The 90-Day Self-Esteem Challenge

Self-esteem can be an unpredictable, fluctuating force. Some days you feel elated and confident, other times unsteady and doubtful. Then you get hit by a toxic shame attack. A crushing heaviness bears down on you, and an inescapable sense of being the shittest human being on this planet grips you — sometimes lasting for many days. Self-esteem can even remain consistently low for months at a time, especially after a breakup or other painful life event.

Self-esteem can be a deceptive force. A person can behave ultra-confidently for long stretches, unaware that they are medicating a chronic sense of insecurity. The true reality — that they are pretending to have high self-esteem — rarely ever enters their consciousness. Deep down they know the truth, yet can never face it, for fear of being swallowed up by it.

Whether you suffer from chronic low self-esteem and know it, or feel unconfident yet over-rely on compensation strategies, the path to healing remains the same.

Telling yourself to be more confident does not work. Mantras will do little to dislodge the core problem. Inflating yourself and ‘punching through’ your low self-esteem always has the opposite effect — the rebound effect will make you feel even lower. This is because these methods either miss the mark or worse, they betray the part of you which feels ‘low’ to begin with. To get to the core of your low self-esteem, we need to go beyond mere words and ego. We need to do the work at the level of mindfulness and emotion, where the repressed shame and self-defeating patterns have poisoned the feeling Self.

90-Days Towards Life-Changing Transformation

Nothing can change without consistency. Using a regular combination of journaling, mindfulness and neutral space-holding for emotions, we will not only dislodge the core of your low self-esteem, but will also use the resulting movement of emotions to reshape your self-esteem into new and empowering forms — fundamentally changing your life in the process.

The process involves putting aside 30–60 minutes at a time for mindful journaling. Each session contains four steps which aim to explore and reveal 1) your shadow, 2) your coping mechanisms, 3) the current state of your life, and 4) your vision of what high self-esteem looks like.

Get a good journal for your 90-day challenge, and separate each entry into four segments as shown above.

It is crucial that you dedicate yourself to this process for a minimum of ninety days. The rate of how you get to that total is up to you. Doing it every day may prove unsustainable, as a session may bring up heavy emotions and truths that need a few days to process and integrate. Try doing it once or twice a week to begin with, and then speed up the interval if you feel confident enough to do so.

Most self-esteem advice tends to focus on positivity. In this case, your journey toward healing your low self-esteem begins by first admitting that somewhere, deep inside, lies someone who believes that they are inferior, unworthy, unlovable, incapable and powerless. Who believes that they are bad to the core.

1. Shadow Revealing

Shadow work involves entertaining the idea that you have a ‘bad’ side. That you have traits, emotions, desires, needs, thoughts, ideas and beliefs that you began to deem as ‘wrong’ at some point in your life.

Your shadow is formed by the rejection and judgement of your loved ones, your community and society at large. Curiosity, confidence, joyfulness, sexuality, beauty, sadness, anger, love; any trait, need or emotion can threaten those around you. When this was the case in the past, especially in your childhood, certain people might have shamed, ridiculed and attacked you for your authenticity. Not wanting to be rejected by your loved ones, your community or by society at large, you repressed these traits, needs and emotions, shoving them deep inside your soul and out of consciousness. This is what the shadow is: A dumping ground for all your disowned authentic parts — a psychological landfill with a sign at the front labelled ‘bad’.

You might have already guessed that the shadow is the primary cause of your low self-esteem. How can you act confidently in the world when there are aspects of yourself that you cannot express under any circumstances? Your shadow makes you into a fraction of who you could be. Therefore you will never become whole until you explore, reveal and integrate what your shadow holds.

Shadow work involves jotting down and acknowledging all the ‘bad’ things about yourself. Start by taking a few deep breaths, and invite your ‘badness’ to come out. This might take a few sessions, but eventually, your mindful intention will reveal darker, more negative emotions. As these feelings arise, write them down. For example: Heavy. Sad. Angry. Grief. Stuck. Shameful. Depressed. Abandoned. Rejected. This will then spur thoughts of your ‘bad’ traits: Loser. Immature. Poor with money. Unlovable. Incompetent. Hideous. Weak. Unworthy. Selfish. Desperate.

How you feel and think about yourself will be unique to you, and will evolve over many sessions as you reveal more and more. This will likely begin with generic concepts, but then grow more specific over time.

Above all, watch out for sabotage from your shadow. Because it has internalised an identity of badness, the shadow does not want to be exposed. Furthermore, it will try to keep you from feeling and releasing its emotional content, since that will destroy its very existence. Days will come when you no longer want to continue the 90-day challenge. Expect this, acknowledge it as attempted self-sabotage, and carry on regardless.

The idea is to allow your shadow to breathe while giving shape to its many parts. This means allowing space for difficult emotions, and acknowledging hard-to-accept truths about yourself.

The most crucial part of shadow work is neutral awareness. You are a scientist. You simply relax into the painful emotions and jot them down. Your job is not to judge them, or ‘fix’ them, or change them. You simply feel and write — nothing more, nothing less.

2. Coping Mechanisms

The shadow is what drives you to hide or to pretend. It is what forces you to dissociate and numb out from life.

To keep from facing the truth about our ‘badness’ or feeling our repressed emotions, all of us develop a series of addictions, distractions and narcissistic behaviours as coping mechanisms.

