Meet Rachel Hailey

We were lucky to catch up with Rachel Hailey recently and have shared our conversation below.

Rachel , so great to be with you and I think a lot of folks are going to benefit from hearing your story and lessons and wisdom. Imposter Syndrome is something that we know how words to describe, but it’s something that has held people back forever and so we’re really interested to hear about your story and how you overcame imposter syndrome.

Actually, I don’t think anyone really does. I think we learn how to navigate imposter syndrome in our everyday lives and function alongside it. Especially for me, being a Black woman entrepreneur, it felt from the beginning of starting my business that I “wasn’t really supposed to be in the space”. Almost as if someone would find out that I wasn’t as good as I thought I was, or couldn’t do the things I had set out to do. But ultimately, it’s about managing that self-talk, the negative self-talk, and the voice in our minds that says we’re not good enough or we’re not worthy. Those are things we get to navigate every single day. And it doesn’t have to be a bad thing! The reason these feelings come up is a form of self-protection. So i do my best to notice the thoughts and feelings I’m having, but go for it anyway!

Being an entrepreneur and a leader in this space sometimes means getting way out on those skinny branches of transformation and being willing to take risks, even though our minds or feelings might be going bananas. So for me, it’s not really about overcoming imposter syndrome, but more about living alongside it, knowing that it’s just a side effect of being a leader and an entrepreneur.

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

Well, a little bit about us at DEI Outdoors. We’re a diversity, equity, and inclusion consultancy focused on the outdoor space, and what that really means is that we help both organizations and individuals—practitioners, too—find ways to create a sense of belonging in outdoor recreation, conservation, retail, and education. We’re really excited about the work we do and the programs we’ve built.

Part of the reason I’m so passionate about this is my own lived experience. I’ve got a lot of intersecting identities, and I’ve noticed that there’s a real gap between the people who want to be part of the outdoor community and those who feel welcome or are actively out there. That’s why we’ve made it our mission to provide organizations and individuals with strategies to foster belonging—a feeling we’re all looking for, I think.

My daughter, who’s almost nine, just told me she wants to hike the Appalachian Trail. And when I think about that, it really brings the heart of our work into focus for me. In 10 years, when she’s ready to take on that challenge as a multiracial young person, I want her to be able to do it without fear or judgment, just fully enjoying the experience. The outdoors belongs to everyone, and that’s what drives everything we do.

We’ve got a lot of ways to support folks—whether through our training programs, our comprehensive audits and assessments for organizations to see where they are with fostering belonging, or our individual practitioner certification, which gives people practical tools to create inclusive outdoor spaces. Our aim is to make the outdoors as accessible and welcoming as it can be.

We do everything from one-on-one and group leadership coaching to partnering with local community organizations to lead community hikes where we connect people with nature and each other. And at the core of it all, we’re community-centered. We really want to lift up and support those who’ve experienced marginalization in the outdoors. That’s what we’re all about—making sure everyone has a place in nature.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

Looking back, I think the three most important qualities, skills, or areas of knowledge that have been impactful on my journey are:

1. Just Start: The biggest piece of advice I’d give is to simply start—no matter what obstacles seem to be in the way, whether it’s fear, commitments, or other obligations. Take the leap, even if it’s just one small step. Whether it’s sending an email, writing a paper, or having a meeting, taking that small step can create forward momentum for yourself. Don’t get stuck in the planning!

2. Fellowship and Mentorship: It’s important to be in fellowship with others. Seek out mentors. I had an amazing group of mentors through a business accelerator program called E4ALL, and they were instrumental in helping me scale my business. Surround yourself with passionate individuals who can shine a light on opportunities or areas you might not see on your own.

3. Rest and Restoration: Lastly, as a new entrepreneur, it’s crucial to build in time for rest. Burnout is real, and it’s essential to give yourself the space to rest and restore, especially as you dive into the passion and momentum of your work.

For those starting their journey, focus on small steps, build a network of support, and don’t forget to take care of yourself along the way.

As we end our chat, is there a book you can leave people with that’s been meaningful to you and your development?

Rest is Resistance- Tricia Hersey

1. Prioritizing rest is important for overall well-being and resilience. The book emphasizes the importance of rest in maintaining emotional, mental, and physical health, and how it can help individuals navigate life’s challenges with greater ease.
2. Rest is a form of resistance against societal norms and expectations. In a society that values productivity and busyness, choosing to prioritize rest can be seen as a radical act of self-care and self-preservation.
3. Rest can take many forms and is unique to each individual. The book explores various ways in which individuals can rest, from physical rest like sleep and relaxation, to mental rest like meditation and mindfulness.
4. Rest is a political and social justice issue. The book delves into the ways in which marginalized communities are often deprived of rest due to systemic oppression and discrimination, and how prioritizing rest can be a form of resistance against these injustices.
5. Rest is a necessary component of any movement for social change. The book highlights the importance of rest and self-care in sustaining activism and resistance movements, and how taking time to rest and recharge can ultimately lead to more effective and sustainable action.

Contact Info:

Image Credits

All images are property of DEI Outdoors

Suggest a Story: BoldJourney is built on recommendations from the community; it’s how we uncover hidden gems,
so if you or someone you know deserves recognition please let us know here.
Resilience
Perspectives on Being an Optimist

We’re often asked if we’ve seen a pattern of success among the many thousands of

Leadership Development
Mastering Communication: Stories & Lessons

“Good communication is as stimulating as black coffee, and just as hard to sleep after.”

Productivity
Perspectives on Staying Creative

We’re beyond fortunate to have built a community of some of the most creative artists,