In Search of a Mentor
I really want a mentor.
I’ve been thinking about this for probably twenty years, and it brings a twinge of sadness to my soul that I’ve never found a person who matches my understanding of what a mentor is. To me, a mentor is someone I really connect with, who understands me as I show up, and who wants to invest some time into the project that is me. (I have. It’s my wife! But she’s not my mentor, as I’ll get to in a moment.)
The Challenge of Dennis
I know I'm not easy to categorize. I'm quirky, sometimes difficult. I have several bad habits that are hard to shake.
But that’s just part of my personality. Knowing what I value most—family, wisdom, creativity, authenticity, and connection—I tend to seek opportunities for growth overall. And that is why the yearning for a mentor is a long, unfulfilled fixation.
Mentors Beyond Mentorship
I have had a lot of luck in having incredible people come into my life and offer opportunities, advice, and share their consistent belief in my potential. I could not have achieved such a rich life without the many people who have invested time and energy in the project that is me.
Many of you who have played a pivotal role in some way are likely aware of your contributions. I’ve tried to send sporadic notes of appreciation to anyone who has lent a helping hand or a listening ear over the years. (There are many more notes to write and thank yous to come!)
My concept of a mentor differs from the types of mentorship and support I've received and sought out over the years. Each has shaped me profoundly, but in different ways. To understand what I'm seeking, I need to first acknowledge what I've already found:
Love
As Scott Galloway often likes to explain, “The most important decision we make is who we partner with, who we marry.”
I found the perfect life partner in my wife, Sarah. Beyond her sheer awesomeness, she has motivated me, as a man and a dad, to push myself in ways I could never have imagined before meeting her.
She understands me well, and she has been a driving force behind most of the risks I’ve taken in my life, especially in creative endeavors and writing.
My wife isn’t necessarily a mentor; she is my muse and a lot more.
Advice
There have been, and are, a large number of people who started as sources of advice and then became friends. Often, I will still turn to a core group of friends for help or insight when facing a challenge or dealing with anxiety, despair, shame, or doubt.
One example is someone whom I met in my days as a journalist and then grew closer to over time. I was able to help him in several ways, and he has served as an incredible resource for brainstorming life and career ambitions and plans. I regard him as a friend more than a mentor. When I was in a particularly low place last winter, I reached out to him for some guidance. He was on vacation in another country, but he immediately called me back to offer immediate support and counsel.
The difference, at least in my mind, between these advisor friends and mentors is that, while always there in a time of need, they have whole lives and multiple responsibilities, including numerous people to whom they regularly share advice in professional settings.
Models
I was fortunate to have a high school football coach as a father. I grew up observing firsthand how to lead, in particular, how to inspire and support young men. To this day, I have men—most of whom are well into midlife and older—who will pull me aside for a quiet reflection and to share their appreciation for the impact that my father had in setting them on the path to success in life.
I was fortunate to have had the experience of playing for my dad, and I learned a great deal about being humble, bold, prepared, and loving from him during that life-changing period. This is a gift I wish I could share with others, especially my own children.
I also have more beautiful, talented, and kind friends than I could have ever imagined. A lot of these men and women have and continue to live their lives in ways that I consistently strive to emulate.
Having people model doing right can help in the formation of one's core values and serve as examples of how to live a value-guided life. I have observed and I am still watching, trying to follow the path you already strove.
Enlightenment
There is a group of teachers who write, speak, and share their ideas far and wide, and who have also left a positive mark on me. Many of these "lighthouses" serve as guides in times of trouble or confusion. They are authors, podcasters, business leaders, musicians, philosophers, and more. Most I will never meet (and, yet, there are a few whom I have been fortunate enough to meet here and there).
I can turn to their work (or them) for the positive vibrations needed to escape the darkness of self-doubt or the uncertainty of what may lie ahead. I can only offer my unending thanks in return.
Ok, Then What is a Mentor?
Being a mentor to someone is a unique experience.
To me, it is a passing on of wisdom, whether sacred, mundane, or esoteric.
Being a mentor is rooted in a tradition that is bigger than our professions or personal aspirations.
It is wanting the next person in line after you to have all the understanding and insight that you have gained through experience and knowledge, which, in all likelihood, was passed down to you from older generations.
It is something that can be traced back over centuries, the keys to life or the wisdom of the ages, as some might put it.
There is a humility in being a mentor—a yearning to give your precious time to make another's life better.
I realize that this concept of a mentor is rare. I have yet to find that mentor. But I still hope to have a proper mentor someday!
Literature's Exemplar Mentors
Of course, literature is a rich vein to mine for a better understanding of mentors.
