Why is this decision so hard?
From Heroism to Authenticity
This essay’s for you if you’re being pulled apart by a decision you can’t resolve. You’re being forced to choose between two mutually exclusive choices despite wanting both.
You’ve tried making this decision by gathering more knowledge and information. You’ve gathered facts, made lists, analyzed trade-offs, and consulted trusted advisors, but felt no closer to clarity.
You find yourself endlessly ruminating about it in the middle of the day and perhaps the dead of night. There’s something heavier underneath all that rumination. Perhaps it’s grief for the path not taken, or shame that you can’t seem to make decisions that others seem to manage with ease, or perhaps you have a nebulous fear that tightens your chest whenever you try to commit.
Eventually, adrenaline overrides this stuckness. You push down your feelings and pull the trigger on one of the options within the decision. Unfortunately, the decision doesn’t stick, and the stuckness somehow comes back even harder.
Exhausted, you avoid making the decision altogether by coasting or letting circumstances decide for you. This fails to contain the stuckness, and its stressful energy starts bleeding into your work, your relationships, and ultimately your health. You become increasingly irritable, less creative and less present. Every decision that would have felt trivial suddenly feels momentous and produces far more anxiety.
However, this coasting somewhat recharges you in an incredibly stressful way. So once again, your adrenaline attempts to push down your fears to override the stuckness, and once again, it doesn’t really work. Going through these cycles again and again leaves you increasingly hollowed out. Each adrenaline-fueled override leaves you depleted, and each recovery takes longer than the last. The decision sits there unresolved while the rest of your life starts narrowing and shrinking.
You don’t want your inability to make this decision define you. You want to trust yourself to navigate complexity, not because you have all the answers, but because you’d like a more reliable relationship with the process of finding clarity. You’d like hard decisions to arouse curiosity rather than dread, and for each challenge to deepen your sense of meaning rather than erode it. You’d like to live a courageous life with meaning, purpose, impact and flow.
Living a life of such flow isn’t fantasy, and it’s reasonable to want it. However, reaching this life requires a deeper understanding of what’s actually keeping you stuck.
This stuckness is what we’ll call a developmental dilemma. These dilemmas are specifically developmental rather than merely difficult because the stuckness doesn’t originate purely from the external situation. It’s a consequence of limitations in your current way of making meaning, which is shaped by your psychological development. A merely difficult dilemma is one where the situation is genuinely difficult, but you have the internal capacity to navigate its complexity. A developmental dilemma is different. It feels irreconcilable because your current relationship with yourself and the world can’t hold both options with the dilemma simultaneously. Resolving the dilemma requires more than just gathering more data or summoning more willpower. It requires growing your capacity to see more clearly.
Here are some examples of such developmental dilemmas:
Should I leave the stable job where I’ve built ten years of trust and security for the sabbatical that could transform my career or leave me with nothing?
Should I stay with someone who loves me steadily but doesn’t ignite me, or end this good-enough relationship and risk being alone?
Should I stay in the rural town where my extended family needs me and my roots run deep, or should I move across the country to a large cosmopolitan city where I finally feel like myself?
Developmental dilemmas like the ones above reduce to a single archetypal question at the lowest resolution - do I change my way of being, or do I stay the same?
A voice in you clearly sees that your current patterns aren’t working anymore. This recognition is an invitation to change, but it doesn’t feel that clean from the inside. Another voice within you isn’t sure whether the real problem is your approach or the genuine difficulty of the situation. You can’t dismiss either voice because both feel legitimate. Change carries inherent uncertainty and therefore fear, but staying the same feels scary if the environment ends up changing out from under you. A developmental dilemma traps you between the fear of changing, and the perceived cost of not changing at all.
What causes developmental dilemmas?
To understand what’s really going on, let’s look at the underlying machinery.
We’re social primates hardwired to meet various needs. Meeting our needs creates value for us.
