How to Make a Difficult Decision

January 8, 2022

It’s tempting but unwise to delay important choices. Grasp the nettle by using both systematic checklists and gut instinct

A couple of years ago, following the publication of my book The Art of Decision Making (2019), I took part in the BBC Radio 4 programme ‘Should I Stay or Should I Go?’ named after the 1981 hit song by the Clash. This is the question we face time and time again, whether it applies to a relationship, a job, the home we inhabit, or any other critical dilemma.

My work as an executive coach involves helping people make these tough decisions for themselves and ultimately by themselves. Unlike a mentor, this is not about giving advice. It is about giving people the tools and confidence to trust their own choices and to act upon them.

In this Guide, I will give you an overview of some of these tools and techniques, and how you can use them to accelerate and improve your decision-making.

Why decisions can be so difficult

Ultimately, what defines a hard decision isn’t so much the decision itself, but how it is perceived by the decision maker. You might feel that a decision is hard because:

-the stakes, for you, are particularly high;

-two or more options weigh the same in your mind; or

-this decision brings back unhelpful memories or fears. This is the case, for example, where a choice is reminiscent of disappointing past choices. It is also the case for the individual whose psychological complexes are triggered by certain challenging situations. For example, a decision might unconsciously reignite a past traumatic event and alter your judgment as a result.

Consider the person who struggles with the decision to accept a more senior position with a considerably higher compensation, when many others would jump on the opportunity. This might be linked to their fear of failing in a high-stakes/high-visibility position.

It could also be because the option of staying in a less senior role is equally attractive, but for different reasons, such as having more free time. Finally, for this person, perhaps breaking into this level of seniority throws up a whole range of issues that originated in their childhood.

I have seen this often with successful professionals whose important decisions are regularly affected by the power of an overactive superego (that is, the image of a parent or another past figure of authority, irrespective of whether they are still alive or not).

In other words, decisions are complex, not necessarily because the choice between two options is complex but also, and more importantly, because human beings are complex.

The etymology of the word ‘decision’ provides further insight. It comes from the Latin word caedere meaning ‘to cut off’. Decisions cut us off from other choices, other opportunities and the possibility of better outcomes. For this reason, the act of deciding can feel like a self-inflicted wound.

Avoiding a decision is in fact a decision

When faced with a difficult decision, it can be tempting to take the easy road and procrastinate. This attitude illustrates what might be the greatest myth about decision-making: that, faced with two choices, we still have the option to not decide and to do nothing. In fact, procrastination is not the refusal to decide, or to ‘freeze’ a decision in time, rather it is the active decision to remain undecided.

It is only when you realise that procrastination is a decision that you will start finding this option less attractive. Moreover, indecision and procrastination do not postpone the pains of a decision to a future day: they multiply that pain by spreading it across every minute of every day, until you finally decide.

Research from the 1990s led by the US psychologist Thomas Gilovich provides further evidence for why it can be shortsighted to kick a difficult decision down the road. Gilovich and his team showed that although, in the short term, people experience more regret from ‘errors of commission’ (taking an action that leads to a disappointing outcome), in the long term it is actually ‘errors of omission’ that lead to more regret – that is, disappointing outcomes that arise from not taking an action.

Therefore, over the long term, it is often wiser to act, and therefore to decide. As Ralph Keeney, a decision scientist and professor emeritus at the Fuqua School of Business at Duke University in North Carolina, put it: ‘Your decisions offer you the only way to purposefully influence anything in your life. Everything else just happens.’

If you struggle with decision-making – generally or occasionally – this Guide will help you understand some of the reasons behind it, and point you in the direction of solutions.

I’d encourage you to read this section with one difficult decision in mind and use the exercises to help you work through it. Ideally, it will be one you are facing right now. If that’s not applicable to you, try revisiting a past decision instead.

Identify the parts of yourself that want different things

When facing difficult decisions, it is likely that different parts of you might want different things. For example, when deciding whether to book a pricey holiday, one part of you (prudent) might think that this expense is unreasonable, while another part of you (hedonistic) prefers to make the most of life and go for it, while yet another part of you (serious) will think that work should come first.

Decision-making involves the deliberation between the different parts of yourself. Resolving this conundrum involves getting them to sit together around an imaginary table to agree on an outcome they can all settle for. In practical terms, try writing down what each part of you wants and seeing if you can identify a solution that optimises the joint aspirations of your different inner selves. Even if you don’t get that far just yet, the simple act of recognising your own competing desires will help you to think through the decision more effectively.

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