My Over 50 Career Journey & Why I Became a Coach Part I

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The Beginning of My Over-50 Career Journey

It’s never too late to start living your dream, even if it didn’t begin as you intended. Seventy percent of the workforce is “actively looking for a career change,” according to GoRemotely. Reasons vary from yearning for higher salaries, living one’s dream, and optimal work-life balance. Therefore, if GoRemotely has accurate statistics, the general working population didn’t begin as intended, or if they did, they aren’t happy where they landed. For me, it was both.

Retire or Work?

Let’s face it, some women my age can retire. However, others don’t want to, and many cannot, especially with a volatile market reacting to certain economic constraints. I fall into both categories. I cannot and don’t want to because I have yet to fulfill my dream, and my constitution won’t allow it; I must stay busy. By busy, I don’t mean taking up a hobby or playing pickleball. Not that there is anything wrong with that. I mean balls-to-the-wall work, earnings to my fullest potential, helping others succeed, finishing and publishing my current novel, writing self-help books, volunteering as a hospice companion, and most importantly, loving and being present for my family.

Societal norms dictate that I have about ten years of working life left. However, on a recent podcast about “Feeling Behind in Life,” Mel Robbins detailed each decade and the unrealistic expectations, noting that these norms were decided in a completely different world. I suggest taking a listen.

As someone in my fifties, I have life and work skills that were gained from my years of living and decades of experience. At a recent networking event, an older gentleman admired my journey and stated, “What a fascinating and interesting life you have had.” I answered, “I am not done yet!”

I flourish when doing it all. Someone else recently hailed it a “Wonder Woman Complex.” I laughed because it isn’t a complex; it’s innate. Don’t misunderstand: I rest and enjoy days off, practice mindfulness and gratitude, exercise, pray, journal, and, on occasion, vacation. Life is beautiful. My happiness isn’t drawn from what I do, but how I feel. I am happy because I breathe each moment as if it were the oxygen for my survival. Bad things happen, and of course, I have other emotions, but I am happy because I choose to be.

Why I Became a Coach

I became a coach to help others succeed, share my success, empower women, and unite the symbiotic relationship of gratitude and life, which is the foundation of who I am. Becoming a coach was a natural progression because of the journey I am about to retell. I coached my family, colleagues, friends, employees, and students. Coaching with Ms. D pays homage to those students who inspired me and coaxed me to be a coach. However, although I coached them, I never realized it was my calling until I found inner peace.

My Career Journey Started with High School

It began there, in high school, quite by accident. As a mother, that sentence baffles me because of the pressure put on teens to know what they want to be and select a college to fulfill that desire. I am guilty of it too, but with much more empathy, understanding, and acceptance. Of my four sons, only one was sure of his passion and drive at a young age. The three others struggled with decisions. That’s OK! (Listen to Mel’s podcast!)

I rebelled from the stigma of being a nerdy, smart kid. This was the eighties, folks, and yes, the movies emulated real high school drama. It was life imitating art imitating life. My parents wanted me to be the first female to go to college, which was not a tremendous feat considering I was the only female sibling or first cousin (they referred to the aunts and extended family).

I didn’t want to take the SATs for any other reason except that I was lazy and convinced I wouldn’t go to college. And, since I am on this honesty regurgitation, I disliked competition. If I wasn’t the smartest in the room, it irked the hell out of me, unlike my sons, who relish it and locate those more talented to emulate (something I am learning to do). So, I withdrew my brain, hiding her behind leather jackets, big hair, and hard partying.

Therefore, as a giant middle finger to my parents, I took cosmetology, which was funny because my dad was a hairstylist before he married my mother. My high school was the central hub in the district and housed vocations such as beauty culture, horticulture, and auto mechanics. If a student added one of those to their curriculum for their junior and senior years, they didn’t need to take the mandatory, three-year academic sequence required for college. I could skate free (glittering roller skates – it was the eighties) through high school, taking the remainder of my Regents’ requirements, which were few at this point, and had easy, breezy electives and even simpler, or so I assumed, as my main focus, cosmetology.

So, I swayed my parents into thinking this was best, and at the very least, I’d learn how to manage my wavy frizz. Ironically, as the only daughter, Mom tormented me with curls, curlers, and pretty dresses until I cut my hair off at the age of 8. Around the same time, she gifted me the Barbie Styling head, which I showed no interest in. But here I was, taking a course to get licensed to do hair, never showing curiosity in the subject.

The first year was rough. I didn’t fit in. I made friends, but I knew I was a fraud and missed classes, which could be detrimental to my license application because the state requires documented hours to test and get licensed. And who knew? It wasn’t as easy as I expected. The academic portion was for me, thanks to my prior academics, but my hands didn’t work like others, and the concepts were foreign because they were never relevant. It took almost 30 years for me to understand why I struggled at the onset. I am a kinesthetic learner, a concept I discovered when I became a cosmetology educator.  

My teacher, my idol, my mentor, hero, Miss Fil, stepped in and laid it on the line. She was the first person other than my mother and recently deceased grandfather who inspired me to be better, who told me I had the talent, and who pushed me. It was tough love sprinkled with encouragement and hairspray. I rose to the occasion, receiving the most improved award in my senior year, and planning at the last minute to attend college for business to open a salon. Oh no, no SATs. Community college for me.

During the summer after graduation, I took the written portion of the state board cosmetology exam, finishing long before others in the testing room. I passed effortlessly but had to wait until the fall to take the practical, which I feared. I made up my hours but missed many of the classes that focused on some of the technical portions of the hands-on test.

Additionally, because I didn’t have SAT scores, the college required a placement test. Woe to me, I was placed in higher-level math and English. I was happy with English, but for the rest of the summer, a hidden gray cloud loomed in my psyche, dreading the cosmetology practical and calculus.

To be continued: My Over 50 Career Journey Part II: Marriage and The College Years.

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I AM NOT A LICENSED THERAPIST OR PSYCHOLOGIST. COACHING SESSIONS ARE NOT A SUBSTITUTE FOR THERAPY OR MENTAL HEALTH COUNSELING. We focus on the present and future. I provide personalized support and strategies to help you achieve your career goals and self-evaluate your progress. Together, we work towards your ultimate success. Schedule your free consultation now!

Do you want to work in the beauty field?

My book, The Future Professional's Guide to Cosmetology, answers all your questions about the industry. Email your inquiries to coachingwithmsd@gmail.com or call me at 732-800-6416 (during EST business hours).

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©Deirdre Haggerty 2025. ALL RIGHTS RESERVED. It is unlawful to reproduce this article or any part without the author’s prior written permission and consent