However, we may not always have a firm grasp on what our needs are, let alone how to meet them. Nevertheless, we take actions in the world in an attempt to satisfy them. We’re not omniscient, so there’s inevitably some error between where we thought we’d end up, and where we actually end up as we attempt to satisfy our needs. The experience of this error and the gap of the unmet need are sensed as an emotional reaction within our bodies, commonly labelled as pain.
Pain is well...painful! We don’t want more of it!
We make sense of and cope with this pain by creating a story around it. It explains what was responsible for the pain, what it means about us and the world, and implies what we should do differently to avoid it in the future.
This process can happen very quickly. We may not have the resources to carefully, rigorously, and consciously calibrate the story we’ve created in the moment to avoid oversimplifications and distortions. Maybe we’re literally running from a tiger or we’re simply overwhelmed by the complexities of the need we’re attempting to meet. So we cope by repressing our pain and its corresponding story within our unconscious until we have the resources to consciously engage with it.
Unfortunately, repression doesn’t prevent our pain and its story from playing an active role in our lives. On the contrary, they give us unconscious justifications to create judgements within our experience. A judgement is our mind’s attempt to operationalize the underlying story and its unhealed pain. It’s what emerges when the story and our unhealed pain distort a clear-eyed evaluation of reality so as to generate proactively protective emotion. These emotions attempt to protect us from experiencing the same pain again and are often variations of fear.
Fear and judgements aren’t necessarily “bad”, and whether they serve us depends on the context.
Suppose we find ourselves in front of a snarling and hungry tiger sprinting towards us with fangs bared. A snap judgement that arouses fear, which in turn motivates our body to run away, would be deeply adaptive! It’d actually be maladaptive to sit there and contemplate whether the tiger’s actually hungry and wants to eat us, whether our judgement is clouded, etc. That’s how we become tiger food!
On the other hand, instead of a tiger, suppose we have a loving and compassionate girlfriend that genuinely cares about us. Suppose we have ADHD and are really bad at staying on top of housework. We’ve shambled home utterly drained after a long day at work. The moment we step in the door, she tells us that she’s really upset because we haven’t cleaned the apartment the way we agreed we would. It wouldn’t be adaptive to impulsively react to the fear from a snap judgement, even if our nervous system thinks she’s a tiger. The snap judgement doesn’t resolve situations like this, and instead adds more unhelpful energy into the system.
Habits get formed by repeatedly acting out behaviors produced by specific fears and judgements. Habits are our brain’s way of creating shortcuts to get our needs met when we don’t have the mental bandwidth for conscious reflection and consideration. They’re self-reinforcing in that the more we engage in a habit, the stronger it becomes. They’re self-organizing in that the stronger they become, the more “creative” they get at attempting to get their underlying needs met, becoming harder to shake off.
Pain creates stories. Stories create judgements. Judgements create fears. Fears create habits. Competing habits create stuckness.
Consider a fictitious man named Varun who was deciding whether to leave his stable job. He took a risk early in his career that he thought would work, but didn’t pay off, and spent months living with the consequences. That’s his pain. He then unconsciously internalized the story that “taking risks leads to ruin, and the only safe path is the proven one.” It generated judgements that surfaced whenever the idea of quitting his job or taking a sabbatical came up. “I’m upset because I can’t just be satisfied with what I have.” or “I should be grateful for my stability instead of chasing something uncertain”. These judgements produced fear and tightened his chest whenever he imagined himself handing in his resignation. That fear drove one of the habits that kept him stuck. Every time he thought of the sabbatical, he’d whip out his retirement calculator, list all the ways it could go wrong, or ask one more person for advice. None of these actions resolved his dilemma and only served to yank him back to the fork - should I stay or should I leave? That is, should I stay within my existing habits or should I attempt to change?
Our habits and the fears that drive them are the final consequence of our desire to meet our needs based on what we value. Life is complex and we often value multiple things simultaneously. We get stuck in a developmental dilemma when we find ourselves seeking to maximize seemingly competing values of equal importance.
