Do You Know What Your Leadership Journey Is?

Phrases like “leadership journey” and “leadership path” frequently are thrown around. We may have an intuitive sense of what they mean as code for the story of our own personal growth. But if someone asked you directly, what is that story for you, could you be articulate?

There is so much jargon, so many “round words” — as a friend once called them — that it is not necessarily easy to express the meaning of the personal “journey” at all. Should you go back to Joseph Campbell and compare your life to the hero’s journey? Words like “wholeness,” “integration,” “actualization” dominate, but these words often are like signposts discovered at a foggy crossroads. Too general, and all roads look the same in that mist.


Many of us resort to simply offering the outer chronology of where we have been, side-stepping the series of inner lessons learned and the turning points, yet it is precisely these inner lessons and changes that come closer to the mark. They illuminate the long-term themes unique to us, ones that even with words attached retain some part of the inexplicable mystery. I may discover my way is about finding a meaningful passion or my true compassionate strength. I may find my lessons are about releasing my authenticity. I may see that it is about understanding what it means to be genuinely open-hearted or that I am learning to surrender to being part of a community, my community. Maybe the theme is about trusting myself with doing the right thing. Whatever that path, I feel it, learning and relearning the lessons, maybe for years to come. For me alone this path exists. From time to time there may be a certain pain in recognizing its presence yet again, and from time to time, it can also bring tears of joy.

Sitting on a high hill in summer, watching the clouds, you can feel that deeper theme moving within, that unnamed path, a “thread,” the poet William Stafford called it. It is life, your life, a life that only goes so far. Your heart understands there is mortality in the equation. If your life, your work are going to be meaningful, that thread must achieve some level of consciousness in time. You must know why you are here, what you are about. Without that consciousness you’ll never know who you truly are or be strong enough to follow that thread all the way to the end. Even if it is only “a story that could be true,” it’s the one you need to be able to tell, especially to those you love.

What advice can be given to help bring that thread into awareness?

Indeed, without getting trapped in the round words or intellectual abstractions, what can you do to raise it from the depths?


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  • My leadership journey is about coming to know and trust my true self. The path began for me in analysis and strategic focus, and has become more contemplative and monastic as I have continued.

    My ability and willingness to share my self with others is rooted in my own recognition and appreciation of who I am.

  • Thanks, Greg, for taking a moment to share how you define your path. What advice would you give someone who wants to articulate their own journey but struggles to find the words?

  • Dear Dan,
    Your posts themselves bring people to define what their lives are about!

    In answer to your question, what can we do to raise our lives from the depths and have some meaning (beyond the built in mortality) … my response is:

    Similar to Greg’s above, I think all true definition starts with the self. I would go further than that and boldly claim that we find our true selves in the face of every obstacle and naysayer.

    Many think of these moments as tests of ourselves yet I think they are essential building blocks to finding ourselves.

    E.G. Being courageous when you never thought you could, being supportive when you are so tired and impatient your lips want to say “Get away from me all of you”, finally taking a journey that keeps coming at you even though you visualized a different one.

    You have touched a chord in me as you can see from my comments. I have been thinking of this a great deal lately.

    Much more to ponder and I have your post to partly thank for that!

    BTW: Happy Birthday to you!


  • This is such a lovely post. It makes one reflect deeply and begs the question: why bring it out of the mist? as some may never need to. But I believe if you have a burning desire to know, if articulating the narrative will help you get closer to the essence of it, the authentic words will come — sometimes from within but often from someone else (or a few someones) who sees you.
    I have been engaged in an ongoing exploration of self-love, intimacy and pioneering — hence, as my “brand” would suggest — the journeys of leadership and love. Thanks for inspiring rich dialogue in the service of creating more meaning.

  • Dan,

    This is a very thoughtful and thought-provoking post. I have never liked the “journey” reference to life or leadership. It sounds too comfortable. It may be more like a “warrior dash” in that we get are hands dirty in the struggles and in the challenges. Through these, we learn more about ourselves and what or how we need to change, if we pay attention and think it through. Self-reflection and being fully engaged together create the environment of understanding and growth.

    We are also, in this process, experiencing the rawness of situations. We gain empathy and the ability within to lead through it with compassion, direction, and renewal.


