Can’t Stop Thinking “What If?”: Why Your Imagination Is Critical to Your Goals

It’s time to think about what might have been.


Max Phillips

2 years ago | 4 min read

I was 11 years old when someone first asked me what I wanted to do with my life. Puzzled, I thought about my talents. I was a keen sportsman, so I settled on athletics.

Twelve years later, I’m sat firmly on my arse writing this article. And I hate running.

But that didn’t stop my imagination from running wild, picturing me crossing the line and becoming Olympic champion one day. Among other things, that’s allowed me to reconcile with my past self, motivate my present, and sympathise with my future.

By letting your imagining off the leash, you can find more comfort in the present, learn from your past, and potentially open up more avenues in the future.

You can then direct everything toward your goals.

The subtle magic of staring out of the car window


Jordan Gross wrote a brilliant article on the power of imagination. Take a minute and read his story:

“My dad, who was driving, shook his head and laughed when I told him what had just happened. “Why don’t you just look out the window?” he said.

Do what? I thought. The option hadn’t even occurred to me […] But that was before the birth of Instagram, Snapchat, Words With Friends, and every other digital distraction that prevents our minds from experiencing that strange feeling known as boredom.

Perhaps my dad’s idea wasn’t so bad. I put my phone in my pocket, and for the first time in who knows how long, purposely gazed out at the Cleveland scenery.”

Jordan makes an important point here. With the distractions available to you reaching a fever pitch, it’s easy to forget the power of your mind. But, whether you like it or not, your imagination is lead by the devices and apps within them.

In many ways, that’s a good thing. When watching something exceptionally creative, I’m often inspired to produce something myself.

But your brain processes everything you consume, storing and using it to make decisions, all without you realising.

Letting your imagination run wild, whether that be through your car window or at 4 am in bed, puts you in the director's chair. You can swing your thoughts into a retrospective, reflective place.

Its power is not to be underestimated.

The power of imagination

According to Harvard psychologists, the more someone’s mind wanders, the less happy they are.

Psychologists Matthew A. Killingsworth and Daniel T. Gilbert say that “the ability to think about what is not happening is a cognitive achievement that comes at an emotional cost.”

Killingsworth goes on to discuss how our “mental lives are pervaded, to a remarkable degree, by the non-present.”

However, with a bit of direction, mind-wandering can initiate some unsuspecting benefits.

Tailor your wandering mind to work for you

To realign yourself with your goals, you must better understand your past, present, and future selves. This can feel tricky given you likely view your future self as a completely different person.

I propose imagining yourself achieve goals that aren’t yours.

For example, when I was younger, I was a good swimmer with potential. However, I decided against competing because I found it boring and lonely, opting for football instead.

Seeing British Olympic athlete Adam Peaty completely dominate the breaststroke awoke my imagination. For a few days, I kept imagining the path I would’ve taken had I chose swimming over football.

Instead of pining for a life that wasn’t mine, it helped me understand why I chose football and the path I’m now on. I appreciate my goals have changed, as I currently imagine writing success. In addition, the team element of football helped me grow confident in social situations, as I now am fortunate to have a few friendship groups.

Moreover, this thought exercise helped me sympathise with my future self. I appreciate his goals might be different from mine, as a lot can change in five or ten years.

Your past self might have had elaborate goals, but you can evaluate why that didn’t happen, understand the lessons, and use them with your present-day knowledge. This way, you're setting your future self up for success and creating a harmonious existence with each version of yourself.

Where this is most useful

There are some more practical uses for this exercise, such as:

  • When you’re suffering from a creativity drought, imagining different paths your life could have and potentially will go to feels like neurons firing in the brain as they form memories. Different perspectives trigger new ideas, something I use all the time as a writer.
  • Self-doubt can be painful. No matter how hard you try, comparing yourself to others is often inevitable, especially if they’re similar to you. When you see how differently your life has panned out, it’s easier to appreciate how the success you’re comparing to is likely not what it seems. Everyone’s path is different — even the various versions of yourself.
  • I quite regularly imagine how my life would have panned out if I made different decisions, such as choosing an alternative university. It helps put regret in the boot and drive me forward in the knowledge the path I’ve explored is the right one.

Imagination is your most potent, accessible weapon

As you grow older, your life is consistently evolving. Goals, relationship dynamics and your general lifestyle will go through massive shifts, so it’s understandable if your identity wobbles.

I’m in my 20s. I’m job hunting again, but I’ve noticed a dramatic shift since last time — a mere two years ago. I know I want freelance writing work. Finally, I have direction, and it feels damn amazing.

This wouldn’t have happened if I hadn’t observed the paths I’ve taken, am currently on, and will potentially take.

If you view your imagination in a similar fashion, you’ll find it easier to compromise, realign, and sympathise with yourself. Essentially, you’re talking to yourself through the time stream.

That doesn’t sound so bad, does it?


Created by

Max Phillips







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