Lead Through Anything Without Losing Yourself
Leading While Lifing™ Intensive
A one-day intensive for executives navigating leadership through life’s hardest seasons—aging parents, health challenges, loss, uncertainty, or simply the weight of holding it all together.
You’ve mastered leading teams, driving results, and making high-stakes decisions. But no one prepared you to do all of that while your personal life demands everything you have. This isn’t about work-life balance. This is about staying whole when both worlds are pulling you in different directions.
The Unseen Burden of Leadership
You're Not Struggling. You're Managing the Unmanageable.
Behind your composed exterior, you might be:
- Supporting aging parents while running a department
- Managing a health diagnosis while meeting quarterly targets
- Processing grief while leading your team through change
- Holding your family together while holding your organization together
- Wondering how long you can keep performing at this level
You’re not alone. And you don’t have to choose between leading well and living fully.
What This Workshop Offers
A Rare Pause. A Clear Path Forward.
Leading While Lifing™ is a one-day workshop designed specifically for leaders who are carrying more than most people ever see. This isn’t therapy. It isn’t traditional leadership training. It’s a strategic session to help you align your work, energy, and priorities so you can sustain your leadership without sacrificing yourself.
In six focused hours with other leaders who understand, you’ll gain:
- Clarity on what this season of your life truly requires
- Permission to redefine success in ways that honor both performance and wellbeing
- Tools to identify what work matters most and what can take a gentler pace
- Community with peers who are navigating similar challenges
- A plan to move forward with intention, not just survival
What You'll Walk Away With
What Changes After This Day
By the end of this intensive, you will have:
A Strategic Lifing Plan
A personalized roadmap that clarifies your priorities, identifies what you can delegate or defer, and outlines how you’ll protect your energy and focus for what matters most—at work and at home.
Redefined Success Metrics
A clear idea for what success looks like now, not according to outdated expectations or someone else’s definition. You’ll leave knowing exactly what “good enough” means and why that’s actually strategic.
A Sustainable Support System
Concrete strategies to build and activate your support network—at work, at home, and in your broader community. You’ll know exactly who to ask for help, how to ask, and what specific support you need.
A Peer Network That Gets You
Connection with other leaders who understand what you’re facing. No explanations needed, no judgment, just genuine understanding and shared experience that continues beyond this day.
Permission to Lead Differently
The mindset shift that allows you to lead authentically instead of performing invincibility. You’ll understand how vulnerability is a leadership strength, not a weakness.
Clear Next Steps
You won’t leave this workshop inspired but unclear. You’ll have specific actions to take in your first week, first month, and first quarter that will immediately change how you’re managing your dual reality.
Keep Showing Up Without Burning Out
Before This Workshop:
Feeling like you're constantly performing strength you don't feel
Questioning whether you can sustain this pace much longer
Struggling to focus on strategy when personal challenges consume your mental space
Isolated in your experience, unable to be fully honest about the toll it is taking on you
Guilty about not giving 100% to work or 100% to life
Exhausted from pretending everything is fine
After This Workshop:
Clear on what you need to thrive, not just survive
Confident in your redefined version of success and high performance
Equipped with practical tools that work in real-world constraints
Connected to peers who genuinely understand your reality
Freed from the burden of doing it all perfectly
Energized by a sustainable path forward that honors all of who you are
Is This Intensive Right for You?
This Workshop Is for You If...
You're an executive or entrepreneur with significant leadership responsibilities
You're currently navigating a challenging personal situation while maintaining your professional role
You're committed to both your career and the people/circumstances that need you outside of work
You're looking for strategic solutions, not just sympathy
You're ready to lead authentically instead of performing invincibility
You want to be in community with other leaders who understand what you're facing
**This Workshop Is NOT for You If…
You're looking for clinical therapy (we'll provide resources, but this is a leadership workshop)
You want someone to tell you to quit your job or abandon your responsibilities
You're seeking a magic solution that erases your challenges
You're not ready to be honest about what you're carrying
WHAT’S INCLUDED
Everything You Need for a Transformative Day
Your Investment Includes:
Six hours of intensive, focused work in an intimate setting (maximum 50 participants)
The Leading While Lifing™ framework and workbook to guide your planning
Lunch and refreshments throughout the day
Premium venue designed for focus and comfort
Access to a private online community of workshop alumni for continued support and connection
Optional VIP Experience:
Upgrade to include an intimate dinner with Terra Winston (limited to 10 participants). Extend the conversation in a private setting with peers, gain additional coaching insights, and build deeper relationships with fellow leaders navigating similar journeys.
WHY TERRA WINSTON
Led by Someone Who Understands Both Boardrooms and Real Life
Terra Winston brings 25+ years of experience coaching Fortune 100 executives, tech founders, and emerging leaders through their most challenging professional and personal moments. As Principal of inTerract, she’s worked with leaders at Google, PepsiCo, Deloitte, Abbott, NBCUniversal, and dozens of other organizations where performance expectations are relentless and personal challenges don’t pause for quarterly earnings.
What makes Terra different:
- She combines “hard” business skills (Systems Engineering, Stanford MBA) with deep coaching expertise (ICF certified)
- She’s coached executives through every life challenge imaginable—and knows the difference between what sounds good and what actually works
- She creates space for honest conversation without judgment while maintaining focus on practical solutions
- Her clients describe her as a strategic thought partner and the coach who “helps me be honest with myself”
Terra designed Leading While Lifing™ because she kept seeing the same pattern: brilliant, capable leaders pushing themselves to the breaking point. This workshop is the program she wishes existed for every leader she’s coached.
Reserve Your Seat
Spaces for the Leading While Lifing™ Intensive are limited to ensure an intimate, impactful and meaningful experience. Early registration pricing available for a limited time.
Questions? Email hello@interractconsulting.com
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