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The Art of Undoing: 3 Unconventional Yet Proven Strategies To Break The Cycle of Bad Habits and Prevent Relapse

Unlock The Art of Behaviour Change With 3 Out-Of-The-Box Methods To Rewire Your Brain, Rewrite Your Habits and Reclaim Control Over Life and Work

Today, I am going to show you how to break free from your bad habits and avoid relapse with three unconventional strategies that prove effective where traditional habit disruption methods fail.

I am going to guide you through a non-linear process based on tried-and-tested approaches that promise to break the cycle of unwanted automatic behaviours and empower you prevent backsliding.

Unfortunately, most people today focus all their energy and time on building new healthier habits, which is good. What they miss, however, is that their bad habits are still there and keep them back often sabotaging the new better behaviours.

Without disrupting the bad habit cycles, it’s impossible to escape autopilot behaviours and build a life with more meaning, purpose and enjoyment.

Your good habits are like strong bricks. Your bad habits are the cracked bricks. No matter how many strong bricks you use to build a beautiful tower, it will never be as strong if you don’t ditch the weak bricks. It may even fall down.

The problem with traditional approaches is that they are based on a more or less simplistic and linear view of habits. 

Popular theories suggest that all that’s needed is a cue that triggers the unwanted behaviour and leads to the reward you crave. They are not wrong or ineffective per se. However, they fail at integrating the element of complexity.

Humans are complex systems. So are life, work, and business. If you try to improve them by using methods based on false assumptions, the results will be poor and vague.

This is why most conventional habit disruption frameworks fail:

  • They are linear and simplistic (from A to B to C)

  • They are surface-level often failing to scratch the “bottom of the barrel” (= the root cause of bad habits)

  • They rely on willpower (which is by the way finite)

You can’t erase unwanted behaviours from your mental maps if you treat the symptoms but not the underlying causes.

And unless you live in isolation (for example, in a cabin in the woods) your efforts to stop dysfunctional and undesirable routines will be jeopardized by the constant influx of distractions.

What you also need to keep in mind at all times is that your reservoir of mental energy for self-control is limited. Willpower is finite (even scientific research points to that). If you use it, you will struggle to resist temptation (that is reverting to bad habits) or maintain discipline.

What’s left? It seems like a helpless battle. It’s not if you adopt a more pragmatic approach grounded on how good habit formation and bad habit disruption actually work.

How do you build and stick to bad habits in the first place?

Imagine your brain is a playground with lots of paths. That seems beautiful but here’s the trick.

First, you accidentally stumble upon a “fun path”. For example, scrolling on your phone when getting bored at work. Your boredom is like a flashing sign telling you “Hey! Start here!”. Engaging in mindless social media scrolling on your phone is walking that path. And having an entertaining break is the treasure at the end of the path. It’s cue, routine, and reward - what most habit theories accept as the foundation of habit formation.

The more you walk that path, the more you like it and get used to it. You find it easily in the mental playground and guess what? Your brain creates super-fast shortcuts to help you find that path next time.

So, next time you are bored at work, your brain automatically screams “Hey! Remember that path? It was so much fun!”. You don’t even think about it. The path is already in front of you and you just walk on it.

The more you walk that path, the more two things happen:

  • That path becomes a fancy super-highway with flashing lights, striking visuals, and compelling messages that call you in.

  • All the other paths (for example, going for a walk, talking to a friend, or reading a book) become hard to find. They get full of weed and you can’t even see their signs.

Even if you want to walk the other paths (subconsciously recognising that scrolling on your phone is not good for you in the long term), you can’t because your brain automatically pulls you to the scrolling highway. That’s easy, fun, and rewarding.

That’s how a bad habit is formed. Now, imagine that 100X for all the -smaller or bigger- bad habits and routines accumulated in your everyday life. That’s a chaotic system of unhealthy, unproductive, negative and undesirable behaviours. You shouldn’t expect to break those cycles with simplistic “A to B” approaches.

