Dayna Steele on Reinventing Life with Guts and Grace
When Everyone Has an Opinion, Listen to Your Own
There's something magical that happens when we reach our 50s and beyond. We've accumulated decades of professional experience, weathered countless workplace storms, and developed an intuition that's finely tuned—if only we'd listen to it more often.
As I sat down with my dear friend Dayna Steele for a recent episode of the Grey Matters Podcast, I was struck by how her career journey embodies what so many of us desire in our second act: the courage to pivot, the wisdom to trust ourselves, and the freedom to design a life and legacy business for women that aligns with our deepest values.
Dayna's story isn't just remarkable; it's a masterclass in overcoming fear of starting over. From rock radio DJ to NASA online store founder to award-winning playwright and actress, she's reinvented herself multiple times while maintaining her authentic voice throughout each transition.
"Ask for what you want," Dayna shared during our conversation. "You never know who will hear it."
This simple yet profound advice resonates deeply with women contemplating a midlife career pivot. We often hesitate to voice our desires, fearing rejection or judgment. Yet as Dayna's story demonstrates, that single act of courage—clearly stating what you want—can be the catalyst for extraordinary transformation.
The Myth of the "One True Path"
Society often sells us the narrative that success means climbing a single corporate ladder. For women leaving corporate to start a business after decades of structured employment, this limited perspective can create unnecessary anxiety.
Dayna's journey obliterates this myth. After 20+ years as a successful radio personality, she faced industry doubters when considering her next move:
"I didn't think I could leave radio and…I did just fine. Everybody had me convinced there was nothing after radio."
How many of us have heard similar limiting beliefs? "You've invested too much time in this career to switch now." "Starting over at your age is too risky." "The skills you've developed won't transfer to a new industry."
These voices—whether from well-meaning colleagues, family members, or our own internal critic—can keep us trapped in careers that no longer serve our highest purpose or joy.
What's particularly inspiring about Dayna's approach is her willingness to question established paths and create her own. When experts told her she couldn't act in her own play about her experience with her mother's Alzheimer's, she trusted her instinct that no one else could tell her story with the same authenticity:
"I know this play is a hit. And maybe someday somebody will go, here's a whole bunch of money. Please come do it on Broadway. But until then, I'm gonna do it my way."
The Pivot That Changed Everything
For many women considering becoming a second act entrepreneur, there's often a defining moment—a catalyst that prompts the consideration of a new path. For Dayna, one such moment came when her mother was diagnosed with Alzheimer's.
This experience—navigating her mother's illness while maintaining her career—eventually led to writing "Surviving Alzheimer's with Friends, Facebook, and a Really Big Glass of Wine," which later became the award-winning play "The Woman in the Mirror."
What strikes me about this transition is how Dayna transformed an incredibly difficult life experience into a source of purpose and connection. Rather than compartmentalizing her personal challenges and professional life, she integrated them—creating work that directly responded to her lived experience and offered genuine value to others facing similar situations.
This integration of personal challenge and professional purpose is a hallmark of successful career transitions for women in midlife. The most fulfilling second acts often emerge from our most authentic experiences, values, and wisdom.
The Freedom to Say "No" to External Expectations
As women building purpose-driven entrepreneurship ventures after 50, one of our greatest assets is the freedom to define success on our own terms. We've spent decades meeting external expectations and standards; now we can create businesses that honor our unique vision and boundaries.
Dayna exemplifies this beautifully in her approach to professional appearance:
"If I can't wear my Chuck Taylors or my cowboy boots, I am not coming to your conference or gala slash shower."
What might seem like a small thing—choosing comfortable footwear over conventional expectations—represents something much deeper: the conscious decision to prioritize authenticity over external approval.
For women reinventing professional identity after years in corporate environments with strict dress codes and behavioral expectations, this reclamation of personal choice can be profoundly liberating.
Dayna took this a step further by choosing to forego makeup during her year of world travel:
"It's been a way of expressing learning to have confidence in myself as I am. And it's given me a newfound confidence in other things…because I don't have to conform."
This evolution toward greater authenticity often coincides with building a business that makes an impact. When we're no longer expending energy maintaining a professional persona that doesn't align with our true self, we have more creative resources available for the work that matters most.
The Art of Taking Advice (Without Losing Yourself)
As we navigate career change after 50, well-meaning advice flows freely from every direction. Colleagues, friends, family members, and industry experts all have opinions about how we should proceed. The challenge isn't in receiving this guidance but in discerning which pieces serve our vision and which don't.
Dayna's experience with her play offers valuable insight into this discernment process. After six years of development and multiple revisions, she found herself in New York receiving feedback that would fundamentally change the nature of her work:
"The feedback we get is, 'Okay, that's great, we love it, but you gotta change it again. The Dayna character has to quit talking to the audience…you gotta take all the Facebook posts out.' The whole thing is a roundup of Facebook posts!"
Rather than automatically implementing these suggestions from industry experts, Dayna reconnected with her original vision and purpose. She recognized that while the feedback came from knowledgeable sources, it would transform her work into something that no longer served her authentic mission.
