How The Gift of Mentorship Changed my Life

by | Jan 22, 2020 | Personal Excellence & Authenticity | 0 comments

In a blog I wrote for Forbes on How to Be a Next-Level Mentor I mentioned that I’ve been formally mentoring others since 2012. But, I can’t say I had consistent, formal mentorship myself until a few years ago.  What follows is the story of how I came to find my mentors over the years. 

Finding Micro-Mentoring Moments Everywhere

Throughout most of my career I blazed my own trail. I have not been afraid to take big risks and leaps because my ability to self-affirm is at an unusually high level. Also, because I generally feel connected to most people and have always (and still do) believe I can learn something from everyone, I never had the sort of ego that would prevent me from asking someone to share their knowledge with me when I needed it. Looking back, like a sponge, I was absorbing micro-mentoring moments all the time. 

Reciprocal, Peer Mentoring

For several years, as a mid-level leader and early executive, I had the great pleasure of having a reciprocal, peer mentoring relationship at work. You can find out more about the different forms of mentoring in my How to Be a Next-Level Mentor article. Over those years, we helped each other grow in many ways, but the core areas where we most consistently supported each other is that I would help him identify and work through instances of workplace politics when they were at play. (He self-identified that he had workplace politics blindness.) He would teach me how to do deeper financial analysis and projections for my budget and miscellaneous business cases. (He alleviated my Excel hell!) 

When the Mentoring Relationship Didn’t Click

In that same timeframe, I once solicited formal mentorship from a member of the executive team I reported to. Of all the execs at the time, I felt the closest to her and that our values most closely aligned. We had worked on several projects together and I admired how her approach with clients and stakeholders felt uncontrived, trustworthy, and elicited ease from everyone around her. However, we met several times for mentoring conversations and it just felt disjointed! Back then I told myself that our communication styles were just so different that it led to our conversations feeling awkward. It is only in reflecting as I write this post that I can put my finger on what really wasn’t flowing. 

At that time in my career I was feeling that I had met my full potential for the role I was in, but that the next role (at that company) hadn’t revealed itself. In short, I felt a little lost about what was next. Would I stay at that company or leave? Did I want to stay in Learning and Development or go back to Talent Acquisition leadership? What were the other options that I couldn’t even imagine for myself? 

What I probably really needed at that time was a coach, not a mentor. I realize now that I fell short on bringing clarity to this relationship, as to what I wanted from her. In a healthy mentoring relationship, the mentee has clear goals they want support with. They know their chosen path (at least in the near term).  It is hard to find the best fitting mentor when you haven’t explicitly mapped out your career goals. My entire career I had crystal clarity and intense focus on the next step. But, when I invited her to this relationship, I was for the first time in my career, unsure about my path. I instead was, unknowingly, heading towards a rather existential crisis at the time. 

Entrepreneurship Led to an Intense Need for a Mentor

After a couple more career moves, I eventually made the leap into entrepreneurship. I quickly found that my needs had changed so much that I needed a different level of support. My experience as a first-year entrepreneur was astoundingly lonely. While I joke that I enjoy the sound of my own voice, the stark echo of it in the early days of solo-preneurship was deafening. 

My greatest challenge in the first couple of years was that I found myself replicating business models as they already exist in the world.  I was painfully clear on how some of them needed to evolve, yet felt paralyzed as to how to build something different. (Heck, if it was easy, other models would already exist). Example: I was putting other high-level coaches to work for Bright Arrow, but the only way to hire high-end coaches is to pay them what they are worth which means, in turn, you have to jack the price up on the client. That doesn’t feel right for me. So, how do we fix that? 

My second big challenge was that I wasn’t enjoying one of the service offerings of my business yet, it was going gangbusters. How do you let go of that?!

My third big challenge was that I was not surrounded by other successful entrepreneurs. My experience in the market I was in was that a faction of entrepreneurs saw other entrepreneurs as a threat or competition so there was little transparency, authenticity, or intimacy. The other faction wanted me to mentor them and show them how they could be successful too. Neither group helped fill my cup and satisfy my own unique needs.

Manifesting My Mentors

In a moment of intense need and loneliness a few years ago, I decided to write a letter to my mentors. You know, the ones I hadn’t met yet. I did this in an effort to get clear on who I had become, what my specific mentoring needs were, and what their profile might be like. Here is an excerpt:


Dear Mentors-

I’m so excited (and relieved) that we’ve found each other. I feel grateful that you see me as talented, capable and a worthwhile investment of your time.

It is important to me that we align in a few areas:

  • You are also an entrepreneur and have built a successful business with (at least a dozen) employees, earned millions in revenue. You continue to grow.
  • You understand what it feels like to risk your own ass with your own money, emotions, stability, and relationships on the line.
  • You’ve bootstrapped it (at least in the beginning).
  • You feel personally tied to the mission of your business because it is making the world a better place.
  • You are inclined to share your knowledge and connections.
  • You recognize that even in sharing your experience and knowledge, there is more than one “right” way.