Suppose we’re at a fork and must choose between values A and B. The moment we start walking towards A, the habits fueled by the fears and judgements from B yank us back to the fork. The same thing happens if we start walking towards B. Because habits are self-reinforcing and self-organizing, the more we struggle, the more “creative” they become at pulling us back towards the fork. This causes us to experience our developmental dilemma as if it’s a concrete wall. The harder we push, the more it resists and the more bruised we become from the impact.
Thrashing against the wall merely increases our stress, which in turn worsens our decision-making. This reduces our effectiveness in the world and makes it even harder to meet the needs underneath what we value in A and B. This in turn makes the fears and judgements from both A and B yell out even louder in our minds, which in turn further increases our stress. It’s a vicious cycle that grows and grows until we crash into a developmental crisis where we’ve hit rock bottom.
It’s sometimes possible to power through a developmental dilemma in a way that optimizes both values simultaneously, by white-knuckling the fears on each side. This approach doesn’t actually heal the fears, judgements, and pain underneath the dilemma. So the underlying patterns that generated the dilemma remain intact. Therefore, overcoming the wall in this way immediately presents another wall of the same taste as the previous one, but with far greater severity. We sometimes manage to overpower that one too, so another one gets produced, and so on. Each one requires more energy than the last, because the thrashing required to overpower a wall reinforces the corresponding habits. Eventually, we’re presented with a wall we simply don’t have the resources to override, and our bodies crumple with exhaustion. This is the experience of burnout.
A typical response towards the dilemma in the face of burnout is complete inaction. This is the machinery that produces stagnation and resignation. It eventually manifests as us being “checked out” or “coasting”.
This is also why treating a developmental dilemma as if it’s purely an information-gap problem doesn’t work, because the wall isn’t purely the result of ignorance about the external world. It’s built from miscalibrated unconscious stories about our unhealed pain, the judgements and fears they generate, and the habits that keep pulling us back to the fork. Clarity is achieved not by collecting more external information, but by peeling back the layers of fear, judgements, pain and finally upgrading the miscalibrated story underneath. More information can’t resolve what’s fundamentally a lack of internal integration.
Heroism versus Authenticity
Heroism is this approach of mustering the courage to push through the wall by defending ourselves from our fears. It’s uncomfortable but can generate incredible results because decisions get made and we move forward. Our culture valorizes such heroism and it’s not “bad”. It’s better than the alternative of being a slave to one’s fears. Developing the capacity for heroism is a natural and appropriate part of psychological development.
However, heroism has inherent limits because it doesn’t go deep enough. Pushing through the wall via sheer force of will overrides the relevant habits, but the story, pain, judgements, and fear that generate the habits remain unhealed. Heroism produces short-term results but guarantees an overwhelming escalation in the future.
The alternative to heroism is authenticity.
Relating to your dilemma authentically involves tracing back through the fears, judgements, stories, and pain, and involves a recalibration at the source. We befriend our fears rather than defending against them. We forgive our judgements rather than reacting to them. We heal and grieve our pain instead of ignoring it. Most importantly, we consciously recalibrate and upgrade the story built to make sense of the pain, so that it can see and explain more of reality than when it was first created.
Shifting these deep stories is a profound experience, because we now gain access to a far more expansive view of our dilemma. This improved clarity often produces alternative choices that seem to simultaneously optimize the competing values. Sometimes it even changes the framing of the dilemma itself, by changing what we find relevant in our circumstances. Moreover, it becomes easier to resolve the dilemma consciously if the two competing values are truly mutually exclusive.
Shifting from heroism to authenticity changes our relationship to discomfort so that it informs our choices rather than hijacking them. Overcoming the wall feels less like pushing through it, and more like getting pulled through it.
The practice of cultivating authenticity
The following process is one possible practice for cultivating authenticity. It’s a skill, so it may seem awkward at first but becomes more natural with repetition. It involves running the four steps below for each option in the dilemma, and then integrating them together:
Making friends with your fears.
Forgiving your self-judgements.
Grieving your pain.
Upgrading your stories.
