A few years ago, I had the opportunity to take Red Thinking in a new direction. And it looked terrifying.

Well, not terrifying exactly but the fear of the unknown had me thinking – and overthinking – my next steps. You’ve probably faced something similar when confronted with a Big Life Thing like buying a house, making a career change, or moving on after a relationship or job has ended. The fear can be paralyzing. What got me moving in my situation was a secret solution. One that no one bothered to teach in school. Or pass down from one generation to the next. 

Trusted Relationships

In the early part of my career, I started to wonder if the only way to succeed was to make tough calls. Unrelenting energy seemed to get things done, yet I didn’t always admire how others met milestones and handled relationships. However, I DID love the fast-paced agency vibe, the quick pivots, the great ideas, exceptional creativity, thoughtfulness to campaigns, and more. 

Fortunately, I saw more good stuff than bad before becoming a business owner. Someone I admire once said, “I know I am only as good as the people I surround myself with.” I couldn’t agree with that more. And I surround myself with much more than a great team and cool clients – I’ve created an exceptional network of trusted relationships. Through trial and error, I now find myself surrounded by, supported, respected, and amplified by some truly incredible people. And it keeps getting better.

Authentic Friendships

They say you are judged by the company you keep. I’m certainly conscious of the people I surround myself with at work and outside of work – because these are the people who push me to be my best. One of my dearest friends happens to also be a coworker. She laid down a 

very insightful view of me at work, explaining to other employees, “Shay drives in a lot of lanes all at once because that’s what her role demands.” It was a wow moment because that phrase captured my management style well. My friend knew me so authentically that she could articulate a truth that even I didn’t recognize. That insight led to other ah-ha moments like recognizing that my multitasking tendencies are why I often find myself able to do my best thinking after five p.m. when the rest of the world is starting to wrap up their workday. I believe you need to allow yourself to have deep friendships and cultivate long-term relationships. Having authentic friends can be an asset when considering a fear-provoking situation because those people know you well and want what’s best for you.


Early in your career, everybody tells you to get a mentor. And your response is probably, What the hell is that? Then one day you realize that you have an older, wiser, or more senior person in your life that you turn to for advice and suddenly you think – Oh, that’s what they meant. I had an unlikely business mentor who took me under his wing at my first agency job. He was a client, and he was tough and harsh, and scary. He was also exceptionally kind, and with extraordinarily high expectations of me, he provided wildly smart guidance. Everyone I worked with said they could 

never work with him. But I loved his unvarnished advice (I miss that, and him). Even now, as a business owner, I find that I still need someone to be my sounding board. When I was wrestling with my fears about Red Thinking, I really needed perspective, and it was hard to come by. What I found is that I could cultivate mentor relationships with multiple people who were already in my life. Some who knew agency life. Some who were super smart about their career. Others who had the uncanny ability to always seem cool and calm. I leaned on and learned from all of them. And it left me with a bit of a revelation: If you’re growing correctly, you should outgrow your mentors.

Raw Honesty

Although I’ve mentioned relationships, friends, and mentors, facing your fears can be a lonely business. Often it boils down to taking time to process things, then having an internal conversation where you are totally honest with yourself. A ‘get over it’ moment. When I was going back and forth about Red Thinking, I remember being scared because I don’t enjoy the operations parts of the business and the first step would be lots of that. My husband saw me struggling and asked, What’s the worst that could happen? I answered, I could fail. He shot back, You’re marketable. If it doesn’t work out you can get a job elsewhere. And after some raw honesty with myself, I concluded: I didn’t want to work for someone else, so failure was not an option. I’m known for making quick decisions, so agonizing for even a few days seems like an eternity to me. That’s how I discovered it was fear stopping me. It’s also how I realized what I really wanted. So, there you have it: The formula for overcoming fear. Trusted relationships + good mentors + authentic friends + raw honesty. I think a lot of us are really talented overthinkers. The next time fear stops you in your tracks, take some time to lean into the people you have around you and do some honest self-talk.