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Step Into 2026 With a Plan You Feel Excited and Confident About
In just two days, you’ll leave feeling clear, focused, and ready to grow.
Join an inspiring 2-day experience designed to help you think bigger, plan smarter, and step into 2026 feeling clear, confident, and ready for growth.
Together, we’ll turn your big ideas into a clear, energizing plan, supported by proven strategy, intentional reflection, and inspiring conversations with other ambitious women entrepreneurs.
Planning Day 2026 is Wednesday & Thursday, Dec 3 & 4, 2025.
Spaces are intentionally kept small so every conversation is meaningful. Reserve your seat today and get ready to plan your next level with clarity and joy.
Lead your growth with intention.
Discover the strategy that keeps your message clear, your actions focused, and your results growing month after month.
Join us for Planning Day, Wed & Thurs, Dec 3 & 4, 2025
Testimonials
Anna de Acosta, Mindset Coach
This was the most value I’ve gotten from any online event ever! And I’ve been to a lot! Thank you so much. My mind is blown!
Leslie McDaniel, Coach & Consultant
Before working with Jennifer, I felt stuck, relying on sheer willpower and self-discipline that always left me discouraged.
With her structure, accountability, and reality checks, I launched three group programs in just three months — and grew my revenue by 80% in one year.
Tera McDonald, Founder of Kalawikk
I wasn’t sure if Planning Day was right for me but I’m so glad I took the leap.
I left with practical strategies, new business leads, meaningful connections, and the motivation to create my best year yet.
Susan McGuire
Only 10% of business owners plan and Planning Day showed me why it’s essential.
I finally had the space to organize my business needs, create timelines, break-down specific activities, and learn even more about marketing and sales strategy.
Now I feel confident and ready for the year ahead.
Picture starting every day inspired, focused, and confident about how you’re growing your business.
During Planning Day, you’ll craft a strategic plan that aligns with your strengths, values, and goals and feels energizing to implement.
It’s not about doing more; it’s about doing what matters most.
👉 With dedicated time, structure, and support, you’ll step out of the daily busyness to think strategically, plan intentionally, and move forward with confidence.
Here's What Will Happen At Planning Day 2026...
Arrive to Planning Day with Clarity, Confidence, and Momentum Already in Motion
You’ll spend intentional time reflecting on your growth, celebrating your wins, and refining your 2026 vision so when Planning Day begins, you’re already grounded, inspired, and ready to lead your next chapter with purpose.
Vision, Messaging, and Sales Strategy
Lay the Foundation for a Focused and Profitable 2026
Day 1 is all about aligning your big-picture vision with a clear, confident strategy that reflects your next level of leadership and success.
You’ll refine your vision, elevate your messaging, and strengthen the sales systems that help you grow with clarity and ease.
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Prep Work Review: Celebrate your 2025 wins and finalize your 2026 vision and goals with clarity, confidence, and alignment.
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Profit Centres: Focus on the offers that drive your 2026 growth so your marketing stays clear, strategic, and effective.
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Magnetic Messaging:Deepen your mastery of the 5 pillars of messaging and practice them live with the Messaging Map and Coffee Talk Makeovers so your words connect naturally and powerfully with the right clients.
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3 Steps to Sales: Strengthen your client journey from lead generation to conversion so your sales process feels natural, not forced.
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Marketing Magic: Discover creative ways to grow your audience and attract aligned clients through connection, collaboration, and confidence.
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Project Plan Your Marketing: Turn your top 2026 strategy into a clear, actionable roadmap with milestones and momentum built in.
By the end of Day 1, you’ll feel deeply aligned with your goals, clear on your client pathway, and confident in the systems that will keep your growth flowing all year.
Project Planning, Integration, and Bringing It All Together
Turn Your Vision Into a Clear, Actionable Plan for 2026
Day 2 is where everything comes together. You’ll refine the details, organize your priorities, and create a practical plan you feel confident following all year long:
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Morning Reset: Begin with takeaways, Q&A, and coaching to strengthen and refine what you created on Day 1.
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Project Planning: Map timelines for your biggest business and personal projects such as launches, podcasts, books, events, and more, so everything fits with focus and flow.
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Personal Priorities First: Schedule vacations, holidays, and what matters most, designing your business to grow around your life.
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Deep Dive Work Time: Use structured sessions and focused time to move projects forward with live support and feedback.