  • Kate —

    As always, your comments reveal your dynamic spirit — courageous, supportive, and open. Many of us define and discover ourselves in the tough moments. We “take it on,” whatever has been given to us, standing up in our own lives (even with our knees shaking), living and speaking with freshness and clarity. That certainly is the way I see you — in your posts and your wonderful work to build the #Peopleskills learning community. You hold a quality of articulate affirmation, Kate, and balance that so well with welcoming and sharing the ideas and views of others. Your presence reminds me of the famous poem, The Invitation (see the left hand column on the linked page).

    I believe there are often patterns to our challenges, and it is in facing and breaking these discovered patterns and cycles, that we find our way.

    Thank you, too, for getting those birthday wishes going!

    All the best

  • Blair —

    Thank you so much for your gracious comment and great question — why bring it out of the mist? To me, that question itself defines a path forward for some. Yes, why, indeed? The answer will be quite personal. In my experience, that answer can have to do with many things, including needing to stop numbing out one’s own emotions and personal truths — for if a person can’t experience the pain, neither can they find the joy. This isn’t to say suffering on its own has value or is the only way to discover meaning.

    A woman in a class I was teaching once raised her hand and said, “I like what you are saying but when I look within I don’t find anything at all. It’s all just dark!” The class chuckled but the woman wasn’t trying to be funny, and her comment created a serious dialogue about how we can all become more intimate with ourselves.

    Although we haven’t interacted for very long, what I see in your comment here, Blair, and in your posts (and the lovely interview you did) is a sensitive and joyfully balanced approach to relationships and life generally. You show us how to break down the false barriers between love and work. And the joyful energy is right there, front and center, even when the stories have their share of angst. What a juicy kind of leadership that is! How you got to such a place must be such a wonderful story!

    Today, I send you this poem by Theodore Roethke, one of his last, I think, for your journey.

    Thank you, Blair

    Best always

  • Jon —

    What a great statement — not a journey but a “warrior dash.” Coupled with the notion of self-reflection, the contrast of energized action with a penetrating and calming intelligence. Perhaps your symbol ought to be a rushing mountain stream that has carved deep pools here and there in the solid rock. One wouldn’t say the water was “taking a journey” so much as to simply appreciate its crashing course and subtle depths!

    I’ve always been impressed, Jon, by your capacity to take otherwise dense material (look at my own!) and give it a simpler, more elegant frame. Who could not sense the great and generous heart beneath your words? Your projects?

    Thank you, Jon, for showing up here in such thoughtful and creative way!

    All the best

  • Dan, once again you hit upon one of the challenges that delineate the difference between theory or head knowledge and the path and struggle to true enlightenment.

    I am not using the term of enlightenment to mean an all at once buddha or christ experience either. (akin to Paul’s road to Damascus experience) Merely the theories and words we may stumble over when things are still only in our heads and not yet birthed through our genuine experiences into the thresh hold of our real lives. Where we take on the being of it as our living, breathing message.

    In part, I haven’t found it to be predominantly something we can do by conscious intention…to bring some things to awareness. It seems that some things will only come to our awareness when we are truly ready for it. And yet, at other times, we are forced into an awareness of things via life events.

    On the one hand, we speak of overcoming fear and yet sometimes, fear may be our ally to prevent us from entering into territory that we are not yet equipped to handle. Something else may need to be strengthened in us first and then, as if by grace, the fear may then give way so we can cross yet another thresh hold into a new state of awareness and growth. And healing.

    Thanks again for another wonderful post Dan.

  • Samantha — Yes, I too believe that we have parts of us that “stabilize” our identities by helping us shy away from threatening situations, and other parts that are more growth oriented. From my standpoint, the stabilizing parts protect us and are often less conscious. The growth oriented aspects are often more conscious and enable us to break through old patterns and ways of being. Sometimes that growth oriented part doesn’t use words so much as images, songs, dreams, synchronistic events to inform us and catalyze awareness. In the balance between protection and growth, we may discover, as you say, the place where we can “take on the being of it as our living, breathing message.”

    I see you as someone who is consciously courageous about your own growth, Samantha — which is a great boon to all who you come to touch. You seem to me to have of what Jon speaks of in his comment, that warrior side, sensitive and probing to find the real ground and stand firmly upon it, while also conveying real compassion for our private vulnerabilities and and perhaps not so private frailties.

