Why I Deliberately Doubt Myself

how to overcome self doubt

Assertive people don’t doubt themselves.

They obsess over their passions. They’re sure of their goals and know how to achieve them. They make five-year plans and stick to their routines with the discipline of a boring accountant.

At least that’s what society wants us to believe.

I tried being assertive.

I made five-year plans. I thought I had all the answers. I could become successful too. All I had to do was follow the ‘successful-lifestyle checklist.’

But my five-year plans didn’t last five weeks. Each time, I came across an obstacle and didn’t know what to do. I tried to bulldoze my way through it. But the obstacle wouldn’t budge.

Life offered hope. It dropped hints, asking me to adapt. But I was too busy trying to prove that I knew what I wanted. I ended up missing those hints. I lost sight of the objective.

I plateaued. I felt defeated… like a failure. And I gave up.

Then I realized the true meaning behind Bertrand Russell’s quote,

The whole problem with the world is that the fools and fanatics are always so certain of themselves, but wiser people are so full of doubts.

People stagnate when they believe they know it all. They might become big fish in a small pond, but they stay stuck in the small pond.

In her bestselling book Rapt, behavioral science writer Winifred Gallagher wrote:

Once you’re familiar with a situation, your top-down conviction that you know what’s going on can cause you to miss even dramatic alterations to it, such as substitution of a horse’s head for a human one. It’s hard to overstate the implications in daily life, from finding fresh solutions to problems at work to keeping the zest in marriage.

I had to accept that I didn’t know what I was doing. And I probably would never know.

So I began to doubt myself deliberately. I accepted that I didn’t have answers and that the ones I had could be wrong. I embraced life as a teacher, allowing it to lead.

What Happened?

I now find my sense of self turning fluid. I no longer know who I am. What I do doesn’t define me. And this is an immensely liberating feeling.

I’ve now adopted a beginner’s mindset instead of trying to prove myself. My skills don’t matter, nor does my history. I’m ready with Plan A, but am aware that it can go south anytime. Hence, I’m now prepared with Plans B and C too.

become a lifelong learner

If B and C fail too, I can regain presence and clarity quickly. I learn from my errors. Josh Waitzkin calls this phase of losing to win, of giving up your current mindset to grow, an ‘investment in loss.’

Investment in loss is giving yourself to the learning process. — Josh Waitzkin

But deliberate self-doubt doesn’t mean beating myself up. It means watching my thoughts and protecting myself against complacency. It means questioning myself, examining what I did and my future plans. It means being ready to try everything before dismissing it.

The result is experiential learning. A lot of it.

I plateau, but I try not to stay there for long. I’ve realized that the battle between proving my worth and pursuing a goal is futile. If I pursue a goal, I’ll prove myself in the process. If I don’t achieve what I aimed for, it’s because I’m not good enough. Yet. I’ll try harder. This approach has made me less emotional and more rational.

Nothing is permanent. Not failure. Not success. I’m not successful. But I’m happier. And in the long run, it’s happiness which leads to the success and not the other way around.

This article originally appeared on Medium.


  1. Suzy February 5, 2018
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