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The OwnTrail team, left to right: Lyle Hazle, principal engineer; Rebekah Bastian, co-founder and CEO; Kt McBratney, co-founder and chief brand officer; and Carolyn Dunn, vice president of engineering. Not pictured: Yvonne Chan, UX/visual designer. (Lisa Elliot Photo)

Does it matter what order you check off milestones like buying a house, getting married and having kids? Do you actually need all three to be happy?

If you choose to have kids later in your career, can you take a break to be a mom and still return to the C-suite?

How do you pick whether you or your partner takes the lead in childcare or tending to an ailing family member?

And what are the right answers to these high stakes decisions?!

Rebekah Bastian says that’s the wrong question to ask.

During nearly two decades working in leadership roles in the Seattle tech industry, serving as advisor and board member to numerous startups and organizations, and being a mom to two boys, Bastian crossed paths with a lot of women. And she started to see a pattern in her conversations.

“There’s been a common theme, which is women really worrying about their path through life, worrying about where they’re going and how they’re going to get there and being afraid that they’re going to get it wrong,” Bastian said.

Bastian has written a book called “Blaze Your Own Trail” to dispel the myth of a one-size-fits-all, perfect path to happiness. To take the message a step further, Bastian has partnered with Kt McBratney to launch the OwnTrail platform to help women further explore and plot their own paths while learning from the routes being followed by others.

“I really wanted to both embrace the idea that there’s no one right path of your life,” she said, “and create this sense of solidarity by weaving data into it, around the experiences that we all share.”

Bastian and McBratney are launching the book and site tomorrow at a sold-out event at the Capitol Hill location of The Riveter. Bastian, who is vice president of Community and Culture at Seattle’s Zillow Group, and McBratney, who is chief marketing officer at Seed&Spark, a Los Angeles-based entertainment company, will announce at the event that they are leaving these roles to work on OwnTrail.

Bastian spent more than 14 years at Zillow, joining the online real estate giant as one of its first employees in 2005. She was vice president of product for two years before taking on her most recent job leading initiatives around equity and belonging, cultural engagement, and social impact products.

“Rebekah has been an incredible force who has helped Zillow from our earliest days,” said Rich Barton, Zillow’s CEO and co-founder, in a statement. “While I am sad to see her leave, I am incredibly proud of what she’s accomplished here that’s ready for our next generation of leaders to carry forward. Rebekah has blazed her own trail since I met her in 2005 and I’m excited to see the new heights she’ll achieve in her next chapter.”

Own Trail will initially be free to encourage new users to join; the team hopes to reach 100,000 users over the next year. Bastian did not share details as to how the site would eventually be monetized.

Some sample trails. (OwnTrail Image)

Early users of OwnTrail have been creating profiles and pathways in a beta version of the site. The platform lets users string together a series of milestones grouped into categories with subheadings. They cover life changes such as moving or trying to have kids, career milestones including issues at work and promotions, obstacles like illness and mental health issues, and other events. Users can add details to flesh out the milestones.

It can feel vulnerable to honestly share the successes and failures, the achievements and missteps, made through the course of life. Bastian and McBratney said they’re working to create an environment to foster sharing.

They said that privacy is a high priority, and the platform will have well-enforced community guidelines to keep it safe and troll-free. Users have the option of posting their paths anonymously, and will need to share their path before commenting on others, once that function is available. The co-founders said the platform will moderate the interactions between users.

“We’re not just creating a safe space for women to share and learn and grow,” McBratney said, “but also a space for them to be brave and be authentic.”

GeekWire caught up with Bastian and McBratney to discuss the launch of the book and platform. Here’s a transcript of the Q&A, edited for brevity and clarity:

GeekWire: The book uses a “choose your own adventure” structure. How come?

Rebekah Bastian: It’s a format I grew up with, so it definitely has that nostalgic value. But I also wanted to create a format that’s very experiential. You tell somebody there’s no one right path and you’re going to be okay through any of them, but the format of being able to experience that through this second-person narrative where the reader is the one going through the decisions and going through the outcomes was a really fun way of exploring that concept.

And I have a product management background. So, to be honest, I kind of think in “decision trees.” The format really lends itself well to my way of thinking.

GeekWire: How did the book become this bigger OwnTrail platform?

Bastian: The book has numerous different pathways — there are 19 different endings — but those are just a subset of the infinite different pathways that a woman might go through in her life.

Being a product person, I started thinking about some cool ways that women might share the trails they’ve blazed. I started off thinking about it as more of a viral feature. But as I started digging into it further, I realized that there are some really meaty problems that can be solved through understanding the different experiences and pathways that women have been through.

When we look around, we see these picture-perfect results shared through the social media facade. And everything’s really separated out into personal versus professional, which I think sells our experience short as women. Our personal and professional lives are just so intertwined.

OwnTrail co-founders Bastian and McBratney. (Lisa Elliot Photo)

And then there’s the issue that it’s really hard to be what you can’t see. So women — and especially those who hold multiple underrepresented identities — have a hard time feeling confident going after aspirations when they don’t see other people who look like them in those places, and that they might not even think of going after.

GeekWire: How does OwnTrail work as a mentoring tool?

Bastian: We know that 75% of women aren’t receiving the mentorship that they want, and 79% of women aren’t giving the mentorship that they want to be giving [Editor’s note: These data come from a mentorship survey that Bastian conducted as part of her market research]. It’s because it’s time consuming and women don’t always have someone to ask to be a mentor. Or if they do, sometimes they’re afraid to ask. And women don’t get asked to be mentors.

So while one-on-one mentorship can be really powerful when it works out perfectly, the idea behind OwnTrail is that we’re creating these micro acts of mentorship, which are women sharing their paths through life. And by aggregating all of those into a neural network of life paths, we believe that we can help provide the guidance and the inspiration that women are looking for in a more scalable way.

GeekWire: Will users be able to reach out to each other for individual conversations?

Bastian: The way we’re planning right now is that the discussions are public if someone wants to ask a question about, say, drilling down on the details of someone’s milestone or how they navigated a certain issue. The whole idea is scalable guidance, so instead of someone answering a question in private again and again, we share the conversation with the whole community so that we can get scalable inspiration from each piece of content.

GeekWire: Do you plan to do data analysis of the life paths?

OwnTrail users plot their paths using milestones that allow them to share more details. (OwnTrail Image)

Bastian: We’re really excited about the data side of this. We’re not aware of anything that’s really gone deep into data of life experiences and life paths and there’s so much potential to be able to say, on an individual level, women who’ve taken the trail that you’ve taken tend to do this next, or on the aggregate level, these are the experiences that women go through, and X percent of women do this after this.

For being half the population, there is kind of astonishingly limited data around women’s life experiences. We plan to share that and help fill that data gap.

Kt McBratney: That really opens the door for offerings that support women during those times. We’ll be able to prove, for example, that something is an obstacle when women are coming back from maternity leave and things like that. It’s not just stories that women can use at an individual level, but can also be used to advocate for change.

Rebekah Bastian: When we know where women are in their lives and they tell us where they want to be headed, and because we have predictive analysis to verify that, we can really make sure that we’re giving them everything they need at each stage in their lives.

Kt McBratney: And the data is used in an anonymized, aggregate way. We’re always keeping our community’s safety and privacy in mind. They’re always in control of whatever identity and information they share.

Editor's Note: Funding for GeekWire's Impact Series is provided by the Singh Family Foundation in support of public service journalism. GeekWire editors and reporters operate independently and maintain full editorial control over the content.
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