Rebecca Callahan is a community builder and career coach for early/mid-career women
Age: 50
Location: Denver, Colorado
Owner, Summer Day
Certifications: ACC (Associate Certified Coach) and CPCC (Certified Professional Co-Active Coach)
I coach early-career women through the “broken rung”‘” leadership transition and build communities that connect and retain customers. Whether you’re navigating a career pivot or creating a space where your customers keep coming back, I’m the strategic partner who stays until you get results.
My rate: varies depending on if the work is hourly or per-project, and whether the client is for-profit or non-profit
I’m in the midst of my glide path
This is a concept I came up with when my husband and I had dinner with longtime friends. We were discussing our next chapters and how we’re going to get there. I explained how my goal wasn’t retirement, it was re-career. That, of course, raised some eyebrows, so I explained it as if I was in a glider. Instead of retiring from something (corporate America), I was looking to retire to something — slowly but surely making changes and re-prioritizing until I landed gently after a long, slow trip down.
My primary goal in this next chapter isn’t monetary, it’s impact. What can I do to help the next generation? What can I do to help purpose-driven organizations thrive? How can I be there for my almost-adult children and aging parents in a way that allows me to be fully not just physically present? My focus on impact means I’m selective about the clients I take on. I want to help early-career women avoid the mistakes I made, and build meaningful communities that are doing good in the world — not just maximize profits (although revenue isn’t all evil!).
My priorities have shifted in the past five years for several reasons.
First, when my daughter (now 17) was in middle school, she wrote an essay on the gender pay gap and was appalled. She couldn’t understand why women were paid less to do the same job a man did. I realized she was watching and I wanted to do something to make a difference.
Between 2020–2022, I lost three parents to stroke, Alzheimer’s, and cancer. And I’m now caring for my father, who also has dementia. Those years were rough. I was working full time in intense roles and while my companies provided me the grace and time to do the things I needed to do, it came at a cost. I was burned out, mentally, emotionally, physically, and spiritually. And, you know what? Watching my parents succumb to these horrible diseases, it became readily apparent to me that what I was doing didn’t matter. Not really.
And what did matter? Well, that’s what I set out to find out.
I started my glide path in 2024 and haven’t looked back since. It was the best decision I’ve ever made. Prioritizing myself, health, family and purpose have been a game changer for me — especially as I’m deep into perimenopause (that’s a whole other midst of!). It’s radically changed my family dynamic AND how my work days look. I start each morning with stretching, meditation, and journaling. I’m learning to quiet my mind and listen more deeply to my body and give it what it’s craving. Sometimes that’s an intense weight-lifting session, sometimes it’s a long walk. Sometimes (and I’m being real here) it’s sitting and staring at the wall until my monkey brain calms down.
Now, instead of ‘I have to’, I find myself saying ‘I get to’. It isn’t just positive thinking — it’s a fundamental shift in how you structure your life and work.
That’s the mindset I help my clients develop, too.That’s the kind of communities I want to build.
This shift in perspective directly influences how I work with clients now through Summer Day. I understand the weight of burnout, the importance of intentional career moves, and the value of creating space for what truly matters. When I help women navigate the ‘broken rung’ or build a community that brings people together, I’m drawing from this hard-earned wisdom about sustainable success.
So, yeah, instead of defining retirement as jumping off a cliff — one day you’re employed and the next you’re not — I’m defining it in my own way. Re-careering as I float down my glide path.
Career highlights
- Helping a client 6 months out of a job land her dream role with a higher salary than she dreamed of asking for
- Launching and growing thriving alumni communities
- Building teams that choose to follow me
- Turning around a failing subscription product
My super powers
I create order out of chaos and get shit done in the service of my clients and colleagues. I’m a relationship builder who sees both the big picture and all the moving pieces. I see people, understand problems (opportunities), and can intuit what’s working and where the gaps are.
I’ve done so much in my career: relationship management, strategic marketing, retention, subscription management, sales, sales ops, product & project management and process improvement. But the throughline of my entire career, regardless of what role I actually held, is supporting others. Whether it’s:
- Making my client look great in front of their boss by running a successful marketing campaign
- Removing obstacles for my team so they could do their jobs better
- Streamlining processes to minimize friction
- Launching communities to bring people together
- Supporting a coaching client who’s figuring out where they want to go
Ideal customers and clients
- Early/mid-career women who are usually in the midst of a transition themselves: new job, new promotion, new move and looking for clarity around the shift. (Also see HR departments looking to invest in their new managers.)
- Organizations offering transformational workshops: Participants leave inspired but struggle to implement changes alone. You want to support their growth and keep them close. A community solves both — providing ongoing support for participants while deepening their connection to your organization.
- Market research and insights organizations: Subscription-based businesses that understand recurring revenue.
- Community-curious organizations: Wondering if community is right for you? Let’s figure it out together.
Open to trades
As my glide path focus is on impact vs. profit, I’m definitely open to conversations with the right organization/individual to partner in creative and mutually beneficial ways.
I tried this in my career but it didn’t work
A long time ago, I owned and operated a mom/baby outdoor workout franchise. I tried to do a grand opening event before I really had enough clients. I spent so much money on food, drinks, and decorations, but only a few people showed up. It was a little embarrassing. I learned I should have waited until I had more clients and brand awareness before hosting an event. A grand opening doesn’t necessarily mean you have to do it right away!
Grown-Ass Lady heroes
Ilona Maher, Sara Blakely, Mary Oliver
How The Midst community can support me
I joined The Midst to be part of a community of like-minded women in a similar stage of life. I’ve been in women’s communities before and it always blows my mind — the connection, support, and kinship that gets cultivated when we lift each other up. Inevitably, when it’s a bunch of women, the conversation wanders from business to families to partners to health to hobbies. It’s never linear and always good for the soul.
My BHAG is to partner long-term with women-run companies to help them grow and succeed. And, yes, I am focused on community and leadership development, but my Create order out of chaos and get shit done ethos allows me to fill so many different gaps. If you know of or are a women-led organization in need of a solid business partner, let’s chat and we can figure it out together. But honestly? I’m here as much for the kinship and collective wisdom as I am for the business connections.
What’s next?
That’s the million-dollar question, isn’t it? I sat here for a good 15 minutes thinking about this question, then stopped thinking altogether and got quiet (this is where staring at a wall comes in handy). Here’s what came up:
Every year, I choose a word or phrase to guide me instead of making resolutions—because let’s be real, those never stick. But a word as a guiding light? That resonates. For 2025, my word is fearless. Actually, it’s fear less.
I follow Nicole Sachs’ work on healing chronic pain (I was a chronic back pain sufferer), and she talks about how we can live our lives from either fear or love. Both will get you results, but one costs so much more. So I’m manifesting fearing less — shifting from “have to” to “get to” thinking, and recognizing that fear often comes from caring deeply about results and outcomes.
Rebecca Callahan is a member of the Founding MidstHer community for solopreneurs, founders, self-starters, and community builders. Learn more about the Founding MidstHer program here.
