The Next Big Milestone in My Trail

Rebekah Bastian
Feb 11 · 6 min read

I was getting coffee recently with a young woman who had reached out to me. I block off my calendar for a few of these coffees each week, and tend to prioritize meeting with people who are underrepresented in their fields — I feel it’s an important opportunity and responsibility of being a leader. This woman, like most of those that I meet with, was uncertain about where she was supposed to be headed in life and how she would get there. She sat there asking me questions: How did I know what I wanted to do? How did I make a big career switch? How did I balance work and motherhood? Did I think she should find a job that she was more passionate about? How could she advocate for herself?

As I gave her answers — all of them in the theme of “it’s ok, there’s no one right path, you’re doing great” — she feverishly scribbled down answers in her notebook. By the end of our coffee chat, she seemed somewhat reassured. Understanding more of the unplanned and imperfect path that I had taken, and being reminded that there’s not a right answer and that the best thing she can do is be open to possibilities, she seemed empowered to go back out there and kick ass. My ability to help build her confidence and inspiration felt really good to me too.

The problem with this story is that there are countless other women just like her who could use a similar coffee chat. Even this woman will need more inspiration and different perspectives as she continues to navigate her own path. And I don’t have a lot of time for this, even as someone who prioritizes these relationships in my life. These 1:1 mentorship interactions just won’t scale to meet the 75% of women who wish they were getting more mentorship, and the 79% of women who wish they were providing more mentorship.

The many experiences I’ve had like this have been the inspiration behind the new company that I am co-founding, OwnTrail. By combining the life paths of a diverse range of women into a self-guided experience, we can scale the ability to give and receive mentorship and inspiration, and help women discover not the right path, but their path.

I actually didn’t set out to start a company. As with most of the major endeavors in my life, I was investing in the work that lead to OwnTrail for many years before I realized I was “doing work” in this space. The first phase of this was the research phase. This included living my own crooked path, experiencing the rollercoaster of massive failures, surprising successes and unplanned experiences that come with a well-lived life; as well as the similarly unpredictable journeys of dear friends that I had the honor of living through in close proximity. I’ve also had the privilege of hearing the stories, uncertainties and perseverance — and the questioning of what their “right path” is and how to navigate it — of countless women who have confided in me, through my leadership and mentorship roles as a tech and culture exec. All of that made up the research phase of OwnTrail, and lasted somewhere between 10 and 40 years.

The next step was writing a book. I woke up in the middle of the night in September, 2018 with the idea for Blaze Your Own Trail implanted in my head. I don’t know how, but it was there and it was vivid, and I had no choice but to write it. Modeled after the Choose Your Own Adventure books I read as a child, Blaze Your Own Trail is a second-person fictional narrative with extensive data woven in, and a decision tree as the table of contents. It explores the choices and paths that a woman might experience in her personal and professional life. The goals of the book are to instill confidence around the idea that there is no one right path in life, build solidarity around the shared experiences that don’t get talked about enough, and foster compassion for the bumpy paths we are all on. I was lucky to find an editor, Anna Leinberger, and a publisher, Berrett-Koehler, that understood and believed in this vision.

As I was preparing for the launch of Blaze Your Own Trail, I started exploring what kind of website I should build to showcase the book. The traditional approach is to create an author website, and talk about the book on there. However, I started to think about how the ideas and goals behind Blaze Your Own Trail could be so much more than just the author who wrote it. There are a finite number of paths to explore in the book, but an infinite number of paths that women really experience. What if I could create a platform that captured and shared those paths? I pulled in a couple of old friends (and extremely talented software developers), Carolyn Dunn and Lyle Hazle, to help me work on a website around this idea. I also asked the woman that designed the cover of my book, Yvonne Chan, to help with the visual design of the website. And I reached out to two badass, brilliant friends, Rebecca Lovell and Sage Quiamno, to advise on the idea. While it’s probably clear to readers at this point that I was working on more than just a book launch platform, I managed to fool myself into thinking that’s all it was for a while. But the more I worked on OwnTrail, the more I found myself lying in bed unable to sleep because of excitement and inspiration over the idea. There was something important there, and I had to go all in!

OwnTrail team: Lyle, Rebekah, Kt & Carolyn (photo by Lisa Elliot)

It was around the time that I was realizing my calling around creating OwnTrail that I went to a Chairman Mom event and met Kt McBratney. She and I first connected about a potential collaboration between our current jobs, but then decided to grab coffee and ended up hitting it off. (Spoiler alert: we have the same Leo birthday! No wonder). I first told her about my book, then started talking a bit about the website. She totally got it. After a couple more energizing conversations, and the realization that her skills were exactly what we needed to make OwnTrail a success, I asked her if she would be interested in being an advisor and — after that went great — if she would be my cofounder. She said yes!

The decision to go all in with OwnTrail required the bitter-sweet decision to leave my 14.5 year career at Zillow. The experiences I’ve had at Zillow reflect much of what I would hope to see in the world. I’ve felt challenged, supported, valued for being my full self, and given huge opportunities. I’ve had incredible sponsors, mentors and role models. And I’ve been able to balance work, motherhood and creative outlets in a way that has been energizing and fulfilling. I’ve also learned how privileged I’ve been in these experiences. There are so many systems and dynamics in the world that hold people back from their full potential and, while none of us can solve all of them, I believe what we are building with OwnTrail can help lift some of the barriers that women and non binary folks experience in navigating their personal and professional lives.

As I am publishing this, we just launched the first version of OwnTrail, at the same time as my book launch. The need for women to see other women who share their identities and experiences, and who have navigated and achieved what they aspire to, is real and urgent. We feel called to build OwnTrail to meet that need, and can’t wait to learn from the inspiring women that share their trails with us!

OwnTrail Blog

Building a platform for womxn to share, explore and blaze…

Rebekah Bastian

Written by

CEO and Co-founder of OwnTrail, writer, mentor, artist, mother, wife, aerial acrobat.

OwnTrail Blog

Building a platform for womxn to share, explore and blaze trails. Follow our journey through the milestones, obstacles and learnings.

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