One of the hallmarks of this American culture is self-reliance. Messages about doing it all on our own, and being strong and tough and persevering abound, not only for men, but also for women. When a woman finds herself in the position of being a single mom raising a son on her own, most people look the other way and tell her to just carry on.


Young boys learn a lot from their Mom, but the value of a male model can’t be understated. Source:

When my son was 4 ½, his dad and I divorced after being separated for about a year and a half.  I was the primary custodial parent, but my son did have contact with his dad.  However, when my son was 12, he and his dad stopped seeing one another.  My son had asked his dad to address some serious issues between them, and his dad responded by pulling away.

Initially, the separation was very good for my son. He and I finally had the space for my son to have a more “normal life.”  Soccer, Red Sox games, movies and leadership conferences all became easier to take part in for my son with his life unencumbered by the issues with his dad.

Realizing that my son needed good male role models in his life, I sought out organizations and activities that allowed my son to interact with male mentors. I found Boys to Men New England when he was 12, and over time, BTMNE became a critical part of the emotional foundation for my son’s life.

One part of Boys to Men is an annual Rites of Passage teen weekend workshop in August.  My son participated in the workshop when he was 13, and staffed it when he was 14, 15 and 16.   When he was 15, it became clear that my son was feeling deep pain from what I have come to call “the father wound.”  Even though he was part of a community of men and boys during the workshop, the absence of his father cut deep.

My son started to ask questions about who his father was and who he might be since his father provided half of his genetic material.  My son wondered why his father might disappear and leave his son. And my son also felt the pain of his parents’ divorce and estrangement.  No matter how hard I tried to support my son’s interests and find resources that also supported his interests, there was a huge void inside of him that I could not fill:  the father wound.

Over time, I came to realize that no matter how good a mom I was, no matter how hard I tried to find resources to help my son and to help him learn to help himself, because I was his mom and not his dad, there were many things I just could not do.

A teenage boy looks to men in his quest to determine what it means to be a man. I was not a man. A teenage boy needs to hear the story of other men’s journey to manhood.  I did not take that journey as a woman.


Young boys can benefit from the stories of successful male mentors. Source:

The mentors in Boys to Men had something to offer my son that I could never give him:  the experience of growing up male in this culture, and coming to define the men they wanted to be through their experiences growing up—with and without the support and involvement of other men.

As my son’s struggle deepened, I realized it was the other men he needed to talk to, not just his mom.  Having a support group of  men who knew him became invaluable as he started to face some increasingly difficult and painful passages in his own personal journey towards manhood, a journey that is still underway.

It takes a village to raise a child, and the village must include male mentors and role models deeply committed to the best interests of each male child.  When my son feels connected to other men who care, his spirit grows.  When my son feels isolated and alone, especially from other men, his pain grows.

I am very clear I cannot do it alone, and I cannot successfully guide my son to manhood without the care, commitment and involvement of other good men. If you are a man who cares about boys in their transition to manhood, become a mentor with Boys to Men. There are many other boys like my son out there counting on you. And even boys who have two parent homes need a village that includes emotionally available men.

Opening your heart to a teenage boy can be the difference between helping a young man learn to fly, and watching someone with great potential crash as his pain weighs down his wings.

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It’s important to remember that both sides of the mentorship have knowledge to impart to the other.

At the Over My Shoulder Foundation, we spend a lot of time talking about the powerful impact that a mentoring relationship can have, both cross-generationally and cross-culturally. Often when people think of a mentor/mentee relationship, they think that the mentee is the primary beneficiary of the relationship as he or she is learning new skills and knowledge from his or her elder, the mentor. However, it’s no surprise that the younger generation also has a lot of useful experiences and skill sets to pass along to the older generation. This increasingly popular concept is known as reverse mentoring.

This unique concept was most famously introduced to Corporate America more than a decade ago by former General Electric Chairman Jack Welch, and it has continued to gain momentum as advances in technology have  further widened the gap between generations. For example, a business owner in his 50’s knows that he needs to have an active presence on social media, so he partners with a 20-something to help him learn the skills for more effective marketing.

The three main requirements for a successful reverse mentoring relationship include formalizing the relationship in some way, building mutual trust, and being open with each other about new ideas. A few of the benefits to establishing this type of relationship include shortening the learning curve, building morale, increasing productivity, and cultivating future leaders.

