New Directions: Nanny Cindy

New Directions

This series called “New Directions” features interviews with former nannies that branched out into another aspect of the business, had to add something to be able to stay in the profession, or left the profession entirely.

My goal during the course of these articles is to show you that you have choices, and that sometimes “new directions” can take you to new growth.

An interview with  Cindy Wilkinson by Glenda Propst

How long were you a nanny? I have been a nanny since 1977.

How long have you been out of the field? During this 33 yr time span, I have worked as a live-in, live-out, and shared nanny for families in Colorado, California, and Connecticut.  I have also taken off several years to teach full-time, but still continued to nanny part-time during those periods in my career.  For example, while teaching full-time during the day, I was once a home game night nanny for a Denver Nuggets basketball player’s children throughout the basketball season.  Then, in 1996, I started a business called Jumpin’ With Cindy where I market my children’s CDs, kids music classes, and performances.  Since that time, I have juggled my music career with my nanny career, sometimes focusing mostly on the music end and other times focusing more on the nanny side.

When did you realize that it was time for a change? Since I have a degree in Early Childhood Education, I have typically started a nanny position when my charges were very young and stayed with them until they were in full day school.  Then I would start over again with a new family with very young children in my next position, continuing this pattern, on and on…  I am someone who loves new challenges, so I began mixing up my career a bit to give me more variety and lots of different types of experiences professionally.  This has aided me greatly in having such longevity in the nanny profession.

Did it come to you gradually, or was it an epiphany when you realized there was something else you wanted to do? Leaving my very first nanny job to begin a full-time teaching job was very difficult.  This was thirty years ago and I knew only one other nanny and felt very isolated in my job.  After two years of living in and working long hours as a nanny, I knew that I needed a change.  It was hard personally, even though I loved my job and totally adored my charges.  This transition was very stressful for me and it took me a few months to actually make the change.  Fortunately, my employer could see that I needed to be in a different kind of work environment and I was able to leave my job on very good terms.  Down the road a couple of years later, I was lucky to be able care for these children again as their summer nanny while we were all on summer break from school.  Over the years, my transitions from one job to the next, whether as a nanny, teacher, or musician, have become easier.  I now have the confidence to trust my instincts and also know that things have a way of working out for the best.

Do you view it as a positive change or negative change? These changes have definitely been positive for me.  Finding the right mix of caring for children in a home environment and teaching in the classroom has seemed to have fallen in place quite naturally.  I feel so very blessed to have found the right balance for me, not only as a nanny, but also as person.

Tell us what you learned as a nanny that is helping you in your current job, career, or profession? My role of nanny allows me to deal with the same challenges that a busy parent deals with each day.  This has helped me to be a more empathetic teacher!  It is easy to criticize the parent who rushes in hurriedly with a child as she drops him off for school or forgets to praise the picture he has painted that day as she picks him up from school at the end of the day.  A nanny gets the chance to walk in the shoes of a parent during her workday.  She must somehow manage the hectic schedules of her charges with keeping every aspect of a busy household together as well.  She sees how difficult it can be to tend to the needs of a cranky toddler while trying to carpool older charges to their activities while also making sure her employers come home to a tidy and organized home.  And she is sometimes the one who must drop off her crying charge at preschool as he clings to her as she confidently says good-bye and walks out the door.  It can all be very challenging and I definitely have a greater respect for the parents I deal with as a teacher.

Tell us how your work in your current job has influenced your charges? My charges have been most influenced by the creativity which I have encouraged in them through our endless art and music activities.  Some of these children have gone on to play the violin or to study ballet.  One of my former charges even designed my Jumpin’ On Down the Road CD cover as a 2nd grader.  But, all of them have felt empowered to create original ideas and blossom into unique individuals, not just following the same road as everyone else.

What advice would you give to other nannies? I don’t see working as a nanny as an either/or decision.  There are so many different types of nanny positions: full-time, part-time, vacation, and on and on.  I just returned from Las Vegas where there are tons of nannies who go to the hotels to care for children there.  And, there are nannies who may just care for children on the week-end or a few afternoons after school.  When I left my first nanny job, I felt I was losing both my identity as a nanny and my relationship with my dear charges in resigning my position with them and moving on to teaching.  But, this was not the case.  I found other ways to fit nanny work into my busy schedule and found ways to stay connected to my former charges as they grew up.  Over the years I have weaved in and out of full-time nanny work and have created a niche that works best for me.  Find that niche that works best for you and be as creative as you can.  Perhaps you too will still be a nanny 30 years from now!!

Tell us a little bit about what you are doing now? I am caring for two young girls as a full-time nanny, while also teaching with the Denver Center Theatre Academy on Saturday mornings, composing for musical theater, and continuing my recording projects.


  1. I’m so glad you highlighted Cindy! My charges love her CD’s, and I learn so much reading her blog and talking with her. We are lucky to have such a multi-talented woman in our field!

  2. I have known Cindy for years through the International Nanny Association both as a friend and as a colleague. I am always impressed when women realize their talents have many sides and explore it to create different jobs. I believe we are better people if we change careers at some point even if it is just a momentary break. I love reading how Cindy has been able to use all her talents!

Speak Your Mind


Featuring Recent Posts Wordpress Widget development by YD

Creative Commons License
This work by Regarding Nannies is licensed under a Creative Commons Attribution-NoDerivs 3.0 Unported License.