For women developing personal branding after 50, this selective approach to feedback is essential. Not all advice—even from respected sources—aligns with your unique purpose and audience. Learning to filter guidance through the lens of your core values prevents costly detours into someone else's vision for your work.
Five Strategies for Trusting Your Gut in Career Transitions
Based on Dayna's experiences and my work supporting women through the Women's Reinvention Collaborative, here are five practical strategies for women navigating midlife career pivots:
1. Document Your Intuitive Hits
Start keeping a journal of moments when your intuition speaks clearly about your professional direction. Note both the mental insight and the physical sensation that accompanies it. Over time, you'll recognize patterns in how your intuition communicates—making it easier to distinguish between fear-based resistance and genuine inner wisdom.
2. Create a Personal Board of Directors
Identify 3-5 people whose judgment you trust implicitly—individuals who understand both your skills and your deepest values. When facing major decisions, consult this inner circle rather than seeking advice from everyone with an opinion. This focused approach protects your vision while still providing valuable outside perspective.
3. Develop a "Try-On" Mindset
Instead of viewing career exploration as all-or-nothing commitments, adopt what I call a "try-on" approach. As Dayna demonstrates with her various ventures, you can experiment with new directions without abandoning everything you've built. This reduces pressure and creates space for authentic discovery.
4. Practice Boundary-Setting Through Small Decisions
Build your "no" muscle by practicing on low-stakes decisions first. Perhaps it's declining an invitation that doesn't align with your values or setting a work schedule that honors your energy patterns. These smaller boundaries create the foundation for bigger ones as you develop your legacy business for women.
5. Connect With Others in Similar Transitions
Find communities of women navigating similar pivots. Whether through a women's business mastermind or informal connections, sharing this journey reduces isolation and provides practical support. Hearing others' experiences helps normalize the challenges while offering diverse perspectives on solutions.
From Expectation to Expression: The Ultimate Freedom
The most profound shift I witness in women creating an encore career for women isn't just professional—it's a fundamental reorientation from living to meet expectations to living as an expression of their authentic self.
Dayna captured this beautifully when she said:
"I know my strengths and I refuse to play them down anymore. I know what I'm good at, and I know what I enjoy doing."
This declaration represents the culmination of decades of professional experience combined with the wisdom to finally prioritize joy and authentic expression. It's the courage to say, "This is who I am, these are my gifts, and this is how I choose to share them with the world."
For women creating a meaningful business after 50, this transition from expectation to expression often manifests as:
Moving from seeking approval to offering value
Shifting from climbing hierarchies to creating collaborative networks
Transitioning from following established paths to designing innovative approaches
Evolving from measuring success externally to defining it internally
The Courage to Begin Again (and Again)
Perhaps the most inspiring aspect of Dayna's story is her willingness to begin again—repeatedly. From radio to retail to writing to theater, she demonstrates that career transition for women isn't a one-time event but potentially a series of evolutions that continue throughout our lives.
"Do something that scares you," she advises. "Getting on stage or not wearing makeup in public and start to develop this weird confidence in other things."
This approach—intentionally stepping outside comfort zones—builds a muscle of courage that serves women well in entrepreneurship. Each time we face down fear and take action anyway, we expand our capacity for future challenges.
For women starting a business after 50, this courage becomes particularly important when facing the inevitable setbacks and pivots that entrepreneurship demands. Having practiced resilience through intentional discomfort, we're better equipped to navigate uncertainty with grace.
Your Invitation to Trust Your Own Voice
As we wrap up this exploration of trusting your gut in career transitions, I want to extend an invitation: What would become possible if you trusted your intuition as deeply as Dayna has trusted hers?
"Be yourself and listen to your gut," she advised as we concluded our conversation. This simple guidance contains profound wisdom for women ready to create their second act business.
Your gut—that complex interplay of experience, wisdom, and intuition—has been gathering data throughout your entire career. It knows your strengths, values, and deepest desires. It recognizes opportunities that align with your authentic purpose, even when they don't fit conventional success models.
When you trust this inner guidance while creating a lifestyle business for midlife women, you build something sustainable not just financially but energetically—work that nourishes rather than depletes you.
The Next Step in Your Journey
If Dayna's story resonates with you and you're ready to explore your own second act with the support of like-minded women, I invite you to listen to our full conversation on the Grey Matters Podcast: Watch the full episode here.
You'll hear more about Dayna's remarkable pivots, her advice for women reinventing themselves professionally, and her insights on navigating major life transitions with grace and humor.
And if you're ready to take the next step in your own career transition coaching for women journey, I'd love to support you through my Women's Reinvention Collaborative—a six-month mastermind specifically designed for accomplished women navigating their second or third professional act.
Learn more about the Women's Reinvention Collaborative here: https://www.beyondthedreamboard.com/the-wrc
Remember, as Dayna so perfectly put it:
"Listen to your heart. Listen to your soul. Listen to your gut.”
What's your equivalent of "this play" in your professional life? What vision keeps calling to you, despite obstacles or outside opinions? That persistent calling might just be your most valuable guide to your most fulfilling second act.
