Imagination is Overrated

Daniel Vassallo
6 min readApr 5


22 years ago, a close friend called me to ask if I wanted to go to a local trade show with him. I didn’t have anything better to do, so I went.

I came home from the trade show with a 12 foot boat. I was 18, and I had almost no money, but I could pay for the boat in installments. The boat didn’t come with a motor or any accessories, but I figured I’d find a way to afford them.

Photo by Nik on Unsplash

However, when I did the math, I didn’t like the numbers. It would have taken me months to save for a motor, and I wanted to use my boat that summer. So I decided to find a part-time job.

This was Malta in 2001, in an economy that was just starting to develop out of third-world status. Despite knowing quite a bit of programming, there were no fancy internship opportunities at tech companies. The only viable part-time work for me was working at a restaurant. So I took a job at one for a whopping $3.40/hr including tips.

18 year old me, boat owner.

2 years later, I was still working at the same restaurant. And that’s where I met my wife.

Today, after 20 years together, we are settled in the Pacific Northwest of the United States. We have 3 kiddos, two boys and one girl. A lot has happened since that phone call from my friend, but if that random call didn’t happen, nothing in my life would have been the same. I wouldn’t have met my wife, I wouldn’t be in the US, my 3 kids wouldn’t exist, and certainly, I wouldn’t be writing this post today.

My family, just before we became 5.

I’m sure you also have some story like this yourself. This is not uncommon. Most of us can recall some random chance encounter that completely changed the trajectory of our life. In fact, almost everything consequential in our lives happens this way: from being born, to meeting our friends, to finding a spouse, to settling in a place, to stumbling on a career, and so on. Randomness drives these things. We might start with a direction, but more often than not, we end up with something that would have been completely impossible to imagine beforehand.

Take being born. Who gets to pick where they are born or to whom they are born? Arguably the most consequential event in our lives is a totally random one. Warren Buffet refers to this as the “Ovarian Lottery.” He says he was incredibly lucky to be born in the United States, a country that rewards buying businesses and allocating capital. If he had been born in Bangladesh or in Afghanistan, his skill of allocating capital would have been almost useless.

My two boys now have a little sister!

So what does this have to do with business? Well, for one, we should embrace and use the random gifts life throws at us rather than trying to brute force our way onto ideas.

For some reason, we like to think that our ideas come to us in the shower. Or on a long walk in the countryside. Or during a brainstorming session. We tend to think we can use our imagination to find good opportunities, just by thinking hard and by avoiding distractions.

But let me tell you this: it rarely happens that way. Our imagination is good at optimizing ideas and extrapolating them. But it rarely leads to new ideas. If I had tried to imagine my life 22 years ago, all the consequential details would have been unimaginable. And the same thing applies to business.

A very common theme I hear among friends who work for themselves is that the things that are making them the most money are things they would have never imagined to be doing just a few years ago. They might have started with a direction, but some random chance encounter led them to try something that a minute before that encounter wasn’t even on their radar.

Sounds familiar?

This is not just an amusing theme. If you want to succeed in business, it’s important to embrace randomness. It might sound counterintuitive, but your goals and dreams can be your biggest obstacle in finding commercially viable opportunities. If you convince yourself that you should stick with your imagined goals, any random opportunity that comes your way that is not conducive to that goal, will feel like a distraction. But almost all good opportunities lie in that randomness.

Business is more random than it seems. It’s very hard to predict (or imagine) what will work and what won’t. It’s not even easy to imagine what we’ll like doing or dislike. We just have to try many things. Many small, safe-to-fail experiments. We learn by trial and error; not only what works as a business, but also what business works for our preferred lifestyle.

But how are we going to try many things? It’s already hard to find one good idea; let alone many. Ah, that’s because you’re trying to use your imagination to find ideas. But as I already convinced you (hopefully), our imagination is limited. It often needs a catalyst.

If we want to have an endless stream of ideas, we need to find an inspiration generator. Something that lets us see random things on a daily basis. Things that without this generator, they would have almost certainly never occurred to us on our own.

Think about how book publishers work. The executives at the company that published Harry Potter didn’t come up with the story themselves. They didn’t sit in a brainstorming session and ended up with a proposal to write a story about a young wizard at a school of wizardry. No, it would have never occurred to them. What book publishers do instead is they open up their inbox, and let random authors come to them with book ideas. Every morning the publisher goes through this stream of book ideas, and then decides which ones to pursue and which ones to ignore.

Or consider venture capitalists in Silicon Valley. Y Combinator would have never been able to imagine AirBnb, Stripe, Reddit, Instacart, Zapier, and Dropbox on their own. Yet, they made billions of dollars from these ideas. Ideas that came from randomness, when some random founder showed up at a random demo day, with a random idea, and YC chose to invest a small amount of money in them.

If you want to work for yourself, my best recommendation for you is to find your own inspiration generator. Something that on a daily basis exposes you to random things that you would have never thought of on your own. Over time, you will improve your selection criteria, and get better at choosing what things are worth trying. But the very first thing to do is to find your inspiration generator.

My own inspiration generator is Twitter. Not me tweeting, or building an audience, but just consuming my Twitter feed. Part of my morning routine is to walk my kids to school, come back home, make a cup of coffee, and spend 30 to 45 minutes scrolling through my Twitter feed. On Twitter I see other people doing things. Sometimes unconventional things. I skim through 99 out of 100 tweets, but there’s usually something I pause on. Something that makes me see an opportunity I had never seen before. I would almost feel the neurons in my brain rearranging themselves. This is called inspiration, and my Twitter feed is its generator.

Every project that I tried (successful or not) in the last few years came from my inspiration generator. The things I’m doing now are things I would have never imagined to be doing just a year or two ago. The things that paid off the most are the things I had the lowest hopes for, and vice versa. I would have found much less success if I didn’t embrace randomness. My imagination is just not enough.

Find me on Twitter if you want to add me to your inspiration generator!

Thanks to Louie Bacaj and Chris Wong for helping edit this piece.



Daniel Vassallo