Meet Jennifer Holmes

We caught up with the brilliant and insightful Jennifer Holmes a few weeks ago and have shared our conversation below.

Hi Jennifer, great to have you with us today and excited to have you share your wisdom with our readers. Over the years, after speaking with countless do-ers, makers, builders, entrepreneurs, artists and more we’ve noticed that the ability to take risks is central to almost all stories of triumph and so we’re really interested in hearing about your journey with risk and how you developed your risk-taking ability.

Wow – that’s a loaded question! Since I can remember I have always been fiercely independent (my mother would have probably used a word like “headstrong”). Being bold isn’t always easy though. I have driven all over the country by myself, moved to Alaska by myself (where I also knew no one), ridden bulls, led a section of state government, worked as a correctional officer and sergeant, been a single mother, and much, much more. Honestly, the scariest thing I have ever done though, was scuba diving.
I grew up in the middle of Wisconsin where, not only is it too cold to swim for most of the year, but there also aren’t many places to do so – especially in the little town of 600ish people where I lived. My parents funds were limited, so they wouldn’t take me to swimming lessons when I was little because we had to go to another town to do so. When they felt my little brother and sister were old enough to learn too, then they enrolled us. I was 13 years old. At that first lesson, I was with kids 4-5 years and more younger than me and had students from my school watching their baby siblings in their lessons – with ME. If I could go back, I would tell myself that those people aren’t anywhere around when you grow up – just do it! You’ll be glad you did. But, back then, I thought my world was over. We were already on the outside because of my parent’s religious beliefs, I didn’t need anything else for them to ostracize me over. So, I refused to attend another swimming lesson as a child.
I take some swimming lessons as an adult over the years, but never really get comfortable in deep water (read, water over my belly button, and I’m only 5′ tall!)
Fast forward to the first time I see the ocean in Florida. I fall in love…
I start working on my underwater tattoo on my back – a turtle, a moray eel, and various other underwater coral and fish.
In 2012 after winning a trip to Mexico, I signed up for a snorkeling trip (still deathly terrified of water more than about 3′ deep).
I put my snorkeling gear and life jacket on and got in the water. I spent the next 30 minutes hyperventilating and holding on to the life ring pulled by our guide. When we got back on board the boat, I told my boyfriend at the time that I was just going to hang on the boat at the next spot. But, when we arrived, I automatically began putting on my gear and was the first person in the water. As I put my face in the water, there, looking back up at me from his home in the coral – just like he is on my tattoo- was a beautiful moray eel. To say I was excited was an understatement. I’d love to say that my fear was gone instantly, but that was far from the case. Several things happened over the next few years – dogged determination to learn to tread water and swim, several more snorkeling trips (including one at Buck Island where I finally learned to trust that a life jacket truly would keep me afloat). The true test was yet to come.
I had attempted a discover scuba class in 2019, with the thought that maybe knowing I could breathe underwater would help, but that was a bust. Then, when I decided to move back to Florida, I decided that I would be a diver before I went. I signed up for an open water course with the plan to get my certification once I arrived in Florida.
I was starting to feel more comfortable in the shallow end of the pool and learning the skills. Then it came time for the giant step into the deep end. I was standing at the edge of the 11-foot deep pool and I couldn’t do it. The instructor was encouraging me and then, seeing that I was not budging, he said, “I didn’t know it was as bad as this.” He told me that he had absolute faith in my ability to do it and that he would be there if I chose to take the step, but that the battle was all mine, that it was a battle taking place in my head. He moved away and gave me time and space.
I was TERRIFIED of taking that step, but I couldn’t walk away because I was also terrified of NOT taking that step. I desperately longed to be in the ocean with the marine life and I knew that the only way that happened is if I took that step. Finally, I let go – I took a breath, let go of the fear, and just did it! I stepped off the ledge.

There was still a long way to go, but I received my certification, continued swimming lessons where I finally learned to tread water, and it’s still a work in progress. As I am writing this, I haven’t dived in 3 years, so this afternoon I am taking a refresher course because next week, I am going diving in the Bahamas.
I read something recently that excitement is simply fear with breath. I like that – and I know that I can use my fear to make me better. I also know that when I face my fears, wonderful things happen!

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?

I currently own my own business, a travel agency that is focused on mindful, purposeful travel. I am also in the process of being certified as a tour director. I work with private individuals, coaches, non-profits, and other businesses who want to travel in ways that benefit our planet and have true impact – environmentally, economically, spiritually, and/or culturally.

I am also partnering with the non-profit, Journeys 4 Peace, to create and lead travel that fosters inner and outer peace, starting with our inaugural Peace Cruise aboard Virgin Voyages in April 2025.

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?

The three things that were most impactful in my journey were:

1. Listening to my intuition and trusting that gut feeling or inner knowing. When I trust, things work out. When I disregard those feelings, I find myself in some sticky situations.

2. Learning from thought and feeling masters like Mary Morrissey, Daniele LaPorte, and Marci Shimoff – both in personal courses and through reading and working through their programs.

3. Having a great support system. I didn’t really have a good support system growing up, so I had to get really good really quickly at building my own. I handpicked my foster family (didn’t give my social worker any choice – did I mention I may have been a little “headstrong”?). To this day, they are my family. I built a great support system of friends and I know that they, and the universe, always have my back. They may not always understand my journey, but they love me and support me nonetheless.

The advice I would give? I would tell you to meditate and do exercises that allow you to hear your own internal voice – and then listen and ACT. It’s no good to hear it, if you’re not going to act on what you hear.

All the wisdom you’ve shared today is sincerely appreciated. Before we go, can you tell us about the main challenge you are currently facing?

The number one obstacle I am currently facing is that I am not a marketing specialist. I sometimes struggle to find ways to reach the audience for what we’re doing.
Case in point – the Peace Cruise. It’s a great cruise with a great company. The company is very committed to safeguarding the environment and the excursion we are doing in the Dominican Republic is all about empowering women and having a positive impact on the economy. We have wonderful speakers, there will be yoga and meditation, wonderful food, and great company. We should have all 30 rooms booked, but we only have 2.
I am reaching out to local colleges working on getting a marketing intern, taking courses to amp up my own marketing abilities (I won an award in marketing in high school – shouldn’t I be a pro?), and working with a marketing expert one-on-one. I am also teaching myself AI to help.

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