Clarity. Courage.
Coaching for What's Next.
For people who know it's time to make a change—and want to meet the challenge deliberately.
For people who know it's time to make a change—and want to meet the challenge deliberately.
Private 1:1 coaching for thoughtful adults 60+ navigating what's next.
A structured group + 1:1 coaching program for managers and leaders operating under pressure.
Are you finding the years after 60 more challenging to navigate than you expected? Do you sometimes wonder who you are at this age or in this time of life?
Have you been knocked off center by:
Are you just not as happy as you want to be, maybe despite living 'a good life'?
If you are ready to embark on the next chapter of your life with greater joy and creativity than ever but feel stymied by the prospect, you’re in the right place. At Reimagined Life Coaching, we understand that life after 60 brings unique challenges along with unprecedented opportunities for growth and joy.
Your Next Chapter Awaits
Life's transitions can feel overwhelming. Whether you're adjusting to retirement, navigating relationship changes, or simply feeling that life could be more fulfilling, you're not alone.
“Working with you was hard but rewarding. Your listening abilities are remarkable and your ideas and feedback are genuinely compassionate and supportive. You made each session rich with great assignments, and permission (encouragement) to grieve all the losses I face. Your investment in me with each session was so sincere, and my investment with you and your coaching was WAY worthwhile.”
Whether you’re seeking a moment of clarity, support to build steady momentum, or you’re ready to fully step into your next chapter, there’s a path here for you—one that meets you exactly where you are and walks beside you toward where your heart is calling.
You’ve spent a lifetime caring for others, showing up, making it work. Now it’s your turn—to reflect, rediscover, and reimagine what’s possible.
Choose The Path That Serves You Best Right Now
A single PAUSE session for a breath of clarity, a SHIFT package to reset habits and regain momentum or a BREAKTHROUGH six-month intensive to step boldly into who you are.
$225
One 75-minute session
Choose this pathA spacious moment to reflect, reconnect, and gain fresh clarity.
$895
Five one-hour sessions over two months
Choose this pathRealign your mindset, habits, and energy to move forward with confidence.
$3,995
Half-day strategy intensive + 20 one-hour sessions over 6 months
Choose this pathStep into who you were always meant to be.
“After our extensive discussions I feel completely empowered and prepared for my next steps to reach my goals.”
“I never had to work at being happy before but at age 73, it got harder to find my 'happy place.' Now I'm dealing with my husband's mental and physical decline and it's become my hardest task. How do I help him while dealing with my own aging challenges? Though I've worked with Gail for a only short time, I have noticed the positive effects of her coaching methods. Her methods work and transform. She has helped me so much that friends have commented that I look and sound happier. It's not a facade. It truly comes from within.”
Reimagined Leadership Project
A structured leadership development experience for managers and organizations
The Reimagined Leadership Project is a cohort-based leadership development program combined with individual coaching support. It is designed for managers and emerging leaders navigating the real, human challenges of leadership — and for organizations that want to support their people in doing that work well.
The project blends:
The result is leadership development that is thoughtful, grounded, and actionable — not theoretical or one-size-fits-all.
Managers play an outsized role in how people experience their work—shaping trust, engagement, performance, and well-being. And yet, many managers are promoted for technical skill or reliability, not for their ability to lead people through complexity.
As a result, managers are often asked to:
...without being trained in the very behaviors that matter most.
The Reimagined Leadership Project was created to address this gap—by equipping managers with practical leadership tools and the personal support needed to use them well.
This Project is designed for:
Individual managers and leaders who:
Organizations and HR leaders who:
While each engagement is tailored to the organization or cohort, the Reimagined Leadership Project typically includes:
This structure allows managers to learn together while also receiving personalized guidance to apply the work in ways that fit their specific roles, teams, and organizational contexts.
The Reimagined Leadership Project is not about fixing people or driving performance at all costs.
It is about developing managers who can lead with clarity, steadiness, and humanity—strengthening both individual leaders and the organizations they serve.
The Reimagined Leadership Project is offered through scheduled cohorts and organizational partnerships. Participants may self-enroll or be referred by a manager or HR leader.
If you'd like to learn more about the Project, or explore whether it's a fit for you or your organization, the next step is a conversation.
Or contact Gail directly at: gailw@reimaginedlife.net
I work with individuals and organizations navigating transition, responsibility, and meaningful change.
I'm Gail Woodard, MBA (Yale School of Management), a leadership and life coach with a broad professional background spanning corporate, academic, entrepreneurial, and coaching environments.
My work supports two distinct audiences:
While these paths may look different on the surface, they are grounded in the same core capacities: clarity under pressure, emotional intelligence, sound decision-making, and the ability to move through change with steadiness and integrity.
Professionally, I bring decades of experience leading, teaching, and advising within organizations, along with an 18-year career as a publisher and business owner. After years of working inside complex systems, I completed formal training in coaching and now bring that perspective into my work with managers and leaders through the Reimagined Leadership Project. My approach integrates neuroscience, applied psychology, and practical leadership experience to help people lead with confidence, clarity, and resilience — especially when the human side of leadership is most challenging.
Alongside this professional work, my personal life has included many of the transitions that come with aging and change: losing my beloved spouse, facing physical challenges, living far from family, stepping away from a long-held professional identity, and asking the deeply human question, Who am I now? I know what it feels like to move through grief, uncertainty, and disorientation — and I also know what it takes to reframe, rebuild, and reimagine a life that feels meaningful and alive again.
These experiences are not separate tracks. They inform each other.
Whether I'm supporting someone through a later-life transition or guiding managers as they grow into leadership, my work is grounded, practical, and deeply human. I help people slow down enough to see clearly, develop the tools they need, and apply what they're learning in real life — personally and professionally.
I don't believe in fixing people. I believe in developing clarity, capacity, and trust — and supporting people as they put those into practice in moments that matter.
If you're navigating a personal transition, a leadership challenge, or organizational change, I'd welcome a conversation.
Let's begin today:
“I've known Gail for a long time. She has helped me through many situations and life challenges. She is sensitive to my needs, not her agenda. She has on occasion masterfully switched gears to provide focused support to help me ride through a very challenging time with attention to unconditional love and allowing. She has also taught me the value of having an accountability system so that I set reasonable expectations and soar as my goals are met. I highly recommend Gail as a Life Coach for anyone who wants to live more joyfully.”