Looking Back to Move Forward

Rebekah Bastian
OwnTrail Blog
Published in
4 min readJan 5, 2021

In our Trail Guides program, the first phase is focused on Reflection. This is because one of the most powerful ways to move forward in our journey is to first take a look at where we’ve been. We take inventory of what tools and resources we can bring with us, what perceptions and patterns served us well, and which we’d like to leave behind.

It is in this same spirit that we’ve been thinking back on last year as we look ahead to the new year. 2020 was strength-testing and world-changing for everyone, and there has been no shortage of struggles and transformations. It was also the year that OwnTrail launched — on February 11, just as the first cases of Covid-19 were headed to the US. My co-founder, Kt, and I had just told our jobs we’d be leaving and were beyond excited to start out on our entrepreneurial journey, with no idea of what lay ahead. Because of our launch timing, we don’t actually have a comparison of what it would be like to grow our company outside of a global pandemic and social uprising.

Looking back on all that we have learned and accomplished and the community that has grown with us, the feeling I’m experiencing most strongly as I enter this new year is gratitude. Gratitude that I had such a strong purpose to focus my energies on, had the exhilaration of entrepreneurship to keep things interesting, and had the staggering support of a growing community to guide me through 2020.

Our goal for our first year was to build out the foundation of OwnTrail, which is formed by a collection of women’s life paths. We were committed to giving women the space to own their stories and the inspiration of seeing others who share their experiences and identities in the places they are and those they aspire to.

We’re excited about the traction we’ve seen so far, entirely organically. We ended 2020 with 616 published trails with an average of 14 milestones each. That’s over 8,600 unique, authentic milestones that you have shared with us. These are real lived experiences that haven’t been shared on purely professional platforms like LinkedIn or on social platforms that encourage a picture-perfect facade. These are the milestones that make up who you really are, and we are beyond honored that you’ve chosen to share them on OwnTrail.

We’re also excited about the diversity of the women on OwnTrail. From day one, we’ve been intentional about not wanting to center a primarily white, heterosexual, cis-gender, able-bodied group of women as so many platforms “for women” tend to do — especially since those are identities that we hold as founders. On OwnTrail, women can opt to add the identities that they hold to their profiles, to support the ability to filter trails to find those with shared identities. That also gives us a view into the diversity of our community. From this we know that 48% of trails and 63% of Trail Guides cohorts are women of color (compared to a 40% US benchmark); 19% of trails and 29% of Trail Guides cohorts identify as LGBTQIA+ (compared to a 5% US benchmark); and the trails on OwnTrail are of women 18–72 years old from 44 states and 27 countries. Our intersectional community of women is a big part of the secret sauce for what makes OwnTrail impactful. It allows women to see people who look like them in the places they aspire to, and to connect with others that are both similar to and meaningfully different from themselves.

We have big ideas for the future of OwnTrail, and they all center you, the women in our community. In 2021 we are focused on building deeper ways for you to connect with each other, scaling our Trail Guides program to support all of your needs around navigating transitions and building deeper connections, and leading the way on a new type of company that we call AuthenTech, which centers the human and turns customers from commodities to community members.

Just as our Trail Guides program starts with Reflection before moving on to Imagination, Aspiration and Action, we are carrying our reflections on 2020 with us as we look ahead. We can imagine endless possibilities for the impact that OwnTrail can have on women’s lives, have huge aspirations for growing that impact with you, and are energized to be starting this new year with the groundwork laid for taking action on this vision. Thank you for being on this journey with us — we can’t wait for the milestones that lie ahead!

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Rebekah Bastian
OwnTrail Blog

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