Cosmopolitan: ‘The New C-Suite Gives Good Advice’: Let CEO Courtney Caldwell Show You How to Protect Your Peace (Professionally)

Hint: email auto-replies play a big role.


Shifting an industry surely doesn’t happen overnight, but for years Courtney Caldwell has been gradually reshaping the cosmetology world. She’s the co-founder and CEO of ShearShare, an app that allows freelance stylists and barbers to rent open spaces in salons all across the country.

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She’s been leading ShearShare since 2017, and working in the salon industry for 20 years—meaning she’s no stranger to running a tight ship and producing impressive results. (That’s why Cosmo and digitalundivided selected her to be in our 2023 New C-Suite Class, after all.) When someone who’s killing it at the top is ready to share tips on how exactly they got to where they’re at, personally, I prefer to listen. If you’re down to do the same, scroll on to soak in some of Courtney’s advice on how to stay productive, patient, and persistent in the ever-changing professional world.

When you’re getting ready for a big meeting or presentation, how do you mentally prepare?

I’m a bit mechanized in my mornings, so before a big meeting or presentation, I’ll get up, do an Appreciation Audit, light a rose candle, meditate, journal, fix myself a cup of hot water, ginger, turmeric, honey, lemon, with a splash of cinnamon, eat a piece of fruit, and then work out and stretch. It’s not until I’ve gone through my self-regulating activities that I can give my best self.

How do you juggle making time for “deep work” versus staying on top of every email, Slack, or notification?

I set up my email autoresponder that lets recipients know that I check email twice a day. This one thing helps me to maximize my productivity, has definitively added to my personal efficiency, and allows me so much grace. 10/10 highly recommend!

When you approach moments of burnout, what’s the best way to overcome them?

During my last season of burnout, I decided to research hypnotherapy. I’d read that many elite athletes, executives, entertainers, and pastors have had success with hypnosis. So I gave it a try. Now when I feel anxiety start to rise, I sit and listen to my customized audiotapes. Night and day difference. Extraordinary Change Hypnosis offers virtual sessions and records them so that you can replay when needed. Ask for Corrin!

What about self-doubt… When you’re not feeling sure of yourself, how do you snap out of it?

One of my favorite books, What Happy People Know, talks about the quarter-second rule. Our brains are so powerful that we can change our entire day with one thought, and it takes just a ¼ of a second to do so. When I’m feeling not so sure, I immediately change my thinking. I’m sure this one little thing has saved me days of depression.

What’s the most common mistake you’ve observed young professionals making lately?

Not exercising patience. And I’ve been there. But I try to advise our new hires or someone I’m mentoring that you can’t skip the process. Put in the work and the activity will always propel you forward.

What questions are important to ask yourself before making a scary career jump?

The one question I asked myself when transitioning out of corporate America into entrepreneurship was, “What’s the worst thing that can happen? If this doesn’t take off and I have to put my RESUME back up on LinkedIn to apply for another 9-5…?” If that’s the worst that can happen, then I have to bet on me and give entrepreneurship a try.

What was your first major career win, and how did you celebrate?

Being in corporate America for 20 years and an entrepreneur for seven, I’ve had many career wins. But I’ll say my first was after I earned my MBA and became head of marketing for an enterprise SaaS company. It was a goal I set for myself as a youth, and I reached it by age 32.

Could you walk us through any embarrassing professional moments that make you laugh when you look back on them now?

Sure! Where do I start? One embarrassing moment that I laugh at now is when we were pitching ShearShare at a demo day. I was the opening pitch and ended up freezing on stage. I had to restart my pitch four times before my brain clicked on!

Where do you sit on the great debate about in-office vs. remote work?

I’ve managed contingent workforces, in-office staff, and everything in between. What matters to me is how to pull the best out of each individual team member. I study my staff, then we determine together what their best work environment is. Sometimes it’s hybrid, sometimes it’s remote, sometimes it’s in the office.

How do you wind down after a long day?

I get outside. I do Navy Seal breaths. I hug on my loved ones. I smile at the future.

What’s the best piece of career advice you’ve ever received?

Just don’t die.

What about the worst?

Don’t work with your spouse. [Editor’s note: Um, Courtney founded ShearShare with her husband, Tye Caldwell! 😂]

What advice would you give to young women of color who want to found their own business?

Just start. And be sure to jump in with a spirit of optimism. That optimism is your competitive advantage.