On Feeling Whole: Wardley mapping, Stoicism and Maturity for Personal Development

Almost a year ago, I created a Wardley map to capture all the things I value and how I perceived the maturity of my practices in living those some things I value. It was a great exercise to try and visualise everything that competes for my time when I’m focused on being the best possible version of me, but truth is almost a year later and as I stopped looking at and updating the map, I’ll admit I’ve done little to no progress at all a year in.

It did allow me to see and improve for a while, but we all know that if we mindlessly go through live we let old habits kick in and take over all our good intentions. I know I’m not alone in this.

This was the map I created at the time:

Personal map of the things I value and maturity of practices

The things I value haven’t changed at all, but a lot of my practices have made little to no improvement and I feel like some of my blind spots are still there. I do feel however that it was me failing the process, and not the process failing me.

In this blog post, I’ll attempt to suggest why I believe mapping our own personal goals might be advantageous and how putting everything on a map can facilitate the visualisation of the “trade-space” which I’ll define better below. Over the next few sections I’ll lay out my thoughts on why I’ve combined these different techniques and what I expect to get from using them together. Let’s start at the beginning though

Back to Stoicism

I’m a big fan of Stoicism, particularly of Marcus Aurelius and though his book “Mediations” has been my bedside reading for years, for the last year-ish that stopped being the case but lately as struggles begin to mount again, I found myself reading it daily and loving it’s results.

Having become an independent consultant working mainly as a contractor for the moment, but with a business partnership and helping a startup, 2 children both of which have their own specific struggles, a wife that’s been struggling a bit with depression, having stopped being as regular in Brazilian Jiu-Jitsu and physical training, and though I’m now recovering having gained over 15kg in the past 1.5 years, the things making me feel ugly and not having the opportunity to support and be who I wish to be in the things I said I value, or better yet, not being who I said I’d be, has had a toll on my mental health for sure.

Book 2 of “Meditations” has a particular passage that struck a chord that helped me get focus again:

“Whatever it is, this being of mine is made up of flesh, breath, and directing mind. []

Quit your books — no more hankering: this is not your gift. No, think like this, as if you were on the point of death: you are old; don’t then let this directing mind of yours be enslaved any longer — no more jerking to the strings of selfish impulse, no more disquiet at your present or suspicion of your future fate. []

Remember how long you have been putting this off, how many times you have been given a period of grace by the gods and not used it. It is high time now for you to understand the universe of which you are part, and the governor of that universe of whom you constitute an emanation: and that there is a limit circumscribed to your time — if you do not use it to clear away your clouds, it will be gone, and you will be gone, and the opportunity will not return.

Every hour of the day give vigorous attention, as a Roman and as a man, to the performance of the task in hand with precise analysis, unaffected dignity, with human sympathy, with dispassionate justice — and to vacating your mind from all its other thoughts.

This reminds me that we’re all human, and that sometimes we all lose track of the things we value if we don’t keep constant attention to what we’re doing, and also reminds me of ‘Memento mori” (Remember you will die) and that life can leave me at any moment and that I want nothing more in life than to ensure my family is taken care of when it happens and that they remember who I am not from the thoughts and pretty words of who I said I’d be, but from the actions they have a memory of me performing. All else is of secondary importance, though a part of my whole.

There are some other passages from “Meditations” that particularly struck a chord with me and the activity of mapping

Always make a definition or sketch of what presents itself to your mind, so you can see it stripped bare to its essential nature and identify it clearly, in whole and in all its parts, and can tell yourself its proper name and the names of those elements of which it is compounded and into which it will be dissolved.

Nothing is so conductive to greatness of mind as the ability to subject each element of our experience in life to methodical and truthful examination, always at the same time using this scrutiny as a means to reflect on the nature of the universe, the contribution any given action or event makes to that nature, the value this has for the Whole, and the value it has for man — and man is an inhabitant of this highest City

To me, this is what mapping is. Thinking about my needs, and stripping naked what constitutes them and when thinking in terms of maturity is about subjecting it to “methodical and truthful examination”. Having metrics whereby I make an assessment of where I actually am.

Your mind will take on the character of your most frequent thoughts: souls are dyed by thoughts

The daily practice of starting the day looking at the map, is a great reminder of the things which are important to me, so I can dye my character with the thoughts that will lead to the results I seek.

As Prasanna K mentioned at MapCamp London 2019 “Once you see a map, you can’t unsee it”. There’s something about the format of a map (visual, one page) that imprints the information in our brains in a way that a simple narrative doesn’t (at least not to me)

Identities and the Trade Space

From the Complex Adaptive System sciences we now know we’re all made up of multiple identities. I’m not just Mario, the Father or Mario, the husband or Mario, the Security professional. I’m all of these and some more.

And in order for me to feel Whole and balanced, all of these identities need to have an expression in the things I do, in what I spend my time doing.

This blog post from the Cognitive Edge website is where I got the “inspiration” to think in terms of my own identities and what’s valuable to me.

