Write because you love to write, not just for the end result. Writing — especially writing a book — is an intense process, full of ups and downs. I wouldn’t recommend that anyone try to write a book just because they want to have a book written. You should do it because you love the journey.
As part of my interview series on the five things you need to know to become a great author, I had the pleasure of interviewing Rebekah Bastian, author of Blaze Your Own Trail: An Interactive Guide to Navigating Life with Confidence, Solidarity, and Compassion. Rebekah is a writer, artist, tech executive, mentor, wife, mother and aerial acrobat. She has held leadership roles including vice president of product and vice president of community and culture at Zillow, and CEO & Co-founder of OwnTrail. Rebekah is a first-time author, is a contributor to Forbes and is a frequent speaker on social impact, career navigation, and corporate diversity.
Thank you so much for joining us! Can you share a story about what brought you to this particular career path?
My career path has been fairly non-linear, and much of it was not necessarily planned or anticipated. I got two degrees in Mechanical Engineering (after a failed first attempt at a music major), and then took a job that was mostly unrelated to my degrees as a Program Manager at Microsoft. After a few years there I started at Zillow when the company was still brand new and in stealth mode. That was almost 15 years ago, and over that time I have grown through different areas of the product, moved into management and then executive leadership, and transitioned from leading our product teams to leading our inaugural Community & Culture team.
I didn’t discover that I loved writing until about 5 years ago when I was asked to write a guest blog post. Since then, I have had bylines in several publications including Huffington Post, Thrive Global and Forbes, and then wrote my first book, Blaze Your Own Trail, that just came out with Berrett-Koehler Publishers on February 11th!
I also just announced that I will be leaving my corporate executive job to start my own company, OwnTrail, which is a self-guided mentorship and coaching platform built from a collection of women’s life paths. I have my own life path outlined on OwnTrail if readers would like more of the juicy details.
Can you share the most interesting story that occurred to you in the course of your career?
The interesting thing about our lives — and particularly those of women — is how intertwined our personal and professional lives are. As such, almost every one of my interesting career stories is also an interesting personal story… and I’ve had a lot of those! One that came to mind with this question was the time I went into labor at work. It was my first baby and, like 15% of women, my first sign of labor was my water breaking. At my desk! My best friend at work, Annie, managed to get me a spare pair of pants and call my husband (I had forgotten how to use my phone in the excitement), and got me stealthily out of the office. When I came back four months later, we had moved offices, gone public, and I had a handful of people reporting to me that I had never met before. It was one of the more jarring transitions I’ve been through!
What was the biggest challenge you faced in your journey to becoming an author? How did you overcome it? Can you share a story about that that other aspiring writers can learn from?
There were two main challenges to becoming an author: writing a book and finding the right publisher. Writing the book wasn’t as hard as one might imagine — I woke up in the middle of the night with the idea for my book, which is a choose-your-own-journey-style exploration of women’s life paths. It was as though the concept was implanted in my brain, and I just had to get it out. It definitely took some commitment to writing every evening (largely on my phone, while putting my children to bed), but I’m lucky that it flowed pretty easily out of me.
Finding a great publisher required some hustle. I started with reaching out to a lot of literary agents, most of who ignored me and a few that spent some time but ultimately declined. Then I posted on LinkedIn, asking my network if anyone had suggestions for getting published. One person reached out to let me know about his own publishing process and when I told him about my book, offered to introduce me directly to his editor. I connected with Anna Leinberger, an editor at Berrett-Koehler Publishers, and she completely got my vision and wanted to help amplify it. She helped me get a contract there, edited my book, and has become one of the people I most trust and admire!
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
I’m not sure how funny this is, but it took me a while to learn how to speak up and advocate for myself. When we’re in more structured situations like school or entry-level jobs, there are pretty clear goals, checkpoints, and measurements of success. So I guess I went into my first job after grad school thinking that the people above me would know what I was contributing and what opportunities I hoped for. It turns out, most managers aren’t minded readers. Some good managers will dig deeper to recognize your contributions and advocate for opportunities for you, but I learned that the most effective approach is to share what you’ve done and ask for what you want. There is no guarantee that you’ll always get what you ask for, but the odds are much higher than if you didn’t ask.
What are some of the most interesting or exciting projects you are working on now?
