EvolveMe #40over40: Rachel G. Sklar

Updated: Feb 25


This is our time! We’re stronger when we work together to lift other women up. EvolveMe's #40over40 list curates profiles of women who have or are in the process of reinventing their careers in their 40s, 50, 60s, and beyond. We're thrilled to share these stories of reinvention - women returning to work, pivoting careers, or launching new ventures!


Meet Rachel Sklar, parent educator and entrepreneur with more than one pivot under her belt. Rachel helps moms raise strong-willed boys to be successful leaders in our society. How amazing is that? Read on to learn about her career journey!


What is the current focus of your career?


I'm working to change the world, one boy at a time, by focusing on the mother-son relationship and all the possibilities it holds. I help moms of strong-willed boys raise their sons to be leaders in society who value relationships, kindness, collaboration, and peace. While I support parents of all types of kids, I have a strong focus on moms of boys who are aggressive, disrespectful, oppositional, unfocused, sensory seeking, and intense.


What prompted your career reinvention?


The #metoo movement inspired me to double down on the parts of my business that focused on raising boys. In 2016, my career as a social worker and parent educator shifted toward the tech industry. I co-founded a start-up that built chatbots to support parents.


Shortly after the company was acquired in late 2019, the #metoo movement hit. It was an obvious call to action. Helping moms raise their sons to respect others and role model empathy seemed like the least I could do to support a social movement against sexual abuse and harassment.


What's the best thing about mid-life career change?


My mid-life career shift came after I checked off society's main boxes. I was married. I had 3 kids attending school. And, by my definition, I had a successful career under my belt. There was a feeling of "having arrived."


My confidence was rock solid, and that gave me the courage to pivot for the joy of it. I had the luxury of saying, "What the heck? Let's try this and see what happens." Sometimes, I think that level of confidence (and perhaps grey hair) inspires trust, respect, and collaboration from those around me


.What's the biggest challenge?


There are simply not enough hours in the day to do it all. When my work is fun and meaningful, it can be hard to draw a line at the end of the day and shift gears toward family. Sometimes, I just want to keep working. The irony is that when I'm most relaxed and taking care of myself, my creative juices start flowing and I get great ideas about how to uplevel my work, albeit at the worst times. That makes it hard to compartmentalize work and play.


What's your personal mantra/mission? Why?


Whether I'm working with a client, doing a corporate speaking engagement, or talking to my Facebook community, I have one goal: Prioritize relationships over being right. That's what I teach and that's how I aim to live. It's a practice, like any other.


Sometimes we fall off the wagon, but it's so important to choose to be in connection and right relationship with others before trying to prove our point or convince someone why they're wrong. Prioritizing relationships over being right goes as far in parenting as it does in business.


Your best career advice for other women at midlife is...


I suggest we all subscribe to the aphorism "a rising tide lifts all boats." If you aim to lift others in your industry, you will be lifted. There's no need to compete if we have a shared mission. We can lift the whole industry together. There are plenty of people that need our services on this planet. There's room for all of us.