. More than likely there’s someone in your community (personally or at large) that can do what you need and do it well. And, according to Jessie, social media can be very powerful when it comes to hiring!
In this episode, Jessie shares how she found Hope, “I [shared that I was looking for an assistant on] my Instagram stories, because truly, right now, that’s where people see me the most. Hope had come to some of my classes and we had started up a little bit of a friendship. She was the one I wanted to hire so I actually put it out there so that she would see it. From that one day of Instagram stories, I had 21 people reach out to me and want to send me a resume. Hope was one of those people and was so persistent in wanting to work with me, which was great because I already wanted her.”
When building your team as a creative entrepreneur, it’s important to clearly train your team members but also leave room for their own gifts to shine.
Now, going from solopreneur to being an employer requires intentionality, especially when it comes to training your team. And, there is often a balance between telling your team members exactly what you need them to do and allowing their own giftings and talents to shine while simultaneously supporting your strengths and creating opportunities for growth. Plus, everyone works a little differently.
To train your team, write steps down. Have instructions for tasks or processes readily accessible. Walk someone through a system, practice, or strategy you have in place until they feel confident doing it on their own. But, leave room for them to make changes and do things differently, because they might know or discover a better way to complete a task and can make improvements to your existing systems.
Hiring isn’t as scary as you think.
Chances are, you started your business because you love what you do. But, when your to-do list is unending and you’re losing sleep trying to get all of your work done, it’s easy to lose your passion and love for your craft and even those you serve.
Adding to your team can help prevent this AND make your business more profitable.
“Don’t let yourself believe the lie that you have to do this all by yourself. Let yourself be free to do what you love.”
If you need help managing your growing business and keeping up with your workload, it’s likely time to build your team!
Want to hear more from Jessie of Roseberry & Co.?
If you’d like to connect and hear more from Jessie you can find her on Instagram at @roseberryandco, on Facebook and at roseberryandco.com.
Links & Resources Mentioned in This Episode
The 7 Habits of Highly Effective People by Stephen Covey
The Goal Digger Podcast – Jenna Kutcher
The Business Boutique Podcast – Christy Wright
Jen Sweeney – @jsweeneydesigns
Cara Rosalie Olsen – @rosaliegwenpaperie
Emily Grey: The Flourish Market
Join the Priority Pursuit Podcast Facebook Community
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