Work Harder or Work Around?

Photo by Selma DA SILVA on Unsplash

This article originally appeared on Forbes in October, 2024. You can see it here, and you can see more of my writing for Forbes right here.

The founder’s journey is hard, no matter how you slice it—and no matter what a slam dunk the business idea seems to be at the outset. It isn’t made any easier by the fact that we live in a culture of entrepreneurship in which we’re expected to follow and measure ourselves against business plans and projections.

Anyone who’s been around this block knows that things never go as planned and projected. In fact, they often go in a better direction—if we have the eyes to see it.

Sure, we start off in the direction pre-defined by the path we’ve imagined, but after that, we have to keep our eyes up as much as our noses down.

The entrepreneurial journey is a process of solving one problem, revealing the next, solving that one and the next, and the next and the next. It’s defined by its obstacles.

Different obstacles require different solutions. Sometimes, the solution is to work harder, and sometimes, it’s better to look up, step back and reassess. One of the foundational skills on this path is knowing when to go through and when to go around.

Go around

Steven Spielberg’s Jaws (1975) made an entire generation afraid to go into ocean water above their knees. But in the two-hour movie, the shark only gets four minutes of screen time, and we don’t even see it until three-quarters of the way through the film.

That’s because the movie’s giant mechanical shark broke early in production. It worked fine in freshwater but malfunctioned in the salty seawater. Rather than exhausting resources to try to make the original shark work, Spielberg went around the problem.

He realized he didn’t need a whole shark, just that ominous, infamous fin. He portrayed the terror of the shark’s victims through tricky, chaotic point-of-view shots that didn’t need to show the shark.

Spielberg, and practically everyone else, agrees that his workaround created a more tense and memorable movie than if things had gone to plan.

We can reach a point in our businesses where we can only solve a problem through overly complicated, impractical solutions—which aren’t solutions at all. In those cases, you’ve got a problem that is more like a brick wall than a hurdle. When it doesn’t make sense to try to go through it, it’s time to think creatively about how you can get around it.

Go through

Sometimes, white-knuckling is the answer.

I spent the summer working on my next startup, Scribbly, which uses AI to paint children into custom storybooks. My first obstacle was trying to figure out how to wrangle the AI into creating stylistically consistent images throughout the story. For a while, I didn’t know if it was even possible. I spent late nights and early mornings prompting and fine-tuning over and over to achieve what I wanted at the quality and consistency I needed.

At one point, I considered bringing on an additional engineer to help me, but at the end of the day, I wanted to figure it out for myself. And I did.

In the process, I gained a deeper level of comfort with the technology that lays the foundation for future projects and explorations. When the next idea strikes, mine or a client’s, I’ll have an even bigger head start on the path to making it.

When we relish and get captivated by doing whatever it takes to get through an obstacle, I’ve found that often, it’s best to turn ourselves over to that passion. Going deep on a problem can not only solve it but also give us knowledge and experience that surpasses it.

Tips for success

• Be fierce in the mission but flexible in the details. The finished product of Jaws looked different than Spielberg’s original vision. But his mission was not to have a shark; his mission was to create a compelling, terrifying movie. He remained true to that. Have a clear and worthy mission, and be open to creative ways of accomplishing it.

• Understand that everything is progress. Sometimes, the path dead ends, becomes unclear or winds you back to a place you’ve already been. It’s always progress. The journey is never a straight line. Keep going.

• Enjoy the challenge. Entrepreneurship is not for people who want to follow a clear, pre-planned path. It’s for people who like to get neck-deep in uncharted waters, think differently and be surprised. Relish the journey and let the challenges energize you.

After working with dozens of entrepreneurs and starting multiple companies myself, I’ve found a place for a strong work ethic and an equally important place for creativity. For obstacles we need to go through, we work hard and go deep. For obstacles we need to go around, we think differently and find new approaches.

Practice the art of knowing the difference, and you’ll go far.