Jailyn Jenkins of Denver Metro Area on Life, Lessons & Legacy

We recently had the chance to connect with Jailyn Jenkins and have shared our conversation below.

Jailyn, really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: When was the last time you felt true joy?
I am grateful to say that I feel joy (or glimmers) multiple times everyday. So naturally, my answer would be today and some of the things that gave me joy today are: 1) a slow start to my Saturday morning, which included a hot breakfast (not meal-prepped), 2) a warm, fall walk around my neighborhood with everything silenced and an ability to engage all of my senses, 3) phone calls with my family, 4) meandering through state parks, 5) getting lost in my books, and 6) lounging on my couch laughing my heart out thanks to a top-tier algorithm.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Jailyn Jenkins, the founder of Teacher Turned Tech. My background is in education— I spent years as an award-winning teacher, instructional coach, and professional learning leader. Over time, I noticed a common challenge: people with strong ideas and meaningful work often get stuck when it comes time to actually implement them using technology.
Teacher Turned Tech exists to bridge that gap. I support educators, founders, and service-based professionals in translating ideas into working systems, whether that’s a website, digital workflows, or basic tech setup or tutoring. Behind the scenes, there’s strategy and systems thinking; for clients, it feels like clarity, momentum, and control instead of overwhelm.
What makes my work different is how human-centered it is. I don’t lead with tools; I lead with how people think, work, and grow. The goal is simple: help clients move from vision to execution in a way that’s sustainable, intuitive, and actually supports their day-to-day lives.

Great, so let’s dive into your journey a bit more. Who taught you the most about work?
Several people in my family have shaped how I think about work, discipline, and responsibility. My mother was my first example. She is a visionary, strategist, and realtor who sees possibility before it is obvious and knows how to bring ideas into reality. I spent most of my time with my mother’s side of the family, and that is where these lessons showed up most consistently in everyday life.
Her parents deepened that learning in different ways. My grandmother was a masterful gardener and cook. From her, I learned patience, care, and the importance of holistic living. My maternal grandfather became the crux of those lessons. I was his shadow, and so much of what I learned came from simply being alongside him. He was a retired lieutenant colonel in the Army, a former real estate agent, and an active entrepreneur who worked hard, took pride in what he built, and also knew how to rest and enjoy life.
Watching him intentionally carve out time for joy taught me that meaningful work is not about constant output. Mondays were reserved for rest, golfing, watching tournaments, and spending time with his granddaughters. Over time, navigating professional systems helped me unlearn the idea that I needed to perform at a machine level to be successful. I have come to believe that doing my best includes honoring my humanity, and that rest and joy are not rewards, but requirements.

If you could say one kind thing to your younger self, what would it be?
Ironically, I was just looking through pictures of Baby Jai, and I couldn’t help but smile and shed happy tears. I had no idea what my life would truly look like, and I am beyond grateful that it surpassed all I could ask for or imagine. So now, I feel prepared to actually answer this. With that said, I’m going to pretend to have one minute with my younger self, instead of saying one kind thing.
I would open my arms wide and say, “Come here!” I would wrap that little girl in the warmest embrace and tell her that I love her, and that I’m proud of her, regardless of which path she takes. I would remind her to pursue progress over perfection, take deep breaths, dream freely, stay curious, frolic in the grass, slow down, and trust that she is worthy of all good things. I would tell her it all works out, no matter what, so trust your gut and move through life with peace, purpose, passion, and people who love you.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. What would your closest friends say really matters to you?
On a superficial level, my closest friends would say that I value working out, reading, joy/laughter, resting, eating good food, quality time with loved ones, and science or STEM.

But at a deeper level, it comes down to what I call the six H’s: Happy, Humble, Healthy, Helpful, Healing, and Humanity.
Happy: Joy is a critical component of the human experience.
Humble: Learning happens everywhere if you are humble enough to listen. Tia Williams, A Love Song for Ricki Wilde, p. 305.
Healthy: My constant pursuit is a holistically healthy life, whether that means throwing weights in the gym, exploring natural alternatives, or looking in the mirror and being real about a pattern.
Helpful: If you can help someone, do it. Being stingy serves no one, despite what capitalism tells us.
Healing: Whether it is in community, over a good meal, in a park, or during a breath work session, healing takes on many forms and it is necessary.
Humanity: We are humans, and humans deserve connection, rest, joy, and more. We must first honor our own humanity if we actually intend to respect and honor those around us.

Okay, so before we go, let’s tackle one more area. What will you regret not doing? 
At this point, nothing. Could I have done things better? Absolutely! But I don’t regret anything. From a young age, I’ve generally understood the concept of “closed mouths don’t get fed,” so my philosophy has consistently been “the worst they can say is ‘no.'” I implemented that when asking to go to Toys ‘R’ Us, requesting more financial aid/scholarships in college, proposing several promotions, and more! That statement is so deeply ingrained in my brain, that when I think about regretting something, I end up addressing it soon after, because “if you weren’t ready, you wouldn’t have the opportunity, and if you weren’t capable, you wouldn’t have the desire.”

Contact Info:

• Website: https://www.teacherturnedtech.com
• Instagram: https://www.instagram.com/techjai_ttt/
• Other: TikTok: https://www.tiktok.com/@teacherturnedtech?is_from_webapp=1&sender_device=pc
  Portfolio: https://ttt-portfolio.my.canva.site/