Planning Day Begins in...
00
DAYS
00
HOURS
00
MINS
00
SECS
Your 2026 Growth Plan
Built With Clarity and Confidence in Just Two Days
In this interactive 2-day event, you’ll step away from the noise and create a strategic, 12-month plan you’ll actually follow through on.
With my proven process, focused time to think, and fresh ideas from other ambitious women entrepreneurs, you’ll leave with clarity, confidence, and the momentum to make 2026 your best year yet.
Planning Day 2026 is Wednesday & Thursday, Dec 3 & 4, 2025.
Say good-bye to wasting time on busy work that gets you nowhere.
Stop throwing spaghetti at the wall with random strategies and posts that never bring real results.
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. I knew I had the ability to succeed, but I couldn’t figure out why I was struggling.
Jennifer gave me the structure, accountability, and reality checks I needed to focus on what really mattered. With her balance of enthusiasm and grit, encouragement and accountability, I broke through my fear of group programs, launched three in just three months, and increased my revenue by 80% in one year.”
Tera McDonald, Founder of Kalawikk
I wasn't sure at first if Planning Day was 'right' for me. But I’m glad I took the leap. Not only did I learn so much more than I expected in a short period of time, I made connections within the class that are business leads and future friendships . Jennifer broke things down into easy to manage chunks of information, provided space to discuss them with other entrepreneurs and then wrapped it all up leaving me motivated and committed to the best year I can dream up!
Susan McGuire
As research tells us, only 10% of business owners plan. This is one key learning for me and why attending the Planning Day workshop was so critical to my growing business.
I was able to take the time needed to organize my business needs, create timelines, break-down specific activities, and learn even more about marketing and sales strategy. Thanks to Jennifer, I'm feeling clear and confident about next year!
Imagine waking up everyday feeling confident and clear about what you need to do to grow your business.
At Planning Day you’ll create a strategy you actually enjoy following. One that plays to your strengths, aligns with your values, and gets the best results for your effort.
This isn’t about hustling harder. It’s about walking away with a clear, doable plan for the next year and the confidence to stick with it.
👉 And because it’s scheduled, structured, and supported, you’ll finally take the time to work on your business, not just in it.
Here's What Will Happen At Planning Day 2026...
Set Yourself Up for Success Before You Arrive
Before Planning Day even begins, you’ll reflect on your 2025 wins, lessons, and growth. Then you’ll map out your vision, goals, and “big why” so that when we dive in together, you’re already focused, clear, and ready to plan from a place of alignment.
Vision, Messaging, and Sales Strategy
Lay the Foundation for a Focused and Profitable 2026
Day 1 is about getting clear on where you’re headed and building the core strategy that will guide everything you do this year. You’ll set your vision, strengthen your messaging, and learn the sales strategies that actually move the needle.
-
Prep Work Review: Reflect on your 2025 highlights, lessons, and wins, then map your vision, income, leadership, emotional, and growth goals for the year ahead.
-
Profit Centres: Identify the offers you’ll focus on in 2026 so your energy and marketing efforts are streamlined and strategic.
-
Magnetic Messaging: Learn the 5 pillars of messaging and practice them live with the Messaging Map and Coffee Talk Makeovers.
-
3 Steps to Sales: Break down lead generation, nurturing, and conversion so you know exactly how to move prospects into paying clients.
-
Marketing Magic: Explore creative strategies to build your list and generate more referrals with confidence.
-
Project Plan Your Marketing: Choose your #1 marketing strategy for 2026 and map it like a project with milestones, timelines, and next steps.
By the end of Day 1, you’ll know exactly what you’re selling, how to talk about it, and how to start generating consistent clients with clarity and confidence.
Project Planning, Integration, and Bringing It All Together
Turn Your Vision Into a Real Plan You Can Follow All Year Long
Day 2 is where everything clicks into place. You’ll roll up your sleeves and map out the details that make your goals achievable:
-
Morning Reset: Start with biggest takeaways, Q&A, and coaching so you can refine and strengthen what you created on Day 1.
-
Project Planning: Create timelines for your biggest personal and business projects from launches, podcasts, and books to websites, events, and beyond. You’ll see where everything fits so you can stop overloading yourself and start planning realistically.
-
Personal Priorities First: Schedule in vacations, holidays, and the things that matter most, so your business grows around your life (not the other way around).
-
Deep Dive Work Time: Use structured breakout rooms and quiet time to dive deeper into your projects and marketing strategies with real feedback and support.
-
Integration & Roadmap: Pull it all together into one clear business plan, organized quarter by quarter and month by month, so you leave knowing exactly what’s happening and when.
By the end of Day 2, you won’t just have ideas, you’ll have a complete 2026 business plan that balances your goals, your lifestyle, and your growth.
Both virtual days will include...
-
Live hot seats so you can get real-time feedback and coaching on your plan.
-
Breakout rooms with fellow entrepreneurs to spark ideas, share perspectives, and build connections.
-
Quiet time to step away from the noise and finally work on your business, not just in it.
-
Q&A time to get your specific questions answered and remove roadblocks before they stall you.
-
Built-in breaks for lunch and recharging, so you can stay focused and energized all day.
By the end, you won’t just have a plan, you’ll have new ideas, new connections, and renewed confidence in your path forward.
Testimonials
Priya Sam, Story Architect
“I went from overwhelm and no plan… to launching my first webinar and group program.”
Before working with Jennifer, I had a lot of ideas but no business plan or structure to bring them to life. It felt overwhelming, and I didn’t know where to start.