I’m really excited about co-founding OwnTrail. After 15 years at the same (fantastic) company, this is a huge leap for me to be venturing out and starting something of my own. The idea for the platform came from my book. While the book has a large variety of paths and 19 different endings, those are just a small subset of the infinite variations that women experience. OwnTrail aims to shed light on all paths to show there is no one right path, to celebrate the bumps in our paths as a form of solidarity, and to combine micro acts of mentorship into scalable inspiration. I can’t wait to see where this vision takes us!
Can you share the most interesting story that you shared in your book?
Because of the choose-your-own-journey nature of my book, it covers a lot of really interesting topics! This includes some of the more expected life milestones, like marriage, child-rearing and career changes. But it also goes deeper into a lot of the experiences that can feel more isolating because they don’t get talked about as openly, such as workplace harassment, infertility, abusive relationships, aging parents, infidelity and existential crises. I think it’s the journey through these experiences that makes the story the most interesting.
What is the main empowering lesson you want your readers to take away after finishing your book?
I hope readers will come away feeling confident that there is no one right path through life and that they are strong enough to make it through even the most difficult experiences. Through the storytelling and supporting data, I also hope that they will feel solidarity in knowing that every experience, no matter how lonely, embarrassing or isolating it feels in the moment, is one that is shared by countless other women. And lastly, I hope that everyone that reads the book — regardless of the identities that they hold — will feel a renewed sense of compassion for others, knowing that everyone is blazing their own trail, making their own decisions, and doing the best they can.
Based on your experience, what are the “5 Things You Need to Know to Become a Great Author”? Please share a story or example for each.
- Write because you love to write, not just for the end result. Writing — especially writing a book — is an intense process, full of ups and downs. I wouldn’t recommend that anyone try to write a book just because they want to have a book written. You should do it because you love the journey.
- Don’t get too hung up on the first draft. You’ll do a better job of crafting the perfect sentences if you just get them out first and then worry about editing them later. And you definitely should edit, regardless of how strong you feel your first draft is. Have some friends read it and give feedback, have an editor look at it, put it down and read it again. You’ll keep finding ways to make it better.
- Read a lot. I can’t imagine being an author without extensively reading the works of other authors. There are so many different ways of telling a story and conveying information, and you can find inspiration within every cover. It’s also great to support other authors — we’re all in this together!
- Try to write every day. I set goals for myself to write at least 300 words a day. That’s not very much, and on some days, I would push myself to the 300-word limit and then stop. But on other days, I would be hit with a wave of inspiration and write thousands of words. Making writing part of my daily habit, while also giving myself permission to have off days, helped me to finish my first draft in about 5 months.
- Don’t be discouraged by rejection. Your book won’t be for everyone, and that’s ok. I got ignored and rejected by a lot of agents before I found an editor and publisher that believed in my vision. And I’m so thankful for everyone that didn’t believe in it up until that point because I ended up with the most visionary and supportive people in my corner!
What is the one habit you believe contributed the most to you becoming a great writer? (i.e. perseverance, discipline, play, craft study) Can you share a story or example?
The ability to trust what comes out of us is key. We are often trained by society to filter our thoughts, feel embarrassed by our creative urges, or question our first instincts. I think that being able to write well requires a level of openness, and that can necessitate doing the work to get back in tune with our creative outputs. For me, all forms of creativity (visual art, aerial arts, music, and writing) have helped open up that creative trust in myself.
Which literature do you draw inspiration from? Why?
I think my inspiration really comes from the wide variety of literature — both fiction and non-fiction — that I read. Every book has a new perspective, style, and story to tell. That being said, I’ll name a few authors that I admire for specific reasons. I loved Cheryl Strayed’s ability to make the raw, vulnerable moments in our lives beautiful in Tiny Beautiful Things. I loved Donna Tartt’s vivid descriptions of both thoughts and things in The Goldfinch. I loved Ta-Nehisi Coates’ ability to both educate and evoke emotion through a first-person letter in Between the World and Me. And I loved both Pachinko by Min Jin Lee and Homegoing by Yaa Gyasi for the way the spanned generations and eras.
You are a person of enormous influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)
That is exactly why I founded OwnTrail — to start a movement! It is a movement of authenticity; of focusing on the journey and not the destination; of feeling confident in our paths, and knowing that we have the strength to make it through any outcome. Historically, women have often been taught to doubt ourselves, to fear the risk, and to silence our voices. All of that is changing, and my dream for OwnTrail is to be an empowering and connecting tool for that change.
How can our readers follow you on social media?
Follow OwnTrail at:
Follow me at:
Thank you so much for this. This was very inspiring!