Solitude, Backpacking and the Art of Leadership

September 1, 2013

Backpacking, Leadership, Solitude


Solitude is not the same as loneliness. It is only when we long for company that we feel lonely. It is as if our life consists of many pieces of music, each in various stages of composition. Sometimes we are content with the music we have but sometimes we become aware of our loneliness only when, for example, the right person comes along to complete our composition.

I spent the other week backpacking with a friend in the Ten Lakes area of Yosemite. My companion was a serial tech CEO, that is to say he starts and/or runs technology companies until they have proved themselves strong enough to stand on their own or, more usually, can be sold to a larger company. It goes without saying that he has strong leadership skills, strong enough to grow and keep together a team of talented employees while selling a yet unsubstantiated vision to hard-bitten stakeholders such as angel investors, venture capital firms and strategic partners. He is your classic Type A personality, driven, constantly alert, always moving and thinking about the next opportunity.

I, on the other hand, make no claim to any special leadership skill or expertise. If you really want to learn about leadership read the work of my blogging friend John Childress, someone who has actually made it his life’s work to study the subject. My own observations below are simply those of a humble backpacker who uses his time in the wilderness to think about what he has read or observed.

When I backpack alone I am careful, deliberate and plan accordingly. When I am in the company of a strong leader such as my tech CEO friend, I tend to be passive, inattentive and leave the planning to him. In short, strong leadership makes a passive follower of me. I suspect this is true of many of us. If someone is willing to take on the difficult and arduous role of leader, most of us are content to follow along more or less passively. However, given the responsibility and incentive to make our own decisions, without the option of having someone make those decisions for us, most of us will do just fine, while at the same time developing and honing our ‘self-leadership’ skills.

Personally, I am tired of strong leaders who flex their leadership skills over others. I am tired of being led into wars, political struggles, financial crises and global campaigns for this or that issue. I am tired of the lying platitudes of corporate leaders who are just as willing to spy and sponge on their own customers as they are on taxpayers.

We need to change the emphasis from ‘leaders’ who lead and ‘masses’ who follow, to a population of individuals who have learned to lead themselves, who are willing to take responsibility for their own lives and who are consequently extremely reluctant to turn over such responsibility to anyone else. Such ‘self-leaders’ need to start by practicing self-control. Without self-control there can be no true leadership. The solo backpacker has learned to take responsibility for him or herself under demanding conditions. The aspiring ‘self-leader’ could do worse than start here.


“Years ago I stopped worrying about how to grow our church and instead focused on growing me.  As I grew me, our church grew.” — Rick Warren (20,000+ people/week)

, , , , , ,

About Malcolm Greenhill

Malcolm Greenhill is President of Sterling Futures, a fee-based financial advisory firm, based in San Francisco. I write about wealth related issues in the broadest sense of the word. When I am not writing, reading, working and spending time with family, I try to spend as much time as possible backpacking in the wilderness.

View all posts by Malcolm Greenhill


Subscribe to our RSS feed and social profiles to receive updates.

48 Comments on “Solitude, Backpacking and the Art of Leadership”

  1. unfetteredbs Says:

    I like your message. Time to wake up and stop being passive. Responsibility.
    Always a pleasure Malcolm


  2. Ulrika Says:

    Reblogged this on Gusto Coaching.


  3. NicoLite Великий Says:

    I do believe we shuld try to be the masters of our own lives. The political leaders that we have are not in the graces of our trust, but only benefit from not being the worse of a pack of devils to choose from, and many CEO’s do not see people, but arrays of numbers. But we do need to follow someone’s lead, once in a while…


    • Malcolm Greenhill Says:

      “But we do need to follow someone’s lead, once in a while…”

      Thank you NicoLite. This may be true but there is a huge difference between an undifferentiated mass mindlessly following a charismatic leader and a group of self-reliant individuals choosing to follow directions to obtain a specific goal that is known to everyone.


  4. Michael R. Edelstein Says:


    On the one hand, your sentiment has much appeal. However, it’s not clear that individuals who show much responsibility and discipline in their own lives also eschew State control.

    Many of them believe something like “I don’t need the Government to tell me how to run my life, but my selfish compatriots do. I can’t trust them to do what’s best for me! We need a strong State to keep them in line.”

    Michael R. Edelstein


    • Malcolm Greenhill Says:

      Michael, thank you for your perceptive comment. While I would like to believe that simply acting responsibly might be contagious I agree with you that this is unlikely. There has to be an incentive for people to be willing to act responsibly and take their life entirely into their own hands. That is why I said: “without the option of having someone make those decisions for us” Freedom once taken is hard to get back. You essentially need faith that the new system will work better than the old.


