Author: Phyllis Reagin is an Executive and Leadership Coach, Leadership Psychology Expert, and founder of At the Coach’s Table. She supports leaders in the entertainment and media industry to lead with clarity, confidence, and purpose.
Here’s something I see almost every week in my coaching sessions:
Overthinking.
It feels like you’re being thorough, responsible, maybe even strategic. But in reality? It’s a sneaky confidence thief.
I was recently coaching Rachel, the VP of Partnerships for a growing production company. Rachel is smart, thoughtful, and deeply respected. But she was struggling to make timely decisions, especially the big ones. She would loop in her head for days, sometimes weeks. She was afraid of getting it wrong, afraid of missing something, afraid of making the “wrong call” and not being seen as a strong leader.
And here’s what happened…
Opportunities slipped through her fingers. Her team started losing confidence. And most painfully? She started losing confidence in herself.
We had to interrupt the pattern! As a seasoned Executive & Leadership Coach, here’s what I know for certain:
Overthinking isn’t a leadership strength. It’s a protective strategy your brain uses when it doesn’t feel safe.
But once you know that, you can start making powerful shifts.
Here are the exact strategies I used with Rachel, ones you can start applying right now:
Regulate First, Decide Second
You know what doesn’t work? Trying to make a confident decision while in a state of fear, stress, or perfectionism. Your brain literally can’t think clearly when your nervous system is in overdrive.
Instead, pause and breathe. Regulate. Take a short walk. Do a quick nervous system reset. When you get back into a grounded state, you will notice your thinking becomes clearer. That’s your executive brain coming back online.
Rachel started doing this before high-stakes meetings. Just a two-minute reset made her feel sharper and more present. And the quality of her decisions changed dramatically.
Choose Your 70% Rule
Perfection is a trap. If you’re waiting for 100% certainty, you’re going to wait too long.
We worked on this mindset with Rachel: “Is this decision 70% good and aligned with my values and goals?” If the answer is yes then go! Move. Decide. The rest gets figured out along the way.
Remember this: Effective and impactful leaders make informed decisions, not perfect ones. And then they lead with adaptability.
Practice Fast, Small Decisions
Decision-making is a muscle. And Rachel hadn’t been working hers often enough.
We created a daily exercise: Pick one small thing to decide quickly. No circling. No spiraling. Just make a clean and quick decision.
Over time, she started trusting herself more. And that trust? It translated into faster, clearer calls when the stakes were high.
You don’t need to wait to become a more confident, grounded decision-maker. You just need the right strategies…and a little belief that you can break the loop.
Next Step: Let’s talk. I’m offering a free 30-minute strategy session where we will unpack what’s keeping you stuck and give you tools to shift into clarity. It’s no-pressure, totally personalized, and designed to get you moving again. Click here to grab your spot.
Meet Phyllis — A former entertainment exec turned high-impact coach. Phyllis is on a mission to help trailblazing leaders in Hollywood and beyond ditch self-doubt or Imposter Syndrome, use their strengths to make the biggest impact, and to start living from their own genius. She’s coached thousands of leaders and teams (from Netflix, Warner Bros. Discovery, Amazon MGM Studios, Google, Meta, Spotify, Atlantic Records, Paramount Global, and more) to lead with greater confidence, influence, and impact. If it boosts leadership impact and builds confident leaders, she’s on it! Read more about her here.