Through our work together, I gained clarity and a concrete plan. When we were preparing my first webinar, I could finally see how all the pieces fit together. That plan gave me the confidence to launch my first group program and it’s continued to grow and expand ever since.
Jennifer helped me lay a solid foundation for my business that I’ll continue to build on as I grow and scale my group program and 1:1 services. Working with her was truly a game changer!
Cheryl Kuchek, Founder Imagination DeZigns
“I went from imposter syndrome and burnout… to feeling confident, free, and excited again.”
When I came to Jennifer, I had lost confidence in myself and my direction. I felt heavy, stuck in imposter syndrome, and convinced I had to keep fighting and hustling my way forward.
Through Jennifer’s guidance, I realized I didn’t need to keep proving myself, I could allow things to come to me, stand in my worth, and show up differently. That shift changed everything.
I stood up for myself, asked for what I wanted, and got it. 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! I'm happy to have been a part of it and get the clarity of what I'm doing right and what else I can do to grow my business next year!
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 2 engaging days with great content, speakers and opportunities to plan and troubleshoot. It will be amazing year. Thanks
Special Guest Speaker
From doing her business planning homework on bare floorboards… to leading 17 clinicians 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.
Testimonials
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 for me. As an accidental entrepreneur I've spent more time doing my work (coaching) v.s. growing my business AND no brainer this = no growth! Now I feel like after years in my career floundering, I have a powerful new mindset and a completed marketing plan to springboard into next year! Best time and money I've spent on my biz all year! Thank you!
Erin Bouchard
I absolutely love planning days with Jennifer. They are the perfect time to get out of your business and focus on the big picture.
Jennifer is the right coach to facilitate these planning days.
She's high energy, and knowledgeable but also straight to the point to keep us on track.
It provides a great combination of learning, personal reflection, and talking it out with like-minded business owners.
TORONTO
MASTERMIND
Friday, Dec 5, 2025
If you’ve ever wished you could take the clarity and momentum from Planning Day and lock it in with even deeper support, this day is for you.
You’ll gather in an intimate group of just 10 entrepreneurs who’ve gone through the same two-day process, which means everyone comes to the table speaking the same language and focused on their 2026 vision.
Here’s what’s waiting for you:
✨ Hot-seat masterminds — get focused feedback, fresh ideas, and honest discussion on your business challenges and opportunities.
✨ New professional headshots — captured by my favourite photographer, Mike Day, so you walk away with fresh images to match your refreshed vision.
✨ Delicious, nourishing food + meaningful connection — because great conversations happen best over a shared meal.
✨ True community — yes, hugs included, along with laughter, insights, and the joy of being in a room full of women who get it.
You’ll leave with sharper strategy, renewed confidence, 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
Toronto Mastermind Day
10am - 5:00pm EST
Early Bird Pricing On Until Nov 16
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 tickets available
Planning Day VIP
- Everything in Planning Day Virtual plus...
- Lifetime Access To Recordings
- BONUS: 2026 Kickstart Call in January
-
BONUS: Discover Your Super Power Training
- BONUS: Become An Abundance Magnet Training
Total Value: $2136
Regular Price: $127
Early Bird: $99
Only 25 tickets available
Planning Day Virtual + Toronto Mastermind
- Everything in VIP Plus...
-
1-Day Mastermind in Toronto, Dec 5
-
Professional Headshots with Mike Day
-
Delicious Healthy Lunch & Snacks
-
Small-Group Feedback + Breakthroughs with Only 10 Peers
Total Value: $4232
Regular Price: $725
Early Bird: $625
Only 10 tickets available
MEET YOUR GUIDE
Hi, I’m Jennifer Trask
For the past seven years, I’ve led hundreds of women service providers through Planning Day, helping them cut through the noise, get laser-focused, and create clear, actionable strategies that actually move their businesses forward.
This isn’t about cramming more onto your plate or chasing every shiny idea. Our proven Planning Day process is designed to help you identify what really matters, build a strategic plan you’ll actually stick to, and approach the year with clarity, confidence, and momentum.
As a catalyst for change, you don’t just need more ideas, you need a framework that ensures you can implement them without burning out. That’s exactly what we’ll build together.
Planning Day is one of my favourite events to host because of the transformation that happens every single time.
I look forward to guiding 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.
🌎✈️ 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.
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
I found the prep work for this workshop really helpful to get me thinking, reflecting and able to get more out of this planning workshop.
I loved how actionable the material is and that I feel like I am well on my way to having a plan on what the next year will look like for success in my business.
Jennifer has an amazing and encouraging energy and I was so inspired by all of the incredible business owners who were also in this workshop!
Kim Cheel
Over the last year I launched my new website, was in my first book acknowledgement, was told by a publisher they were impressed by my developmental editor work for a client they signed.
I finished my quiz, re-discovered the joy of writing just for me, got better at manifesting, had a lot of manuscript assessment clients, finished a manuscript for a ghostwriting client (and she loved it and is starting to work on her next book!)
And finally, I'm happy to announce that I'm no longer living paycheque to paycheque!
GET BETTER RESULTS BY DOING LESS & FOCUSING ON WHAT MATTERS MOST
FOR 2026
The Planning Day process is designed to strip away the busywork and shiny-object distractions that keep entrepreneurs spinning their wheels.
Over two days, you’ll:
- Identify the projects and strategies that actually drive growth
- Cut out the clutter that drains your time and energy
- Map out a plan that feels clear, doable, and motivating
You’ll leave with a focused 2026 strategy, the confidence to follow through, and the excitement of knowing every step you take is moving your business forward.
JOIN PLANNING DAY 2026