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The Struggle with the Mature Masculine

Editor’s Note: From the Mentor Discover Inspire (MDI) Mission Statement, the identity of the “mature masculine leader” may have its challenges. First defining it and second living it. The shift to maturity could also be experienced as the shift from a boy-like mentality to an adult mentality. See the bottom of this page for a comparison of Boy vs. Man. To focus men on their most powerful selves, a new MDI Training “The Mature Masculine Workshop” – led by Jim Ellis and Dylan Stewart – will reveal and delve into a list of 20 mature masculine qualities. Of these 20, one was chosen as the most challenging by Ellis, Stewart and MDI President Ian Kennard, with ideas of how they can address such a challenge. Story about the workshop HERE. Register for the workshop HERE:


Dylan Stewart, Co-Facilitator of The Mature Masculine Workshop

The Mature Masculine Quality I struggle with the most is #15: “I ask for help.”

In truth, I try to do most things alone, and usually get deep into a project before I realize I can’t do it myself. It is only when I really come across my own limitations that I reach out and ask for help from those around me. And when I get the help it just makes everything easier, and makes me wonder why I wait so long to ask for it, and why I have to keep learning that same lesson.

What am I doing about it?

I am on a powerful men’s team, and my men push me and challenge me to stretch myself, and remind me that they are there when I am ready to ask for their support. Slowly I am getting better!


Jim Ellis, Designer of The Mature Masculine Workshop

I am perfect in all ways. Oh wait, no that’s not true at all. That would actually be boring. For me, I have a challenge with the mature masculine quality: #9: “I do not carry grudges or ‘lists’– and I clear with men swiftly and directly.”

Though I desperately want to be clean and clear with all men, I falter in cleaning things up right away and carry some discontent and resentment over time. Of course my brain says, “I will get my chance when the time is right, or when there is some grand exercise to clear lists.” Then again, I secretly hope it never comes to pass. Not because I don’t want to clear up any messes, but because I am too much believing that I will not get the response intended.

I want to have a man listen, take in my input, and be open to cleaning up if there are any broken words or commitments.

My hope tells me that could happen, as it has in the past. My fear says that it won’t happen, and a man will get defensive, shame and blame me for even bringing something up, or simply turn from me and depart. Which has also happened in the past.

Therefore what I can do about this is to simply commit to the “swiftly” part of the quality and give myself no more than 12 hours to contact the man and start the process of clearing any grudges – with the most important part being the purpose of the clearing: so that he and I can be unified as one force for the good of ourselves, our relationship and our team.


Ian Kennard, MDI President

I was asked the following question by the Legacy editor to pick one of the 20 mature masculine qualities and explain why it challenges me the most. 

I will go with #10: I am confident.

This one resonated with me for a particular reason. I am confident in my abilities as a leader, as an entrepreneur, partner, father, brother etc. 

However with that confidence comes a quiet voice which occasionally gets louder and asks: “who the fuck are you, and what could possibly make you think you are any good at ____________?” Imposter syndrome.

What am I doing about it?

  1. I recognize that it is just a voice and that I have a stronger voice.
  2. I smile, embrace and acknowledge the voice for what it is telling me. Rarely is any of it true.
  3. I have a mantra that I use to quickly break out of the cycle: I repeat “Manifest Greatness, Manifest Greatness, Manifest Greatness” until the voices are quiet. The context I hold around “Manifest Greatness” is that it is not only for me, but also for the people around me. It is what I am here to do.

Boy Vs Man – A Comparison

The mature masculine man doesn’t act like a boy. And what would the difference be? Well, let’s see where you stand in this summary of situations. Answers may vary … and they may change over time.  

  • When dissatisfied within the collective he stands, the boy plays the victim and blames the rest of those in the collective. The man steps up and enrolls members in solution.
  • When encountering a “team” dynamic, the boy fights to get his individual needs met. The man works to determine what is best for the the entirety of the team.
  • When spending time on some form of team or collective, the boy waits for the leader or coach to call on him. The man is proactive and reaches out to the team leader to help his team win.
  • When enticed into engaging with a weaker opponent, the boy debates and bickers and fights. The man moves not, and – simply and honorably – listens.
  • When the going gets tough, and challenges heat up, the boy falls into problem-mode and complains and bitches. The man embraces the challenge, summons support and takes action.
  • When encountering a difficult task, the boy hopes someone will come in and do it for him. The man sees the task through to final completion no matter what the situation asks of him.
  • When things are falling apart all around him, the boy points outward, irresponsibly, in order to divert attention away from himself. The man looks within to find his part and does what he can to alter the course of the situation.
  • After dropping standards, breaking his word and being out of honor, the boy hides and hopes no one notices. The man comes out proudly and asks those impacted what they need from him.
  • When showing up “late” for a meeting or gathering, the boy thinks “Oh no, I’m in trouble.” The man thinks, “I’m letting my men down.”
  • When called out by his circle of men, the boy defends his need to be right. The man humbles himself with trust, and is open and willing to learn something new.
  • When in a situation where he is not held accountable, the boy celebrates the fact he can get away with shit. The man holds himself responsible to his best.
  • When faced with a consequence, the boy believes he is bad and is being punished. He hides and hopes no one points out the faltering. The man ONLY knows a return to honor and steps up immediately and responsibly to attend to the matter.
  • The boy looks up in reverence to the men. The man is a peer to all.

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