From Daydreams to Doing: A Candid Conversation with Tamara Kroeker

Meet Tamara Kroeker, one of our host partners and this weeks Pop CoLab #PopStar.

Tamara is an Enneagram coach and teacher who left her comfort zone to pursue true freedom for herself and everyone she works with. In her revealing interview with Pop CoLab, Tamara shares how creativity, self-awareness, and a touch of play can transform your life and career goals.

“My goal isn’t to get everyone to quit their job but to uncover the best versions of themselves in and outside of the workplace. It’s not about what we do, it’s about becoming our best selves in whatever we do—that is true freedom!”

Inspiration

Can you share the story of how you turned your dream into reality? What were the first steps you took?

The short answer is: I woke up one day and realized I would rather be five years into what I really want to do than start something in five years.

The longer answer is: I’ve been growing and learning about myself for two decades using the Enneagram, therapy, and so many other wonderful modalities that woke me up to patterns that were no longer serving me. One of those patterns was staying comfortable in a job I didn’t hate but didn’t love.

The most freeing day of my life was the day I finally said to myself, “I need to quit my job.” Everything after that point has been a dream - choosing to start a business, growing my vision and offerings, meeting people and working towards my goal - bringing the same freedom I experienced into organizations in Winnipeg and the wider Canadian landscape.

My goal isn’t to get everyone to quit their job but to uncover the best versions of themselves in and outside of the workplace. It’s not about what we do; it’s about becoming our best selves in whatever we do - that is true freedom!

What inspired you to pursue your dream, and how did you stay motivated during the journey?

My inspiration started with me. I knew I wanted more in my life, more freedom, more creativity, more everything! As I began living as a truer version of myself, I realized I wanted the same for everyone I met. By getting my expectations and assumptions out of the way I was able to open my mind to the creativity and curiosity of everyone around me. People are amazing - they motivate and inspire me to continue growing and creating!

What role did creativity and play have in shaping your success?

Creativity blooms out of every moment when you start a business - it has to! The days I feel the most stuck are the days when I get fixated on one way to move forward. When my mind is open to creative and out-of-the-box solutions, anything is possible, and the best things happen!

Overcoming Challenges

What was the biggest challenge you faced while pursuing your dream, and how did you overcome it?

The biggest challenge for me was the process of dreams coming true. When I quit my job, I thought, give me a couple of months, and everything will be sorted out - hahaha! I used to think every meeting would end in a contract and every tweak to my website would be the last. When I stopped waiting for the arrival point and began enjoying the moments of process, my stress began to decrease, and my joy and freedom grew exponentially!

How do you handle fear of failure or self-doubt when chasing big goals?

Day by day. I believe in becoming an example for what I am teaching. I am in the process just like everyone else - no one has figured it all out. The best lesson I’ve learned is to be honest about moments of fear and self-doubt and share them with people you trust. Life isn’t about avoiding or mastering tough moments; it’s about learning to ride the highs and lows with the people in your corner.

Can you share a moment when things didn’t go as planned? How did you pivot or adapt?

I suppose this whole endeavour didn’t go as planned. When I started my company I thought I would do workshops and coaching - I was basically overlaying my previous job as a teacher onto my current job because it was what I knew! As I had conversations with people and got to know the needs of organizations, I realized that what I offered was co-created with the people in front of me.

The one thing that has stayed, and will always stay, is, I care about people being seen and heard. Everything else can be adapted so that objective can happen most effectively.

Practical Tools & Tips

What advice would you give to someone struggling to figure out what their dream truly is?

This is a great question and actually a byproduct of what I do!! When you’re struggling to figure out what you want to do it’s often because you’re spending more time thinking about what others want you to do than what you really like and want. So … spend time figuring yourself out! Find a tool like the Enneagram, journal, talk to friends, try a bunch of new things, learn who YOU are and the rest will happen naturally.

What are the top three habits or practices you recommend for staying focused on your goals?

I’ve been through a lot of different habits and practices over the last few years - some are helpful, and some get abandoned within days. The practices that I seem to always come back to are some form of alone time and journaling. I need time and space with me, myself and I, to refocus and tune into what I really want. When I am centred on who I am and what I value, my work and my goals follow suit.

Are there specific tools, resources, or techniques you use to bring your ideas to life?

I use the Enneagram a lot in my planning. The Enneagram is a personality system so I use it to imagine my ideal customer along with their wants and needs. I also use a lesser-known Enneagram system known as the Process Enneagram. The Process Enneagram is an exploration of the natural progression of human development and growth. This system helps to process problems and get curious about patterns. Both systems help to ground me in what the real issues are I’m trying to solve and give me step-by-step processes to move me towards new ideas and solutions.

