Marking Your Own Trail and Defining Success on Your Own Terms with Jennifer Chambers

Jennifer Chambers turned her enthusiasm for hiking and the great outdoors into a key component of her career – a career that has had many of the twists and turns of her beloved trails. Her titles include teacher, published author, chair of the American Hiking Society, entrepreneur, and community leader. In this PowerChute, Jennifer reflects on how her passion has informed her decisions and transitions throughout her career.


Lauren: You are an avid hiker and a strong advocate of education. How have you used those passions to guide your career path – which has included a wide array of titles from published author to entrepreneur to teacher.


Jennifer: Wow that sounds so superwoman-esque! But it all evolved organically over time so it never really felt like that. I have always loved hiking and had an intense passion for the earth and the environment generally. I’ve also always been a devoted educator. Early in my career, I decided to teach, and would spend my weekends hiking. When my husband and I decided to have kids, I scaled back my teaching so that I could be around more. It was during that time that I started to see my passion for hiking as an opportunity to create a business. Ultimately, I concocted the idea of Hiking Along, because it combined my love of hiking and the outdoors with my love of education.


Lauren: So tell me what Hiking Along is.


Jennifer: When I started Hiking Along, it was a company that coordinated and facilitated group hikes to teach children the science behind what their senses experienced along the trail. I worked with schools, groups of kids for birthday parties, and Girl Scout troops – LOTS of Girl Scout troops! Over the course of 12 years, I grew the business in different ways, and enjoyed introducing so many people, especially children, to an activity that I love. Along the way, I got very involved in the American Hiking Society and Leave No Trace – organizations focused on promoting outdoor activity and protecting the environment. And I also wrote my books, Watershed Adventures of a Water Bottle and Best Hikes with Kids: Washington, DC The Beltway & Beyond. So there were a lot of moving pieces, with Hiking Along being just one. But starting in 2015, I lost the spark I used to feel when someone would call to ask “will you lead my kid’s birthday party hike.” It just didn’t excite me anymore. For a year, I let that feeling sit so that I didn’t give up on something without being really sure. Then about the same time, I was offered a full time position at The Siena School, and it was good timing to reevaluate and think carefully about my priorities. I decided to focus on what was important to me, including teaching, marketing my book, and being a present mom to my kids, who were in 6th and 10th grades at the time. So I closed Hiking Along in 2016 and pursued those other activities.


Lauren: Wow. That must have taken so much courage to recognize that your company had run its course and you were okay with letting it go. Have you missed it?


Jennifer: I don’t miss the actual part of leading the hikes, but I do miss the title; I’m a former business owner now, but I don’t regret the decision.


Lauren: People often come to Parachute thinking linear careers are the only option. How do you get comfortable saying no to a linear career in favor of a “piece-it-together” or “portfolio” kind of career?


Jennifer: It really happened naturally. I wanted to keep teaching, but also wanted to be home, and then needed additional stimulation and interaction with people outside of my immediate family, and Hiking Along was born. At that point, I was doing some of this and some of that, and it was all working nicely. So I didn’t specifically design my career that way; it just sort of evolved and I was open to it. Reflecting on it now, I think having the different outlets kept me engaged and interested in all the pieces because I didn’t do any one thing too much. That said, one drawback I found was that working in several arenas made it harder to think of myself as an expert in anything. In fact, when I was voted onto the board of the American Hiking Society in 2008, I remember thinking, “Why are they picking me? I’m not an expert!” Even down the road when I became Chair of American Hiking Society (AHS) I still thought that.


Lauren: So do you feel like an expert now?


Jennifer: Yes. I do. Reflecting on it now, writing my books along with being the Chair of AHS have been the two greatest challenges of my life professionally and because both were successful, it gave me the confidence to recognize and acknowledge myself as an expert. I was able to garner buy-in, work collaboratively to build an organizational foundation, and synthesize communication effectively. Due to my internal feelings of success, I am more comfortable now in my skin and in my head.


Lauren: How did you decide to write Best Hikes with Kids?


Jennifer: I started writing the book in 2008 with monthly trails reviews for Our Kids, but didn’t pitch it to Mountaineer Books until 2012. After writing trail reviews for multiple years, it dawned on me—I could turn this into a book. It took one year to do all the hikes and write about them, and then another year to edit.


Lauren: There are a lot of people who have great ideas and want to write a book, but few ever get past the first stage of writing it all down. How did you take that first step?


Jennifer: The trail reviews served as a practical, bite-size starting point for me, and having something like that can be helpful. But no matter what, I think a big brainstorming session is key. I took out a giant piece of paper and wrote down snippets of ideas and thoughts. I was able to find the unexpected connections and linkages, and once it was all out, I could create a plan for execution. But bigger picture, you really have to come at it from a place of passion, because it’s easier to write from your heart than from your head. If you have it in your heart, the details and the words will come out more easily, and then you can edit afterwards. Also, in the hard moments – the writer’s block, the fear that nobody will buy or like it, the tough deadlines – it is passion that keeps you moving forward. For example, when the book proposal was accepted, I took a huge gulp. The thought of taking this on was so overwhelming. However, I knew I loved hiking and I was able to quiet the voice that said “It’s going to be so hard” and lift up the voice that said “You can do this. It’s time to step out of your comfort zone. You’ll be sharing your passion through this book.”


Lauren: What feedback have you gotten from the book that has been particularly fulfilling or even surprising?


Jennifer: The best feedback I get is when someone says they bought the book and used it, and can point to a particular hike they really enjoyed or loved. Whenever someone shares their experiences, it gives me so much joy to know that other families are getting outside. I just know they are going to look back and say that they have an ethic and grounding force to enjoy the outdoors and thus be its steward.


Lauren: What is your favorite hike?


Jennifer: The Rachel Carson Greenway Trail – it is closest to my house, and the hike that I have shared the most time with kids participating in Hiking Along, my students and my family.


Lauren: That’s awesome! I’ll have to check that one out. We’ve done a bunch of the hikes and I have a goal (that I haven’t really shared with my kids yet!) of hiking all the trails in the book by the end of next summer! What is something that you do every day that keeps you focused on your goals?


Jennifer: Exercise. Each morning, I read for 20 minutes with a cup of coffee, then walk or swim or practice yoga. On weekends, I take a 5-7 mile hike. Sometimes I listen to podcasts and it helps me have good conversations in my head about relationships or goal setting. Other times I want peace and quiet. This is how I keep centered.

About two years ago I realized that even though I like the peace and quiet when hiking, I also missed having people around. My family will come if I ask them to, but I think I’ve hiked them out. They have developed their own hobbies and interests that fulfill them and I want to support them in those endeavors. So I started an informal women’s hiking group, which started out with a few friends and has turned into almost 200 women on a listserve who can choose to come hike with me when they wish. It’s very casual and completely free—but at this point in my career it’s making me happier than I would be leading similar hikes for a profit.


Lauren: What do you think is the next step for you in your career?


Jennifer: I really want to do what I can to protect this amazing planet. I’m starting to explore how I can do that now and over the next couple of years. But I know I have three real passions: teaching, hiking, and loving the ocean and land. I don’t know where these things will lead me. But I will come up with an idea or have an opportunity or conversation with someone that will inspire the next path in my professional journey. I love change and variety. I am beginning a transition where my kids are not going to be in the house anymore, when they are going to have their own lives. It’s bittersweet, but I love the challenge of change, and I’m open and excited for what comes next.


Lauren: The challenge of change. I love it. Jennifer, thank you so much for your time and thoughts.


Jennifer: My pleasure! Thank you so much for asking me.


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Eliza Coleman