Trail Mavens


Skill-based camping and backpacking trips for groups of extraordinary women. Ready to build fires, read maps, pitch tents, hike, laugh, and drink wine around the campfire? Join one of our weekend adventures.

For Busy Professional Women Who Want To
Take Charge of Their Story

Photo by Jenna Carando

Photo by Jenna Carando


january 14-16

adventure type:

camping retreat

activity rating:


registration deadline: thursday, january 5 

Remember twelve months ago, when 2016 started?

Whether you made a resolution or not, one thing was for sure: this year would be different.

This would be the year you broke out of that rut and made a meaningful change; the year you would finally apply to law school, or launch that business, or start drawing again.

The year you would feel the sense of accomplishment and f-yeah satisfaction that comes with acting on the ideas that are meaningful to you.

And then...what happened?

  • Emails flooded in. 
  • Bosses and colleagues popped into your office.
  • Partners, friends, and family gave you dates to remember.
  • Your to-do list grew arms and legs and started whispering in your ear as you slept.
  • ...and even more emails. Curse you, emails!

And because you’re Superwoman,
you mostly succeeded in doing it all.

You used your magical get-shit-done powers to make sure everyone else’s needs were met.

But now here we are again, at the end of the year, and you’re still itching for something that will feed your soul and help you remember that this is the life you were meant to be living.

Itching to stop prioritizing everyone else, and give yourself the attention and space and light you need to flourish.

What would life feel like, anyway, if your goals were
the non-negotiables TOPPING your to-do list?

We’re not going to bullshit you. Manifesting your dreams - as touchy-feely as it sounds - isn’t easy.

It can be terrifying to be so close to what you want. But you know what? The flip side of terrifying is an exhilarating, awake-to-everything, full-to-bursting sense of agency and pride in yourself.

And bottom line, is it scarier to put your dreams into action, or to wake up in twenty years and realize you never did?

Introducing Outside  In

The three day storytelling and nature retreat
for busy professional women who want to take charge
of their story, and take action on their dreams.

Photo by Emi Day

Photo by Emi Day

what's included

  • Three days in the redwoods near the Russian River
  • Small and supportive posse of awesome like-minded women
  • Solo and group coaching to clarify what you want, what’s getting in the way, and what’ll get you there
  • Fresh, healthy vegetarian meals included
  • Top-of-the-line camping gear, so you only have to bring your clothes, your toothbrush, and an open heart
  • Optional guided morning meditation
  • Fresh air, trees, sky, stars
  • No calls to answer / inbox to check / errands to run / partners to please; just deep presence and intention for this life (the only one you’ve got)


  • Say adios to the limiting stories that keep you where you are
  • Create a clear and inspired vision - your trail map - for 2017
  • Get to know your Inner Leader, and learn how to consult her when you’re not sure what comes next
  • Leave with a practical action plan to hit the ground running

Your leaders:


About Sasha:

Sasha Cox is a certified life coach and founder of Trail Mavens. Several years ago, she realized her calling was to enable people - but mostly women - to step into the boldest, bravest versions of themselves. She uses a high-powered blend of intuition, humor, love, and butt-kicking to help her clients create the lives they feel like they get to live (instead of the ones they've got to live). The first question is: what do you really want?

About Jess:

Jessica Mastors is an adventurer and wilderness guide, storytelling coach and strategist who helps daring professionals and early stage entrepreneurs make the next bold leap in their careers and organizations. She’s helped clients use the power of story to wow investors, secure huge donations, get hired in new industries, and negotiate their highest salaries yet. What leap is calling to you?

(Weirdly enough, we've both ridden elephants in Thailand.)


Every single Trail Mavens trip starts with strangers. But don't worry - if you're nervous about not knowing anyone or not being skilled enough, everyone says this before they go.

To feel more confident before signing on, check out our FAQs.

Join this transformative nature retreat for only $997


our commitment 

You can rest easy knowing your investment comes with a 100% money-back guarantee. If you don't find the experience valuable, just let us know within seven days of your return to civilization and we'll give you your money back. Plus, the first five women to sign up will receive a full scholarship to Jess' 'Conscious Storytelling' online course in 2017.


We don't want finances to be the thing that gets in the way of your coming on this retreat, so we  offer installment plans. To learn more, email and we'll get you set up.


Before I started working with Jess, I was concerned about what kind of return I would get from working together and understanding my stories. Honestly, I can’t tell you how game-changing it was to work together; how much I was able to learn and understand about myself and the stories I told myself that simply weren’t true and were limiting me; and how much motivation and positive energy I’ve received from working with Jess during the hard times of having multiple interviews and a lot of pressure.

- Simon T


Jess! Wow. You are the type of woman I aspire to be. You are an incredible leader, communicator and teacher. Your balance and grace is amazing. Thanks for a perspective-changing weekend.

- Caitlin D.

Sasha, what can I say that so many grateful women have already said? Thank you for helping me find strength, confidence, silliness, truthfulness, and love in one short weekend. I feel blessed and full of positive energy. I. Got. This.

-Erin M.


Initially, I started coaching with Sasha in hopes of improving my effectiveness at work. After working with her, I have become a better and bolder version of myself - both professionally and personally. She helped me identify the areas that were holding me back from feeling truly happy and empowered. Interestingly enough, much of the work we did was tapping into my own vulnerabilities and allowing myself space to accept things I couldn't change. I ended up leaving a toxic work environment that was taking up most of my emotional energy. Now, I have the time to spend on areas I care about and with people who matter the most. 

I'd highly recommend working with Sasha if you're ready to make a positive change in your life and willing to put in the work. She's incredibly smart, fun, and intuitive, but she's also firm and will hold you responsible for the goals you set.

- Marissa H.


It’s scary to acknowledge how powerful you are.

Once you’re aware of what you’re capable of when you put your mind to it, you stop having excuses for why you’re not getting out there and doing it.

Incremental shifts - going to the gym three times a week instead of twice, eating out a little less - are nice. They are not what this weekend is about. It’s about putting on your big-girl pants and taking a stand for who you are and what you want.

You in?

Additional questions? Email