10 valuable lessons I learned from running a small company

Running a small company for four years changed me in ways I can’t even count. It’s my proudest accomplishment, the thing I’ll hang my hat on for a long, long time—at least until the next big thing comes along.

But, until then, here are 10 of the most valuable lessons I learned from running a creative business.

#1: You can fight through imposter syndrome.

In the bingo card of life, the last thing I ever expected was to become the COO of a company. And I’m not gonna lie—it made me really uncomfortable at first. I felt inexperienced; I felt unworthy. The company had a very flat structure up until then, and I didn’t think anyone there would respect any kind of authority from me in a million years, title be damned. And for people outside of the company, I kept thinking: they’re all going to think I didn’t earn this. And they’re right. What the hell do I know about running a business? I’m a creative!

Well. It turns out I knew a lot more than I gave myself credit for. And if I didn’t know something? I figured it out, just like I always had throughout my career. Soon, the voices wondering what everyone else would think got a lot quieter. It just goes to show: imposter syndrome is based in external fear. Other peoples’ opinions don’t matter. Only you know what’s inside of you.

#2: Don’t solve problems; ask questions instead.

As someone who took a lot of pride into figuring stuff out and making s#it happen, this one was a tough pill to swallow. But if you’re constantly trying to brainstorm how to solve problems for people, they’re never going to learn how to do it themselves. It’s time to let them do their job so you can move on to a bigger picture, where you’re meant to focus.

Another fun layer of jumping into fix-it mode? You might be chasing the wrong problems. It’s important to ask the right questions not just to get to the root of the matter, but also to help your people learn how to think…and gain their own confidence, too.

#3: Running a business is just like going to the gym.

Some days you don’t want to show up. Some days you feel like you could run forever, and some days you can’t remember how to breathe. There are certain exercises that make you think, “I can’t possibly do one more rep, because I am going to fall apart.” But guess what? I can’t remember the exact statistic or percentage, but your mind starts to give up when you still have 30% left in the tank. You can push through that rep. Same is true for your business.

#4: Your rhythms set your results.

Our business coaches taught us the importance of setting regular cadences for important tasks: team meetings, client meetings, strategic planning, etc. Lock them into your calendar, make them repeat, and honor the rhythms. This pretty much guarantees that you’re doing all of the important things you need to do to give your team safety and move your business forward—motivation be damned. (Motivation is fleeting, anyway. It’s discipline you need, and that’s what rhythms give you.)

#5: Do the thing you don’t want to do—or don’t think you can do.

There were so many times, especially in the early months of the business, that I’d feel myself filling with panic because I’d never done something before, I didn’t know how, I didn’t want to be a squeaky wheel or a bother. But there was a moment when I took a breath, told myself that no one was gonna do it for me, and if I messed up, then so be it: you made the best moves with the information you had, and there are few things that can’t be fixed by being nice. So just do it, because…

#6: It’s better to act than to be right.

I pride myself in being a pretty good discerner: I can generally tell a great idea from a shit one quick. But sometimes, it’s impossible to know how an initiative is going to shake out. Hey, if it was easy, everyone would take business risks, right? Clarity comes from doing. It’s better to take a small, calculated step toward the thing than wring your hands and wonder about it. If you’re planning properly, you can always pivot.

(For the record, that doesn’t mean you should be doing everything. That’s a recipe for disaster. There’s a big difference between ‘no’ and ‘not now,’ a very important communication lesson I heard loud and clear from my biz coach.)

#7: Ask the dumb questions.

How many times have you been in a meeting, and you didn’t understand the point someone was getting at, but you didn’t want to ask because everyone else was nodding along and clearly tracking? Yeah, well, I can guarantee that half the room wasn’t tracking. Be the brave one who asks the “dumb” question.

I saw this modeled by the CEO of one of my Greenville agencies—she asked questions with abandon, never came across as dumb, and clarified messages for everyone in the room. In my own company, this was one of the first behaviors I adopted, and probably one of the best.

#8: Creating a knowledge base changes the game; push to do it even if you’re getting eye rolls.

When someone came to me and told me something that they’d improved or put together for the good of the company, I’d always say, “Great! Did you write a process and save it on the drive?” It kind of became a running joke, but soon the team would say, “I did this thing, and yes there is a process.” But guess what? When we got new team members, they’d spend their first few days on the process drive learning all about how we did things—and they did it without being told. And when someone came to ask me how something happened or worked, I could point to that drive. As more team members took on leadership-type roles, they’d tell me, “It was so great to be able to point to the processes—it saved me so much time!”

#9: It’s okay to feel lazy.

Most of the time, your job is to encourage a team to do the work, not do the work yourself. It’s a hard shift to make when you’ve been a top-tier executer for most of your career. But that energy needs to go into teaching others. Instead of feeling like you’re slacking or not working hard, focus on all the opportunities you’re giving young team members—opportunities you would have killed for when you were their age. And use all of that experience to pour into them, and help them be better than you.

#10: You can’t pour from an empty cup.

If you want to support your team and your business to the best of your ability, you have to take care of yourself. You need to make time for things that fill you up: journal, exercise (whatever that looks like for you), dedicated time with your spouse or family, and—yes—vacations.

Bonus: I can do anything.

If I have one giant takeaway from the whole experience, it’s that. The amount of challenges I worked through, the things I figured out on the fly, the work I was able to put out…man. I went from imposter syndrome to quiet confidence in no time. Nothing scares me anymore. And that’s something I’ll always hold close.