In 2015, we ran a story about Julia Kelly, an entrepreneur who makes a six-figure income as a caricature artist.
Where is she now?
We decided to follow up her story. How sustainable is her business? How passive is her income?
Here’s Julia, with a follow-up in her own words. Take it away, Julia!
How to Manage Two Successful Businesses (and Why One Wasn’t Enough)
— written by Julia Kelly, special guest contributor
When we left off, I was running JK Expressions and I was a couple of months away from finishing my degree. I was beyond excited to be done with my degree and focus on the business full time – I was pretty sure I would be living the dream!
I was in for a disappointment. About eight months after graduating and focusing on nothing but the business, it was hitting record revenues but I was dissatisfied, bored, unmotivated and thinking seriously about getting a “real” job.
I was confused. Everything looked great from the outside: I was my own boss, had a super flexible schedule, tons of time for hobbies, and good money.
What was the problem?
It probably would have worked for a lot of people — there’s tons of advantages to running a business like that:
Major flexibility. Gigs are anywhere from two hours to a couple days long. You show up, you do the work, you go home. There’s very little scope-creep which left me with plenty of time for other things.
Travel. I’ve been all over the country for gigs. It’s pretty cool to travel all around without having to pay for it.
Creativity. You can be as creative as you want. People have to be happy with their drawing, but you have major latitude to switch up your style, process, “look” etc.
But, it turns out that those weren’t the things I really valued.
The disadvantages stacked up pretty well too:
Loneliness: I got lonely running the biz by myself. I didn’t have accountability or community. My schedule was getting really slack with nothing but my own internal drive to keep me motivated.
No consistent recurring revenue: For gig work, you’re starting from zero every month. A great month wasn’t a guarantee of the next month being great. I value consistency and predictability and this type of industry can’t guarantee that.
Too much time on my hands: Kind of a blessing and a curse. I had been filling up my time with a full course load in upper-division accounting and now I suddenly had scads of time to fill up. I tried a few hobbies, but I got bored. I needed to be busier.
I wasn’t challenged: My passion wasn’t wrapped up in art and I didn’t want to push myself artistically. I was more interested in other domains unrelated to drawing and cartooning.
It’s not like there wasn’t any growth potential in the business, but if I wanted to grow JK Expressions into a big company, I would have needed to expand into other types of corporate entertainment, hire a bunch more people, and turn into an agency-type model.
For some reason (I found out later what it was), every time I thought about running a business like that, it didn’t appeal to me at all.
After a year of running JK Expressions full-time, I decided I needed a new challenge, but I wasn’t sure where to look.
In 2016, it kinda just fell into my lap.
Starting a Second Business: Rigits
A good friend of mine (Elizabeth, but everyone calls her Bitty) and her husband moved next door to me in the summer of 2016. During dinner a week or so after they moved in, she mentioned that she wanted to branch out on her own (she had a full-time job in accounting).
It clicked! She had the expertise in bookkeeping and accounting, and I had the business development experience! We already knew that we got along and worked well together, so a few weeks later we hammered out a business plan.
We named our company Rigits (a portmanteau of Remote and Digits). We offered bookkeeping, accounting, and tax prep for small businesses who use QuickBooks Online.
Our first client was a friend of ours whose bookkeeper was taking another job. Bitty worked nights and weekends on our new company, and after six months, we had enough business for her to quit her job and go full time with Rigits.
Three years in to starting the biz, we have over 50 clients and five employees making up an awesome team of humans doing work that’s valuable, important, and (for me at least) fun!
I still run JK Expressions and do a decent number of the gigs myself. Turns out, I’m much happier when drawing caricatures is my side gig and it’s balanced out with more analytical type of work.
How I Manage Two Businesses
The first and most important key is that I’m not managing two businesses by myself.
Bitty manages our employees and does the bulk of the account management. She definitely carries the brunt of the workload there. My job at Rigits is to bring in new business, make sales, and onboard new clients.