About me:

I was born into a family that brought tremendous challenges. I had to overcome substantial obstacles early in my life as part of my path to success. I have a unique and powerful personal story that I’m preparing to share with the world. I’ve been on my own since I was 15 and while I had to work harder than many people for a good portion of my life, I no longer believe everything must be “hard.” Instead of always forcing opportunities to grow or appear, I now try to balance that with “allowing” them to show up.

I grow quickly (it will make your head spin). I am always seeking out growth opportunities via experiences, reading and have a huge hunger to know more (about myself and the world).

To date, I have blazed my own trail. There were never parents or formal mentors to call for guidance. I have invested in myself by having an executive coach over the past few years, but that is also not mentorship. (Though it was and is essential to my growth!) Over the last few years I’ve been asked who my mentors are. People seem surprised when I tell them I don’t have one and never have. However, (and I mean this even as cheesy as it sounds), I have and continue to learn from everyone around me. I’m a human sponge for information and learning by proxy. It has allowed me to live many lives and acquire more knowledge than a single mentor could have imparted.

But I now wonder what it would feel like to have people in my corner in a bigger way. I do not see it as a badge of honor that I haven’t experienced formal mentoring. It also isn’t a ‘miss’. It just wasn’t meant to be yet. But I feel it now. I feel the need. I’ve managed to acquire a breadth of experience on my own, but now I want depth.

Since becoming an entrepreneur, my (already small) peer group has dried up! I am no longer surrounded by people going through similar challenges. Instead I’m surrounded by people who are “inspired” by me or think I’m “brave” or “could never do it themselves.”  I feel alone.


I go on to describe the first three years of growth of my business; service offerings, contractors, and financials as they had come to pass. I shared my business philosophies and personal truths. I described how I had recently turned down a half-million dollars in revenue in order to stop offering a service that wasn’t fun for me anymore. I emphasized my desire to make money by serving others and approaching every interaction with a “service first” mentality. I spelled out the business challenges I wanted to solve. 

Then, ceremoniously, I sent it to myself via email. As if I were sending it to them. Those people who did not yet exist in my life. The gesture felt great. 

When the Student Is Ready, the Teacher(s) Will Appear

I didn’t have to wait very long for the mentors to show up. In an interesting twist of fate, I shared this letter with my executive coach. What follows is a testament to the power of getting clear within yourself and being honest with others about what you need.

Years prior, when I was the head of Learning & Development for another company, she was the facilitator for a coach training workshop I attended. I later hired her to do some leadership training for the company. When I left that organization and moved into a higher level executive role, I hired her to be my own executive coach. Then a couple years after that, I contracted her again as my executive coach while on my entrepreneurial journey.  

She, a wildly successful executive coach with 10+ years of tenure to me, admitted that she had never before had an interest in mentoring another coach. In fact, I already knew that she exclusively worked with CEOs of prestigious organizations so the fact that she was even coaching me to begin with was an exception to her norm. But, neither of us could deny that she fits the bill based on what I needed in that letter. And so, as we had over the five years prior, we allowed our relationship to evolve again. To this day, she is a dear friend, my go-to coach, and a mentor.

She modeled for me (and still does) what it means to be “all in” with a mentee. Handing me clients, making powerful introductions, tirelessly cheering me on, giving me business tools, attending my events, reviewing my presentations and videos of talks I’ve delivered and giving me feedback, allowing me access to her at a deeply personal level, sharing her own wins and challenges with me so that I can grow through her, reflecting back to me who I am, making me believe I can conquer the world and that I’m doing things that nobody else can. Nobody has ever told me they believe in me the way she does. And I believe her. 

In the next year, I unexpectedly ended up attracting another mentor who I would consider a spiritual mentor. Like my business mentor did, she also approached our relationship as if we were peers. She speaks to me as if I already know the things she is telling me. Her ability to do that while dropping existential knowledge on me that makes my jaw hit the floor is nothing short of an art form. To be challenged spiritually, with deep love, is like nothing I have ever experienced. What I’ve experienced with her has done more than change my life. It has expanded my heart. 

What a life, heart, intellect, and business changing experience it is to be in close relationship with mentors. It has called me to mentor more people and in deeper ways than I knew possible before I met them. We are all called to mentor others. It is one of our greatest acts of love and service to the people around us. Where do you need to be serving as a mentor yourself?  And what might you do to secure the unique mentoring you need at this point in your life and career?


Love this post? For a regular dose of empowerment delivered right to your inbox, sign-up for Bright Arrow Digest here.

0 Comments

Submit a Comment

Your email address will not be published. Required fields are marked *

Share This