    Mary Oliver is one of my favorite poets — she reminds me of this same balance. There is a fierce side to her work and one so soft it easily brings tears to my eyes. Which poem could I send you? There are too many — so I’ll just send this one as a proxy for them all.

    All the best to you

  • Well it just so happens that you selected my favorite poem by Mary Oliver. It’s a miracle! (grins)

    ‘You do not have to be good.
    You do not have to walk on your knees
    For a hundred miles through the desert, repenting.
    You only have to let the soft animal of your body love what it loves.’

    Oh how this goes against the grain of what would demand years of flogging and torture of penance for real and/or imagined human failures. That prison that our own psyche learns to confine us to based on outer world conditioning.

    Something so simple. And yet, how we resist and struggle against it. How hard it is to reason with our own internal jailer. : )

    Thanks for your ever-encouraging words and for the poem. I’m still smiling that you happened to pick my favorite!

  • Dear Dan

    Two of my favorite people in one post.
    Joseph Campbell and Dan Oestreich!

    What is my leadership journey?

    Every day I remind myself that others want to be loved just like me.
    Every day I remind myself that others want joy just like me.
    Every day I remind myself that others have pain and struggles just like me.
    Every day I remind myself that others are tired just like me.
    Every day I remind myself that others make mistakes just like me.
    Every day I remind myself that the others want respect just like me.

    You see Dan my leadership is a reflection of what I see within all of us.

    Thanks for allowing me to journey into the depth of my leadership.

    Lolly Daskal
    Lead From Within ALWAYS.

  • Lolly —

    This is a great leadership poem that can take any of us to a profound place. That place is about our greatest capacities for empathy and trust. We can move from self-involvement and isolation to generosity, care and sacrifice. We can, as you have done so well, build a community. I’m honored you have dropped by to share your heart-felt path.

    I often test my own work against the first verse of a poem by William Stafford, “A Ritual to Read to Each Other.”

    The first verse, which I’ve repeated many times on this blog, is this:

    If you don’t know the kind of person I am
    and I don’t know the kind of person you are
    a pattern that others made may prevail in the world
    and following the wrong god home we may miss our star.

    #Leadfromwithin, your creation, offers nearly a half-million people an opportunity to know each other and find that common star.

    Your journey, your story, is a guidebook for the rest of us.

    All the best

  • Dan,

    Your words wrapped itself around me and enveloped me! I feel your heart.

    You are the kindest most beautiful man I know.



  • Hi, Dan – interesting post:)

    Specific comments to your post:

    Like others, I enjoyed seeing Joseph Campbell’s thinking in the discussion. Campbell’s concepts are so iconic and valid that any discussion of individual development should include them.

    I also really resonate to the idea of leadership journeys as resembling a “thread”, and I think this fits somewhat into the comments below which I made before I read your post.

    The “thread” idea addresses what I have experienced, where leadership is a variable concept, one that can vary in the details quite a bit from time to time and place to place. However, the “thread” is the connecting dynamic that holds everything together. Maybe this is about learning to lead:)

    My earlier thoughts on the general idea of a leadership journey posted to the People Skills groups earlier:

    My leadership “journey” is more like an aimless stroll around the edge of a metropolitan area than a planned march toward a destination. I have experienced leadership in corporate environments, on college campuses, in therapeutic circles, the military, and with more groups of various sizes and design than I can remember.

    When I reflect back on all that, the only clear things for me are these:

    1) Leadership is a journey, but not necessarily one with a destination at the end … more like an endless spiral.

    2) Sometimes the leadership part of life is clearly marked, with titles, descriptions, mandates, and all manner of supporting paraphernalia.

    3) Sometimes leadership is just a group of people and how they interact.

    4) Leadership truly is available to anyone, but not equally.

    5) Following someone else is sometimes the best form of leadership.

    6) Like all long journeys, sometimes you are moving toward or away from a thing, and sometimes you are just chilling by the side of the trail.

    Thanks for asking this one:)


  • John —

    Thank you again for sharing your insights — I replied on the G+ one before seeing you’d added further comments here! As I said there, I resonate most deeply with the “spiral” imagery.