Our entry point is fear because that’s what we experience most immediately when we sit with a dilemma. Jung observed that “when an inner situation is not made conscious, it happens outside, as fate”. Rather than heroically powering through our fears, the first move is to slow down and relate to them as an early warning system. We ask our fears questions to better understand what they’re warning us about in the best way that they know how. This shifts our relationship with fear from something to overpower into something to listen to and befriend.
Befriending our fears allows us to see the judgements underneath more clearly. It’s worth distinguishing a judgement from an evaluation. A judgement is what happens when a clear-eyed evaluation gets distorted by pain we haven’t yet healed. Our judgements towards others are ultimately a reflection of self-judgements we haven’t yet owned, because these distortions originate in our own pain. So the next step is to practice compassion to self-forgive each judgement that we’re bringing to the dilemma. Forgiveness doesn’t mean that the judgement is totally devoid of truth. Rather, forgiveness allows us to separate out the evaluation within the judgement from the pain distorting it.
This then creates the space for us to consciously sit with and grieve our pain. We can use our earliest memories of the pain to get a better sense of what aspects of our mind need the most love and healing. Bringing tenderness, care, and compassion to this pain creates the conditions for genuine grieving. Processing this grief loosens the grip the underlying stories have on us, so that they can be upgraded.
Our stories built around our pain were our best attempt at making sense of an overwhelming experience. They were often constructed under duress and haven’t been updated since. Upgrading our stories involves working through a number of journal prompts that progressively widen the aperture of our stories starting with venting/blame, to asking how this entire experience might have been something we uniquely needed. This progression matters because each level of questioning can only land once the previous one has been genuinely processed. For example, trying to skip to “how was this experience for me” before the blame has been heard will feel hollow and forced.
Unpacking each option in the dilemma
The following contains journaling prompts for you to help unpack each option in the dilemma. Each step contains a different theme of journaling prompts which will offer more insight as you progress through the steps.
Describe the situation. Map out the choices within the dilemma with some explanation of how you got here. Probe the situation to find all the negative emotions associated with the dilemma. Find all the statements of the form “I’m upset because...” that feel real to you.
Explore these feelings.
What are you feeling about the situation?
What emotions are coming up for you?
Connect to the body. Where in your body can you feel these feelings?
Make friends with the fears underneath these feelings. Ask those fears the following questions and engage in a dialog with them.
What are you scared and/or upset about?
What are you trying to warn me about? What are you trying to protect me from?
What are you afraid it would mean if that happened? What is the worst case scenario that you’re worried about?
What is your positive purpose? How are you serving me the best way you know how?
In addition to safety, what other positive goals or outcomes are you trying to help me create?
Give appreciation and acceptance to your voice of fear. Remain connected with the fear via that part of your body, and tell it that “I appreciate your positive purpose, and I’m grateful for how hard you’ve been working to help me meet these goals, the best way you know how.”
Would you be willing to work together with me, as friends, to move forward with these goals in ways that might feel scary at times, and would also be safe?
What would you want or need from me, in order to better do so?
Is there anything else you want to share with me?
Conclude by genuinely thanking your voice of fear, and praise it for its efforts.
Explore any judgements underneath these fears that you’ve placed on the situation, the other person, or yourself. Remember that judgements you hold against other people are often mirrored by judgements you hold against yourself that you haven’t yet owned.
“I’m upset because...”
“They should...”
“I should...”
Practice compassionate self-forgiveness. Remember a time when you felt particularly connected and loving. Bring that feeling into your body. Take this feeling and practice compassionate self-forgiveness for any of the judgements you’ve innocently placed on yourself and others. Keep going until you either feel “done” or “lighter”.
I forgive myself for judging myself as $BLANK.
I forgive myself for judging $BLANK as $BLANK.
I forgive myself for judging myself for $BLANK.
I forgive myself for judging $BLANK for $BLANK.
I forgive myself for buying into the belief that $BLANK.
Find the earliest painful memories. Try to find the earliest painful memories for each judgement. Ask yourself what pain these judgements were attempting to protect you from, in the best way that they knew how. Write down these memories as clearly as you can.