  5. Ishaiya Says:

    I share your philosophy Malcolm, and very beautifully expressed in this post. The philosophy is sound because it is based on tried and tested observation as you say, and as I know from my own experience. In order to lead others you must be able to lead yourself and take control of the life you lead. Your life begins with you and ends with you, and everything in between is based on your own unique perception of what you experience, so choose to perceive it well and with confidence.
    Enjoy the rest of your Sunday!


  6. Morgan Mussell Says:

    Great post. In considering the seeming passivity of the populace, however, I think you have to figure in “learned helplessness”

    The phrase entered the language after a key psychological experiment in which dogs were subjected to electrical shocks with no way to escape. They became entirely passive, exhibiting canine signs of clinical depression. Later when an escape mechanism was added – they could avoid the shock by jumping over a small net when a buzzer sounded – they had to be taught, physically carried over the net.

    Right now, isn’t our situation analogous to the dogs before they had a means of escape? Individuals, through solitude like you, or by other means may begin to reclaim their power, but as a nation under the thumb of a corporate oligarchy, where is the net we can jump to avoid the next war or crisis or economic disruption?

    In this past week of remembrance of the March on Washington and all the other mass demonstrations of the ’60’s, one contrast with the present that wasn’t mentioned was that then the battle lines 50 years ago were clear. Everyone knew who the good guys and bad guys were. You were either for or against desegregation. You were either a hawk or a dove on Vietnam.

    Now it’s so much more diffuse. It’s a slow, ever so slow process to begin to even see where the problems lie. The Occupy movement gave it a name – “the 1%.,” and this summer’s revelations about the NSA and our current Syrian sabre-rattling makes clear that the entire governing class is part of the problem – the fantasy of a “good” and a “bad” political party breaks down.

    The first signs of nets to jump over emerge as individual initiatives flying under the radar, implemented (to grab your metaphor) by solitary backpackers. I’ve tried to celebrate a few of them on my blog – the micro-gardeners and mini-library entrepreneurs, and everyone who struggles to find a satisfying way to make a living. If we cannot “change the system” perhaps newly empowered and formerly passive people can begin to find the 21st century equivalent of “dropping out” – trying to live our lives and inspire others to live decent lives in spite of our so-called leaders.


    • Malcolm Greenhill Says:

      Morgan, thank you for these very interesting comments. Personally I’m not convinced that our problems are more insuperable than say the problem of freeing the slaves during the heyday of slavery, or the colonialists facing down the greatest military power on earth. It’s all a matter of perception. Change people’s perception of the problem and the problem often disappears. I obviously don’t have all the answers as to how we go about doing this but you have mentioned a few strategies in your comments and clearly “trying to live our lives and inspire others to live decent lives in spite of our so-called leaders” is key. Albert Jay Nock called such people the “remnant” and believed that one day they would be called upon to provide a beacon for the multitudes. It is also possible that the elites will bring about an economic collapse which might not end as badly as most people think. After all there are significant advantages to starting afresh with no government debt 🙂


  7. Penny L Howe Says:

    Yes, yes and yes! I agree. An excellent article!


  8. Clay J Mize Says:

    Love your opening line. Well done.


  9. becwillmylife Says:

    Peggy Noonan wrote an interesting piece in the Wall Street Journal where she referenced some interesting insight about President Ronald Reagan and his leadership style. “Really good politicians don’t try to read the public, they are the public. they don’t try to be like the people, they actually are like them.” Amen. This is the culture I want to live and work in.


  10. Lisa Chesser Says:

    Very true and sometimes that’s the only way we become confident.


  11. Michele Seminara Says:

    So true, and so pertinent to our times! The ideas you presented also got me thinking about parenting styles, and the way we may be taking away our children’s drive to ‘self -lead’ by sorting everything out for them – thereby setting them up to expect, and accept, a government that will do the same. So interesting Malcolm, thank you.


    • Malcolm Greenhill Says:

      Michele, that’s a great observation and yet, from personal experience, it’s a difficult habit to break. As parents we want our children to do well so we give them less chores as long as they concentrate on schoolwork, but then they grow up to be less responsible individuals. Who said life was easy? 🙂


  12. carmenw503 Says:
    Hi Malcolm. You could have a read here as well. It’s my pleasure to visit you. See you again. Take care.


  13. Mike Says:

    Good advice. Thanks for reminding us!


  14. Kavita Joshi Says:

    nice read Malcolm…simple but true facts and observations that you have presented here…I love the quote a lot about growing oneself ..thanks a lot for any upcoming backpacking trip?


  15. ohstacy Says:

    Brilliant! So true!


