Bootstrapped Founder #101: Why Reading Fiction Is Important for Entrepreneurs

Dear founder,

I recently heard a saying: "leaders read, and readers lead." It made me reflect on my reading choices over the last few years and what I have discovered from switching things up a little.

A few years ago, you would have been unable to find any fiction in my library. All I consumed were non-fiction books from founders, entrepreneurs, industry giants, and all kinds of successful people. I believed that my time — being fully employed as a software engineer — was too precious to spend on stories. I wanted knowledge, and I thought that I could find that most readily in how-to books and non-fiction tomes.

Well, that has changed. I've been devouring a lot of fiction in the recent past, and I have found it to be more instructive and helpful than I ever could have guessed.

Prefer listening over reading? Listen to this on my podcast.

I started increasing my fiction consumption right when I went all-in on Twitter. The more I interacted with people on a daily basis, the more I found fiction to be beneficial to my work.

Well-written literary fiction allows me to shift my perspective into other people's minds. That's not very surprising, as the mere act of reading makes the reader imagine the character in their head and see the fictitious would through that character's eyes.

What I found incredible is that this perspective shift trained me in empathy. In slipping into those characters, I learned that even though someone might think, feel, and behave very differently from me, they still act as a generally coherent human beings.

When I first realized this, I immediately saw this applicable to my entrepreneurial life. Fiction shows flawed beings with flawed world views yet still acting consistently on the individual level. And that's a reality for any business owner! Your customers, your prospects, anyone you interact with are equally flawed and lacking the knowledge you have. They behave oddly from your perspective, but they perceive themselves to be very consistent.

Understanding this — and deeply empathizing with the lived reality of the people you want to serve and empower — makes interacting with "complicated" customers much easier. To them, your argument or knowledge of your own product doesn't matter: what matters is the consistency of their own worldview. The more you can help them integrate new knowledge without completely shifting their mindset, the easier it will be to help them, sell to them, and retain them as long-term customers of your business.

Another great learning that fiction provides is the focus on the narrative. Every good story has a hero's journey at its core. The better a storyteller the author is, the more you will relate to that journey, and the more you will care about it.

You want to be a storyteller yourself when you talk about your business, be it to your customers or even to yourself. The more fiction you read, the more you will learn what makes a narrative interesting, what role suspension and foreshadowing plays, and how it's not just "the one thing one person does" — fictional narratives are complex and interwoven.

As an entrepreneur, it's your responsibility to reduce this complexity and turn it into an easy-to-understand narrative that attracts compatible customers to your business. Talking about your business in terms of pure outputs is not enough, just like telling a story without noticeable levels of character development feels shallow and uninteresting.

Your personal story, the origins of your business idea, and how it relates to the lives of your prospective customers are all parts of the bigger hero's journey of your business.

And since we're talking about heroes: you'll want to make your customers the heroes of your business. Reading fiction will train you in understanding how heroes stand out from the background characters. It's about vibrancy: vibrant descriptions evoke vibrant emotions. In reading literary fiction, you'll expose yourself to vocabulary that resonates with you and the people you want it to resonate with. You can then use it in the website and email copy you use to engage with your customers to massively improved effect.

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In addition to learning how to narrate your journey better, fiction exposes you to new and previously unthinkable concepts that will impact the course of that journey.

Fantasy and science fiction are particularly good at this. They often depict worlds and societies that have developed from completely different assumptions than what we are used to. The social dynamics of those groups will wildly differ from what you know, yet they still make sense to anyone in that group.

Particularly in the early stages of building a business, this will come in very handy. When you do Embedded Exploration — the act of embedding yourself in your target audience's communities to learn as much as your can to find a critical problem worth building a business around — you will undoubtedly encounter communities with rules that you don't immediately understand. Knowing that they still make sense because of the underlying assumptions and learnings from long before you joined their community will help you blend in and become one of them.

Finally, fiction teaches you critical thinking. In trying to empathize with the characters of a story and what drives them, you'll undoubtedly agree more with some than others. You'll consider their internal motivations and judge their actions from an "in-between perspective," somewhere between your own moral position and the elaborate socio-ethical world view that the author instilled in the book. This mix of empathy and judgment is incredibly helpful for founders trying to be leaders and peers in a community they chose to serve and empower. Fiction trains you to maintain that balance.

One of my biggest learnings from reading fiction was that coherence could come from wildly different assumptions. Just because you're more knowledgeable doesn't mean that you're right. The concept of maintaining a consistent worldview is important to people, and the more you help them do that, the more they'll show appreciation. This doesn't mean that you can't stand behind your own truth. Just know that it might look a little bit different for the people you interact with.

Fiction teaches empathy. The best thing about this is that you don't need to do anything else but read. There are no worksheets or tests. Just gobble up more stories, and you'll see an improvement.

So, if you've been avoiding fiction because you felt it wouldn't help your entrepreneurial ambition, think again. It's a tool in your arsenal that can change the way you think about communities, people, and world-changing concepts. It's definitely worth a try.