Hold compassion for the pain. Practice holding compassion and care for the pain in these memories. Create space to grieve for this pain if you need it.
Identify the stories. What are the stories you created to make sense of this pain? Write down all the ones that come up.
Upgrade each story through progressively higher levels of thinking. Answer the following questions for each story:
Why me?
This is yet another opportunity to grieve the pain from the story. Give yourself permission to vent whatever you need to vent that you haven’t already vented above.
This is also your opportunity to vent about the difficult decision you’ve found yourself in (e.g., if you find it unfair).
Who is to blame?
There will be parts of you that want to ascribe blame. It’s okay that they’re doing this, and they’re trying to help you the best way that they know how. This is your opportunity to give them a voice, even if you’re not going to immediately react to that voice.
Figure out who (including you?) was responsible for this pain.
Figure out who is responsible within the current context for why you’re facing this difficult decision, and how it seems related to your pain.
How do I fix it?
What would it take for you to internally and externally fix your pain? It’s okay if you don’t have the answers. If you don’t know how, who could you ask for help?
What would it take for you to internally and externally fix your pain within the current situation? Again, it’s okay if you don’t have the answers. If so, who could you ask for help?
What would it take for you to feel/act with more integrity both within this situation and in relation to your pain?
How can I learn and heal?
Your pain is an experience to learn and grow. What’s the positive lesson behind your pain?
What sorts of constructive behaviors can you turn into habits to “bake in” what you’ve learned from this pain?
What sorts of constructive behaviors can you engage in to heal from this pain?
Again, if you don’t know the answers to these questions, who could you ask for help?
How was this for me?
Beyond learning and healing from the experience, how were both your original pain and this specific dilemma a unique gift for you to practice receiving from the universe?
What was the positive purpose of this entire experience, uniquely and idiosyncratically for you?
Integrating the upgraded stories
Going through the steps above for each option in the dilemma will often change your relationship with the dilemma itself. The journal prompts below attempt to integrate all of these insights into concrete decisions you can now make.
Explore alternative choices.
Having upgraded the stories from both arms of the dilemma, were there any core confusions keeping you stuck?
Are there any possibilities that you can now see that you previously couldn’t, even if they involve asking for help from someone specific?
Are there any possibilities that would let you grow from this situation?
What new constructive behaviors would be necessary for you to work towards these new possibilities?
Commit to constructive habits.
Given the constructive behaviors from the last step, how can you establish them as habits? What kind of support do you need to turn them into habits?
This entire process is much easier with the help of a therapist or executive coach. But you can still make meaningful headway by yourself.
Conclusion
Hopefully, your original dilemma will look and feel different after doing this work, not because the external circumstances have changed, but because the fears that were distorting your perception have been recalibrated. In some cases, the dilemma itself may shift such that you view the entire context very differently.
Note that this process isn’t something to be done only once. This process is most valuable when established as a habit that you practice for the difficult decisions that you encounter on your path. Each recalibration doesn’t just resolve this specific dilemma, but rather builds your general capacity to navigate the next one authentically. This practice compounds over time, and what once required step-by-step effort starts to become a more natural way of relating to stuckness.
This practice is a doorway to a life where difficult decisions bring curiosity rather than dread, where each challenge deepens your sense of meaning and clarity rather than eroding it.
Wisdom is the capacity to see more clearly rather than knowing more. Each developmental dilemma is an invitation and opportunity to see more clearly than you could before. In some sense, this practice results in the cultivation of wisdom as practiced through the doorway of difficult decisions.
Acknowledgements
Thank you to Brian Whetten for teaching me everything I’ve articulated in this essay. I cannot emphasize how incredible he is as a coach. All the valuable insights from this essay are his. All mistakes, lack of clarity, etc. are mine.
If you liked this essay, I’d highly recommend reading his book Yes Yes Hell No! The Little Book for Making Big Decisions. There’s an incredible amount of value packed in that one little book.