Switching from individual to identity and from formal structure to constraint management offers us an interesting alternative to this focus. As the problem increases in complexity we increasingly change the nature of constraints, loosening coupling to allow rapid readjustment to a dynamic situation, reversing the process as the situation stabilises again. Critical to this is a reduction in the number of things that have to be managed and a focus which builds experimentation into change. So this exploration is going to bring in my prior development of a typology of constraints. Just to be clear, it’s not going to be complete in one blog post! However, getting a chance to teach this on an advanced Cynefin Course in Sydney last week helped get a lot of things straight in my mind. So let me start by listing some types of identity:

Role based identities such as crews, in which people are training in role and role interaction.

Activity or socially triggered identities; how we feel in different contexts. The example I normally give is that these days over a weekend I can shift between rugby supporter, hill walker & opera goer wearing different clothes, having different conversations while maintaining a degree of integrity around a core.

Task based identities (often overlapping with crews) in which a common task working with familiar people creates a different perspective. However smaller constructs, such as pair programming offering some interesting possibilities that I want to develop here.

Context triggered such as in a crisis where wholly different patterns of expectation and interaction form without design

Authority and power based entities both formal and informal.

Life’s complex, and we all have but 24 hours in a day. And what I most struggled with is with the hiding behind virtue as a procrastination method not to do the other things that keep me whole and balanced.

For instance, spending much more time on books and learning to somehow justify why I’m not going to the gym or Brazilian Jiu-Jitsu practice.

So in order to feel balanced, one must first understand what are those identities which mater to us and what they’re made of in terms of practices.

And this is where Wardley mapping comes in, as it allows me to identify ‘User needs”, in this case, what I need to feel whole and then make an initial list of a value-chain of what practices are required in order to fulfil that need.

For me, nothing changed since I last did that map. What I value and the identities I wish to spend my energy on are still the same, and they are:

  • The Educator
  • The Strong man
  • The Nurturer
  • The Protector
  • The Provider

These are the main identities of who I want to be, who I said I’d be, and now it’s up to me to ensure I live up to it and develop the practices that will deliver against these identities, so I don’t feel a fraud.

The main challenge is how do I deliver against all of these, how much time should I spend with each, what gives when I decide to take time and effort away from one to work on the other.

The challenges I’ve identified I need to address are the following:

  • How do I deliver against these ?
  • How much time should I spend with each ?
  • What gives when I decide to take time and effort away from one to do another ? (the trade space)
  • How do I think of progress in a holistic way so that my metrics for “good” and “best” have in consideration my multiple identities ?

This is where I think Wardley mapping and particularly Practices are a ready tool to be used to visualise in one page what our goals are and the trades we’re constantly making.

This is what my map looks like:

Personal map of the things I value and maturity of practices

Maturity Mapping and OODA

Chris McDermott has a brilliant blog post here on medium about using Maturity mapping you can access here

One of the sections that most struck to me was this:

To improve what really matters is that we understand our own context, the challenges we face and our ability to adapt and learn to meet these challenges. That is, we need to focus on “present thinking”. I’d suggest that for a maturity model to provide utility it must reflect the context, and provide some guidance for improvement that can be selected dependent on that context.

Understanding context is key, and the identities need to be relevant to you. Your identities are likely to be different than mine, as I appreciate I’m a bit of a dull boy myself.

Breaking down these different activities to Practices allows us to start visualising how mature we are in each of them (more about this later) knowing we should leave room for adaptation and improvement over time or even activity replacement as long as it’s coherent with the different identities.

Personal map of the things I value and maturity of practices

I’ve done personal transformations in the past, so I now know what to expect. And what transpires to me from having lost over 60kg of weight and keeping it off for over a decade, is that you ultimately change your wiring and things don’t just get easier and automated, they become part of our implicit guidance (the way we do things automatically without having to think about it) but it takes time to develop that level of implicit guidance and knowing it will take significant cognitive effort to get to that stage helps us appreciate the challenges ahead, especially where we’re not where we want. This is a reference to the OODA Loop (below), in that we should remind ourselves that it will get easier in time.

The other side of the same coin, is that for the things that are more mature practices we’re likely to find ourselves having to decrease the amount of work we’re doing in that space if we’re to have a fighting chance of feeling whole and balanced between our multiple identities.

Personal map of the things I value and maturity of practices

Knowing how you’ll fail, so you don’t

I’ve written in my philosophy blog before about Mr. Ugly

From that article:

And what’s dangerous about Mr. Ugly, is he never goes away. It’s the little voice that second guesses your decisions. It’s the voice saying you can rest today, you always have tomorrow or the day after. It’s the voice that tells you don’t need to live with a sense of urgency. Basically, it’s bullshit and those who permanently succumb to Mr. Ugly cannot expect to improve on the long run. It’s making excuses, and not adjustments. Rationalizing weak behaviour and patting yourself on the back for a job half or not done. The reason why I like to call him Mr. Ugly is because when he comes and when he takes over and I myself exhibit weak behaviour, I know that he’s pushing me away from my dreams and I’m doing things that make me Ugly, because that’s who I am and how I look when I’m not relentlessly pursuing my dreams and instead succumbing to the things that make me weak.