You do not need to fix or change anything here. Simply write down all the addictive, distracting and selfish behaviours you notice about yourself. Distractions might be: Scrolling social media. Playing video games. Over-thinking. Binge-watching television. Addictions might be: Gorging on chocolate. Taking drugs. Sex. Alcohol. Binge eating. Finally, look at your relational behaviours. This might include: Acting arrogantly. Punishing others. Stonewalling. Controlling others. Lying. Indulging in fantasy.

With relational coping mechanisms, it can be easy to deceive yourself. We are experts at concealing our ‘bad’ behaviours in relationships from ourselves. It may take practice, and you may surprise yourself as the weeks of journaling pass by.

Remember: No judgements or actions are needed here. Simply write everything down and mindfully consider it. Keep a watchful eye for judging thoughts, and do your best to remain neutral and accepting of what you reveal about your coping mechanisms.

3. Gratitude And Progress

We can now finally emerge from the underground and into the light. Take the time to look over the current state of your life. What do you have to be grateful for? Your critical thoughts will fight you hard at this stage: You have nothing to feel grateful for. Your life is horrible. Stop trying.

Start with: I am alive. I am breathing. I am safe from harm. There is alwayssomething to be grateful for. Eventually, you will grow more attuned to the beauty of your life. Even if you have a difficult relationship with your mother, for example, you might be grateful that she fed you dinner and was in a good mood for a change. If not, who in your life thought of you, said something nice to you or did something nice for you? Write it down. You might be grateful for your car or your health. Maybe the sun is shining today. There is abundant beauty in your life. Make a practice of meditating on and revealing it, one journaling session at a time.

Next, think of all the ways you have made progress and improved in your life. Finding a job. Drinking less. Improving a relationship. Saving more money. Finishing a course. Becoming fitter. Think about the previous months and years, and look at where you are compared to where you were. Continue to reveal these changes, which you might not have previously acknowledged.

4. Manifesting: Daring To Shine

Now that you have lovingly acknowledged your shadow and allowed it to breathe without judgement, you have loosened its emotional contents. What gradually emerges from this is your True Self; the authentic part of you which holds your potential. A repressed shadow keeps this aspect of us blocked, cutting us off from our power, leaving us feeling incapable and inferior to others.

Now, you have movement. While it might feel heavy and painful, it is movement nonetheless. This is the moment of truth. Many people with low self-esteem make a bad habit of getting stuck in their painful emotions. Negative feelings create negative thoughts, which spur more heavy emotions, spurring more critical thoughts, leading to a self-defeating, downward spiral into lower and lower self-esteem.

Manifesting is about reversing this downward trend through the practice of attraction. If low self-esteem is all you know, nothing will ever change. True transformation begins when you introduce the idea of high self-esteem into your consciousness.

What does high self-esteem look like to you? What qualities would you have if you dared to shine bright? If you were all that you could be? Some qualities which might come to mind are: Worthy. Lovable. Attractive. Magnetic. Capable. Joyful. Approachable. Fascinating. Well-off. Well-dressed. Loving. Grounded. Open-hearted. Courageous. Standing tall.

With each quality you write down, imagine how it would feel to embody it, and how it might look in your life. Visualise scenarios where you have those qualities. How do people react to you? Which direction does your life take?

This energetic practice takes patience and time. Your shadow might try to sabotage your attempts at manifesting. You might also feel nothing when you first start. If you can persevere, you will notice a shift. Visualising yourself as magnetic, for example, will eventually bring a magnetic feeling into your body. As you begin to feel magnetic, people will respond to you positively. When people respond to you positively, positive emotions will emerge, feeding the sense of being magnetic, and the cycle is reinforced in an upward spiral.

Parting Words

The 90-day challenge is a beautiful promise; an act of self-love, when perhaps we have little love for ourselves. In this way, it becomes an act of faith, and an act of courage. Every session will feel different, and will reveal different things, depending on your life situation or your mood. Even the moon cycle might affect it. The only consistency required is in your capacity to sit down and honour your promise to yourself.

You will need to remain steadfast in the face of doubt, sabotage and crushing painful emotions. When it gets too much, you might need to take a few days off. The idea is to lean over the edge without re-traumatising yourself. Facing repressed emotions and confronting self-truths is no game. Be sure to reduce external stress where you can, practice self-care, and above all, to be kind to yourself. Harsh judgement and self-criticism will only hinder the process. If you do fall into a negative thinking loop, simply observe the thoughts and wait for them to pass.

Never try to manipulate the process. Don’t try to force yourself to be anything other than what you are in that moment. Reveal what is repressed in your shadow and invite it to come out. It will release when it is ready, and not a second sooner. When manifesting the qualities you desire, your invitation will be enough. Let your True Self and the world around it do the work. As for your addictions, be diligent in exposing them to the light, but once again, do not judge them or try to push them away. As you manifest more goodness, and more pain is released, your distracting and addictive behaviours will transform on their own. Do not force anything.

Just as life springs from death, goodness can emerge from your ‘badness’. That is your reward for enduring this challenge. When all is written down and done, you will gain a sense of inner peace, worthiness and wholeness. You will possess an effortless confidence in your capacity to manifest your potential. Is that not worth toiling and struggling for? Is that not worth living for?

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