Further Along My Bike Rides: 8 Additional Leadership Lessons

In May 2018, I contributed my thoughts on 5 Timeless Leadership Lessons from my Bike-Rides. There, I posed the question: “What can the act of riding a bicycle possibly teach us about leading well?” 

Now, 2 years later, I continue to ride. In addition to having fun, I continue to be interested in knowing what more my bike rides can teach me.

In this reflection piece, I ask the same question from two years ago, and I add eight additional leadership lessons to the previous five. This will make my gift a ‘baker’s dozen’. In what follows, after each ‘leadership lesson’ learned, I will ask a few reflective questions. I encourage you to complete them in your own time either individually or as a team.

Lesson #6: Some Questions Are Timeless

But, you might ask, why raise the same question again? Is it not time to move on to new questions? Surely there must be 50 ways to leave your same question! 

Imagine simply asking a question once, and never feeling the need to raise it ever again. The courage to raise the same question again is testament to the belief that there is more that can be learned from that question. This belief lays the groundwork for the significance of raising a ‘same ‘ol same ‘ol question’ as one worth asking.

We may be too hasty in our desire to ask ‘new’ questions and wanting ’new’ solutions even when those new solutions create more problems. On the other hand, we may hold on so tightly to old solutions that we shackle ourselves to them. 

We may be bored or even irritated when someone raises ‘old’ questions. We may adopt an attitude that says “been there, done that!” We might even treat a person asking the same questions as a ‘gadfly’, or a nuisance. In fact, in his Apology, Plato used the term ‘gadfly’ to describe Socrates’ acting as an uncomfortable sting to the Athenian political scene, like a spur or biting fly arousing a sluggish horse. And Socrates paid with his life.

Our times may have changed, but leadership questions like:“why do we study leadership?” or “what does it mean to lead well? – these continue to be eternally relevant and significant. Questions like these enable us to stay focused on purpose and direction. 

Purpose and direction, in turn, focus our attention within the context of change. In changing times, any information that is disconnected from the issue of purpose and direction – or questions that remain silent on purpose and direction - is just noise.

Reflection Questions: 
Is the information that we are requesting 'simply more noise'?  
How are our questions connected to ‘purpose and direction’? 
What is the point of choosing to do this?

Lesson #7: Shifting Gears – Shifting Assumptions

This year, I bought myself a new bike. I offered my daughter my old De Vinci bike. Today, I ride a Fuji Traverse 1.3. Nothing fancy, though it is a hybrid. As I rode my new bike, I found myself constantly shifting gears to get a feel for the bike. Yes, like all relationships, it was also my way of getting acquainted with my new riding partner.
 
As I shifted gears, I was reminded that ‘shifting gears’ can be akin to the mental practice of shifting paradigms or shifting from our own ingrained assumptions. We all carry our own assumptions, do we not? 

Our assumptions are themselves part and parcel of our socialisation. But that is neither here nor there. The point is this: imagine what our lives would be like with each other if we only allowed ourselves to be influenced by our own assumptions. This would be a mark of a unilateral rather than a reciprocal relationship with the other party. It is a choice to live in a non-egalitarian world. It is a voice that says “my way, or the highway”. In the long term this is a recipe for disaster. 

The willingness to ‘shift gears’ is a willingness to engage in an open conversation without feeling the need to protect one’s own assumptions. It is an openness to genuinely inquire into the meaning of what each of us hold to be ‘true’. It is not to ‘politicise’ opinions for that would only lead to division.  It is an openness to reason through the best of what the other has to offer. The act of ‘shifting gears’, then is also like shifting from a ‘politicising stance’ to taking a ‘conversational stance.’ 

So, can we talk?  

Reflection Questions:
Are we conversing openly or are we simply protecting our own assumption-al-positions? 
How do we know that we are conversing openly? 
Let me offer you one measure for the second question. If you both feel heard, then you are on the right track to both talking and listening.

Lesson #8: Riding with a friend and the gift of a promise

Unlike my rides in 2018, this year I found myself riding with a dear friend. “So what?” you might ask. Riding with a friend raises the bar from, “I am going for a bike-ride tomorrow,” to “I will meet you on the McGillivray Bridge at 9am,” and to actually be there at the scheduled time.

It is to make a promise with someone other than yourself and doing all you can to keep the promise. It is about being accountable to the other and to the promise made. 

Why do we make promises? We make promises because we live in unpredictable, uncertain, and changing times. In times of unpredictability and uncertainty, making a promise and keeping a promise (as best as we can) is one way of returning ourselves to some degree of stability. 

