5 Powerful Questions to Boost Your Decision-Making Confidence

"The risk of a wrong decision is preferable to the terror of indecision." ~ Maimonides

In a world filled with endless choices, making decisions can feel overwhelming. Whether you're facing a career change, a major purchase, or simply choosing what to have for dinner, the ability to make confident decisions is a crucial skill. This guide will explore five essential questions to help you navigate the decision-making process with clarity and courage.

The Importance of Decision-Making

Every day, we make countless decisions that shape our lives. While many of these are minor, the cumulative effect of our choices significantly impacts our overall well-being and success.

Even the minor decisions can be hard at times. Every ‘yes’ we say is a ‘no’ to something else and let’s face it, not many of us like saying no. And yet not making decisions leaves us stuck, unable to move forward towards our goals.

One of the key principles I used to teach aid workers preparing to work in conflict zones was "make a decision". When the proverbial is hitting the fan, indecision only ever seems to make a situation worse. And I think the same applies to whatever challenge you’re facing in life.

Learning to make confident decisions not only reduces stress but also moves you forward toward your goals and aspirations. So how can you make decisions with more confidence? Here are some of the questions I ask myself when I’m struggling to make a decision.

5 Questions to Guide Your Decision-Making Process

1. What's the Bigger Picture?

One of the first questions military planners ask is "What is my aim?", followed by "What is my commander’s intent?"

In plain English, what’s really important here?

Before diving into the details of a decision, it's crucial to step back and consider the broader context. Ask yourself:

- What is my ultimate goal or vision?

- How does this decision align with my values and long-term objectives?

Personal Example:

When I faced a decision about what to do with my flat, I found myself caught in a web of options – sell, rent, or stay put. The economic climate added another layer of complexity. Reminding myself of my vision for my life put the brakes on going round in circles and see the route out of the maze - like taking the bird’s eye view of my life. I have a couple of mantras that help me with this:

"I live a life I don't need a holiday from."

"I collect experiences, not stuff."

I come back to these time and again as a North Star to guide me through difficult decisions and help me see the bigger picture.

2. Can I Reduce the Options?

Decision fatigue is real. The more options you have, the harder it becomes to choose. Try to simplify your decision by:

- Setting clear constraints or criteria

- Eliminating options that don't meet your essential requirements

Case Study:

When planning my wedding, I quickly decided on a venue despite the myriad of options available. A friend expressed surprise that I had already come to a decision, which got me reflecting on how I (sometimes) can be uber-efficient in making decisions. The key? A strict budget. By setting this financial constraint, I automatically ruled out numerous venues, leaving me with just three viable options. This made the final decision much more manageable.

3. Does It Really Matter?

Not all decisions carry equal weight. Sometimes, I can agonise over choices that, in the grand scheme of things, don't significantly impact my life (like what to wear today or what flavour of gelato to order - seriously, I have reduced myself to a sweaty, teary mess over this one at times). Ask yourself:

- Will this decision matter in a week, a month, or a year?

- Am I overthinking a relatively inconsequential choice?

Practical Tip:

For minor decisions, try setting a time limit. If you can't decide within that timeframe, choose randomly and move on. This technique can be particularly helpful for day-to-day choices that often bog us down.

4. What Would This Decision Look Like if It Were Smaller?

Big, life-altering decisions can be the worst. I see lots of clients struggling with decisions because they’ve made them massive, existential questions. “I don’t know what to do with my life”. “Who do I want to be?”. Questions that size don’t have nice neat answers.

The trick is to break them down into smaller, more manageable steps.

My friend Sarah has a lovely frame of deciding if she wants to do something for a season. Sometimes, saying this is something I’m choosing for now takes the pressure off and opens up more space in your decision-making.

Another way to think about it is trying a 10% project - is there a way of trying out this new thing without having to commit 100% to it? Essentially, we’re finding ways to treat the decision as an experiment rather than the only answer - or as one of my teachers likes to put it, you’re taking the decision out on a date, not getting married to it.

- Can you test the waters before fully committing?

- Is there a way to implement your decision gradually?

- Could you choose an option for a defined period of time?

Expert Insight:

Dr. Robert Cialdini, a renowned psychologist and author of "Influence: The Psychology of Persuasion," suggests that people are more likely to commit to big changes if they start with small, consistent steps. This "foot-in-the-door" technique can be applied to decision-making too.

5. Is There a Way Back?

Knowing you have a safety net can provide the confidence to move forward with a decision. Having a "plan B" doesn't mean you're planning to fail; it's a safety net that allows you to take calculated risks.

Perhaps that’s going back to the same or similar role. Maybe it’s having a savings buffer to carry you through. Having some kind of contingency plan and, again, treating it like an experiment - if this doesn’t work out, I can take a step back and then try to move forward in a different direction.

Consider:

- What's your contingency plan if things don't work out?

- Write a list of what could go wrong and, most importantly, write down what you could do if that happened.

Personal Experience:

I’ve quit my career twice with very little idea of what I was going to do next. Both times, the thing that gave me the confidence to move forward was knowing I could go back if it didn’t work out. Yes, I wanted to move on and I could see that where I was wasn’t all that bad. Knowing that if I tried something new and it didn’t work, I had something to fall back on made the whole thing much less scary and gave me the courage to leap

Putting It All Together: Your Decision-Making Framework

Here's a simple framework that brings all that together for you to use next time you feel stuck.

1. Define the decision and its context (bigger picture)

2. List your options and apply constraints (reduce options)

3. Assess the importance and impact (does it matter?)

4. Break down the decision into smaller steps (make it smaller)

5. Identify potential exit strategies or alternatives (way back)

You are not all-knowing and you cannot predict the future - sorry and welcome to being human! All you can do is make the best decision you can with the information you have at the time.

Final Thoughts

If you're still struggling with a decision, maybe these will help nudge you forward.

My general experience is that I regret the things I don’t do, rather than the things I did do.

Remember that there is nowhere to get to. The purpose of life is to enjoy the journey so put one foot in front of the other and trust that each step is taking you somewhere interesting.


Want to tap into your body's wisdom to support your decision-making? This guide will help get you started.

My Planning With The Seasons ebook combines cyclical living with military planning processes. Download it for free to get a practical yet intuitive approach to planning and decision-making.

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