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Jill Drader

002: Struggle is Your Success with Jill Drader

In this very first official episode of the People Teaching People podcast, I’m joined by Jill Drader. 

Jill has been a mentor for me since we connected in 2014 when we worked on building a curriculum together. Jill has an incredibly kind and generous heart and is someone who has inspired me to follow my heart and those nudges. 

Jill Drader is a natural connector, teacher, visionary, and intuitive. She’s launching her new venture – OwlSeek – where she will continue her executive coaching and leadership practice, and re-launch her retreat series in spring 2023. 

Her non-for-profit Struggle Is Your Success, was partnered with Trellis this year, the largest NFP in Calgary, which supports youth initiatives. Jill’s past education is varied – a degree in International Development and African studies where she studied in Ghana through the University of Calgary – a journeyman status in tile setting – and a degree in counselling where she does more spiritual care and spiritual direction. 

Jill’s past awards include being named Honorable Albertan by the Alberta Legislature, Distinguished Alumni by the University of Calgary, and Top 40 Under 40 by Avenue Magazine. Jill always operates from a heart of service – caring deeply about those who struggle and suffer with mental health or addictions, and gives her time to various Calgary agencies helping people. 

Listen in as we talk about:
  • Looking at our vocation. Jill asks us to question what we’re told is our calling vs. what we actually want to do.
  • Struggle is your success. How do we look at success differently? Jill shares how she challenges the ideals around success and shifting young minds and perspectives in the process.
  • Being guided through recovery and filling our own cup up. Jill talks candidly about her struggles with alcohol and drugs and how her path through recovery is what opened up her mind to new possibilities. She shares how she fills her own cup up first and what that looks like for her on a daily basis. 
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Jill shares about how she started to question her vocation. What was she being told was her calling? And what did she actually want to be doing instead? She talks about the power of changing our direction and embracing the unknown. She realized she loved working with people, teaching and continuously learning. By embracing her inner calling, she found her vocation and followed the path to where she is today.


As we move forward, the importance of connection and looking for new ways to facilitate connection will be key. We need to be intentional in ensuring the wellbeing of both teams and individuals. Jill says that a safe work environment needs to be in place; one in which everyone feels heard and understood.


We need to reflect on the things that are challenging for us otherwise we bottle them up and things in our bodies become unbalanced. Jill talks about the importance of looking outwards by doing things like reading and listening (really listening!) to other people. Being caught in a cycle of overdoing and busyness can be connected to an obsessive and unhealthy mindset.

Quote_Struggle is Your Success

“When you enter into an environment that’s a higher vibration environment, where there’s hope for you and acceptance, that’s life changing.”

Jill is one of the co-founders of Struggle Is Your Success. One of the other co-founders, Musap, wanted to reflect on his own journey of immigrating to Canada, as well as the cultural dynamic that he learned around masculinity, education and questioning if this was a cycle he wanted to repeat.

He wanted to change things, and change meant teaching and inspiring other people like him who had the same questions and curiosities.

The hope with Struggle Is Your Success is that it gets them to be able to really feel the possibility that they can do something with where they’re at and with how they think. It gives an opportunity to explore another way of thinking and exposing them to careers that they don’t know exist.

Quote 2_Recovery


“The journey through recovery is to take personal responsibility and do what you need to do to live a different life in every aspect.”

As someone who struggled with drug and alcoholism, Jill learned through her recovery journey how important it was to learn from others and be open to new possibilities. She shares about why outside connections and community are critical, how to know when to set a boundary, and when enough is enough. 

She talks about transforming her life through her deep connection to nature, which she prioritizes every day.

Jill says that observing patterns in nature, as well as the natural disasters or life and death cycles helps her to grow. She’s a big fan of advocating for your own health, because unless something’s really wrong, nobody’s going to do it for you. 

Jill Drader
  • What is something that you would love to learn about or something that you would love to learn how to do? The mechanics of the car and how to restore a car
  • What is a place that is at the top of your travel bucket list? Thailand, Indonesia, and Peru
  • What is a book, podcast, or TV show that you have enjoyed recently? 
  • If you could sit down and have a conversation with someone that you would love to learn from, who would it be? Dr. Wayne Dyer

1:00 Meet Jill Drader

2:50 Jill’s Story

5:00 Jill’s new venture Owl Seek – an executive leadership and retreat platform 

6:50 The role of teaching and learning in Owl Seek

8:15 The best teachers are also learners

10:40 The non-profit Struggle is Your Success, co-founded by Jill, helps youth unleash their potential

17:30 How Jill gives herself permission to change

21:20 How Jill defines recovery and how we all need to recover from something in the interest of growth, stronger connections, and positive mental health

28:50 The importance of building connections 

33:00 How Jill supports her own mental health and fills up her cup

34:30 Jill’s favorite teacher – her high school psychology teacher 

39:00 What Jill is most proud of looking back on her journey so far

41:44 Jill answers some rapid fire questions

44:20 Jill’s words of wisdom 



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