Prior to my life in higher education, while working in organisations as their Senior Change consultant, I was often asked to assist my clients through the process of coping with change. Sometimes, in no uncertain terms, they had been told by senior managers that people affected by change would need to learn to compromise by making concessions. 

Let’s take a closer look at the language of compromise. It consists of com (meaning, together) and promise (a declaration or an assurance). It is not about making an agreement or a settlement that is reached by each side making concessions. However, the essence of com-promise is not one of making concessions of any kind but making promises together (a co-promising).


The act of making promises, for a political theorist like Hannah Arendt (see her book on The Human Condition),  arises simultaneously out of the basic unreliability of human beings who can never guarantee today who they will be tomorrow, and unpredictability, namely the impossibility of foretelling the consequences of an act within a community of equals where everybody has the capacity to act. 

In a democratic society, the power of making promises is that it enables human beings to stabilise their relationship with each other while in the face of unpredictability and unreliability. It is precisely because of our own unreliability, and the unpredictability of the consequences of our actions, that we make promises. It is a choice that offers an alternative to controlling the unpredictability of the consequences of any action and controlling the unreliability of others through force. 

Reflection Questions:
What are we co-promising ourselves as we live with the certainty of uncertainty? 
How do you feel when you or the other makes a promise? 
How do you feel when promises are broken? 
For those of you who are coaches, how might you frame/reframe this understanding of ‘co-promise’ for your clients? What will you risk in doing just that?

Lesson #9: I am not in a race

Riding with my friend was also a reminder that I was riding for the sake of enjoying the ride. So, as my friend sped up, I did not feel the need to keep up to her speed. And God forbid! What if others knew that I could not keep up with my female friend? (Ouch! Now, YOU do). Oh! The pain of my suffering male ego! 

In 2018, I offered Lesson #2: Enjoy and respect the companionship. At the time, I asked my readers to orient to those whom they lead as companions and not as subordinates. Now, I ask my readers to imagine orienting to those whom they lead as companions and not as competitors. 

I suspect that we all know a thing or two about competition. Every man or woman for themselves. It’s a dog-eat-dog world. From this perspective, competition is a reflection of scarcity, fear, and not one of abundance. Is this the best that we can do for ourselves? What would it mean to shift gears from this understanding of competition? Well, again, let us look closer at the etymology of competition. It consists of two words, com (meaning, together) and the Latin petere (meaning, to pray). So, we might ask: at what point in our human history did praying together become translated into competing against one another? 

What if I also said that it is not about either being in front or being behind. From an ecosystemic thinking perspective, we cannot think of one without the other. It is not an either-or option. The concepts of ‘front’ and ‘behind’ are concepts that stand in a relationship with each other. I understand one (behind) by understanding the other (front). Unlike the common adage that goes ‘it takes one to know one’, ecosystemic thinking would say it takes two to know one. 

Another part of the challenge with competing against one another is that it excludes the possibility of real collaboration. As I reflect back on my high school experience in Malaysia, I am struck by the lack of collaborative learning in our school system. It was, and I believe it still is, an exam-based educational system and structure. At the end of the day, all students returned to their respective corners (homes) – cope with their own limitations or build on their strengths – and learn (memorise the instructions and information) by themselves and for themselves. 

At the end of the year, they would be required to enter an exam hall and individually regurgitate their memorisations to the best of their abilities. In this educational system, there was a singular absence of the possibility of students to learn and study together. 

In that system, there was an absence of the possibility of students helping students. Herein lies a particular irony. We first prepare our students to be competitive (each student for herself or himself). And then, when they get to the workplace, we want them to be collaborative and work as a team. Huh?

Reflection Questions:
Are you competing against one another in the community or in the workplace or are you truly working together? 
How do you feel when you work together or work against one another? What is really at stake for YOU? What is really at stake for US? What is really at stake for our community? 
What can you do to promote collaboration, and is it even an option?
What would collaborative learning look like in your schools, organisations, and in your world?

Lesson #10: I am not in control

In 2018, I offered another lesson (lesson #4). I named it ‘Read the Signs’. This time around, while I read the signs well, I did not quite fully appreciate the prairie headwinds that I would face while cycling in the open, with no trees to act as a barrier to the winds. I was fully exposed to the power of nature. 

Nature, in this instance, was indifferent. It did not care that I – or anyone else for that matter – was cycling. 

