The freedom in hard choices: Why your toughest decisions define who you are

Which career path should you pursue? Should you stay in your relationship or leave? Do you take the safe route or the exciting one?

We have all faced decisions that left us paralysed, staring at pros and cons lists that refused to lead to a clear answer. We assume we are missing information or not thinking hard enough. But philosopher Ruth Chang, a Professor of Jurisprudence at the University of Oxford and a leading scholar of rational choice and value, suggests something radical: the problem is not that we are confused, but that we are asking the wrong question.

When the maths stops working

Chang describes how most of us approach difficult decisions by weighing what she calls practical reasons. We calculate measurable outcomes. Should Adam choose the intellectually stimulating job or the financially secure one? He tries to quantify how much stimulation matters versus how much money matters. He makes his list, does the maths, and still finds himself stuck.

That is because some choices are not actually mathematical problems. They are something else entirely. Hard choices, Chang explains, are hard not because of us or our ignorance, but because there is no single best option. When we are genuinely torn between alternatives, it is not a failure of reasoning. It is evidence that both options are legitimately valuable in ways that cannot be directly compared.

You cannot meaningfully compare intellectual stimulation to financial security in the way you can compare the price of two houses. They exist on different dimensions of value. Chang challenges the traditional decision-making framework that assumes one option must be better, worse or equal. Instead, she introduces the idea that some choices are on a par – qualitatively different yet living in the same neighbourhood of worth.

Creating reasons by committing

This is where Chang’s insight becomes transformative. When practical reasons run out and the scales refuse to tip, we have the power to create a reason by choosing one side or the other.

This is not arbitrary. When you are torn by a hard choice, you are invited to commit to a version of yourself. In our example, Adam is not simply choosing between jobs; he is choosing what kind of person he wants to be. Does he want to be someone who prioritises using his mind every day, or someone who provides financial stability for his family?

Every time we commit to a relationship, a project or a career path, we are also committing to a future version of ourselves. The practical reasons might be balanced, but through choice we create what Chang calls an existential reason: a reason rooted not in external incentives, but in who we decide to become.

Chang calls this our normative power - our human capacity to make reasons for ourselves, to author our own direction. Hard choices, then, are not traps or tests. They are the moments when we step into agency over our lives.

The coaching connection: From stuck to self-authored

This lens is deeply resonant in coaching. Coaching often begins in the same space that Chang describes, the moment when the analysis stops working and questions of identity begin.

When clients come to coaching, it is rarely because they have not analysed their options enough. It is because they have reached a threshold where reasoning cannot decide for them. They sense that the decision is not about getting it “right”, but about finding what is true and aligned.

In this space, the coach does not offer answers. Instead, we explore questions such as:

·     What values are being expressed or challenged in this decision?

·     What identity, story or aspiration might each option represent?

·     Who are you choosing to become through this act of commitment?

Hard choices invite a kind of self-authorship. Coaching gives structure and support to that process, transforming indecision into clarity rooted in values. The aim is not to optimise outcomes, but to act with integrity and intention.

The question that changes everything

Chang reframes decision-making by inviting a new question: “What will this choice make of me? And is that who I want to be?”

This changes decision-making from calculation into an act of self-creation. It shifts us from seeking validation in outcomes to cultivating alignment with our evolving selves.

Consider someone deciding whether to move across the country for a relationship. The practical reasons may be balanced: career opportunity on one side, emotional connection on the other. But the real question is not which yields a better measurable outcome. It is whether you want to be someone who prioritises love and connection, or someone who prioritises professional advancement and stability.

Neither choice is wrong. Both are deeply human. But the act of choosing, and committing, reveals and shapes who you are.

Why This Matters Now

In a world obsessed with optimisation and data-driven decisions, Chang’s philosophy is liberating. Not every choice has a best answer waiting to be found. Some decisions are invitations to author your own life.

This matters profoundly in professional life, where many of us are haunted by the pursuit of the “right” path: whether to stay at the stable company or join the risky start-up, whether to specialise deeply or stay broad, whether to prioritise balance or growth.

Chang herself once faced that crossroads, unsure whether to pursue law or philosophy. Fear of being an unemployed philosopher led her to law. It was not who she was. Later, through that lived experience, she turned back towards philosophy, and towards the subject that had defined her own struggle: how we make hard choices.

The truth she discovered applies universally: safety is not always the right reason.

The power of self-authorship

Chang’s framework removes the burden of having to find the objectively correct answer while preserving the gravity of decision. You are not flipping a coin. You are exercising your power to stand behind one set of values over another.

That is the work of self-leadership, and it is also the work of coaching. Both rest on the same insight: that freedom is not the absence of constraint, but the ability to choose meaningfully among your own values.

So, the next time you face a hard choice, where the numbers will not add up and both paths hold promise, remember you are not stuck because you are missing information. You are standing at a crossroads of self-definition.

That is not a burden. That is freedom.