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Integration & Roadmap:Bring it all together into one clear business plan, organized by quarter and month, so you leave with clarity, confidence, and momentum.
By the end of Day 2, you’ll have a complete 2026 plan that aligns your goals, lifestyle, and growth and the confidence to bring it to life with ease.
Both virtual days will include...
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Live hot seats Get real-time coaching and feedback to refine your plan and strengthen your next steps.
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Breakout rooms Connect with fellow entrepreneurs to share insights, spark ideas, and build meaningful relationships.
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Quiet time Step back from daily distractions to think strategically and move your business forward.
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Q&A time Ask specific questions, gain clarity, and clear any obstacles with guided support.
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Built-in breaks Recharge and refocus throughout the day so your energy and creativity stay high.
By the end, you’ll walk away with a plan you feel confident implementing plus new ideas, connections, and inspiration for your next level of growth.
Special Guest Speaker
From doing her business planning homework on bare floorboards… to leading 17 staff across two thriving locations (with a third on the horizon), Katie Michaud has built something extraordinary in just two years.
At Planning Day, you’ll get to hear Katie’s story firsthand. Not as a glossy highlight reel, but as a real case study in what it actually takes to build a business that grows quickly and sustainably.
She’ll share:
✨ The messy middle moments (and how she got through them)
✨ The marketing + sales strategies that fueled her rapid growth
✨ How she overcame confidence blocks that nearly kept her small
✨ The biggest risks she took and what made them worth it
✨ What she’d do differently if she was starting all over again
Katie’s journey will inspire you, but more importantly, it will give you practical insights you can bring into your own 2026 plan.
This is your chance to learn directly from someone who’s walked the path and is still walking it with courage, clarity, and big results.
TORONTO
MASTERMIND
Friday, Dec 5, 2025
Refine Your Strategy. Deepen Your Confidence. Expand Your Community.
If you’re ready to take the clarity and momentum from Planning Day even deeper, this intimate in-person mastermind is for you.
You’ll gather with a small group of 10 accomplished women entrepreneurs who’ve completed the two-day experience all aligned around the same 2026 vision and language of growth.
Here’s What’s Waiting for You:
✨ Hot-Seat Masterminds
Refine your sales strategy, receive focused feedback, and explore new perspectives that elevate your next level of results.
✨ Professional Headshots
Captured by my favourite photographer, Mike Day, so you leave with fresh images that match your refreshed confidence and brand.
✨ Nourishing Food + Meaningful Connection
Enjoy a beautiful meal and heartfelt conversation with like-minded entrepreneurs who inspire and support your journey.
✨ True Community
Yes, hugs included. Expect laughter, insight, and the joy of being surrounded by women who get it and get you.
You’ll leave with sharper strategy, renewed self-trust, and deeper relationships that will continue to support you throughout 2026.
Toronto Testimonials
“Planning Day is a gift of self-care. Making the commitment to work ON your business as you take a short break from working IN your business is the gift that keeps on giving. I found the combination of different activities, break out rooms and guest speakers a brilliant combination! I loved the addition of the Toronto Integration Day. It was warm, inviting and personal. It was a great use of time and such a fun, creative and meaningful way to look at planning.”
-Suzy Rosenstein, Midlife Coach & Podcast Host
"The Mastermind Day is my favourite out of the Planning Day workshop. Its a day to not only "integrate" the info we learned but also to integrate the energy of it and getting to spend a whole day with Jennifer is truly inspiring and pumps you up.
Jennifer is a walking example of living a life and running a business not just through passion but fulfillment and happiness. It is a joyous journey and it is possible for all of us."
- Magda Juliana Diaz, Mentor & Coach
“As a mom of five, it's hard to find the space in my home and uninterrupted time for planning my business. So just getting away and being with other women for a day is so powerful. The connections you make, the deep conversations that you can have, it's unlike any other environment.
Jennifer does a really great job at creating a safe space where you can fully be yourself. I felt supported and witnessed in the group by the incredible women. It was a privilege to be there in person among them."
- Anna de Acosta, Intuitive Guide
“The Planning Mastermind Day in Toronto was one of the highlights of my year. There is something magical when a group of women come together to encourage and support each other.
Jennifer curated a perfect day of connection with business and personal growth - at times light-hearted, at times down-to-business, and always captivating and joyous. Thank you Jennifer, for creating a day to celebrate and boost my business. A perfect way to wrap up the year."