You need a more holistic approach that targets the root cause, accepts and adapts to the chaotic life and work circumstances, and personalises the experience reinforcing your commitment to break free (you can’t rely on your finite willpower).

Why should you care that much about breaking your bad habits if you also build new good ones?

Imagine your mental capacity for meaningful and productive action as a scale. On the left side are the good habits. On the right side of the scale are the bad habits. 

If you keep adding good habits to the left side without taking away any bad habits from the right side, you will struggle to tip or even balance the scale. The reality is that we humans have more bad habits than good habits.

If you want to tip the scale with your good habits, you must become a superhero striving to build healthy routines all day long, day in and day out. That’s far from reality.

To tip the scale in your favour, you need to subtract bad habits (while mindfully loading the left side of the scale with good ones).

Here’s another example. Imagine your life and work are like a video game. 

When stressed or overwhelmed because of work or a life event, you mindlessly turn on the video game and start playing. There’s a flashing sign screaming “Enter the gamezone! It’s going to be fun!”. 

You play and feel numb (=superficially better), and all of your stress and overwhelm seem to go away. Playing feels interesting, challenging, fun, even rewarding (when you get points and level up).

The more you play, the more your brain connects “stress” or “overwhelm” with “games”. New neural connections are quickly made so that next time you feel the same again, “playing the game” pops up as your automatic brain response. “It’s fun. Remember last time? You even managed to level up! Come play again!”.

It’s like creating a secret passage (in videogame terminology) from stress and overwhelm to fun. Shortcuts and highways, remember? It’s the same mechanism.

The more you play, the mightier a castle is built. Its walls get higher and higher and you can’t see anything except going into the castle and playing the game. Any other healthier option lies somewhere on the ground near the castle walls, but you can’t see it in the mud.

You can’t expect to escape living and working on autopilot without combating your bad habit collection. They hold you back and there will never be a surplus of awareness, intention and meaningful action. 

You will run your “economy” on deficits and that’s never sustainable. 

To shift from deficit to surplus, you must get creative and move beyond the traditional linear models that neglect how complex your brain, life and work are.

Here are 3 unconventional approaches to help you reach a breakthrough (especially if you feel stuck on autopilot mode and struggle to live and work with meaning, purpose and enjoyment).

#1 Controlled Chaos Shot

Drawing on the principles of Chaos Theory, the idea is that small interventions and changes to your environment can disrupt habitual patterns.

This comes in contrast to traditional approaches based on the (false) assumption that life, work, and business are linear and controlled systems.

Although I find existing theories and books useful (and ground-breaking at the time they were published), I can’t but think that a “from A to B” approach is not the solution.

We live (and occasionally thrive) in chaos. Assuming that you simply have to fix the cue (by making it invisible), make the habit difficult, and downgrade the value of the reward (in that order) doesn’t make much sense anymore.

The essence is still valid. We just have to tweak the execution.

We are creatures of habit and our lives and work are perplexed in chaos. They are complex systems and changing a few things expecting them to work as planned is a utopia.

So, instead of controlled, laser-focused linear interventions, you shake up the whole system. What does that mean?

Disrupting the pattern with the purpose of shaking the bad habit mechanism and cycle to the ground.

How can you do it? Introduce random “chaos” into your environment and routines to destabilise the context supporting the habit loops.

Those loops rely on predictability. You see X (the cue) and do Y (the bad habit) to get Z (the reward). That’s how the brain works, remember?

Now, shake that up. Change a crucial element of the equation or even take it out altogether and see what happens. Your brain can’t find the shortcuts and highways it created. It gets puzzled about what to do or choose next so the “obvious” bad choice is no longer automatic.

It’s like forcing it to restart or recalculate the route, much like Google Maps does when you turn right (instead of left as it instructed you).

Let me demonstrate how to do it with a few examples.

If you have a daily habit of endlessly scrolling your LinkedIn feed on your mobile phone right after lunch to “engage with other users and do business development by connecting with them” right after lunch (I did that at some point), break the pattern and introduce controlled chaos. Stop taking your mobile phone with you when you eat your lunch (or have it buried deep in your bag if not at home). Or take a book with you when you head to your kitchen or the restaurant. Your brain will automatically search for the mobile phone to initiate the LinkedIn feed scrolling but guess what? It can’t find it.

