Many businesses talk about implementing systems like Traction and EOS—but far fewer actually follow through with the discipline required to make them work.

In this episode of The Stroke It Podcast, Jenny Townsend shares a raw and honest look at what really happened behind the scenes during her team’s first year implementing EOS—and why simply having the framework wasn’t enough.

For the first six months, the team had the language, the meetings, and the intentions… but they weren’t consistently tracking results or holding each other accountable. It wasn’t until mid-year—when they committed to uncomfortable conversations, ownership, and real follow-through—that things began to shift.

Jenny introduces the concept of “Grind Season,” also known as planting season—the period where the most important work happens long before results show up. It’s the season defined by urgency, discipline, and doing the unglamorous work required to create momentum.

She breaks down how compressing timelines, focusing on a critical number, and leaning into high-effort marketing strategies helped the business go from falling behind to building real traction toward their goal.

You’ll learn why giving yourself too much time can actually hurt performance, how urgency sharpens focus, and what it really takes to execute on systems like EOS in the real world.

If you’re a business owner, entrepreneur, or someone working toward a big goal, this episode is a reminder that success isn’t built when things feel easy—it’s built in the seasons where you choose to show up anyway.

In This Episode

• Why most teams fail when first implementing EOS
• The difference between having a system and actually executing it
• What “Grind Season” (Planting Season) really means for your business
• Why Q1 can determine the success of your entire year
• How urgency eliminates distractions and increases productivity
• The power of setting and focusing on a critical number
• Real examples of grassroots and community-based marketing strategies
• Why compressing timelines can accelerate results
• How accountability and uncomfortable conversations drive growth
• The mindset shift required to create long-term momentum

Order Stroke It now at jennyaldaytownsend.com/book. Your order includes a signed copy, shipping and handling, and great Bonus items!

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Check out more about Jenny Alday Townsend by visiting http://www.jennyaldaytownsend.com

Did you know there are free downloads available on my website? Go to All Products | Jenny Alday Townsend and snag the 4 Ground Rules to Elevate your life. Planning your future? Develop your 1-3-5 and change your life path!

Many people spend decades planning financially for retirement—but very few plan for what life actually looks like after they stop working.

In this episode of The Stroke It Podcast, Jenny Townsend sits down with former CFO turned retirement coach Lisa Haynes to explore the emotional and identity shifts that happen when a career ends and the next chapter begins.

After more than 30 years in corporate America, Lisa Haynes realized retirement isn’t simply about leaving work—it’s about reinventing yourself, rediscovering purpose, and designing a life that still feels meaningful.

They discuss why traditional retirement is changing, why more people are choosing entrepreneurship later in life, and why planning your purpose is just as important as planning your finances.

You’ll learn how to prepare for the transition before retirement arrives, avoid the isolation many retirees experience, and start asking the bigger questions about legacy, fulfillment, and what you truly want your life to look like.

If you’re approaching retirement, considering a career pivot, or simply wondering what your next chapter might hold, this conversation will challenge you to think bigger about what comes after your career.

In This Episode

• Why retirement today looks different than it did for previous generations
• The emotional side of retirement most people never plan for
• How identity shifts when you leave your career behind
• Why many retirees end up “unretiring”
• The importance of rediscovering purpose and passion
• How to reinvent yourself at any stage of life
• Practical strategies like pause before you pivot and stack small wins
• The legacy question everyone should ask themselves

Connect with Lisa Haynes

Website: https://retiredandkillingit.com
LinkedIn: Lisa J. Haynes
Instagram: @retiredandkillingit

Order Stroke It now at jennyaldaytownsend.com/book. Your order includes a signed copy, shipping and handling, and great Bonus items!

Follow the Stroke It Guide on socials to stay connected and to get tips on how you too can get your STROKE on'!

Instagram: https://www.instagram.com/jennyaldaytownsend/

Facebook: https://www.facebook.com/thestrokeitguide

Check out more about Jenny Alday Townsend by visiting http://www.jennyaldaytownsend.com

Did you know there are free downloads available on my website? Go to All Products | Jenny Alday Townsend and snag the 4 Ground Rules to Elevate your life. Planning your future? Develop your 1-3-5 and change your life path!

In this episode of The Stroke It Podcast, Jenny sits down with entrepreneur and operations leader Emily McSherry, founder and CEO of Advize—a platform helping students explore careers through short, coffee chat-style alumni interviews and AI-powered recommendations.

Emily shares how a major pivot accelerated her path: after graduating from UCLA Anderson and getting laid off when her department was cut, she went all-in on Advize at the moment she had the least to lose. She opens up about the real tradeoffs of entrepreneurship—moving, saving, living lean, and choosing long-term impact over short-term comfort.

This conversation goes beyond careers into confidence, relationships, and action. Emily explains why students hesitate to reach out, how shared connections (like being alumni) make networking easier, and why a clear, specific ask changes everything.

Jenny and Emily also talk about health, balance, values, and boundaries—why rest matters, how burnout shows up, and how structuring your time around your values can reduce anxiety and help you work smarter.

They close with practical entrepreneurship lessons: stay close to the customer, test assumptions early, and build what your customer cares about. Emily leaves listeners with a challenge: write down your dream life, step into that identity, and take one aligned action today.

If you’re a student, parent, or professional craving clarity, this episode is a reminder that clarity follows movement—and opportunity can start with one conversation.

Resources Mentioned:

Advize (free student access): students.advizehub.com
LinkedIn: Emily McSherry
Advize Newsletter

Chapters

00:00 – Common ground + connection
01:20 – Meet Emily
03:00 – Layoff → going all in
05:00 – How Advize works
08:30 – Why students don’t reach out
12:30 – Action builds confidence
15:30 – Values + the “thirds” framework
20:00 – Workplace relationships + networking
27:00 – Make a clear ask
37:30 – Entrepreneurship tradeoffs
39:00 – Build for the customer
46:20 – Visualize it, then act

Order Stroke It now at jennyaldaytownsend.com/book. Your order includes a signed copy, shipping and handling, and great Bonus items!

Follow the Stroke It Guide on socials to stay connected and to get tips on how you too can get your STROKE on'!

Instagram: https://www.instagram.com/jennyaldaytownsend/

Facebook: https://www.facebook.com/thestrokeitguide

Check out more about Jenny Alday Townsend by visiting http://www.jennyaldaytownsend.com

Did you know there are free downloads available on my website? Go to All Products | Jenny Alday Townsend and snag the 4 Ground Rules to Elevate your life. Planning your future? Develop your 1-3-5 and change your life path!