  16. Hanne T. Fisker Says:

    Malcolm, wonderful post. It’s been in the back of my mind until the time felt ripe to reflect here too in your comment section. I’m much attracted to solitude, it’s so rich with flavors, colors and silences. It is only when we long for company that we feel alone. I might have a slightly different experience/perspective on this, or perhaps what comes before the longing of company. It is only when we have lost touch with our own true nature and walk in life that we feel lonely. When we have let ourselves down. When we have been so occupied with the outside world, it’s demands and commands and thereby poured all our energy out there leaving nothing to nurture our inner world, forgotten in the rush. Then loneliness appears and the longing and possibly need for other people grows stronger, in an attempt to fill up an empty hole, where perhaps the deeper roots to longing is more about returning home to oneself… ? I read somewhere long time ago, but somehow it has stayed with me, something in the lines of this: When a depressed person went to a medicine man he would ask the person 4 questions: When was the last time you danced? When was the last time you were singing? When was the last time you were enchanted by stories? When did you stop finding comfort and peace in solitude?

    Regarding leadership, yes and yes indeed. As for being a leader, there is always a good question to be asked regarding what kind of leader someone is; do people follow him/her out of respect and inspiration or out of fear?


    • Malcolm Greenhill Says:

      Hanne, I love your description of solitude as being “rich with flavors, colors and silences” which is so true. Solitude is never just one flavor. You provide an interesting perspective as always. You seem to suggest that loneliness is always pathological as if someone truly in touch with their “own true nature” would never feel lonely. On the other hand, I think loneliness can be pathological but I also think it can be fine depending on our character. Someone said “sheep are lonely but the shepherd is never lonely” which suggests that whether or not we feel lonely depends upon our nature. I love the story about the medicine man but of course depression is not exactly the same as loneliness. Thank you for all these rich pearls to reflect on.


      • Hanne T. Fisker Says:

        Malcolm, you have a very good point in loneliness depends on the nature of a person. Speaking for myself, the loneliest place in the world can be among people, whereas loneliness never occurs when I’m alone. Hence perhaps why I often chose solitude. I do all my journeys alone (and meeting wonderful people along the way) part of it is solitude part of it is the wish for freedom to go where ever my feet and gut-feeling takes me and when. Rarely do I bring company on my hikes either, unless its purpose is to show friends beautiful spots off the trails. As a friend once said: “you just want nature to yourself” There is truth to that 🙂 I like the solitude but also the stillness, humans tend to talk a lot 🙂 It changes the feel of a place. Regarding the medicine man, my fault, I didn’t intend on equal depression with loneliness it was the remark on finding comfort in ones own solitude that intrigued me.

        There is a book on horses called “Passive Leadership” challenging the alpha-theory by Mark Rashid, where he explains how very often we believe the leader of a herd is the strong stallion, every horse obeying and moving out of his bites and in safe distance of his kicking hooves. Whereas in the herd there is also the passive leader, very often a mare. She has only one thing in mind; how to save energy, energy needed for flight in case of real danger. She is calm, waits and observes and doesn’t try to fight for leadership against the stallion, which she already knows is futile and in a horses mind equal waste of precious energy. What happens is, other horses begin to follow her and her example, they feel safe around her and her decisions. The interesting thing here is, she doesn’t command or demand leadership, she’s not the slightest interested, however she is chosen, by the herd. Apology for putting human terms/reaction on a horse, don’t know how else to explain it. I’m not quite sure where I’m going with this story, only I find it fascinating in the context of the art of leadership…


  17. Michele D'Acosta Says:

    I visit your blog knowing I will find inspiration. I love the approach you’ve taken with this post and, incidentally, I’ve adopted your philosophy. Couldn’t agree more that we need more self-leadership, taking ownership of our lives and not looking to our official leaders to solve the big problems. In this time of total information awareness everything we need to know is already written down. The heavy lifting is joining the dots, joining hands and looking in the same direction. Malcolm, thank you.


  18. principalpollak Says:

    Malcolm, I am a school leader who believes in the ideal of leadership. Expecting passive followers is the opposite of good leadership. Doing so is just being the boss. Leadership is building capacity in those you lead, so they may become leaders by example in their own right. That is how change happens. Check out my blog which is one way I do lead.


    • Malcolm Greenhill Says:

      “Leadership is building capacity in those you lead, so they may become leaders by example in their own right.”

      Thank you. I agree that this is the ideal but, as you know so well, give a task to any group of people and a leader will emerge who, by sheer force of intellect, personality or presence, will play a dominant role. The dictionary defines leadership as “the action of leading a group of people or an organization”. It doesn’t say anything about how a leader leads. So maybe my post was discussing the abuse of leadership skills or just addressing one aspect of leadership. I defer to the experts on this one and will certainly check out your blog to learn more.


  19. Malcolm Greenhill Says:

    Thank you for the linkback.



  1. Leadership: Standing Four Square | - September 10, 2013

    […] Solitude, Backpacking and the Art of Leadership […]

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: