MS: What was your pivotal moment in life that made you take this direction? 
JD: I started working with a coach who made me realize how crucial it is to create your own personal brand - even if you're working for someone else. About three months into building my personal instagram account, I started offering advice to the salon owners and they didn't seem perceptive to any of it. I brushed it off and kept working on my own stuff. Out of nowhere, they let me go. I felt shattered. I didn't understand at all. I thought, "What am I doing? Should I even be doing hair? Maybe I need to find a new career."

MS: What made you want to be what you are now? 
JD: I'm first and foremost a hairstylist. My high school art teacher told me I'd be a good hairstylist. Honestly, all I knew was that I didn't want to waste my time and money in college when I had no idea what kind of career I wanted; but I trusted her a lot, so I basically just went for it! I knew I'd have the ability to be creative, and I love being around people so I thought it would be fun. I love my job, and I definitely have a lot of fun but it's nothing like what I expected!

After a few days of spiraling, I realized I needed to make a choice. I needed to either pick myself up and go into business for myself, or shut down my career. I decided I had so much more to give, and took a leap. I invested a lot of money and time into starting my own business, Hair by Jessie Ryan LLC. I'm grateful every day for the life and career I have now because of that one choice. I'm even grateful that I was let go from my job, because it would have taken me a long time to do it without that push.

MS: What are your favorite parts about what you do? 
JD: There are so many things I love about what I do. Maybe my favorite thing is seeing my clients transform from the beginning of an appointment to the end. I know everyone loves an IG transformation post, but for me it's more than just the hair. We go to a new hairstylist hoping that we come out feeling better, but so many people have had bad experiences that it can be scary to try someone new - again. I don't think anyone expects the experience they have with me. I really strive to make each person feel seen in my chair, no matter what's going on in their lives.

MS: What are your short-term and/or long-term goals at the moment? 
JD: My short term goal is actually a personal monetary one that I'm happy to share! I'm going to be debt free by November 2021. Long term, I'd like to invest in more coaching to figure out what my next business moves are. A lot of people expect me to open a salon someday, but that has never felt true to who I am. I'm an entrepreneur - control and freedom are why I like working for myself. We talk a lot about this kind of stuff on my podcast, and I could quite literally talk for hours about all of this! (Shameless plug: If you're interested, my podcast is called The Ditto Podcast: for creative entrepreneurs. I have two seasons of audio where we talk about all the most relatable things in entrepreneurship! Again, our stories are all more alike than you'd think, and it's really comforting to know you're not the only crazy one out here doing the dang thing!)

MS: Do you have advice for people interested in the same field? 
JD: My advice for anyone who is thinking of entering the cosmetology field is to shadow someone in your desired position, for as long as possible, before you even go to school. In Connecticut you only need to attend 1500 hours of school and pass a written state board test to get your licence. This career is so much more than what they teach you in school. I honestly don't know if I would have done this if I had known from the beginning how much work it actually is. Only 4 people from my graduating class of 20 are still doing something in this field of work after 8 years. 

MS: What is something(s) you wish you knew in the beginning? 
JD: Something I wish I knew in the beginning is that it's okay if you don't fit in at the first place you work. It took me 8 years and 5 salons to find somewhere that I didn't have to hide and be like someone else. That charade doesn't last long. Fake it til you make it, is a scary game to play. Be yourself, love yourself and the rest will fall into place. Corny, but 100% true.

MS: Who/what are your biggest inspirations and why? 
JD: So this is gonna be a weird answer. I don't actually follow a lot of hair stylists, so I think my inspiration actually comes from the creative entrepreneurs that I interview on my podcast. So many of us are doing whatever it takes to make our clients feel good. That's really what it's all about for me. I'm always taking hair classes and learning new techniques, but I wouldn't say that I have any single favorite artist who I follow.

MS: What is your favorite food/drink-related memory?
JD: Oh this is a good one! It's so hard to answer because I REALLY love food! haha! I have to say the most unique eating experience I ever had was at the Essex Restaurant with you, Monique! We got to experience a tasting menu where I literally had no idea what was coming next. It was so exciting but I don't really like a lot of cheese so I was worried about that. I know, you think I'm crazy but I like to taste my food and cheese just makes everything taste like cheese!!

MS: What is your favorite quote(s) and why? 
JD: Okay this one is really hard. I love to read, so quotes are where I go to feel understood. I think this one has to be my favorite by St. Therese - though I have adjusted it in my mind to fit my beliefs. "May today there be peace within. May you trust that you are exactly where you are meant to be. May you not forget the infinite possibilities that are born of faith in yourself and others. May you use the gifts that you have received, and pass on the love that has been given to you. May you be content with yourself just the way you are. Let this knowledge settle into your bones, and allow your soul the freedom to sing, dance, praise, and love. It is there for each and every one of us."

MS: What are some things that keep you going? 
JD: A few things!
- Knowing how lucky I am to be as busy as I am right now.
- Knowing that I'm making a difference, even the slightest, in my clients' lives.
- Knowing that seeing me succeed helps those around me realize their own potential. Then watching them succeed on their own!!
- I'm becoming successful without having to change who I am to do it. I will stay high-vibrational, positive, kind and honest no matter what.

MS: What is something you wish people learned or knew more about in your industry? 
JD: Many of us have worked long, hard hours to continue to be the best at what we do. The amount that you pay us is due to the many hours that we've spent perfecting our work, as well as using only the best products available and keeping a beautiful space for your experience. Asking us for a discount, or refusing to pay after a service, are maybe the most disrespectful things you can do. Do some research, and have an open conversation with your stylist about your budget so that we can avoid these situations.

MS: Do you have advice or encouragement for ways to support local? 
JD: Well, I really think that a lot of supporting local business is just being aware. Keep an eye out for new stores, and make a point to actually visit them when you can. If you know people who have online businesses, then do whatever you can to support them. If you're on a budget and you can't afford anything, then share it on your social media pages, or send it to a friend who you know would love them! There are really so many ways to help get the word out about a great new shop that you want to support!

“Even if you work for someone else, you have to advocate for yourself and work like an entrepreneur. Your success depends on how much effort you put in. That's the truth for anything in life, truly.”


“My real job is to help my clients find, and embrace themselves. We are all more alike than we realize. We're vulnerable, excited, optimistic, but careful and observant.”