This was a humbling reminder that I am not in control – even as much as I would like to think that I am or was. Riding against strong winds while feeling all the aches and pains of my steadily aging body, I was left with several options: 

1. Stop Riding. Call my Ever-Supportive Wife to Pick Me Up.  
2. Continue Riding and Complain Till the Cows Come Home. 
3. Curse Nature. 
4. Call on the Goodwill of Others to Bring Me Home – a variation of (1),
5. Curse Myself for Choosing to Ride while I Continued to Ride, or
6. Learn to work through my aches and pains, by adjusting (shifting to lower gears, slowing down) and riding through it. 

Option 6 is an option for resilience. While resilience is a choice that accepts defeat as a possibility, it chooses not to be defeated. Resilience is a measure of how much we want something and how much we are willing and able to work through our aches and pains. It is connected to both our mental and emotional strengths in ways that allow us to reframe purpose and direction. 

I could berate myself by saying: “I am never doing this again! This is simply no fun anymore!” But then again, honestly, who ever declared that fun is equal to the absence of challenges? While the physical challenges of riding a bike may at times not be ‘fun’, I can still opt for ‘fun’ by entertaining myself with the possibility of telling a story about that which is not in my control. (Did I just break the fourth wall?)

It is here that I am reminded of the reason why we need stories. 

Author Isak Dinesen, for example, noted that “all sorrows can be borne if you put them into a story or tell a story about them”. Adding to ‘Isak’ Dinesen’s thoughts (See Arendt’s text Men in Dark Times) philosopher Hannah Arendt suggests that we need stories because they “reveal the meaning of what otherwise would remain an unbearable sequence of sheer happenings”.

So yes, imagining myself telling my story as I rode through the aches and pains of cycling, revealed the purpose of my bike rides – and that made my ride bearable. 

Reflection Questions:
What did we do when we felt the fun being taken out of work? List out your responses.  
How did each of the responses make us feel? 
What did we choose to do when the going gots rough? 
What stories have you told yourself (yourselves) when the going gets rough?

Lesson #11: I am in it for the long-haul

Here’s a bit of craziness. This summer, along with my friend, I have been riding an accumulated total of a minimum of 70 km on weekdays and then long rides of up to 80km on Saturdays. These long-rides have taught me that a life well-led is not a sprint. I’ve begun to think of it as more of a marathon. But the more I think about this, the more I shift gears to argue that it is more than a marathon. It is, I would suggest, more like a relay. 

Like in a relay, leading well is about being concerned about what we are handing off to our younger generations – those who come after us. How we treat our land; how many mountains we may blow up for material gain; how many trees we cut down permanently – these may give us the impression that we, human beings are in control. 

Some are arrogant enough to treat our limited natural resources as if they are unlimited. In our destructive tendencies towards our natural resources, what do we leave behind for our children and our children’s children? This very question inspires us to entertain the possibility of restraint from indulging our desire to control nature. Imagine our relationship with nature without restraint.
 
Whereas long bike rides of 65km, 70km, or 80km may sound crazy, they do have a finite end. However, to think in terms of being in this journey of life for the long-haul is to think about the legacy we choose to leave behind when we each face our finite end (death). This idea transforms the practice of longer rides, from a sprint, to a marathon, to a relay. Our lives may be short (finite) and it will only last for a brief moment, but our legacy will always be long – albeit as long as we have humans to remember, and as long as we do not blow up our planet. 

Reflection Question: 
What legacy do you want to leave behind for those who come after you? 

Lesson #12: Acting Deliberately

Allow me to return to my starting point in this essay. It is about my goals and why I chose to ride for short and long hauls. 

When I began riding with my friend, she expressed her desire to culminate her summer achievement with a 100km ride. This was her goal. Now I feel like I need to ride those 100km because I do not want to disappoint her. “Really?” – I asked myself.

Goals are not only laden with values – they are also laden with both complementary and contradictory values. This is what makes the language of goals tricky in that it can bring people together and it can separate them. For now, let me stay with the notion of accepting another person’s goals without the need to feel obligated to take on those goals as one’s own. This is a way of asking: how can I act deliberately in the face of another person’s goals?

While we were on our 70km bike ride, for example, we met a gentleman from the Bahamas. He too was on his bike and was taking a short break. 

Gentleman: “I aim to ride 45km today...and I am working up to 80km this summer.” 

Me: “How come 80km?” 

Gentleman: “Because I turn 80 this year” 

We all have our reasons for the goals that we set for ourselves. And, as I noted earlier, our goals are laden with our values. Here, for example, was a man who was turning 80 years of age. Within his context, riding 80km was meaningful for him. But wait. I must clear this up. My friend is not turning 100 this year. Far from it! She wanted to ride 100km for her own reasons and I respect that. At the same time, I need to remind myself that the 100km ride was and is not my goal. 

