5 Stories That Prove It’s Never Too Late to Change Careers

By Jenn Rose Smith
Ashley Woodson Bailey

Maybe it’s the un-PC nature of our biological clocks, or just good old-fashioned societal pressure, but it seems that women are especially susceptible to timelined expectations in life. Many of us want to achieve status in our dream jobs by 30, be married with multiple kids by 35, sell the company by 40… etc, etc. I don’t know about you, but my life hasn’t played out that way AT ALL. It’s actually been better than that, in ways I could never have designed. But first, I had to be open to embracing the natural flow of my own timeline, and let go of other people’s ideas and expectations that I was taking on as my own. Last week I set out to find five other women who threw the conventional timeline to the wind to discover their own dream jobs, and reap major rewards. If you think it’s too late to shift gears or go for the career you’ve always wanted, read these five stories and ask yourself the ultimate question: why not?

Ashley Woodson Bailey, 44
photos by amber fouts

former career path: I was a florist for a very long time, on-and-off for 20 years. I worked on large scale weddings and events in Houston, New York, Savannah and Austin.

current gig: Artist/Photographer of Flowers/Product Designer

what inspired you to change careers: I honestly didn’t want to change careers but was forced to when I was involved in a near fatal car accident. Physically, I was unable to continue the manual work of being an event florist after the accident. It’s funny, when a really terrible event ends up being the best thing that ever happened to you.

how old were you: It happened in the summer of 2012, so I was 39.

what you love about your new career: I love that I get to work with flowers in my own way on my own terms now. I photograph them and use the images to create art prints and textiles. Hands down, the most rewarding part of my new career are the people I’ve met and that I get to work with.

the hardest/scariest thing about changing careers: I wasn’t scared to launch my business because I had literally almost died. I figured it couldn’t get much worse than that.

your best advice for career changers: If you’re a creative, make sure you have insight from someone with a mind for business. It will seal your fate as a business woman.


Aimee Speer, 41
photo by hannah mayson

former career path: I founded and ran Hem Jeans, a premium denim boutique in Austin, with my sister, Loree. With the incredible support of the Austin community we shared a decade of success and it was a part of my life that was filled with growth, both professionally and personally. I raised my first two baby girls at the store, but after 10 years of being married to a brick and mortar business, I decided I needed to make a change.  

current gig: hat maker at Covet Hats

what inspired you to change careers: After the birth of my third daughter, I wanted to be able to have more freedom to be with my family, and have the flexibility to travel and express my creativity. I loved working in fashion and knew it was a path that I still interested in. I wanted to have more of a creative voice and work with my hands. My love of hats kept calling to me and I became obsessed with figuring out how to make them. I was able to find a local milliner who taught me some hand-sewing techniques and blocking skills, but what I really wanted to learn was how to make a proper cowboy hat the way they were made in the early 1900s. I found a cowboy hat maker in Utah that had been making hats for 40 years. His direction and advice helped me decide that hat making would be my next chapter. I’ve been collecting tools and self-teaching ever since. I’ve been making hats now for 3 years and professionally for a year and a half. With the incredible support of my husband Scott,  I have been able to focus all my energy on building my business.

how old were you: I was 39 when we closed the boutique and I began to explore millinery and hat making.


the hardest/scariest thing about changing careers: The hardest thing was jumping. Once my mind and heart were committed I knew I could accomplish what ever I set my sights on. I consider myself to have a very strong work ethic.

what you love about your new career: Seeing people wearing, enjoying and living their lives in my hats makes me super proud. I love creating hats and I put all of myself into every hat, each of which I consider a work of art.

your best advice for career changers: Do it! Life is short and you’e wasting your time if you don’t invest in your own happiness. The longer you stay at a job that is unfulfilling the more you resentment you feel, which is no way to live. Your intuition is the key and your inner voice is guiding you… Listen!

