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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