The 3 tactics I suggest there and how Mr. Ugly can be useful are the following:

  • Understand he has valid and relevant concerns
  • Understand he’s about fear and doubt, and both are personal choices
  • Focus on the next task, stop dealing with all possible problems at once

Using a personal example, Nurturing doesn’t come naturally to me. I’m the Logic driven person that deals with everything in a rational way, and when I feel the feelings I go back to safety which to me means over-analysing the situation and defining a coherent plan to get unstuck, and talking about feelings is just horrendous to me. So the work there for me is huge, as I WANT to be the person my wife and children can talk with without just giving them solutions to problems. Acknowledging feelings is a huge part of being a supportive father and husband, something I want to develop but in no way it’s easy for me to do. So I need to find a way to capture myself when I’m not being helpful with other’s feelings and do something else instead, and the way I measure my maturity in that space needs to acknowledge that.

Going back to the second section on “Identities and the Trade Space”, it’s key to understand the constraints to maturing each of the components of the identities and make an attempt to define metrics which are helping us address those constraints.

What can Maturity mean for our Identities ?

I reserve the right to come back to this at a later point, and particularly to revisit some of specific metrics or components which are part of my identities, but I’m a great believer in simplicity especially to begin with.

This is likely to be something I evolve over time, but for now I’ll be coming back to OODA because it provides some good insights into how decision making.

OODA Loop — how fast you go through the OODA loop relates to the quality of your decision making. Particularly if your implicit guidance leads to where you want, or if you require longer loops (cognitive effort) to reach it

For me, I’m choosing to think about my different Identities and how I’m performing them, in terms of the Cognitive Effort required required for me to be at what I believe my best should be.

For instance, if thinking about my Identity of being Strong, to which some of the Components are ‘Clean eating’ and ‘Gym training’, I’ll see it as maturing the less conscious effort it takes from me to do “the right thing”, avoiding junk food and going to the kitchen and naturally grabbing the apple, not the chocolate.

Thinking in terms of OODA loop, it’s about Deciding and Acting (the longer loop) until the same decision starts being made by ‘implicit guidance’, and I can start trusting myself that the way I naturally operate is conducive to bringing me the results I desire.

The more I become mature in each, and can rely on implicit guidance to keep a high level of performance, the more I’ll be able to focus on other aspects or on my other identities. Maybe even removing them from the map, if they no longer require any cognitive effort to sustain.

What about metrics ? How will it be measured ?

I’ve been thinking a lot about this particular aspect, and decided to take what I think is the simplest approach I could take.

The key thing here is to think about the constraints. And at least for now, I believe the main constraint is time. For many different reasons, I’ve left myself go somewhat over the last year-ish, whilst I’ve hidden myself behind work goals/objectives in order to disregard some of my other identities.

And the main challenge I’m now having, is how to get time to work on all of these identities in a way that I can see all of them moving forward but without disregarding the whole or any of the parts of the whole.

So instead of generally focusing on hard metrics or performance, what I really need right now is to get into the motion of doing all these things I value, and once I’m at a place where time is no longer giving me results or when my implicit guidance gets me to do the motions automatically, then I can revisit and select other types of metrics.

One problem at a time. It doesn’t have to be right, it only has to be useful.

Personal map of the things I value and maturity of practices

It also allows for the greater amount of flexibility, so I can mix and move my week and activities as circumstances allow themselves to unfold, and not get into the defeatist habit that I often find/found myself in of “I couldn’t go to the gym this morning, so let’s overeat for the rest of the day”. If I’m just measuring time, then if I can’t do a full gym session, maybe I can do a few hundred bodyweight squats and pushups instead.

It reduces the specificity of the goal, makes it more flexible and I have a better chance of meeting my goals and keep working and improving my identities.


This is the longest blog I’ve ever written, and a bit outside of what I’m know to write about though I do have an almost defunct now Philosophy blog which I’d like to resurrect hosted at http://lettersforrafael.blogspot.com/

I’m certain I’m not the only one, as the world is getting more and more complex by the day. And part of the challenge for all of us, is that being online we always see people who are better than us at some of the things we value, at some of our shared identities.

What we don’t see is what trade-off’s they’re making. What we don’t see is how they deal or what they’re not doing in order to focus on a particular identity. For instance, I have friends who do 4 or 5 Brazilian Jiu Jitsu classes a week. But they don’t have 2 kids or are running a business and still figuring out what that will actually mean in the long term.

So resetting my own expectations on what is achievable, and not expecting that across all of my identities and its components that I’ll ever be at “Best” across all of them is the main thing I need to keep in mind.

What mapping it allows me to do is to visualise the trade-space, and to provide a visualisation so I can focus on the things that are important to me, and hopefully catch myself next time I start trying to hide behind a particular goal and see the implications or impact it has in my other identities.

Because, at the end of the day, all any of us want is be who we said we’d be. And do it our own way.