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Make 2027 the Year Your Sales Feel Consistent, Not Lucky
One focused day to celebrate how far you’ve come, choose the few things that will actually bring in clients and revenue, and map out a 2027 plan that fits your real life.
Planning Day is Thursday, Dec 3, 2026
You’re busy. You’re posting, showing up and saying yes to things, and it’s still not translating into the sales you want.
You’ve had real wins this year, but you haven’t stopped long enough to celebrate them, let alone figure out why they worked.
You plan big every January, and by spring you realize you signed up for twice what one person can actually do.
And somewhere in the back of your mind is the question: am I even working on the right things?
What if you had protected time to step out of your business, look honestly at your year, and plan the next one with women who get it?
That’s Planning Day.
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!
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.
Femy Praseeth, Sunshine & Chai
I recently pivoted into creative writing and had no idea what my business could look like before joining the Planning Day.
By the end, I had clarity on my bigger vision, a solid problem-solution framework, a detailed project plan, and fresh, creative ideas for marketing my Substack and the business I’m building.
How Planning Day Works
Planning Day Is for You If…
• You’re tired of being busy without knowing what’s actually working.
• You want consistent clients instead of luck.
• You do your best thinking with other women who get it, and you’d love a room full of them to bounce ideas off.
• You know your message and offers (Planning Day), or you’d love a refresh before you plan (Learn + Plan).
If you nodded at even one of these, you’re in the right place.
Come exactly as you are, with your messy notes and big ideas, and we’ll turn them into a plan.
It’s not for you if you’re looking for a shortcut, a done-for-you plan or overnight results.
Planning Day is for women who are ready to make peace with their pace and build something real.
Imagine It’s the First
Monday in January
Instead of wondering where to start, you open your plan, and you know...
- Your 2027 revenue goal, and exactly how many clients it takes to get there.
- You stop wondering if you’re doing the right things, because you chose them on purpose.
- You have 1 to 3 priority projects, and real permission to let the rest go.
- Your marketing is mapped by quarter, so clients come from a plan you understand, not luck.
- Your vacations and family time are in the calendar first, and your business fits around your life.
- You’ve actually celebrated 2026, so you can talk about what you do with pride.
- You show up as a CEO who works with intention, not just effort.
Testimonials
Clerisa Varghese
Before I joined Planning Day, my exposure to business planning was in a corporate setting where you make fancy charts and pull your hair out to obtain the necessary metrics. So, I was concerned whether this planning day was going to be full of FLUFF or not.
It did not disappoint. The BIGGEST WIN for me was the breakout rooms where participants got time to share their marketing ideas and business projects and get insights from peers. WORTH the time and money investment.
Cathy Minz
Planning Day gave me the clarity I didn’t even know I was missing. Seeing the real numbers (my pricing, my capacity, my actual hours) grounded my big dreams and showed me exactly what’s possible with the time I have.
I walked away excited, a little nervous, but more confident and capable than ever.
Alyssa M, Founder of Kalawikk
I walked in with a website and some hope. And walked out with structure around my ideas, a plan and some tangible deliverables that made my business REAL.
I met other wonderful, warm, kind women, all at different stages of their business. Planning Day was a game-changer.
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.
Two Days, One Choice
Day 1 is for learning. Day 2 is for planning. Come to both, or just the one you need.
The Sales & Marketing Masterclass
Wednesday, December 2 · 10am to 4pm ET
Get clear on what you say and what you sell, so your plan has something strong to build on.
• Magnetic Messaging: walk away with a Messaging Map that makes your ideal client think “she gets me.”
• 3 Steps to Sales: see exactly how a stranger becomes a client in your business, and where it’s leaking.
• Magic Intro Offer: design the entry offer that turns interest into paying clients.
• Breakout rooms: test your new message and intro offer with other women entrepreneurs and get real feedback.
Best for newer business owners, or anyone whose messaging and offers need a refresh.
Planning Day
Thursday, December 3 · 10am to 4pm ET
Leave with your 2027 sales and marketing plan done, not “started.”
• Wins & Lessons: celebrate 2026 and decide what to repeat and what to leave behind.
• Capacity & Commitment: set a revenue goal that fits your real hours, energy and pricing.
• Project Planning: choose your 1 to 3 priority projects and map them across the four quarters.
• Your 2-Page Business Plan: dedicated quiet time to finish it, with live hot seats for your questions.
Best for everyone, including returning planners who just want to plan.
Both days include live hot seats, breakout rooms, quiet work time and built-in breaks, with more time to work on your own business than ever before.
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 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 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 29 Spots Remaining*
Toronto Mastermind Day
10am - 5:00pm EST
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
Your Price: $97
Only 50 17 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
Your Price: $127
Only 25 12 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
Your Price: $725
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.
Bree BV
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!
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.
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.
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!
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.”
