Meet Chez Chesak

We’re excited to introduce you to the always interesting and insightful Chez Chesak. We hope you’ll enjoy our conversation with Chez below.

Chez, so good to have you with us today. We’ve always been impressed with folks who have a very clear sense of purpose and so maybe we can jump right in and talk about how you found your purpose?

I think I’ve just always been relatively well-attuned to my own internal passions and needs. I see that as the first step toward finding a purpose. I developed this sort of internal ear because I was often left alone as a child so thought a lot, and deeply, about the world around me, trying to figure it all out. When I’ve been tempted by opportunities that might have been more lucrative, I eschewed them in favor of things that I had a passion for, rather than just making a money grab. This then led me, perhaps unintentionally at first, to develop a career that is more experience-based rather than financially focused. I’ve just sought out opportunities that provided me with real, ideally fascinating, life experiences rather than simply funds. That road has been sometimes harder and with less resources than other options but has provided me with a much richer, more fulfilling life.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?

Currently I wear three ‘hats’. My day job is running the Outdoor Writers Association of America as their Executive Director, where I provide for 600+ members, all vetted, conservation-focused media who report on camping, fishing, climbing, hunting, biking and other outdoor pursuits. We are particularly excited to be planning our 100th anniversary, which kicks off in 2026 at our conference in Madison, Wisconsin.

My ‘side hustle’ and passion is writing, which I currently do as a freelancer. I primarily write about outdoors and adventure travel but also pen destination pieces, stories about family travel, reviews of spirits (bourbon, whiskey, etc.) and other adjacent elements of the outdoors and/or travel. My works have appeared in The Los Angeles Times, Fodors.com, Matador Network, Rails-to-Trails and dozens more outdoor/adventure publications and websites. I’m also a regular ‘expert’ for USA Today’s 10Best series.

As a volunteer, I’m currently the President of the Society of American Travel Writers. It was an honor to preside over their convention in amazing Detroit in 2025 and I look forward to being the Past President of SATW for their convention in 2026, which is in pastoral and bucolic Haywood County, N.C.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

I really think that knowing yourself is the key toward finding the right path for yourself. And to really know yourself starts with honesty. You have to be honest with your self about your abilities, skillsets, core beliefs – and certainly where you fall short too. This is the key and why you must be honest with yourself first. And there’s certainly no shame in understanding where your mind, your experience and your skillsets might be lacking, indeed it’s the first step in helping or correcting your abilities in those areas.

This was where my journey to develop an experience-based career, rather than one focused solely on financial gain and assimilating things, began. I just knew that if I entered a world of cubicles, board rooms and suits, that I would die (certainly emotionally if not actually physically).

One of our goals is to help like-minded folks with similar goals connect and so before we go we want to ask if you are looking to partner or collab with others – and if so, what would make the ideal collaborator or partner?

What can I say, I’m a team player. As a former college football player and U.S. Army veteran of Iraq, I know the incredible strengths that come from working as a team. This is why I think I also gravitated toward associations, as they are communities within themselves and if they don’t at least cooperate, they will certainly not thrive and could possibly even wither away. And the right team will help compliment your skills, provide support for any shortcomings and ultimately elevate you to greater heights. So I’m always on the look out for a good collaboration.

One example comes from the Outdoor Writers Association of America. Since we have a community filled with vetted outdoor storytellers, brands and destinations want to get in front of them. So in the past we’ve developed press trips where a destination hosts several OWAA members (to ultimately get exposure in media) but we also bring in an outdoor gear brand to provide product for the media to use and test while exploring the outdoors there. In the past, these collaborations have then spun out where the brand and destination might also have a sweepstakes, catalog photo shoot in the destination and other partnerships. These partnerships create true ‘win/win/win’ opportunities.

Contact Info:

Image Credits

Juliana Broste, Paul Queneau, OWAA, SATW

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