    I think Stafford catches the sense of that thread we follow so well in his poem. I have a sense that you like leaving some of the mystery in tact, which is exactly where I am, too. I believe we need to open ourselves and go beyond literal, logical, teleological and otherwise culturally constrained views of leadership and growth. When I work with the question that defines this post in learning events, I find I do use models, but I also always hasten to add that no model could ever do justice to the learning and development of a human being. Metaphors often work better than formal diagrams and logic. An intuitive image drawn on a scrap of paper may draw a person into deeper self-understanding faster than data from a 360 degree assessment. No one else, it seems, can tell us what the words should be to describe our own path or passage.

    As the saying goes, “when you catch the fish, throw the net away.”

    I’m so appreciative that you found this post and took time to share your experiences and your wisdom.

    Best to you

  • Theteapixie wrote:

    Hi Dan,
    I love that you challenge the language that we have fallen into using to discuss leadership.  From my first day of university I discovered the human need to differentiate and create exclusivity through the use of unique language.  Considering the ubiquitous nature of leadership, it is curious that we have found ourselves in the place of using “round” words (I love that).

    This seems like a magical place to be a leader in opening up the language of leadership to reflect that everyone leads at one time or another – whether or not they recognize it or can even talk about it.  You have taken a courageous step in challenging the status quo of the assumed language of the leadership discussion.

    While language is a way of creating community, it can also exclude.  Perhaps an important note is that the “round” words we have assumed for discussing this topic are more about the community of discussion than about the experience of leadership.

    My experience of leadership began when I was very young, leading school teams and projects.  It transformed into corporate leadership, entrepreneurial leadership, leadership as a Mom, and international volunteer leadership.  And then I discovered that the skills that made me a leader were not about “leading” or showing the way (a traditional description) – they were about facilitating the excellence of others.  I now focus my leadership skills on facilitation of strategic visioning.

    My experience of leadership is quite simple: recognize in others where they excel and, like building racing car sets, present the requested road pieces so that they can build their own path.  It used to be that I set the path, but in working in the volunteer world and as a parent, I discovered that when people worked with natural talents – the work that comes easy – success was inevitable.  Anyone who identifies with their “ease” (as I like to call it) will become a leader, setting pathways.

    It is when we connect with our ease that we lead without aggression, and with a quiet confidence that makes room for, and encourages, the excellence of others.

    Thank you for opening up the language for this discussion. Great, thought-provoking write.


  • Theteapixie —

    So many wonderful insights! Thank you for noticing that piece about the language, and how exclusionary — and I’d also say parochial — it can be.

    And I absolutely love this notion of identifying with one’s ease, and how that facilitates leadership. (I’m stealing this right away). Perhaps there is a connection in something I’ve noticed over the years with clients. Those who were hooked into “how I should grow, what I should do” typically don’t act on these, their own imperatives. The action plan never gets done. The person does not become who they say they should be. But those who follow the true energy of what they want to be, want to do, find the growth and opportunities they desire.

    In this sense, I try to help people see the future as following a river downstream (with ease) rather than climbing a tough mountain.

    Theteapixie, thank you so very much for sharing your experiences, history, and elegant understanding of question I posed! Awesome!

    Many best wishes

  • Theteapixie wrote:

    Thank you, Dan. I am honoured by your compliments. You have done a lovely job of discussing the concept of ease – I am hoping that everyone is quick to adopt it. 🙂

  • Awesome post Dan! You know what? This gave me a thought… I should sub-theme my blog “My Leadership Journey”. My writing started off from what I was learning about leadership and penning some thoughts around it.

    The passage that outlines my leadership journey is from a blog post I wrote some time back titled NAKED & UNASHAMED: LEAD FORWARD

    “Leaders embrace the challenges they face, yet all my life I ran away from my demons. When I confronted them, I got the courage to embrace my ability to deal with them. When I took leadership of my innermost soul, I led others with purpose and joy.”

  • Dear Kimunya~

    I so glad this post was inspiring to you! I recommend anyone who reads your comment also immediately clicks the link to read your great post, “Naked & Unashamed: Lead Forward…” It is testament to your strength of character and willingness, as writer Annie Dillard once termed it, to “ride the monsters all the way down.” Thank you for blessing this post with such a powerful personal story. As someone said to me during a dark time, “I hold your journey in the light.”

    All the best to you, Kimunya, and thank you again.


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