What To Ask When Making a Tough Choice

Mo Issa
4 min readApr 16, 2022
Photo by Gian Cescon on Unsplash

Many, many years ago, when I was in college, I was stuck in a toxic relationship. It was clear to my friends that I should walk away, but I didn’t. The relationship ended after she unceremoniously dumped me. I didn’t have the strength to leave, and I suffered accordingly.

Last summer, I wanted to create a Podcast. I built a room for it, bought all the necessary equipment and was ready to start. Then I had some problems at work, which meant I had to spend more time there.

If I went ahead with the podcast, I had to sacrifice writing and the upcoming book I’d planned to write. So I thought about it and instinctively decided to pause the podcast project. I don’t know whether it was the right decision, but then, it felt right.

A month ago, I’d wanted to start running outdoors again when I got a call from a friend who wanted to form a cycling group and had pencilled me in as a critical member.

I didn’t know what to say. I wanted to do both but knew that time wouldn’t allow it. If I chose one, I felt I was missing out on the other. The longer I sat on the decision, the more anxious I felt.

Whether it’s a life-changing decision like leaving a toxic relationship or a smaller one like choosing what outdoor activity to do depends on the quality of the questions we ask ourselves before deciding.

We often default to what is most comfortable to not upset others or the ecosystem around us. But, if I can summarise all the learnings from self-help, we tend to grow most when we start making difficult choices. The road less travelled is the way to personal development.

Another question we ask is whether the choice makes us happier? This is so subjective to render the question meaningless. We project our feelings toward everything, and it becomes hard to know what makes us truly happy.

In defining happiness, we look at alternatives in our lives, not because we want the happiest option, but only because we’re bored with what we are doing. We are bored, not due to a lack of choices but rather because we are not content with ourselves.

We feel that we are missing out on something. So we compare what we are doing with what others are doing and presume it would give us more joy to do the things they are doing.

A few weeks ago, I came across the most insightful question to ask via a podcast when I heard Oliver Burkeman, author of Four Thousand Weeks, recount Jungian therapist James Hollis’s simple words:

“Will this choice enlarge me or diminish me?”

Instead of chasing comfort or asking what makes us happier, we should allow our intuition to elicit a far deeper response. That’s precisely what I did with dropping the podcast, but I didn’t consciously know it. However, I treat writing as sacred, so it’s always easier to make decisions concerning it.

The reality is that we know what the right choice is deep down. When we remove all the noise surrounding us, we can see what actions enlarge us. We can envision an image of our larger self, smiling, satisfied in doing what we love.

In deciding whether to run or cycle, I recalled how I’d felt while running in the rain one day.

It was late July, and rain was imminent. Perfect conditions for running. I put on my shoes and ran toward the dark clouds filling the sky. The slight breeze suddenly picked up and became a strong wind. The trees started to shake violently, and the leaves began to scatter across the ground. I kept running; I didn’t stop. Rain pelted down from the now completely black sky. I was the only one on the road — no cars, no vendors, not even stray dogs. I felt a chill run down my spine, and tears rolled down my cheeks. But I wasn’t tired, and I didn’t feel any of my usual running pains. I was on some kind of high, and for a few minutes, everything was so clear that I was at one with this universe. The swaying trees were dancing to the music from the sky, and I was the composer.

If running didn’t enlarge me, then nothing else did.

I knew that I wanted to run, and if my knees withstood the test, running not only enlarged me but nourished my soul. I can’t seem to find the solitude and freedom I feel when I’m out running.

Though it was a hard choice, I called my friend and apologised, telling him that I’d committed to running and perhaps I could join his cycling group in six months. No doubt he was disappointed, but he understood.

I wish I could return to my younger self and ask whether the toxic relationship I was stuck in was enlarging me or diminishing me. It was evident to everyone but me that my soul was being crushed, yet I stayed for far too long.

Today, whenever I’ve got a hard decision to make, the first thing that comes to mind is whether the choice enlarges or diminishes me. Then I quickly think of how I felt when running in the rain, and if I don’t get that awe-inspiring sensation, then it’s a NO.



Mo Issa

I rise daily at 5 am, meditate, read and journal on my Self-awareness journey. Some of my reflections make it to my blog; others don’t. (http://mo-issa.com)