Camilla Marcus, 32

former career path: For whatever reason, I’ve always enjoyed rowing a lot of boats at once. I have a varied, cross-disciplinary background including stints in business development, creative consulting, angel investing, and real estate acquisitions.

current gig: owner and founder of west~bourne restuarant in NYC

the hardest/scariest thing about changing careers: Uncharted waters are always scary, especially if you don’t really know anyone where you’re headed. I like being part of a group and team, so that initial period when I felt alone (for me) was the toughest. That said, I try to remember that the initial discomfort is temporary and take it day by day. It’s also good to remember that anything worthy can’t be easy or everyone would do it.

what you love about your new career:  First and foremost, I love the people I get to collaborate with on a daily basis. The west~bourne community — from our branding and design teams Foda Studio and Studio Mai, to our California collective of independent makers like the Cartorialist, Robert Siegel Studio and Hedley & Bennett, to our restaurant family, to our heroic charitable partners The Door and the Robin Hood Foundation. I get to be inspired by and learn from unbelievable humans and every day heroes.  At west~bourne, we believe in neighborhood hospitality: cooking for ~ and giving back to ~ our community… so that’s absolutely what gets me up in the morning smiling and ready to make an impact.

your best advice for career changers: This one comes from my mom, and I remind myself every day: you have to be your biggest fan before anyone else can.  

Marnie Duncan, 33

former career path: I worked in online advertising in New York. I started in sales at Yelp.com, the online review site. Then I moved to Glam Media, a women’s lifestyle network. I was in the online industry for 5 years before making my career change to fitness.

current gig: Owner and Founder of MOD Fitness

what inspired you to change careers: Fitness has always been my passion. I started teaching barre fitness at 22 years old after a neck injury. Barre fitness helped me rebuild my strength and transformed my body. It became my passion and I always dreamed of having my own studio one day. 

how old were you when you made the switch: I was 26 years old when we moved to Austin in 2012, it was the perfect opportunity to start my own business.


the hardest/scariest thing about changing careers: The scariest part was the fear of failure. You never know if a business will be successful and if your vision will resonate in a new area. I was new to Austin but was lucky to find a supportive community for small business owners and female entrepreneurs. 

what you love about your new career: The best and most rewarding part of my job is the clients and people we meet at the studio. MOD is a place where friendships are made and people come together. I love that our staff is helping individuals meet their fitness goals, see results, and are a part of their health and fitness journey.  

your best advice for career changers: Be passionate and confident in what you want to do and you will succeed. 

Kristen Helmsdoerfer, 25

former gig: I taught middle school for three years. 

current career path: pre med student

what inspired you to change careers: I went from teacher to student again within the same week! 

One day before the morning bell, a teacher across the hall and I were monitoring the students sitting in the hallway. A lot of them were eating Hot Cheeto’s and other unhealthy snacks for breakfast (despite our school’s meal program), which led to a discussion about poor nutrition. She said, “It’s so sad because it’s clear that some of them have the signs of early onset diabetes. Just look at the discoloration and bunched skin on Hipolito’s neck.” Later that day, I was standing at the whiteboard teaching something about writing to my 7th graders, and I saw that same student walk in late. Even though I had taught this child for four months, it felt like the first time I actually looked at him closely and vividly remember thinking, “I wish I could be your doctor right now and not your teacher.”

I couldn’t believe the extreme amount of health disparities and lack of providers in the Valley, and came to find out that the county in which I lived in was part of what was called the diabetes capital of the nation; I knew that I wanted to come back to a place like the Valley and serve. At the time, physician’s assistant and nurse practitioner were buzzwords I heard repeatedly; however, when I was driving home from church on November 13th, 2016, I had this epiphany or “eureka moment” and called my mom and said, “I am going to apply to medical school. Why not?” She affirmed me and said I could absolutely do it.

the scariest/hardest thing about changing career paths: The true hardest part about my career change was saying no. It meant openly admitting that I was unhappy, and going against my ingrained instincts to commit and not quit.

what you love about your new career path: I feel completely alive when I’m in the hospital. I feel more purposeful and joyful than ever. As a volunteer, I love going into patient rooms and listening to their life stories and providing small means of comfort, like a cup of coffee. When I shadow the doctors, I love the process of differential diagnosing and interacting with other staff, but more importantly, I enjoy getting to know the patients. Entering into the art of medicine has felt like a beautiful awakening where my heart is matched to my calling and I can fully thrive.

your best advice for career changers: In Spanish, there’s a phrase “Tirarse en la piscina” which means just diving right into the deep end of a swimming pool. Dare to disrupt what you think your life should be like. Always keep your heart and eyes open to opportunities, even if it feels completely illogical. Trust. You’re not  too old. Who defines what “old” is anyway? Be nontraditional and quirky. Never compare yourself to others for you’ll rob yourself of what you’re uniquely meant to do. Love others, love yourself, and love what you do.