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HOW TO MANAGE TWO SUCCESSFUL BUSINESSES

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.