We caught up with the brilliant and insightful Madison, Ava And Elle MacGregor a few weeks ago and have shared our conversation below.
Hi Madison, Ava and Elle, thanks for joining us today. We’d love to hear about a project that you’ve worked on that’s meant a lot to you.
When Madison turned 25, she had a quarter-life crisis. It sparked deep conversations with her younger twin sisters, Ava and Elle, who were 22 at the time. Together, we realized just how confusing and overwhelming your 20s can be. Determined to make sense of it, Madison began digging for answers. That search led her to The Defining Decade by Meg Jay, a book that reframed her thinking and revealed how this decade can shape the rest of your life.
That discovery sparked an idea: what if we started a podcast where we could talk about the highs, lows, and messy in-betweens of your 20s? A space to share transformative stories and help others feel less alone, more inspired, and a little more equipped to navigate it all.
Now at 26, and 23, we’ve launched the first season of The 20 Something Playbook, which premiered on June 3, 2025.
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
We’re Madison, Ava and Elle, three sisters who have been collaborating creatively since we were 13 and 16 years old. Growing up dancing and acting professionally, we developed a deep passion for storytelling early on. At 16 and 19, with many after-school work sessions under our belts, we successfully published a young adult novel P3: The Inevitable Truth through a Kickstarter campaign that raised $15,000 in just 30 days.
Around that same time, we began working with the mental health non-profit Teaching Everyone About Mental Health (T.E.A.M.), founded by Forbes 30 Under 30 honoree Mackenzie Drazan Cook. Through T.E.A.M., Madison began honing her public speaking skills, that had started when she was 8 years old, speaking at fundraising events for the Canadian Cystic Fibrosis Foundation, the life-threatening illness Madison was born with. She went on to host interviews with Olympians, scientists, Ivy League professors, Forbes 30 Under 30 founders, and mental health professionals as the host of T.E.A.M.’s podcast.
As sisters, our 20s have been anything but straightforward. When Madison was 20, cystic fibrosis began to take a serious toll. The average life expectancy for someone with CF is between 18 and 30 years old, and Madison’s health rapidly declined. She dropped to 88 pounds and had to use a wheelchair. Ava and Elle needed to take on new responsibilities and had to grow up fast to support her. All the while, we were balancing the excitement and pressure of having just published our novel P3.
Three years later, everything changed. A breakthrough drug became available to Madison, transforming her health virtually overnight. For the first time, she was able to live like a “normal” 20-something. That’s when the quarter-life crisis hit, because without the distraction of a life-threatening illness, she was finally left to face the daunting question of what to do with the rest of her life.
In 2021, during the height of the COVID-19 pandemic, we began adapting our Young Adult novel into a pilot (first episode of a tv show) script. The process was full of rejection, trial and error, and hundreds of cold outreach messages. Over the past few years, we’ve developed the show alongside a production company and are currently in the process of trying to get the series made (not an easy task in the ever-changing entertainment industry). Our vision is massive… and so we persevere.
Are there any resources you wish you knew about earlier in your creative journey?
One resource we wish we had understood earlier in our careers is the power of social media. In our early 20s, as we were developing our skills in screenwriting, we believed that success came down to one thing: networking. It was all about who you knew. And for a while, at least when we first started in the industry, that was true. If you had a great script and could attach a credible producer, director, or actor, you were on your way to being green lit (meaning your show/movie secured funding and is moving into production.)
But the landscape has changed.
Today, having a personal brand often matters more than traditional industry connections. Gone are the days of being “discovered” out of nowhere. Instead, we are expected to prove we can connect with an audience before a network or studio takes a chance on us.
When the three of us realized this shift in the process of creating our podcast, the importance of launching The 20 Something Playbook became even more clear. We’ve found building an online presence, as well as starting a podcast from scratch, has been a steep learning curve, but it’s also been empowering to create something without having to ask for permission or funding. It’s no longer just about having an interesting idea; it’s about finding a way to connect with the people who care. That, we’ve learned, is the real power of digital platforms.
Have you ever had to pivot?
A time we had to pivot? One of the biggest moments came after we self-published our young adult novel through a successful Kickstarter campaign. After raising $15,000 in 30 days, we set our sights on getting the book picked up by a traditional publisher. We took calls with people in the industry and quickly realized something: the publishing timeline was incredibly slow, 10 years, in some cases, just to get traction.
At the same time, we received tough but honest feedback from an Amazon bestselling author who told us that, while the effort was impressive, the crowd-funded version of our book wasn’t strong enough to compete in that space. That was really hard to hear, but it sparked a necessary shift in thinking.
We asked ourselves: Why are we doing this? The truth was, we always saw P3 as something bigger than a book, we envisioned it on screen. And we wanted to play these characters while we were still the right age to do it. That was the moment we pivoted into screenwriting.
It was a scary leap, but also one of the most fulfilling decisions we’ve made. Writing for screen lit a creative fire in us, and it’s allowed us to grow not just as storytellers, but as entrepreneurs. Looking back, we’re so grateful we had the courage to change direction when we did.
Contact Info:
- Website: https://linktr.ee/20somethingplaybook?utm_source=linktree_profile_share<sid=b1f74546-94f6-42c5-bff9-6db1a44773d8
- Instagram: https://www.instagram.com/20somethingplaybook/?igsh=YmkyenAxNTdzeWls
- Youtube: https://www.youtube.com/@20SomethingPlaybook
- Other: TikTok: https://www.tiktok.com/@20somethingplaybook?_t=ZM-8uRKOZCcsKb&_r=1
Spotify: https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=bb5f5111a1b14020
Apple Podcasts: https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743
Image Credits
Photos of the three of us, minus the one on the beach and the selfie, are credited to Audrianna Martin Del Campo