- Chris Swail, Life Coach
“The Toronto Mastermind Day was an incredible experience surrounded by such inspiring entrepreneurs.
There was a lot of great sharing and good laughs. I learned that I need to stop listening to the outside chatter and focus on my goal to help my clients.
This day set me up for success next year because it helped me break through my limiting beliefs. I realized that being among like-minded entrepreneurs is key to supporting each other throughout this remarkable journey."
- Tanya Cullen, Dietician
"The Toronto In-person Day was amazing. I loved the opportunity to network with other amazing business owners trying to make a difference in the world.
I enjoyed the pace and the discussions.
If you want to feel energized for your next business year, you MUST attend this event. So worth it!
Thanks Jennifer for coordinating and facilitating this wonderful event. I'm looking forward to next year's In-Person Event."
- Lynn MacDonald, Consultant & High Performance Coach
Your Vision Deserves More Than a To-Do List. Let’s Build a 2026 Plan You’ll Stick With.
Planning Day 2026
Join us online via Zoom on
Wed & Thurs, Dec 3 & 4, 2025
10am EST - 4pm EST
*Only 75 60 Spots Remaining*
Toronto Mastermind Day
10am - 5:00pm EST
Early Bird Pricing On Until Nov 16
Spaces are intentionally limited to keep Planning Day intimate and high-impact. If this feels like your next step, now’s the perfect time to reserve your seat.
Planning Day Virtual
- Prep Work Package
- 2 Full Days of Interactive Planning with Hot Seats, Breakout Rooms & Quiet Time
- Your 2026 Strategic Business Plan Framework
Total Value: $1,391
Regular Price: $97
Early Bird: $75
Only 50 38 tickets available
Planning Day VIP
- Everything in Planning Day Virtual plus...
- Lifetime Access To Recordings
- BONUS: 2026 Kickstart Call in January
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BONUS: Discover Your Super Power Training
- BONUS: Become An Abundance Magnet Training
Total Value: $2136
Regular Price: $127
Early Bird: $99
Only 25 22 tickets available
Planning Day Virtual + Toronto Mastermind
- Everything in VIP Plus...
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1-Day Mastermind in Toronto, Dec 5
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Professional Headshots with Mike Day
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Delicious Healthy Lunch & Snacks
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Small-Group Feedback + Breakthroughs with Only 10 Peers
Total Value: $4232
Regular Price: $725
Early Bird: $625
Only 10 2 tickets available
Testimonials
Heather Beck
This past year I surpassed my client goals, l landed my first 5 figure deal and had a ton of fun planning some speaking events - and executing them.
I also said NO to 2 different opportunities, as they didn't 'feel' right. This was huge for me!
I did all of this while also going on my regular bike rides and prioritized staying regulated emotionally.
Meghan Conway
My business now feels like it's just an extension of me. It doesn't even feel like it's necessarily a business. It's just a joy.
Within a few months I had four Ikea kitchens booked. Between September to December I did six Ikea Kitchens and about five to six online design plans.
Bree BV
The prep work was so helpful. It got me reflecting and made the workshop itself even more impactful.
I loved how actionable everything was, and I finally feel on my way to having a clear plan for success next year.
Jennifer’s encouraging energy and the inspiring group of business owners made it an incredible experience!
Kim Cheel
In the past year I launched my new website, was acknowledged in my first book, and even received praise from a publisher for my developmental editing work.
I completed my quiz, re-discovered the joy of writing for myself, and supported multiple clients through manuscript assessments and ghostwriting projects. Best of all—I’m no longer living paycheque to paycheque!
MEET YOUR GUIDE
Hi, I’m Jennifer Trask
For the past seven years, I’ve had the privilege of guiding hundreds of women service providers through Planning Day, helping them focus on what truly matters, create clear, strategic plans, and step into the year with calm confidence and renewed excitement for their business.
Planning Day isn’t about doing more or chasing every idea. It’s about doing what moves the needle with purpose and joy. Using a proven framework, we’ll map out a plan you’ll feel genuinely excited to follow, one that supports your goals and your wellbeing.
As a catalyst for change, I know that real growth comes from clarity, focus, and aligned action, not hustle. That’s exactly what we’ll create together.
