Being an entrepreneur means experiencing a range of emotions, sometimes in quick succession: there’s frustration, inspiration, exhaustion, glee, satisfaction, anger, excitement, despair — to name a few. It’s a rollercoaster.
Success hinges on being able to manage those feelings, and not letting them unbalance the even keel needed to keep going through the highs and lows. But there is one emotion I always make a special note of, every time I feel it: surprise.
Surprise is what prompted me to start my company, Jotform. It was 2005, and I was working as a developer at a New York media company, coding custom web forms for editors who needed them quickly. One day, after building yet another nearly identical form, I did what any burned-out developer would do — I searched for a tool to make the process easier.
That search turned up nothing, and there it was: surprise. Could it possibly be that such a tool didn’t exist? It didn’t. And that’s when I knew I had a good idea on my hands.
Over time, I came to understand that surprise isn’t just a fleeting emotion. It’s a signal. Evidence that something’s been overlooked, or that an assumption that seemed widely accepted might, in fact, be wrong. And for entrepreneurs, those moments — if you know how to pay attention — can be the starting point of something big.
Related: 70 Small Business Ideas to Start in 2025
When surprise strikes
When something surprises me, I don’t brush it off — I investigate. I’ve learned that those unexpected moments often contain more insight than hours of brainstorming. If you stumble on an idea, the next step is to build a minimum viable product, or MVP, and get it into users’ hands as soon as possible.
Obviously, not every surprise will lead to a product — a lot of MVPs end up dead in the water, which is why I advise building them quickly. But the practice of noticing and reflecting on the unexpected builds a kind of mental radar, one that keeps you alert to opportunities others miss.
The same is also true for less pleasant surprises. I once had a Jotform customer — a well-known brand — ask me to send a salesperson to their office to learn more about our other products. I was completely caught off guard. Salespeople? We had no salespeople. Until that point, Jotform had been entirely self-service.
I was so stunned that I sent no one, and didn’t go myself, either. Surprise! We lost the client to a competitor, one that had a sales team. But that moment stayed with me and became the impetus to build Jotform Enterprise, which today is growing so quickly it will surpass our self-service version within a few years.
Surprises like these, pleasant or otherwise, are rarely random. They test assumptions and expose blind spots. And if you’re paying attention, they can reveal what should come next.
Systematizing surprise
You can’t plan for a surprise, obviously, but you can get better at spotting it. Over the years, I’ve learned to build what I think of as a “surprise radar:” a system that keeps me tuned in to the unexpected, even in the most ordinary moments.
The first step for me is to always stay curious, even — or perhaps especially — when doing routine tasks. It can be easy during these times to switch off your critical thinking brain. But those are often the best moments to notice inefficiencies or strange patterns. Why does this process take so long? Why do we always do it this way?
This way of thinking is what’s called a beginner’s mindset, and it can be tough to adopt if you are not a beginner in your field. Once we’ve gained enough knowledge in a given area, our brains forge shortcuts that, while timesaving, also reduce our capacity for surprise. It becomes easy to stop questioning how things are done.
Related: The Accidental Entrepreneur: 3 Tales of Entrepreneurial ‘Eureka’ Moments
One strategy to keep your brain from slipping into autopilot is to conduct a time audit, which can help you figure out where you’re sinking your precious time. There are plenty of different platforms for this, like Reclaim or Toggl, but what matters is that you can clearly understand what tasks are taking up too much of your day.
From there, search for automation or AI tools that can relieve the burden for you. If it’s been a few months since your last search, do it again — AI technology is evolving rapidly, and options that may not have existed just last week may well exist now.
If you’re still coming up short, consider this a potential opportunity. Someone will probably fill this void eventually. Why not you?
It’s also critical to get outside of your comfort zone. Read books and articles on topics seemingly unrelated to your job. Talk to people in different industries, with different expertise or whose ideas don’t align with your own.
Will this be uncomfortable? Sure. But that’s the point. Surprise exists at the edge of expectations, just outside of what you thought you knew. If you only stick to the familiar, you’ll rarely be surprised. And without surprise, innovation is unlikely. The more you train yourself to notice the unexpected, the more you’ll start seeing it not as a disruption, but as a guide.
Being an entrepreneur means experiencing a range of emotions, sometimes in quick succession: there’s frustration, inspiration, exhaustion, glee, satisfaction, anger, excitement, despair — to name a few. It’s a rollercoaster.
Success hinges on being able to manage those feelings, and not letting them unbalance the even keel needed to keep going through the highs and lows. But there is one emotion I always make a special note of, every time I feel it: surprise.
Surprise is what prompted me to start my company, Jotform. It was 2005, and I was working as a developer at a New York media company, coding custom web forms for editors who needed them quickly. One day, after building yet another nearly identical form, I did what any burned-out developer would do — I searched for a tool to make the process easier.
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