To learn more about reverse mentoring and how you can benefit from such a relationship, please contact us at the Over My Shoulder Foundation.

Image Source: bujiie


Take time to get to know your mentee.

At the Over My Shoulder Foundation, our mission is to raise the awareness of the positive impact that mentoring can have, both cross-generationally and cross-culturally. If you are interested in helping guide a younger person to success, we wanted to share some helpful tips for how to become a mentor courtesy of Management Mentors:

  • In order to build a strong relationship, you need to first take the time to get to know each other. While it’s important to share your wisdom, it’s even more important to listen to what your mentee has to say.
  • Discuss what each of you expects to gain out of this mentoring relationship and outline goals that you would like to achieve.
  • Be open about your ideas, thoughts, and feelings about the mentoring relationship and encourage your mentee to do the same.
  • Determine up front how often the two of you will meet and the preferred type of communication, whether it be in person or on the phone.
  • To be most efficient, come up with a rough plan of what you plan to talk about with your mentee prior to your meetings, and be ready to adjust your agenda as necessary.

It’s always important to keep in mind that it takes two people to build a strong mentoring relationship, and establishing expectations of each other up front can help the relationship to be mutually beneficial.

To learn more about how to become a mentor, please contact us at the Over My Shoulder Foundation.

Image Source:  U. S. Fish and Wildlife Service – Northeast Region


If you ask successful people what they attribute most to their career growth, many of them will tie their accomplishments back to having strong mentors along the way. The same could be said for Sheryl Sandberg, the current COO of Facebook. Throughout her professional career, she played a hand in the IPOs for both Facebook and Google, and served as the chief of staff for the United States Department of Treasury. She was recently named the fifth most powerful woman in the world by Forbes magazine.

Facebook COO Sheryl Sandberg

Sheryl Sandberg contributes much of her success to strong mentoring relationships

When it comes to mentors in the business world, Sheryl Sandberg mentions in this CBS News piece that we often think of a man-to-man mentoring relationship versus one that is comprised of a man and woman. She shares that it’s natural for two men to share a beer and have this type of camaraderie in a hotel lobby while traveling for business, but may send out the wrong signals if a man and woman were to have a drink in the same environment. For this reason, she explains the importance of more senior and tenured professional women taking on younger women as mentees to help guide them along the way in their careers.

Just like Sheryl Sandberg, Patti Austin and Dawn Carroll attribute much of their success to the strong mentoring relationships that they have developed throughout their careers. Wanting to spread the word on the power of “Mentorology,” they founded the Over My Shoulder Foundation. The goal of this non-profit organization is to raise the awareness of what a positive impact mentoring can have across generations and cultures.

For more information about the Over My Shoulder Foundation and our mission, please contact us today!


Photo Credit: Drew Altizer Financial Times



Sofia Vergara is just one celebrity who has made the transition.

When Grammy Award winner Patti Austin made the decision to pursue her dream as an interior designer, songwriter and designer Dawn Carroll mentored her to make this dream become a reality. This successful mentor/mentee relationship helped to inspire the two women to establish the Over My Shoulder Foundation, which aims to raise the awareness of the positive impact that mentoring can have both cross-culturally and cross-generationally.

Patti Austin is not the first entertainer to cross over to the world of interior design. Listed below are several other celebrity interior designers that have successfully made this transition:

  • Justin Timberlake: First a singer, then an actor, and now a designer, Justin Timberlake is a co-curator for HomeMint, which offers high-end home furnishings, decor, and art.
  • P. Diddy: In addition to his music and acting career, P. Diddy also has his own clothing line and home collection known as Sean John.
  • Cindy Crawford: Aside from being one of the world’s most recognized supermodels, Cindy Crawford has her own home decor line called Cindy Crawford Style.
  • Sofia Vergara: This actress has not only come into her own in her role on Modern Family, but recently launched an affordable home furnishing line for the bedroom and bathroom called Sofia by Sofia Vergara.
  • Lenny Kravitz: This rock star has also created his own upscale home design collection called Kravitz Design, which includes custom-made furniture, crystal lighting fixtures, and bold wallpaper designs.
  • Brad Pitt: This actor turned his passion for design into a partnership with furniture maker Frank Pollaro to offer high-quality inventive designs.

Who are some of your favorite celebrity interior designers that have had successful careers in a variety of industries? Do you think the benefited from a mentor relationship while they made this transition?