Planning Day is one of my favourite experiences each year because of the transformation that happens when women come together, reconnect with their vision, and leave ready to lead their next chapter.
I can’t wait to guide you through it.
If You’re New to Me, Hello and Welcome!
I’m Jennifer Trask, and in addition to my well-earned “in the trenches” degree in entrepreneurship (from building my own business and helping over 2350 of clients and customers grow theirs), here are a few “official” facts you might like to know:
⭐️ Voted Toronto’s Best Life Coach (2019 & 2020) and Toronto’s Best Business Consultant (2022 & 2023) by Toronto Star Readers.
👩🏻🎓 Holder of a Bachelor of Commerce in Marketing and an MBA in International Business.
🙋🏻♀️ Certified NLP Practitioner with a passion for mindset and transformation.
🙌🏻 ’m also proud to give back through my volunteer work with North Star Startups, where I mentor entrepreneurs weekly on mindset, strategy, marketing, and messaging. I co-created the organization’s Mindset Curriculum, which equips founders to move past self-doubt, strengthen resilience, and grow with confidence.
🌎✈️ A lifelong lover of entrepreneurship and adventure, I lived the digital nomad lifestyle for three years across Australia, South America, and the US. And I’m heading out again in 2026 for another year of work + travel! So far, I’ve explored 27 countries, and lately I’ve been enjoying road trips across beautiful Ontario
☕️🍁 Coffee + autumn are my happy place. Give me nature’s rainbow of fall colours and a steaming mug, and I’m in heaven.
💫 When I’m not coaching clients or leading members inside The Joyous Journey, you’ll probably find me at a local café, cycling, or sitting by the water in a Muskoka chair feeling deeply grateful.
GET BETTER RESULTS BY DOING LESS & FOCUSING ON WHAT MATTERS MOST
FOR 2026
The Planning Day process is designed to help you focus on what truly moves your business forward and simplify your strategy for sustainable growth.
Over two days, you’ll:
• Identify the projects and strategies that create the biggest impact
• Streamline your efforts so your time and energy are used intentionally
• Map out a plan that feels clear, achievable, and inspiring
You’ll leave with a focused 2026 strategy, renewed confidence in your direction, and the excitement of knowing every step you take is creating meaningful progress in your business.
JOIN PLANNING DAY 2026Testimonials
Mary Ellen Flesher
Planning Day was Awesome! I got so much out of the 7+ hours including more clarity on my niche, great ideas for marketing and a lot of motivation going into next year. Jennifer is an excellent business coach who has many helpful answers and creative ideas when you're stuck.
Francesca Massi
Within 1 week of our conversation I built my online store which I have been wanting to do for a year!
Josie Smith
Planning Day was a total game changer! As an accidental entrepreneur, I used to spend all my time coaching instead of growing my business and of course, that meant no growth.
Now I have a powerful new mindset and a complete marketing plan to springboard into next year. Best time and money I’ve spent on my business all year!
Erin Bouchard
I absolutely love Planning Days with Jennifer! They’re the perfect chance to step out of the day-to-day and focus on the big picture.
Jennifer brings the ideal mix of high energy, deep knowledge, and straight-to-the-point guidance that keeps us on track. It’s the best combination of learning, reflection, and connecting with like-minded business owners.”
Priya Sam, Story Architect
I went from overwhelm and no plan… to launching my first webinar and group program.
Jennifer helped me create a clear plan, gave me the confidence to execute it, and laid the foundation I’m now building on as I scale my business.
Working with her was a game changer!
Cheryl Kuchek, Founder Imagination DeZigns
When I came to Jennifer, I had lost confidence in myself and my direction. I felt like an imposter and was convinced I had to keep fighting and hustling my way forward.
Through Jennifer’s guidance, my confidence came back in a whole new way... not arrogant, but grounded.
I’m finally taking time off, enjoying my business again, and showing up with energy and freedom I never thought possible.
Roxana Radescula, Leadership Coach & Trainer
This is my second year attending Planning Day with Jennifer and it's even better than last year!
Jennifer's insights and training, the group discussions, breakout rooms, handout, speakers, everything is so well thought and prepared!
Marianne Preston
I feel more energized, focused, excited and prepared for next year!
This was a fabulous opportunity to plan. Jennifer’s skill and experience set the stage for two engaging days with great content, speakers and opportunities to plan and troubleshoot. It will be amazing year.