Your brain gets monentarily confused and can’t direct you directly to the super-highway of your bad habit. If you are old enough to remember the video games of the early 2000s, you will resonate with this: it’s like your brain keeps bumping on a mental wall that it can’t go through in the same way your videogame character bumped on a wall again and again, stuck in this loop (because of poor graphics and interface).

Here’s another life example. Let’s say you have a bad habit of eating unhealthy snacks when working on your home office. This is what you conditioned your brain to do: work on your laptop, get a little stressed, bored, or tired, get up, head to the kitchen, open the cupboard, take the snacks, start eating them on the go, sit down at your desk, continue work while devouring the whole bag.

Let’s bring some chaos in the setting. That’s a real-life example (I did that myself). Go to the kitchen and rearrange the cupboards. Put cans where your snacks used to be. Put the snack box in the complete opposite cupboard, different self. Now, empty the snack box and replace the snacks with apples and pears. Do that for a few days. Then take the snack box (now filled with healthy options) and hide it somewhere in your living room (a cupboard or big drawer you have there).

Here’s what happens. The next time your brain puts you on autopilot to go grab snacks from the kitchen, you go to the cupboard where the snack box used to be. You see the cans. Then you try to remember where the snack box is. You open that other cupboard and take out the box. No snacks (as expected) but apples and pears. Your brain is “burning”. “What should I do now? I don’t have a clue!”, it screams. It gets worse when you put the snack box in your living room. “What the heck happens?”, your brain screams.

Even if you mindlessly go grab a snack (while feeling overwhelmed by a project, tired so not thinking anything, or consumed by your stressful thought patterns), you simply can’t. The box is elsewhere, the content of the box is different.

With time, not only do you break the pattern of grabbing a snack in seconds (you have to search for the box) but you also replace unhealthy snacks with fruit. 

That is a complete turnaround. You made it happen by simply introducing controlled chaos into your life and work. 

Trust the process (and chaos). It has the power to disrupt every single one of your undesirable habits, one by one.

#2 Black Box Reverse Engineering

Habits are unfortunately automatic and opaque, like “black boxes” - mystery boxes where we can only see the outside and not the inside while knowing that the inside holds all the critical information.

It’s like an aircraft’s black box. The pilots know how they fly the airplane (that’s the input) and they also know how the aircraft responds to their commands (output). They are trained and knowledgeable about airplanes but they don’t know all the internal processes (between the input and output).

This is why investigators look for the black box when there’s an aviation accident. It’s their way of looking at what really happened.

In the same way, our habits are the black boxes and we can only see the obvious: the cue that triggers the unwanted behaviour, the bad routine we engage in, and the reward (the output in a way).

However, habits are much more complex processes and unless we look inside their “black boxes” we can’t find a sustainable way to disrupt the unwanted routines and habits.

Reverse engineering is about dissecting something and break it down into its components. If you are an engineer or craftsman, you can do that literally. As a knowledge worker, all you can do is take a sneak peak inside the mystery box and try to figure out how it works.

The goal is to get to the root cause of your bad habits. Otherwise, it’s difficult to break the cycles. A simplistic, surface-level approach is not enough.

Let’s take inspiration from real-life reverse engineering and see how engineers or craftsmen actually do it. First, they carefully open the object and study its components. Then, they carefully take out the components. Deconstructing it piece by piece helps them understand the role of each piece in the whole system. This is how they can extract the knowledge. Then, they meticulously reconstruct the object making improvements (subtracting or adding components) so that the system works smoother.

This method is like working backwards from the finished product to uncover the blueprints or construction methods.

You can do the same with your bad habits. You must deconstruct the habit to its components in order to uncover the root cause (not the obvious, “surface-level” symptom). It’s a deep, introspective dive to understand the hidden rewards or functions the habit serves beyond the obvious. Then, you can tweak the system to make it stop working, plain and simple.