I began this reflection by saying that I choose to ride for the fun of it. At the same time, riding my bicycle was an opportunity for me to work a few things through in my own head. My goal was and is related to the question: “I wonder what leadership lessons I will learn from my bike rides?”  

That too was fun for me. 

My goal was not to ride 100km. Consequently, I cannot be concerned about joining (pleasing) or not joining (disappointing) her and her friend for an upcoming 100km ride. But what if I did overly concern myself with her goal?

First, there will be a lack of clarity – “whose goal is it, anyways?” 

Second, this lack of clarity may suck me into a feeling of ‘obligation.’ If I gave myself into feeling obligated, then I would be distracted by and feel stressed over the options of pleasing or disappointing. If there is one thing that I have come to learn over the years, it is this. Living out of obligation is not fun. 

Third, it will be to forget why I chose to ride in the first place. So, one way of acting deliberately, would be to remember why you are doing what you are doing, in the first place.

Reflection Questions:
Why are we on this journey called life? 
What is your goal and what are the underlying values of your goal? 
Have you confused your goal with someone else’s? 
How do you feel while in the middle of that confusion? 
What would it take for personal goals to become shared goals? 

Lesson #13: On the language of a ‘cycle’

Perhaps it will be appropriate for me to end my reflections by speaking to the intellectual framework informing my reflections. The language of a ‘cycle’ moves us away from thinking in terms of scientific, linear cause and effect relationships. 

At best it is a unilateral relationship of independent variables affecting dependent variables. And yes, we can also get to be really fanciful by introducing intervening variables. In a scientific model, observers are required to separate themselves from the observed. 

The language of a cycle, however, offers the possibility for the observed to ‘cycle back’ to the observer and for the observer to ‘cycle back’ to the observed. The image of the figure 8 comes to mind. It raises the possibility that both the observer and the observed stand in a reciprocal relationship with each other – there is the possibility of a co-influence.

Indeed, where can we be in the world and not not be a part of it? 


In this respect, the scientific model is inconsistent with the concept of reciprocal relationships. This is the perspective of systems theory. I believe that systems theory offers us a better lens through which we can develop a meaningful understanding of our relationship with our practices. It can offer us a better understanding of what it means to lead well.

The language of a ‘cycle’ and ‘cycling back’ (systems theory) introduces us to the idea of leadership as a reciprocal relationship among leaders and followers. It also reveals that unilateral relationships are the signature of power-wielders. Systems theory also introduces us to thinking about our reciprocal relationship between practice (for example, riding a bicycle)) and learning. 

The language of a ‘cycle’ and ‘cycling back,’ inspires us to make a fundamental epistemological shift (shifting gears) from considering oneself as an independent and detached observer who innocently watches the world go by, to considering oneself as a participant in the drama of mutual interaction and of the give and take in the circularity of human relationships. 

If you accept the validity of what I am saying, then you will accept the linear language of cause and effect as a language of unilateral relationships that is devoid of reciprocity. If you accept the validity of what I am advocating, namely for a systems theory approach to understanding leadership, then, you will also accept the complexity of how we come to know what we know. 

While we (observers) cannot exist in isolation from our world (our observations) – in our attempts to know, we (as observers) also assume a position outside of the system. The relationship between the observer and the observed is complex in that they are both inside and outside the system at the same time. 

Let me add to the complexity. In practice, I am riding my bike and not riding my bike, at the same time, as I reflect and talk about riding my bike. Indeed, this is a call to be a self-reflective leadership practitioner-scholar.

Systems theory invites practitioners to take a scholarly interest in their practice. Practitioners, in other words, are invited to open themselves to the process of thinking about their thinking about why they do what they do. 

At the same time, systems theory invites scholars to think about their thinking which informs their practice. It is in this way that systems theory – through the language of ‘cycle’ and – ‘cycling back’ – enables me to offer practices like remembering purpose-direction, collaborating, co-promising, shifting gears, being in a relay, raising the same question again and again, staying resilient, and acting deliberately, as both significant and worthy of our attention and especially as they relate to my question of what it means to lead well.

Reflection Questions:
How are your practices an example of reciprocity? 
How are your practices an example of unilaterality? 
What are the consequences of reciprocity or unilaterality?

Concluding Thoughts

As I noted 2 years ago, I continue to collect my bicycle riding experiences/stories as I write on this topic of what it means to lead well. If you have any bicycle-riding experiences that you would like to share with me, I invite you to do so. You will definitely add a unique flavour and another perspective on what it means to lead-well.