The Clarity Edit #3: Why big decisions feel hard and 6 ways to make them easier

You’ve already made dozens of choices today. Maybe you scrolled past Slack notifications before getting out of bed. Maybe you grabbed the same breakfast as yesterday without a second thought. In the moment, none of these felt like decisions. They were automatic.

But then there are the other decisions. The ones you consider for months or years. Should I finally leave this job? Move to another country? Have a child? End this relationship? Find a co-founder?

Suddenly, all that easy, automatic decision-making ability vanishes. You’re stuck, ruminating, Googling, talking to friends, rereading your own pros-and-cons lists. And still, you can’t make progress.

Even small decisions can feel draining. If you’ve studied a restaurant menu for 15 minutes and still defaulted to the same dish you’ve had last time, you know what I mean. Multiply that by a thousand, and you’ve got career decisions.

Psychologist Herbert Simon once described two broad styles of decision-making. Some people are satisficers: they spot an option that feels good enough and move on. Others are maximizers: they chase the best possible outcome, comparing every option. It sounds clever, but maximizers often feel less satisfied, even when their choice is objectively better.

Other research links decision-making style to personality. One of the most widely used personality frameworks in psychology is the Big Five, which measures people on five broad traits: openness, conscientiousness, extraversion, agreeableness, and neuroticism. And research shows these traits don’t just shape how we relate to others, they also shape how we make decisions.

High openness makes you curious, but also prone to overexploring, which makes committing to a course on action very difficult.

High conscientiousness helps with careful planning, but can spiral into perfectionism.

And high neuroticism often means replaying risks and regrets on a loop, making every choice feel heavier than it is.

So yes, part of it comes down to personality. But even beyond that, two common forces make decision-making more challenging than it appears:

The good news? You don’t need to reinvent your personality to get better at making decisions. What you need are some practical tools that take the weight off and bring more clarity.

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Economists remind us that every yes is also a no. When you choose one option, you close the door on others.

That promotion you accept might come with an impressive title and better salary, but also less free time, fewer evenings with friends, and a creative project set aside.

The real question becomes: Do I want this more than the things I’m sacrificing?

Naming those trade-offs brings hidden costs into the light. Without that, it’s easy to fill your life with commitments that look impressive but leave you feeling unfulfilled.

A deceptively simple tool: fast-forward five years and ask yourself:

Which choice will I regret less?

By shifting perspective, you cut through the fog of short-term concerns. Many decisions feel overwhelming in the moment, but when you zoom out, the path often becomes clearer. You’re not predicting the future, just asking which choice aligns more closely with the kind of life you want to look back on.

Not every decision benefits from weighing endless factors. Sometimes the most effective filter is your own set of values.

Values are the guiding principles you decide to live by.

For example: Career success is important to me, so I only take on work that helps me grow.

Or: In this phase of my life, I prioritise my well-being, so I will chose a low stress work environment over one that pays higher, but is more demanding.

With values in place, you don’t need to re-argue every choice, you simply check whether the option aligns.

The strength of this approach is consistency. It ensures your decisions reflect who you are and what matters most, even under pressure. Instead of asking, is this a good opportunity the question becomes does this opportunity align with my values.

You might be familiar with a postmortem, the meeting held after a project wraps up. The team looks back at what worked, what didn’t, and what they’d do differently next time. The goal is to learn from experience so future projects run more smoothly.

When faced with a big decision, most people imagine success. A premortem flips this around: imagine it’s a year later, and you’re not happy with the decision. Then ask: what went wrong?

Maybe you underestimated the workload in the new role. Maybe you ended up not liking the team culture. Maybe you didn’t plan for financial stress if you started your own business. By walking through potential points of failure in advance, you uncover risks you might otherwise miss.

A premortem doesn’t mean abandoning bold moves, it means making them with eyes wide open. You can build safeguards, set boundaries, or prepare contingencies, so the leap feels less like a jump into the unknown.

The sunk cost fallacy convinces us to stay stuck in a situation because of what we’ve already invested in it.

Maybe you spent five years in a role, trained for years, and put in endless hours of effort, so how could you throw that all away and start from scratch? But just because you’ve invested a lot of time and effort into something it doesn’t mean you can’t move on from it.

When dealing with the sunk cost fallacy, ask yourself: If I were starting from zero today, would I still choose this path?

It’s a bracing question. Sometimes the honest answer is no, and that’s when you know it’s time to stop pouring energy into a path that no longer serves you.

Some decisions aren’t about which option to choose, but what to do first. That’s where the Eisenhower Matrix helps move from thinking to action.

Here’s how it works. It divides tasks into four categories:

The real power lies in the second category: important but not urgent. This is where long-term progress lives — writing the book, developing new skills, building relationships. And yet this is the category we neglect most, sacrificing it to endless urgent tasks, even though it’s the work that shapes the life we want.

Once you’ve reached a decision, use the Eisenhower Matrix to figure out how to start bringing it to life.

We can’t change our personality, but we can use these tools to sharpen how we make decisions.

Opportunity cost, regret tests, values, premortems, sunk cost checks, and prioritization are all lenses. They won’t eliminate uncertainty, but they can help you see choices more clearly and act with greater purpose.

In the end, better decisions aren’t about finding the perfect answer, they’re about learning to move forward, one choice at a time.

And if you’ve been circling the same decision for months, sometimes what helps most is a sounding board. That’s the work I do as a coach: helping ambitious professionals cut through the noise and move from rumination to action. You can learn more about working with me here.