Chasing Dreams Interview with Kayla Kleinman: Launching Holistic Happenings, a Wellness Events Company

Kayla Kleinman is a woman of many talents. She's an actress-turned-marketer, fitness blogger, yoga teacher, and grad student among so much else. Kayla's also the co-founder of a new wellness events company in NYC named Holistic Happenings.

She's navigated her way through a variety of small jobs and exploring her interests in order to start creating a life on her terms, which I know so many of you desire to do.

Find out how chasing her dreams has gained big time attention from companies like Teen Vogue, Arianna Huffington's new company Thrive Global and Modell's.

Let’s dig in!


At what point did you know you wanted to follow this career path? How did you know this was the right direction?

Oh gosh, it's been a long journey to get here, but one thing has led to another.

I graduated college with a BFA in theater but fell in love with fitness while I was in college. Because of that I decided to become a personal trainer and started my blog Kayla in the City.

I was then recruited by a start-up thanks to my blog and twitter account and totally fell in love with marketing because it combined my creative background with the more analytical part of my brain.

From there I worked in marketing at various start-ups in the wellness industry. Last year at this time I thought I had my dream job as the marketing lead at a small fitness fashion company, but I didn't feel 100% satisfied. I really, really, really wanted to be my own boss and craved the excitement of starting my own business.

So I decided to go to grad school while also launching Holistic Happening... and that's where I am now!

What are the biggest struggles you've faced while trying to achieve your dreams?

Sometimes I wish there was a guidebook essentially called How To Launch A Successful Wellness Event Company.

Every little aspect has been a learning process -- my co-founder Leslie and I are learning what works and what doesn't work and doing our best to learn from those failures.

Right now our biggest struggle is also getting the word out. I'm learning you gotta be loud and proud and promote the cool things you're doing every opportunity you have.

Owning your own business can be tough on the body and mind, between long days, instability and really putting yourself out there to reach your goals. How do you stay healthy? Do you have any rituals that help you stay centered?

I always, always, always workout first thing in the morning. If I don't do it right after I wake up, it's probably not gonna happen!

I also try to make a conscious effort to walk 4-5 miles a day, which is pretty easy in NYC. If I realize I've been spending too much time sitting around, I force myself to get up and take a long walk. It always leaves me re-energized and refreshed.

Speaking of putting yourself out there, overcoming rejection is a big part of chasing dreams. How do you bounce back?

My mom jokes that nothing can be as painful as the rejection I experienced as an actor and while studying theater in college. It's kind of true.

I'd be lying if I didn't admit that it hurts, I recently auditioned to be an instructor at one of my favorite fitness studios and didn't get the job. I try to remind myself to not take it so personally. It doesn't mean they don't like me, it might just mean I wasn't the right fit.

What do you do when you're having an off day—maybe feeling down, struggling with self-doubt, or just unmotivated?

I'm a total podcast junkie. On those super blah days, I try to take an extra long walk while listening to a motivating podcast (a current favorite for entrepreneurs is Being Boss!) and it usually gets the creative juices flowing.

Or sometimes I just listen to what my body is telling me and use that as a day to catch up on boring, menial tasks which don't require as much motivation and creativity.

What is one misconception people have about you and/or your profession?

That I'm super outgoing, ha! While I'm fairly bubbly and sassy online, I'm also super awkward in most social situations and joke that people are probably really disappointed when they meet me.

What is one of the biggest lessons you’ve learned along the way?

I've become a believer that everything happens for a reason. I'm grateful for the jobs that have rejected me and the jobs that have fired me because I know it happened so something better could come along.

What advice would you give to someone who wants to follow a path similar to what you have?

Just do it. I'm glad I approached my Holistic Happening co-founder about making our first event happen like legit right after I had the idea. I didn't give myself a chance to chicken out and think it was a dumb idea.

When do you feel the most inspired, alive and the most like YOU?

I love getting to teach yoga classes and lead events for Holistic Happening because it brings back the same feeling I used to get as an actor.

After our events, I'm always this beautiful mix of exhausted and exhilarated and I come home with this wild smile on my face. It's addicting and after our first event, I knew I needed to feel that feeling again soon.

What people, books, music, etc. inspire you?

I'm insanely inspired by other bloggers and solopreneurs who are making shit happen. It's scary to strive for a non-traditional career path -- people thought I was crazy to go to school for theater and now people think I'm crazy that I don't want a 9-5 job.

In addition to my love of podcasts for motivation + inspiration, I'm also a total non-fiction junkie and love books like #Girlboss and Make Your Mark which both energizes and inspires me.

Describe your favorite moment or accomplishment in your career so far.

When I found out I was featured as one of the top fitness Instagrammers to follow in Teen Vogue in May. I was seeing a show with my best friend and looked at my phone right at the end of intermission only to see my Instagram was legit exploding with notifications and people tagging me in some post about top fitness Instagrammers on Teen Vogue.

I spent the entire second act of that show thinking I made the whole thing up or misread what happened. I was so insanely honored to be featured.

Yes, of course, it was awesome to get my 15 seconds of fame, but it was also exciting to be recognized as a source of motivation and positive vibes when that's not always true about the fitness industry.

What’s the most exciting thing going on in your life right now?

As of this weekend, the Holistic Happening event calendar is booked SOLID until May. People and companies have started approaching us about events including Arianna Huffington's new company Thrive Global and Modell's! I legit screamed for a good 5 minutes when I found out we were doing the event at Thrive, I was so flipping excited.

About Kayla Kleinman


Hi Guys! I'm KaylaKleinman -- I'm the co-founder of Holistic Happening, a NYC-based company creating interactive wellness events. I'm also a fitness blogger over at Kayla in the City and grad school student studying Social Media Marketing (yes that's a thing you can get a Master's degree in!)

Website // Instagram // Twitter

This interview is part of the Chasing Dreams interview series. I’ve interviewed a variety of entrepreneurs and small business owners who have chosen a different path in life in order to go after his or her dream career. Have an entrepreneur in mind you’d like to learn more about? Let me know!


Danielle Zeigler

I'm Danielle, an SEO and Digital Marketing Strategist on a mission to help creatives and entrepreneurs harness their strengths, personality, and energy to easily + authentically market their work to exactly the people who need it.
I specialize in SEO and content marketing as ways to attract clients TO you. I'm extremely introverted, so I'm allll about the inbound marketing!