The goal is to discover why your mind clings to that bad habit.

You need to investigate questions like:

  • What unmet need does this habit fulfill? You just have to go deep and identify the root cause. There’s an example coming up to help you understand better.

  • What emotions does it help me avoid? Every bad habit is a gateway to a state of more positive emotions. Instead of feeling bored you engage in a bad habit to give you joy and pleasure, for example.

  • What subtle benefits do I derive from this? Be brutally honest and identify what is the real reward (not the obvious one).

Let me give you an example to further help understanding the deconstruction - reconstruction process.

Imagine you work at your desk and you are about to start a big new project for a client. You have everything outlined and it’s very clear what you have to do. However, instead of jumping in, you open Youtube to put some lo-fi background music to boost your productivity. 

The YouTube homepage is designed to draw you in, though. You see a video from your favourite artist who has just released a new song. Below is a new video from the content creator you follow. It’s so interesting and you will learn a lot so you automatically press play to start. You promise to yourself, “I will only watch a few minutes to get the idea!”. 

Before knowing, it’s 30 or 40 minutes later you realise that you still have not started the project. “It’s just in the other tab to the right, waiting. I will just get to it. Give me a minute!”. The time goes by, you still watch videos mindlessly while work still waits to be done.

Press pause (literally and metaphorically). Ask yourself the three questions above.

  • What unmet need does watching YouTube videos fulfill?

    • Entertainment or relaxation. Your initial goal was to put some background music while working, remember? Dive deeper.

  • What emotions does that help me avoid? 

    • Boredom or feeling tired are the obvious responses. Go deeper. You are perhaps overwhelmed by the project or you didn’t want to take on it in the first place. It’s discomfort and the lack of joy that drive your behaviour. Perhaps it’s also a hidden fear of inadequacy, that you don’t have what it takes to complete it successfully and with high quality.

  • What subtle benefits do I derive from this?

    • Nothing special. It’s not about being entertained or relaxing. It’s a temporary cognitive “pause” (you literally stop thinking about work that stresses you out), or perhaps a way to avoid discomfort caused by stress or overwhelm. You disconnect from immediate responsibilities (your client’s project) and release the tension.

Put simply, you avoid doing the unpleasant work and numb yourself until it’s too late or you start feeling tired. That’s a nice excuse to abort the work altogether. “I can always start tomorrow when my mood and energy will be better!”.

You have now deconstructed the bad habit of mindlessly watching YouTube videos while you should be working. 

Let’s now reconstruct and improve the pattern to break the cycle.

All you have to do is to look at it from a healthier perspective. If you have fear of inadequacy and believe you can’t do the work, you have two options: a) reject the project and make sure you don’t take on similar projects in the future, b) identify what skills you miss and work on them. You may also start the project and educate yourself along the way as you identify gaps in your knowledge or skills. The latter is much healthier.

If you feel like YouTube is a constant trigger, block it from your browser and hide the YouTube app in your phone so you tweak the “black box” making YouTube not easily accessible.

However, this process also helped you identify that you take on projects you don’t want to work on (you do it just for the money). You can shift from that money-focused mindset because it doesn’t serve you in the long term. You may earn some money but it’s going to consume so many of your limited resources (time, energy, attention and focus) that it doesn’t make sense anymore. You could have used them for a more meaningful project that would also help you grow your business and enjoy it more.

#3 Ritualistic Cleansing

Rituals have always been a part of human culture. Since the early days of humankind, people would create certain rituals to celebrate something good or cast out something bad.

In our case, bad habits are the ones to cast out. Drawing inspiration from anthropological concepts of ritual and symbolic cleansing, this framework treats your bad habits as unwanted “entities” that have taken root in your life.

You are about to leverage the immense power of ritual and symbolism to create a psychological break from your bad habits.

This has nothing to do with the sacred. It’s very pragmatic and uses rituals and symbolism as vessels for sending your bad habits away.

