Don't Overthink, Just Start

How I overcame overthinking to start my own journey.

Yesterday marked a small but significant milestone in my journey – one of my apps received its 200th payment. That's 200 instances when some random person on the Internet trusted my app enough to enter their credit card details and make a purchase. This small achievement is a validation of the work and the potential of the journey I embarked on.

In hindsight, it took me a while to get started on this path. I realized that I had been overthinking many aspects of the journey, which delayed my initial steps. From worrying about perfecting every detail to doubting my capabilities, overthinking was a constant barrier that held me back from achieving early and small successes like this one.

In this post, I share how I realized I was overthinking, the common reasons for overthinking and offer practical strategies for overcoming this habit. It's about moving from a state of paralysis to action, from endless planning to executing, and from doubting to believing in your capabilities.

How I Realized I was Overthinking

Back in January 2022, after 14 years as a software engineer in New York, I was ready to start working for myself. I carefully calculated all my expenses – mortgage, child care, vacations – to make sure I could afford it. Everything looked good until I realized I forgot to include my family's healthcare costs, which could be up to $24,000 a year. Even though I had enough savings to cover it, this mistake made me doubt my entire plan. 'What else did I forget?' I thought.

Because of this doubt, I didn't quit my job that year. My careful planning turned into overthinking, stopping me from taking the next step. It was a clear case of thinking too much and doing too little.

A year later, in January 2023, I was in the same situation. I wanted to work on my own ideas, planned for my expenses, etc. But this time my thinking had changed. I understood that looking for perfect certainty was useless. I told myself, 'I can't control everything.' I had to embrace uncertainty. This change in mindset helped me stop overthinking. I finally quit my job and began my self-employment journey.

Three Reasons for Overthinking

I have realized that the three reasons of overthinking are fear, self-doubt and guilt.

1. Fear by far is the biggest reason that leads to overthinking. We all struggle with different kinds of fear. Fear of loss in social status, money etc. I struggled to make the decision to quit my job because of such fear. What if I turn out to be a public failure? The opportunity cost for this decision is hundreds of thousands of dollars. Why am I ready to part with that kind of money? I would disrupt my corporate career growth.

2. Self-Doubt is another factor that led me to overthinking. I never had a world changing idea or a grand vision that I wanted to pursue. I had never sold a thing in my life to a stranger. The idea of making a living on your own terms was foreign to me. I doubted myself since I didn’t have the skills required for the journey I wanted to embark on.

3. Guilt may not be a common reason for overthinking. However, it was holding me back. 15 years ago I immigrated to the US for better opportunities and life. And I was lucky to experience them. I worked at the biggest tech firms on cutting edge problems and a well-paid job. It allowed me to live a comfortable life with my wife and two young kids in the suburbs. I have seen my parents work hard to provide me the best education and resources they could afford. I want my kids to receive the same. Then why would I want to ruin my chances of continuing a comfortable life for me and my family? Wouldn’t I let down my parents and my kids with such career altering risky decision?

How to Overcome Overthinking

One practical technique to overcome overthinking is to think in terms of "Two-Way Door" decisions. These are decisions that are reversible, allowing you to course-correct quickly. They were popularized by Jeff Bezos within Amazon’s corporate culture.

For me, Two-Way Door decisions are a practical way to limit my downside while maximizing the upside. For instance, when I finally decided to embark on my own journey, I gave myself one year to experiment with my ideas and experience the outcomes. This period should be enough to determine:

1. Whether I enjoy the self-employed journey, and

2. If being self-employed is financially viable.

If things didn't work out, I could always rejoin the workforce. The downside would be limited to a year's worth of expenses and lost salary. The upside, however, remained unknown.

Another practical strategy is time-boxing decision making. For example I have decided not to spend more than 2-3 weeks to launch an idea. If the idea gains momentum, then I can justify spending additional time on it. Creating time based boundaries helps the brain to prioritize what’s important and filter out the noise. More importantly it helps fight paralysis of analysis.

My rational mind agreed to this plan, but my emotional mind still grappled with thoughts of failure, self-doubt and guilt. Failing is hard, but over the years, I’ve realized that growth happens whether you fail or succeed. However, failure helps identify your blind spots. The sooner I know them, the better. If I fail due to lack of skills, I know where I need to improve. If it's due to lack of motivation, it’s a sign this journey isn’t for me. Similarly, if a lack of confidence is holding me back from executing my plans, that's a clear indication this path may not be right. The only way to find out was to just start and stop overthinking.

But what about the guilt? I asked myself: Would I be proud if my kids remembered me for exploring new possibilities rather than sticking to the traditional path?

The answer was clear -

Don’t Overthink, Just Start.

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