Meet Nicole Gregory

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

Hi Nicole, thank you for being such a positive, uplifting person. We’ve noticed that so many of the successful folks we’ve had the good fortune of connecting with have high levels of optimism and so we’d love to hear about your optimism and where you think it comes from.

Optimism is a fascinating word. I think in some ways with the rise of ‘positive thinking’ it has lost its beauty and potency. The definition of optimism: “hopefulness and confidence about the future or the successful outcome of something”.
Growing up, I had the honor of watching my father live out the truest example of what optimism has become to me. We had very little to our name and to many standards, we fit into the poverty sector. As I have grown into adulthood and look on my childhood in hindsight, I have found myself studying my father’s belief system and what enabled him to wake up as a husband, a father of 12, a business owner (back in the time when ‘black-owned business’ wasn’t something that remotely played to one’s favor) – fully embodied in his perspective and belief that life was going to be ok. What I have come to realize is that optimism is parallel to faith and faith is what my father had buckets of. The most poetic and well-rounded definition of faith that I know is: “the substance of things hoped for and the evidence of things unseen”.
What I have learned is that life allows us the option of hope or despair. I compare them to lenses- we have the option to experience life through whichever lense we decide to put on and every experience will be filtered through our choice of lense. I have decided that while I live, I choose hope, while always holding in my reality that as predictable as the sunrise is, so are heavy clouds and rain-filled days and the beautiful thing is, is that even the rain-filled days eventually get filtered through that hope.

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?

My professional career for the past 15 years has been in Hospitality and Food & Beverage. In 2021, I opened Staycation Coffee which had a location in Richardson for four years and has a corporate bar location in Uptown, Dallas. Although I am a coffee lover and educator, my time in both industries has been fueled mainly by my love of gathering around beautiful, sense-ual moments created through intentionally designed spaces, artfully inspired elements and the combination of those to create moments of authentic and life-shifting gathering with other humans.
Running a business that put me in the public almost daily, revealed to me that I needed a pivot that would give me a bit more space and time to devote to creating, while still pursuing the same goal of a storefront space – inspiring gathering, conversation and FEELING through beautiful and heart-led work. I believe this to be vital- not only for finding touch points across this messy line of being human but also for individual evolution.
This has me returning to my piano and music composition along with writing as I muse on what is next by way of a brick-and-mortar. My first dip back into this pool was an immersive art installation co-created with my sister, the artist Jessica Vollrath, Spring 2025 at South Dallas Cultural Center. I am wildly excited for what this current exploration holds.
Alongside these creative outlets, Staycation the brand, is currently undergoing its own pivot as my attention turns more towards coffee education and curated products mostly by local artists, that support people in creating sense-ual moments for their own gatherings. Our updated website will go live in December!

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

Whoa… what a great question.

1. I’ve learned that every pursuit comes with its own set of ‘DIFFICULT’. I believe this to be an aspect of achievement that we cannot avoid. What I have learned is that somewhere along the way, we have to decide if the pursuit is worthy of its ‘DIFFICULT’ because that will determine if we see it through. I think it is critical to understand that we have the power to choose what ‘DIFFICULT’ we want to take on but we don’t get to decide IF it comes. It WILL come and if it’s something worth that trade, we will show up for it day after day after day until it becomes the masterpiece in our dreams. Saddle up and be ready for the ride.

2. Becoming acquainted with stress and where it originates from was one of my biggest game shifters as a business owner and creative. I’ve had a difficult history with stress and due to some health issues that came from this, I made a decision to understand stress dynamics: what is IN my control vs what was not. I learned that while there is definitely stress from external things that we cannot control (the very act of being alive is its own stressor) there was also an internal stress that I was feeding. For example: I hadn’t put consistent practices in place to assist in my daily time management so I’d often find myself behind schedule; or I allowed myself to worry about something far outside of my wheelhouse of responsbility; or I was mentally bloating an issue that was not as tedious as I was making it out to be. To be able to understand what I could shift, drastically changed my life. I saw a marked difference in how I show up for projects, business, creative pursuits, etc.

3. Authenticity above comparison is something I live by. I often chuckle to myself when I see another trend pop up whether it’s in art, music, food and beverage, fashion…
In my industry, the trend would usually be a coffee beverage that quickly spread to every coffee shop in the neighborhood. Is following a trend good for the bottom line? Usually and trust me, I understand wanting to put that first and foremost when you own a company but for me, I realized that I find joy and richness in following an original idea. Is it risky and oftentimes scary? Yes, because you are working with no data except “I love it!” yet on the flip side, you have the chance to stand apart and you live with the satisfaction of knowing YOU are out in the world expressed in your uniqueness.
-and what is life except showing up with our own original stamp? No comparison. Only authenticity.

If you knew you only had a decade of life left, how would you spend that decade?

Living every day, waking up and asking, “how do I put life back into the world today?”
As I see our world and try to make sense of it from one day to the next, I am so aware of the fact that there will ALWAYS be people pushing for agendas that are destructive. We see destruction on many levels: our planet, our communities, our economy, our identities, our families, our atonomy, etc. and oftentimes it’s really difficult to contend with what our response should be to what feels like an overwhelming energy that we are helpless to.
I think beauty inspires hope.
I think kindess brings life.
I think creative output seeds curiosity.
I think true community can save us.
I believe a painting, a poem, a product, a song, a book, a good meal, a good cup of coffee or a perspective shifting conversation can bring moments of joy that put the energy of light back into the world around us.
So I intend to keep creating as long as I have breath in me; be it a company or a composition- and to endeavor to put the life back into the world as often and as potent as I can.
That is how I would spend my next decade.

Contact Info:

• Website: www.nicoleleahgregory.com, www.staycationtx.com
• Instagram: @staycationcoffee
• Other: Note: our Staycation website (referenced above) is under revamp and will be live again in December!

Image Credits

The Rchive Collection

Hillary Bridgeman Photography