Crafting and using a ritual provides structure and meaning to things that are usually vaguely conceived or understood in their entirety (exactly what happens with your unwanted behaviour and routines).

Anthropologists observed that most rituals in human culture and history emerged in times of uncertainty and stress. Does that ring a bell?

Let’s dive into how you can craft a personalised symbolic ritual for your bad habits. I call that Ritualistic Cleansing because the main goal is to cleanse you from deeply rooted beliefs, assumptions, unconscious patterns and automatic behaviours that don’t serve you.

Here are the steps:

  1. Pick a bad habit. Clearly identify it (the cue, the routine, the reward) and acknowledge the negative impact it has on your life and work. Be honest and realistic. It’s okay to feel overwhelmed, disappointed or frustrated by acknowledging the dire consequences and impact of your unwanted habit.

  2. Choose a physical object. That can be anything related to your habit. It may represent it (for example, a cigarette if you want to quit smoking, or an unhealthy snack if you want to shift to healthier eating habits). It can also be something that is not physical per se but can have a physical dimension. For example, if you are addicted to a social media platform or dating app, that object can be the app icon on your phone. Now print the icon on a sheet of paper. It’s important to have it physical. If it’s something digital (most probably), print it out.

  3. Create the symbolic cleansing ritual. That can be any action that has the meaning of release. If it’s a piece of paper, you can tear it up or burn it (always safely, take all necessary precautions and don’t burn the house down). You can also bury it in the ground and put a stone over it so that you remember you left that bad habit there for good. If it’s a physical object, you can throw it away. For example, you can just throw away that unhealthy snack or the cigarette you chose in the previous step. You are not done yet! Read on.

  4. Declare your intent and commitment. While performing the ritual, state what you intend to do (or stop doing) loud and clear. It’s important to do that as the closing act of the ritual. Remember, rituals usually mark endings and new beginnings. This is what you want to achieve and “celebrate”. Mark the ending of your bad habit and the beginning of a new era free from it.

This process is short but very real, pragmatic and physical. And it has nothing to do with mysticism for sure. It’s a symbolic act of releasing the old habit which has immense psychological power (it can help you stick to your commitment).

Just a few more things about this framework:

  • Give it time. Don’t rush to go to the kitchen, take the snack and throw it away. The ritual requires that you slow down, go mindful, become fully aware of what it is you cast out and why, and release it with conviction.

  • I would like to stress again the importance of awareness in the ritual. Without awareness, you won’t be able to release the bad habit mentally and psychologically. It’s not about the physical act (tearing up the paper, burying the object, throwing it away). It’s the symbolism behind it, and for symbolism to have a positive effect on you you need to practice mindfulness and gain awareness: take a few deep breaths, concentrate on the habit and the object, stay present and don’t judge (you may think “That’s BS. What am I doing here?” or other negative self-talk may pop up in your mind). 

This symbolic cleansing method can also be used with anything you want to release from your life or work. 

Another example is this. Write down on a paper all the things that hold you back or the tasks you feel are blocking you. Anything that is negative and you want to let go. It can be all the manifestations of your procrastination or perfectionism (they are very common as a solopreneur). Then, tear that paper up emphatically and declare your commitment to break the cycle and shift to healthier thinking and acting patterns and behaviours.

That declaration can be as literal as this: “I release myself from the burden and suffering from perfectionism. I am now free to opt for good enough and improve on the go”.

Here’s a recap of the strategies 

What’s next?

It’s all about mindset and strategy. As ancient Greek and Roman philosophers taught, we can only control our minds, thoughts, and actions. Focusing on this can help you avoid unnecessary struggle, get unstuck, and move forward faster.

If you need guidance getting unstuck and making those crucial mindset shifts, I can help, especially if

  • you are a currently struggling introverted solopreneur (stuck in a wrong mindset and with bad habits that don’t serve you)

  • you want to quit your 9-5 job and create your one-person business, but your bad habits keep you back for good

DM me on LinkedIn, and let’s explore how Mindset Coaching can help you move forward and claim what you desire and deserve for a life with purpose, meaning and enjoyment.

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