One example of literary mentorship that has always stood out for its uniqueness is that of Abbé Faria and Edmond Dantès in The Count of Monte Cristo.
Imprisoned, Faria becomes everything a mentor should be: a guide, a father figure, and, most importantly, the impetus for Dantès' transformation into the greater man he will become. There is a mutual benefit for both men, as Faria can mentor and pass on wisdom to Dantés. There is a shared vulnerability between the men, a need for companionship, and a desire for hope.
What is idealized for me here is that there is a deepness in the human connection between the mentor and mentee that makes both live richer.
Joe Gargery in Great Expectations is another kind of mentor, one we often fail to recognize until it's too late. The relationship between Gargery and Pip makes me wonder if I have missed my opportunity to have that influential mentor.
The blacksmith, who serves as both a father figure and a brother to Pip, represents all the mentors we overlook in our hunger for something grander. While Pip chases his great expectations, Joe remains at his forge—steady, kind, offering a different model of manhood that Pip can't appreciate until he's been thoroughly disillusioned.
The wisdom Joe shares is about treating people with dignity, regardless of the situation, and finding contentment in simple things. These are lessons Pip—and many of us—only value after we've exhausted ourselves chasing other definitions of success.
Which brings me back to the present, to my own search, and to a conversation that happened just weeks ago.
The Modern Mentor
At the first meeting of The Wild Gentleman book club, a conversation on relationships between men in The Great Gatsby eventually led to agreement of a common experience feeling a void in our lives (both personal and professional) that mentors should inhabit.
There was an acknowledgement that we all yearned for other men to offer their wisdom and guidance, but had not experienced such mentor relationships in our lives.
For many men, both seeking a mentor and offering to be one can be an uncomfortable experience. We resist because searching for a mentor requires admitting we need help, and serving as one requires us to acknowledge our worth and recognize that we have value to share with other men.
Both require acknowledging vulnerabilities that go against some conventional notions of masculinity.
This is where The Wild Gentleman's vision of masculinity becomes essential. We don't need to buy into the perception that mentoring comes through hierarchy, with the successful, "arrived" mentor dispensing wisdom downward.
What if we could own our vulnerabilities and ask other men for support, and admit our ongoing struggles to realize that our experiences can offer value to others?
How to Find a Mentor
For me, the most immense chasm to cross in finding a true mentor is "the Ask." I consider myself willing to put myself out there, yet I have a deep-seated fear of being rejected. I feel that is even more true in a potential situation of rejection by other men that I look up to and admire. (There are all sorts of hangups connected to shame, fear, and other similar feelings that make me, and I think a lot of men, emotionally uncomfortable.
But, if anything, The Wild Gentleman is an adventure in practicing what I preach. So, here is how I plan to continue my search for a mentor.
Who to Seek: Write out 5 to 10 men who you think could serve as good mentors; these are probably folks with whom you already have a good, established relationship and who have lived admirable lives. Build stronger connections with anyone you might want to be a mentor to down the road, even if you are not close yet.
Narrow Your List: Be realistic about the consistency and availability of potential mentors. You want someone whose existing time needs and current responsibilities won't be infringed upon.
Be Humble: Acknowledge the vulnerable role a mentor/mentee relationship might create for you both. Be honest about why you want this person as a mentor, considering your needs and the experiences you hope to gain from a mentor.
Expect the Unexpected: Meaningful mentorship requires a real leap of faith from both parties. Don't be surprised if some people ignore or are unsure of how to answer your query. However, you might be surprised by the responses you get from those who are really interested in stepping up as a mentor.
On Being a Mentor
How do you guide someone else through waters you're still charting yourself?
There's something beautiful and terrifying about mentoring from any position in life. If someone reaches out to you and feels bold enough to ask you to play the key role of serving as a mentor, be honored that someone sees the wisdom you have gained through what has undoubtedly been an adventure-filled life.
To be a successful mentor, I believe the key to success is to admit that you don't have all the answers while still offering the wisdom you've gathered.
Go forth. Be vulnerable. Ask someone to be a mentor. Pass on that hard-earned wisdom.
I'm already taking my own advice here; writing this piece is itself an act of vulnerability—a public admission of yearning that goes against every instinct to appear self-sufficient.
That twenty-year ache I mentioned at the beginning? It's still there.
The Wild Gentleman exists because I needed it to exist. This piece exists because I needed to write it. And if you've read this far, perhaps you needed to read it.
Maybe you're that potential mentor. Maybe you're seeking one too. Maybe you're somewhere in between, with wisdom to share and gaps still to fill.
I'll let you know how my mentor search goes. But more importantly, please send me a note if you do your own seeking—or if someone reaches out to you. This is how we build the community we are seeking. Let's build this together.
