Why Does Making a Decision Feel So Hard?

There’s a recurring theme that’s been showing up lately – in coaching sessions, over coffee with friends, even in quiet moments of reflection. It’s the struggle to decide. The dilemmas vary: Should I take a job overseas? Is now the right time to start postgrad study? Where should I base my business? Which school should I choose for my child?

What’s so hard about choosing X over Y, or Y over Z? On paper, it sounds straightforward. Weigh the pros and cons, gather information, make a call. Done, right?

But anyone who’s stood at a crossroads knows – it’s never that simple. Beneath the surface, something subtler, psychological, and persistent is at play. Of course, some decisions carry more weight than others. Career moves, relationships, big financial or life changes – these aren’t light choices. They shape our lives, it’s only natural to want to get them right.

Optimal Over Perfect

Here’s where most of us get caught up: we’re not just trying to make a decision, we’re trying to make the best one. The perfect, regret-proof decision.

But what if the idea of 'best' is the problem?

I often encourage clients to drop that word entirely. Instead, I steer them toward making the optimal decision. Optimal reflects reality. It’s based on who you are now, the information at hand, your constraints and priorities – not some mythical gold standard.

Take a client I worked with recently, deciding where to base her business – Sydney, Melbourne, or a regional centre. We walked through the usual process: identifying business needs, examining lifestyle preferences, weighing pros and cons, costs, opportunities. Logically, we landed on a vibrant regional city an hour from Melbourne. Infrastructure, market access, lifestyle – ticked all the boxes.

But then – out came that question: "Is this the BEST place?"

What she really meant was: "How do I know I won’t regret this later?" And that’s when we hit the deeper stuff. The forces beneath the surface.

The Myth of the Best Decision

Here’s where people often get stuck: the chase for the best decision. Not just a good one – a perfect, hindsight-proof choice. And beneath that, two psychological forces quietly fuel the struggle:

Counterfactual Thinking – That mental habit of imagining how things could have turned out differently. Psychologists call this the “what if” spiral. It keeps your mind fixated on the path not travelled – all the hypothetical versions of your life you didn’t live. It’s seductive, but corrosive.

Cognitive Dissonance – Once a decision is made, dissonance creeps in – "Was this really the right choice?" You feel torn between your past self (who decided) and your present self (who doubts). It’s an internal tug-of-war.

We Aren’t Static – And Neither Are Our Decisions

One thing we forget: we’re not static. You made that decision based on the resources, values, and context you had then. But life shifts. You evolve. Circumstances change. It is impossible to expect your past self to make a choice that satisfies every future version of you. That’s why chasing a singular, eternal 'best' choice is only going to set you up to fail.

Beware the Maximiser Trap

Psychologist Barry Schwartz’s research is handy here. Maximisers exhaust every option, hunting for the perfect choice. Ironically, they tend to feel less satisfied – more prone to regret, decision fatigue, second-guessing.

Satisficers? They figure out what's good enough, make the call, and move forward.

The Illusion of No Regrets

A recent chat with my cousin summed it up perfectly. He was contemplating a career move, weighing options.

"What’s the best move here? I don’t want to take A and miss out on B. But I also don’t want to choose X and neglect Y."

His real question wasn’t about A, B, X, or Y. It was: "How do I choose without regretting it later?"

I jokingly replied? “I’m only a executive coach. If certainty’s what you’re after, maybe head to the local temple and chat to the palm reader. They might offer you a clearer forecast. But me? I can’t promise regret-free living.” Because regret isn’t proof of a bad decision. It’s proof you’re human.

The Inevitability of Regrets

Why are regrets unavoidable? First, change is constant. What feels right today may feel off in five years – not because you chose poorly, but because you’ve grown.

Second, every choice is a trade-off. By choosing one thing, you're necessarily not choosing another. What gets us tangled is thinking there’s a way to avoid giving up anything – when every choice means walking one path and leaving another untraveled.

Third, hindsight bias messes with us. Once the dust settles, it’s easy to convince ourselves we 'should have known better' based on information we never actually had at the time.

The Convenient Amnesia of Success

While we’re talking outcomes, let’s take a quick side trip. Not every decision leads to regret. Sometimes, you make a call – and things turn out better than you hoped. Your business takes off. The job you took opens doors. The school you chose fits perfectly.

And what happens then? That little voice in your head pipes up: "See? I made the best decision." It feels amazing!

But here’s the kicker – we conveniently forget what happened between Point A (the decision) and Point B (the success). We skip the hard work. We erase the tears, the resilience, the messiness. Instead, we craft a neat story: I chose well → I succeeded.

That’s classic confirmation bias and to be clear – this isn’t a flaw or failing. It’s a perfectly normal human trait. Our minds are wired to smooth over complexity, to craft coherent stories about ourselves. The trouble is only when we start believing the story means there’s a replicable formula for perfection.

Closing Thought: Regret as Feedback, Not Failure

Regret will show up. It’s part of life. But here’s the shift: regret isn’t an indictment. It’s information. It’s a signal that something has changed – either in you or in your context. Use it as data, not a weapon against your past self.

When you understand why you made your choice – anchored in your values, your knowledge, and your situation at the time – you’ll have something solid to return to when doubt creeps in.

And remember, a decision is simply the act of deciding. Some decisions will shape years, even decades. A few may feel permanent. But most of the time, life gives us room to adjust, recalibrate, and choose again – armed with new information, shifting priorities, or fresh perspective.

As for the path not travelled? Let it stay where it belongs, in the realm of imagination, not self-judgement.

Ready to make peace with your next decision? If this resonated and you'd like support navigating the process—whether it's a big life move or something closer to home - feel free to reach out. Sometimes, having someone help you untangle the noise makes all the difference.

Want to Dig Deeper?

If some of these concepts resonated, or if you'd like to dive a little deeper into the psychology of decision-making, here are a few resources worth checking out:

• Maximiser vs Satisficer:

👉 Do Maximisers or Satisficers Make Better Decisions? (BBC Worklife)

A thoughtful look at the difference between maximisers and satisficers, and how each approach impacts satisfaction.

• Cognitive Dissonance Explained:

👉 What Is Cognitive Dissonance? (Verywell Mind)

A practical breakdown of why we experience inner conflict after making decisions—and how it plays out in everyday life.

• Counterfactual Thinking & The ‘What If’ Trap:

👉 Why We Can’t Stop Thinking About ‘What Might Have Been’ (Psychology Today)

A deeper dive into how we mentally replay the paths not taken—and why it’s so hard to let go.

• Bonus – The Paradox of Choice:

👉 TED Talk by Barry Schwartz

A classic exploration of how modern life overwhelms us with options, and what that abundance of choice does to our satisfaction.