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The Sideline CEO Starter Challenge

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A simple, 5-day challenge to get your team (and your sanity) organized before the first whistle blows.

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In this challenge you will:

Create an easy-to-manage home for all your important team information.

Make sure everyone who needs to be “in the loop” can stay connected and informed

Choose an organization system that helps you stay on top of tasks without overwhelm

Take small, confidence-building steps that make your season feel lighter and more under control

hey there,

I'm Erin Walker

A few years ago, I found myself saying “yes” to co-managing my kids’ hockey team… and immediately wondering if I’d made a huge mistake. I didn’t feel qualified, I didn’t know what I was doing, and I was terrified of messing it up for my kid, for the team, for everyone.

That first season was a blur of stress and scrambling. I was booking hotels in tiny towns, chasing down missing game socks, answering endless emails, and hoping I hadn’t overlooked something important. I was doing my best, but it often felt like someone was always disappointed and I was constantly wondering if I was the only one feeling this overwhelmed.

Over time, things shifted. I learned through trial and error, built systems that worked, and started to feel proud of the experience I was creating for the kids and their families. Then other new managers started coming to me for advice, and I realized: no one should have to figure this out the hard way.

I created this challenge as the gentle first step I wish I’d had a way to help new team managers get organized, feel supported, and start their season with confidence, instead of chaos. Because when you feel calm and capable, everything changes: parents feel informed, kids have a better experience, and the whole season runs smoother.

If you’re stepping into the team manager role and want to start strong without the overwhelm, this challenge is for you.

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