How do you set actionable goals while still dreaming big?

My favourite method of goal-setting is through a system I used to use in education, referred to as backward design. I start with my biggest dreams and goals and work my way backwards to my current moment in time. This system helps me see the practical steps I need to take now to see my dreams realized in the future.

Collaboration and Support

How important is community or collaboration in making a dream come true?

It’s everything. “We need you and we need each other because together we can do more.” No one operates in a vacuum, even solopreneurs. Every achievement builds on countless small interactions and support from others - whether it's advice, encouragement, collaboration, or simply being part of a wider network that opens new doors and opportunities.

How can someone find the right mentors, partners, or supporters to help along the way?

This is a great question. Not everyone is the right fit for one another - even when it comes to mentors, coaches or therapists. Trust yourself when you meet someone - do you feel supported and seen? We shouldn’t be looking for a bunch of “yes” people in our lives - sometimes we need to have difficult conversations - but I know difficult conversations go a lot better when I trust that the person I’m confiding in believes in me and my business.

What advice do you have for maintaining balance between following a dream and managing other responsibilities?

It’s always a balancing act. Some weeks you do more dreaming than doing and other weeks it’s the reverse. Keep your dreams at the forefront of your mind as you grow your business and forgive yourself when you have an off week.

The Role of Play and Creativity

How do you use creativity and play to fuel your goals and navigate obstacles?

To me, play is the lightness of life, its the moments that we realize nothing is as serious as we thought it was, it’s laughing at something instead of crying, it’s being curious about mistakes instead of punishing, it’s letting life be the quirky path that it is and skipping along with it. With lightness comes an ability to see beyond obstacles, to see what is possible and engage with solutions more creatively.

Can you suggest fun exercises or activities to help participants spark inspiration and dream bigger?

When I used to work as an elementary teacher, I used games and competition to add excitement and energy to any lesson - how many jumping jacks can you do in a minute? The same principle works just as well with adults.

Do a brain dump. Set a timer and write down as many words you can think of for past success or current problem - no judgment or assessment, just dump them out (maybe grab some paint pens or crayons to make it fun.)

Challenge a friend to a “post-off” on social media - 30 days of engagement in a row; comment or repost for one another and track the growth; or maybe an account take-over!

And my regular and favourite way to add fun … grab some markers, stickers and a fun notebook for your next task or to-do list - life doesn’t need to be that serious!

Encouragement and Reflection

What’s one piece of advice you wish you’d received when you started pursuing your dream?

I wish instead of people telling me - “starting a business takes a long time” - I heard, “enjoy the ride, every little moment is what running a business is all about.”

What does success mean to you, and how do you celebrate milestones along the way?

“Success is liking yourself, liking what you do, and liking how you do it.” Maya Angelou

I keep a folder in my photos full of little moments of success for anything and everything that makes me feel like I’m moving towards my dream.

If someone feels their dream is unattainable, how can they reframe their thinking to make it feel achievable?

Check-in with your body and see how it feels when you say your dream out loud. What makes you think your dream is unattainable? Is it you or someone else? Because the only opinion that matters is yours.

How do you keep the momentum going after achieving a big goal? What’s next for you?

Celebrate with someone!! Invite someone into your successes. It will not only fuel your next idea but theirs too!

What’s next for me is capitalizing on my momentum. I’ve used 2024 to build connections and awareness for my passion - self-development work at work! I firmly believe self-awareness is the link to success in all areas of our lives - when we know more, we do more.

For 2025, I’ll be focusing on deepening client relationships, scaling my workshops and assessments, and expanding my influence in Winnipeg and beyond. I have many dreams and plans in the works for expansion and growth to contribute to the every-changing landscape of leadership development and help create long-lasting transformations in this field.

Lastly, If you could turn any childhood hobby into a full-time career, what would it be?

Crafting. (I did for a bit during covid … might need to do it again)

Better Together: Nine Perspectives on Collaboration

Discover how the Enneagram can transform the way you work with others in this engaging and interactive workshop. "Better Together" dives into the nine different ways people approach collaboration and teamwork, helping you understand the motivations, strengths, and blind spots of each type. You’ll gain practical insights to elevate your team's dynamics while having some fun along the way.

Want to experience Tamara's Workshop, Better Together: Nine Perspectives on Collaboration? Let's Talk