The HomeStretch – Where the Meaning of Life Awakens Within You
Together, we will chart the paths that lead deep within as you rediscover what gives your life meaning and where your spirit is guiding you next. Your HomeStretch is not the end, but the beginning of your most meaningful chapter.
Join a Community of People Redefining What Their Next Chapter, Their HomeStretch Means
“HomeStretch gave me permission to dream again.”
— Sarah M., Retired Executive
Does This Sound Familiar?
“I worked for 30 years and now I feel… lost.” The structure that defined your days is gone. Monday feels like Thursday. The calendar that once overflowed now echoes with emptiness.
“My identity was my career—who am I now?” When people ask what you do, you stumble. “I’m retired” feels like saying “I’m done.” But you’re not done. You’re just… stuck.
“I have no genuine purpose now.”
You used to solve problems, lead teams, make things happen. Now you’re wondering if your best contributions are behind you.
“I thought I’d have a perfect life spending time with family and traveling, but something’s missing. Is this all?” The golf games and grandkid visits are wonderful, but they don’t fill that deeper need for meaning and momentum.
You’re not alone. And you’re not broken. You’re simply ready for what comes next.
What If the Best Really Is Yet to Come
Set aside everything you’ve heard and learned about financial planning for retirement.
You’ve got that covered. This is about something more than money—rediscovering who you are when you’re not defined by what you do.
HomeStretch isn’t about managing your retirement. It’s about igniting your renaissance.
Discover What’s Possible
Rediscover Forgotten Dreams
Unearth the passions you set aside “until someday”—that someday is now
Create Your Personal Roadmap
Design a purposeful path forward based on YOUR values, not society’s expectations
Build Meaningful Connections
Join a community of kindred spirits navigating the same exciting transition
Wake Up With Purpose
Replace “What will I do today?” with “I can’t wait to start”
How It Works
Your 3-Day Transformation
01
Rediscover
Uncover Your Core Values & Forgotten Passions
We’ll dig deep to identify what truly matters to you now—not what mattered at 30 or 50, but today. You’ll reconnect with dreams you’ve deferred and discover new ones you didn’t know existed.
02
Reimagine
Design Your Next Chapter Blueprint
Using our Five Pillars framework—Family & Friends, Spirituality, Health & Wellness, Adventure & Discovery, and Continuous Learning—you’ll craft a personalized vision that excites you to jump out of bed each morning.
03
Reignite
Create your Living Action Plan & Support
Transform insights into action with a concrete 90-day roadmap and accountability partnerships that ensure you don’t just dream it—you live it.
About Chris Elliott
Your Guide to What’s Next
Chris Elliott isn’t your typical retirement coach. After he began thinking about his next chapter and seeing other family, friends, neighbors, and even strangers struggling with the “now what” of retirement despite financial security, Chris discovered that the real challenge isn’t managing money—it’s rediscovering meaning.
With over 25 years of experience helping people navigate major life transitions, Chris created HomeStretch to address what traditional retirement planning ignores: the human side of this profound life change.
“I believe retirement is outdated terminology. You’re not retiring FROM life—you’re transitioning TO your next adventure. My mission is to help you make this next chapter your best chapter by taking responsibility for the life you’re creating and making choices that are intentional and self-respecting.”
Real Stories, Real Transformations
"I went from dreading Mondays to celebrating them"
“Before HomeStretch, I was successful but purposeless. I’d built companies, led teams, achieved every professional goal—then retired and felt like I’d disappeared. Chris helped me see that my experience wasn’t my identity, it was my foundation. Now I mentor young entrepreneurs, write the novel I always promised myself, and feel more alive at 68 than I did at 48.”
Michael Thompson, Former CEO, Retired at 65
"I discovered I wasn't done growing—I was just getting started"
“My husband kept asking why I seemed unhappy. We had everything—health, grandkids, financial security. But I felt guilty admitting something was missing. HomeStretch gave me permission to want more. Not more things, but more meaning. I’m now leading a community garden project, taking art classes, reconnecting with my faith and spirituality, and having deeper conversations with everyone in my life. The workshop didn’t just change my retirement—it changed me.”
Linda Chen, Former Teacher, Retired at 62
"From feeling useless to feeling essential"
“The hardest part of retirement was feeling like I didn’t matter anymore. Three days at HomeStretch completely shifted that story. Chris helped me see that my decades of experience weren’t obsolete—they were exactly what someone needed. I’m now consulting part-time on my terms, volunteering with purpose, and traveling with intention. Best of all? I know exactly why I wake up each morning.”
Robert Martinez, Former VP of Operations, Retired at 67
Frequently Asked Questions
How will I know if this workshop is right for me?
Great question—and we’ve built in a safeguard. Upon registering, before any financial investment / commitment, you’ll have a required discovery call with Chris. During this conversation: (1) Chris will address all your concerns and answer your questions, and (2) together you’ll determine if the workshop is the right fit for you at this time. Both you and Chris have the ability to decide whether participating would be effective for you. No pressure, just clarity.
What if I'm not fully retired yet?
Planning ahead of actually leaving your professional position is ideal! Many of our most successful participants attend 6-12 months before retirement. This gives you time to process, plan, and hit the ground running when your retirement date arrives. Think of it as training for a marathon—you wouldn’t start running the day of the race.
What makes this different from other retirement programs?
This isn’t about retirement at all—and it’s certainly not about your financial future. Financial advisors help you afford retirement; we help you love it. This is about reclaiming and discovering your purpose and happiness after your professional life. While others focus on making your money last, we focus on making your days matter. This is about making this stage of your life the best chapter of your life. We believe the best is yet to come—and we’ll prove it to you.
What's the time commitment?
The workshop is a three-day program, typically running 9 AM to 5 PM. Depending on which session you choose, it can be three consecutive days or spread over four days (½ day kickoff, 2 full days, ½ day finale). We keep groups small and intimate—maximum 12 participants—to ensure everyone gets personal attention.
Is there any pre-work or pre-reading?
Currently, there’s no required pre-work, though this may evolve based on participant feedback. You’ll receive a welcome packet with logistics and optional reflection questions to get you thinking, but nothing that feels like homework. We want you to arrive curious, open minded, and not stressed.
What if I'm an introvert or uncomfortable in groups?
We’ve designed the workshop to honor all personality types. While there’s group interaction, there’s also substantial individual reflection time. No one is ever put on the spot, and sharing is always by choice. Many introverts tell us the small group size and Chris’s facilitation style made them feel safe to open up in ways that surprised them.
Is this workshop religious? What about the spiritual component?
While spirituality is one of our Five Pillars, HomeStretch is not tied to any specific religion or faith tradition. We recognize that connection to something greater than ourselves—whether you call it God, the Universe, Nature, or simply your highest values—is often essential for finding meaning and purpose. The spiritual element of the workshop focuses on exploring what gives your life deeper significance and how you connect with that source of meaning. Participants from all faith backgrounds (and those with no religious affiliation) have found this approach respectful, inclusive, and valuable for their personal journey.
What is Circle of Life, and how does it relate to HomeStretch?
Circle of Life is a transformative travel experience that Chris also Co-facilitates, designed for those seeking adventure combined with deep personal reflection. For more details, visit: https://explorerspassage.com/circle-of-life-sri-lanka
Your Next Chapter Starts Here
Ready to stop wondering "what now?" and start living "what's next?"
The truth is, you’ve been preparing for this moment your entire life. Every challenge you’ve overcome, every skill you’ve developed, every relationship you’ve built—it’s all been leading to this.
You don’t need to have it all figured out. You just need to take the first step.