For JK Expressions, I have a great virtual assistant who’s been with me for over two years. She’s slowly taken on more and more of the administrative tasks, bookings, and email communications for me.
Over the years, we’ve found a couple of ways to approach work that minimizes how much time I have to spend on it.
Optimize your communication style: Email is my scourge. A cluttered inbox will stress me out quicker than anything else. Because of that, I encourage my assistant to text me for quick questions. If there’s a bigger question, I’ll call her on the phone. Anything to reduce my inbox is completely worth it for me. When email is down, Jules is happy, so I’ve optimized my communication around that principle.
When in doubt, delegate: There’s so many tiny tasks I do in the day that aren’t the best use of my time. But because it’s faster in the moment to “do it yourself”, those tasks pile up. The danger is that you’re spending the bulk of your day on the urgent, but not important, tasks. To mitigate that, I’ve tried to form the habit of delegation. The easiest way for me to do this is to record a screen capture where I do the task while narrating it. The task gets done, and now I have instructions ready-made to hand over. Recording a quick video has removed the barriers to delegation and allowed me to make it a habit.
Make the robots work for you: There are a few key pieces of technology that have allowed me to automate what used to be very time-consuming tasks. For instance, writing emails – I have several dozens of email templates accessible in my inbox for almost everything: sales, follow up emails, frequently asked questions, requests for referrals, notifications, onboarding, you name it! If I have to use any type of copy more than once, I’ll make a template for it.
Here are some of the tools we use to collaborate and reduce my workload. I’m not an affiliate for any of these tools, I just use them every day and they save my sanity!
Zoom: I use this for screen sharing with clients and our remote team. It can be so much easier to explain by doing instead of having a lot of back and forth over email, so screen sharing has been really useful for me. I also use it for recording screen capture videos that I use to delegate tasks.
Yesware: A Gmail plugin that stores categorized email templates and sets reminders if you haven’t received a reply. The templates integrate beautifully with Gmail and make follow up a breeze. I never have to set calendar reminders to follow up with someone – the email will boomerang back to me on the date of my choosing.
Hiver: Another Gmail plugin that allows my assistant and I to assign emails to each other, leave notes and comments on an email, and “close” the email when it’s handled. We’ve probably cut down our internal email threads by at least a third.
By using these tools and principles, I probably spend less than an hour a day on JK Expressions unless I have a gig.
The whole gig process is automated, too. All I have to do is check my calendar, where my assistant has put all the information I need to get to the gig and make contact with the client. She creates invoices and contracts, writes blog posts, books other artists, collects timesheets, and keeps everything running smoothly. I couldn’t function without her.
Finding Alignment Between Work and Values
I wouldn’t recommend starting a second business to everyone who is feeling uninspired or going through plateau in their main business. But it was the right decision for me.
The biggest improvement has come from working in a team. Having a business partner—and now a team—is such an exponential improvement from working in (relative) isolation like I was with JK Expressions. I have people in my corner who are just as invested in the success of the business as I am. Bitty helps to balance my weak points and keeps me on track. It generates a ton of momentum and keeps me striving and pushing.
I also knew I wanted to have a bigger impact on the world, and I wasn’t motivated to do it with a caricature company.
Don’t get me wrong—it’s absolutely possible to have a major impact with that type of business and plenty of people do it. But JK Expressions wasn’t the way I wanted to leave my mark on the world.
In the year that I ran it exclusively, I kept trying to “solve” why I was resistant to growing the business.
Finally, I trusted my gut and started something new.
After Rigits got some traction, it became clear to me that we had what it took to tangibly improve people’s lives and businesses in the world of finance and accounting, and that’s what feels right to me and motivates me to grow the business.
So I guess I’ve come full circle. Drawing caricatures started out as my side hustle, became my main hustle for a while, and now it’s back to my side hustle.
It’s been a wild ride—certainly never one that I would have guessed. It may be an odd journey, but it’s mine, and I love it!
— written by Julia Kelly,
in her own words,
as a guest article for Afford Anything