Dealing with ‘what-if’ questions

What if I had taken that full-time job offer when I was graduating university? What if I had not left my job to go back to full-time studies?

Things would have been different. That’s for sure. But on the other hand, life would not be what I’m experiencing now.

The trajectory of our life is made up of the decisions we make daily. Some decisions are inconsequential, like the outfit we choose to wear on a particular day. Others might have a greater impact on our lives, like the universities we go to or the jobs we accept.

But regardless of what decisions we finally make, the voice that accompanies us daily won’t fail to torment us with never-ending ‘what-if’ questions.

What-if questions of the past

What if I had made that decision? What if I had not made that decision?

Some might think that it’s actually bad news. That there is no way we can turn back the time and undo any decisions that we have made.

But I think that’s good news.

The fact that we can’t go back in time makes our lives easier. It means that there’s no point trying to answer the ‘what-if’ questions for the decisions that we’ve made in the past. We’ve already made our decision. And the only thing left is to live life forward.

Instead of spending energy wondering about the ‘what-if’ questions that can’t be changed, we can spend the energy to seek the wisdom we need to make better decisions in the future instead.

What-if questions of the future

Dealing with the ‘what-if’ questions of the future is harder. While the past can’t be changed, the future is uncertain and influenced by your decisions.

When you feel that you need to make a significant change in your life to pursue a new career path, will you do it? And when you don’t know what the future will hold, what could you do?

1. Explore multiple possibilities before you make a choice

You might want to try an exercise called the Odyssey Plan1, where you imagine any number of parallel lives that you could live for the next 5 years.

Sample of Odyssey Plan. Template available here.
Image credits: Belinda Rowse

Each path would be separate on its own. And you might want to put aside any practical considerations for a moment. There’s nothing stopping you from dreaming as big as you want. At least for a start.

We could explore as many possibilities we want before we even make a choice. From each parallel life we dream about, we can then ask ourselves:

  • What if I chose this path?
  • Will it lead me to where I want to be in 5 or even 10 years?
  • Can I make new options by combining different possibilities from different lives?

The whole point of this exercise is to get you into the flow of brainstorming.

When it comes to making important life decisions, we tend to feel that we don’t have many options. We feel like we’ve got one life to live and we want to live it well. But the problem is, that makes us fearful of making wrong decisions.

I think what the Odyssey Plan exercise emphasises is that all the possibilities you map out are great choices. And there is no single right one that you have to follow.

2. Answer as many questions as you can

As long as it’s a decision that impacts the future, you could and ideally should answer as many ‘what-if’ questions as you can.

Thinking about whether to make a career switch?

Ask yourself what would happen to your finances, your happiness, your family? Ask yourself whether you would secure your next employment or client before you make the switch. Or would you be comfortable with quitting first, taking a break, before finding what’s next?

What if you fail? What if you succeed?

The more future ‘what-if’ questions you can answer, the greater your understanding of the consequences of your decisions.

3. Decide when to stop and make your choice

At some point, you have to stop asking the ‘what-if’ questions and make your choice. Otherwise, you would be stuck in analysis paralysis and never make any choices at all.

When you don’t make a choice actively, remember that you are still making a choice by default – the choice of inaction. And there could actually be a cost of inaction.

The longer you choose not to do anything, the harder it will become for you to make a career switch. The older you get, the greater the cost of you going back to full-time studies again. The higher your pay, the harder it will be to let go of the job that torments you to pursue a new gig that interests you.

Ultimately, you would have to stop overthinking and as Nike puts it well, ‘just do it’. There is no way you will be able to answer all the ‘what-if’ questions. It’s impossible to plan your future to such great detail that you will have an infallible plan.

Plans will always change no matter how great your plan is. So remain open and flexible. Sometimes, after doing enough research, the

The journey of a thousand miles begins with a single step.

Lao Tzu

Will you choose to take that step forward and not let uncertainties hold you back?


1 Designed by Bill Burnett and Dave Evans. More information in their book.


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