On the theme of business, I’m really excited to introduce you to today’s guest, Charlene Bailey, a figure skater. After leaving the world of competitive skating at 19, she realized there was a void in her life. Through an inspirational, entrepreneurial journey, she found her way back to the sport as a coach and fashion designer. What is so powerful about her story, in particular, is the way that she just put one foot in front of the other to follow her passion. Charlene epitomizes this idea of ‘if you really want something’ you make it happen.

Her story is inspiring and relatable, and it was such a pleasure to be able to sit down with her and talk with her about her entrepreneurial journey, as well as her visions for her figure skating fashion business, her dos and don’ts as an entrepreneur, and ways she finds balance between her busy entrepreneurial schedule and her core health values.

Key Takeaways:

[1:43] Introduction to our guest today, Charlene K Bailey.

[3:25] Charlene takes us through what she’s been up to, her background, and the current business she’s building for herself.

[8:30] Charlene’s visions and frustrations for fashion in figure skating.

[10:35] What feminism means to Charlene and how it’s infused into what she’s creating.

[12:53] Charlene’s advice to those who are unsure of where to start.

[13:54] The steps Charlene took to get started with her business.

[16:55] How Charlene learned to become an entrepreneur.

[18:08] Charlene’s recommendations, to-dos, and ‘don’t-dos’ to entrepreneurs on a similar journey.

[19:34] How and what Charlene is outsourcing to other people.

[20:45] The criteria of ‘letting go’ as an entrepreneur to allow yourself to grow.

[22:16] What has helped Charlene through her journey as an entrepreneur.

[24:00] How Charlene went about finding her mentors.

[26:56] How Charlene finds a balance between a busy entrepreneurial schedule and her core health values.

[30:04] What Charlene would like her legacy to be.

[31:26] Charlene’s key-performance indicators!

[35:15] Where to find more about what Charlene is up to.

Mentioned in This Episode:

Gary Vee’s Youtube Channel

The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life, by Mark Manson

The Revolution Magazine

Toronto Fashion Week

More About Charlene Bailey

Bailey is the Director Creative of cb., established in May of 2015. She has two studio locations: One in downtown Toronto, and the other in Richmond Hill.

She designs and creates figure skating garments tailored for the competitive skater. Charlene runs her business very differently than most others in the industry; with a client-centered brand. She holds each relationship with every one of her clients very dear and works hard to ensure each one of them feel and look their absolute best the second they step out onto the ice!

Connect with my Guest:

Websites: CharleneKBailey.com and The Revolution Magazine.

Social Media: Facebook, Instagram, and Twitter.

If you enjoyed our conversation and would like to hear more:

Please subscribe to The Entrepology Podcast on Stitcher or iTunes.

We would also appreciate a review!

Join our badass Women’s Facebook Group, Legacy Performance Labs

If you want to be something amazing, you need to surround yourself with amazing people! The Legacy community is made up of badass women living — not leaving — their legacy every single day. If you are on a mission and get it that your health is the key to your unlimited potential — Join us on Facebook!


See where you stack up and take this month’s quiz right here!

Part of improving your health and performance as an entrepreneur requires that you take inventory of your current state of health. To this end, we have prepared a monthly quiz related to the health and performance of entrepreneurs and go-getters. 


This week I want to challenge you to try something new and get outside of your comfort zone. Maybe it is taking a new fitness class, signing up for pottery classes or teaching yourself to sew as Charlene did. Whatever it is, share your commitment on our Entrepology Facebook page. Because when you are accountable, you  are helpable.


“[In figure skating] there’s a theatrical element to the athleticism. You don’t need to look like you’re in a circus; I think you could look super glamorous — and that’s what I kind of want to bring to the table.” — Charlene Bailey

“In no other sport is there an element of fashion. … It’s a marriage of something that could be very feminine but also it’s super sporty — which is feminism at its finest in my opinion.” — Charlene Bailey

“At the end of the day, life isn’t that complicated; It’s about being happy.”
— Charlene Bailey

“I think the #1 thing is keeping in mind why you started [your business] in the first place and really being grounded because … it’s very easy to get carried away with everything that’s going on.” — Charlene Bailey