Why you should stop fighting and start embracing your self-doubt

The most successful people continuously question themselves.

Why you should stop fighting and start embracing your self-doubt
[Photos: manyakotic/iStock; liorpt/iStock]

In the startup world, it’s easy to get caught up in the seemingly overnight success stories of others, such as unicorn founders who launched billion-dollar companies in their 20s. Maybe they even dropped out of college to do so.


So we tell ourselves that this is what it takes to build a successful business. Rather than playing the long game, we’re eager for instant gratification, which, in startup terms, often means securing major VC funding. But I’d like to suggest that perhaps there’s another way to make it in the business world. This route is much more manageable and less fraught than the unicorn route. It’s a slower path that leads to a more rewarding destination.

And though many will tell you that sheer confidence is the key, I’d argue that the road to achievement is paved with self-doubt. With that in mind, I’m offering some tips to consider for developing a healthy habit of self-questioning.

But first: Why does the fast road to success seem so attractive?

We’re prone to quick pleasure

The bad news is: Studies show that most of us are prone to opting for immediate gratification, rather than holding out for more significant rewards.

You may have heard of the widely cited Marshmallow Experiment. Stanford psychologists offered young children one marshmallow that they could enjoy right away, or two if they waited a bit. As you might expect, researchers found that most of the children couldn’t resist the sweet treat. Only a few of the participants delayed gratification to receive the second marshmallow.


More interesting were the follow-up studies, which found that children who waited to receive the second marshmallow ended up faring better in various aspects of life. This included higher SAT scores, lower levels of substance abuse, lower likelihood of obesity, better responses to stress, and better social skills—as reported by their parents. The takeaway? It pays to put off pleasure, even if for most of us, our instincts push us to do otherwise.

It might not feel like it, but we can practice slowing down. Here’s why that matters.

The benefits of some self-doubt

Self-doubt get a bad rep, but it can lead to high-quality thinking and, ultimately, better results. In other words, a second marshmallow.

When we take the time to question ourselves, we trade a faster result for a more thoughtful, long-term one. We get a result that takes into consideration both the immediate consequences and the effects down the road. This concept is captured by the idea of second-order thinking, a practice that involves continually asking yourself, “And then what?”

Stopping to consider the future impacts is what separates good business decisions and great ones. Back when I was still working as a programmer for a media company and moonlighting for my fledgling startup, JotForm, I thought of quitting my day job and going full-time with my dream. Had I done so, my life would have changed overnight.


Instead, I bided my time and chose the bootstrapping route. Thirteen years and 5 million users later, I’m all in, and I’ve maintained full control over the company. For me, that’s the second marshmallow, and I wouldn’t have done it any other way.

I’m not suggesting that my path is for everyone. I do know, however, that I reached the best outcome for the business and lifestyle I wanted when I slowed down and asked myself the hard questions, such as:

  • What kind of culture do I want to create?
  • What will I sacrifice by becoming VC-funded?

Building a sustainable business takes time, but if you’re providing real value to your customers, eventually, results will emerge.

Here are some tips for building a (healthy) level of self-doubt into your day-to-day lives.

1. Build time into your schedule for reflection

Bill Gates instituted Think Weeks, twice-a-year retreats during which he completely disconnects at a hideaway cottage. Mike Karnjanaprakorn, founder and CEO of Skillshare, does the same.


We might not all have a secluded cabin to escape to, but I think it’s crucial to build regular time in your schedule for totally unplugging.

2. Get comfortable with alone time

Solitude can help us to tap into our deepest level of thinking. Some of my best ideas have come during quiet times—with a window seat and a few hours to myself.

Being alone can feel uncomfortable at first—we do nearly anything to avoid it—so start small, with a walk or a coffee. Pretty soon you’ll notice that each time it becomes easier, and you’ll eventually start looking forward to the ritual.

3. Become a “second-order” thinker

Technology has made decision-making more straightforward than ever. A potentially life-altering decision can be one reply-click away.

Before making any important decisions, always run through the potential impact—both the immediate and further down the line. Ask yourself: What do the consequences look like in 10 minutes? Ten months? Ten years? Don’t just think about yourself either; make sure to consider what the impact will be for those around you.


With practice, we can cultivate a healthy level of self-doubt. And if you’re already prone to self-questioning, embrace that quality in yourself.

Aytekin Tank is the founder of JotForm, a popular online form builder. Established in 2006, JotForm allows customizable data collection for enhanced lead generation, survey distribution, payment collections, and more.