Why You Don't Need a Perfect Plan

You’ve probably felt it before. Staring at a big decision, waiting for the perfect answer to appear. You tell yourself: once things are clearer, then you’ll start.

In the 1950s, Nobel laureate Herbert Simon studied this human tendency and called it bounded rationality.

He found that we rarely make perfectly rational decisions. We don’t have complete information, unlimited time, or the ability to predict the future. So we ​make the best possible decision​ given what we know now.

He called it satisficing, a blend of “satisfy” and “suffice.” It’s not about perfection. It’s about moving forward with enough clarity to act.

And yet, most people wait. They think clarity means certainty—that if they think longer, research more, or plan better, the fog will lift. But that’s not how real progress happens. The fog only clears once you start walking.

How I Found My Path Without One

Before Wolo Yoga or AppSumo, I studied Culinary Arts and worked at restaurants, coffee shops, and bars—as a chef, bartender, and barista.

Later, I sold insurance, ran a catering business, opened a café, started a coffee blog, and launched a cold-brew brand. Then came freelance design, WordPress themes, Quora writing, and eventually, growth marketing.

It wasn’t glamorous. I often felt lost, switching directions while friends built stable careers. At times, it looked less like ambition and more like confusion. But every step—even ​the ones that didn’t work​—revealed something. Each experiment gave me feedback to adjust my direction. I didn’t find clarity before moving. I found it because I moved.

Back then, it felt like wandering. Now I see it was exploration disguised as chaos. As Steve Jobs once said,

You can’t connect the dots looking forward; you can only connect them looking backward.

That’s the paradox of clarity: it’s earned through motion, not discovered in thought.

How to Move Without Perfect Clarity

You don’t need a perfect path. You simply need a compass that evolves. Here’s how to build one.

1. Act to learn, not to be right

When Jeff Bezos left his hedge-fund job in 1994, he didn’t know if selling books online would work. What he did know was that the internet was growing 2,300 percent a year. And that he’d regret not trying.

That became his Regret Minimization Framework: act in ways your future self won’t regret, even if the outcome is uncertain.

Most people overthink because they want to be right before they move. But progress starts when you treat decisions as experiments. Bounded rationality says we never have all the data anyway, so act to gather more of it.

Motion is information. Start small, start now, ​start before you're ready​.

2. Use curiosity as your compass

Neuroscientist George Loewenstein found that curiosity arises from the gap between what we know and what we want to know. That discomfort—the information gap—pushes us to explore. In decision science, it’s called the exploration vs. exploitation tradeoff.

You can’t explore forever, but you also can’t grow by staying put. Curiosity helps you strike the balance: explore just enough to update your map, then exploit what works.

The feeling of “not knowing” isn’t confusion. It’s a signal you’re learning something new. Curiosity is your radar in the fog, not for finding a straight road, but for noticing what lights up when you move.

3. Seek progress, not perfection

Harvard researcher Teresa Amabile found that the biggest motivator at work isn’t money or recognition, it’s the feeling of making progress. Even small wins matter. Psychologists call this the progress principle.

Every small step is a feedback loop. It teaches you what’s working, what’s not, and what to try next. Progress isn’t a feeling, it’s information. We often think we need motivation to act. But most times, action creates motivation.

The key isn’t to have everything figured out. Instead, it's about doing something today that moves the story forward.

4. Design for flexibility, not certainty

Nassim Taleb calls it optionality: the ability to benefit from uncertainty by keeping your options open. When you stop chasing the perfect plan and instead build reversible, low-risk moves, you turn uncertainty into opportunity.

Optionality looks like developing skills that apply across domains: storytelling, design, communication, and product thinking. I call these the ​meta-skills​.

Each one compounds in multiple directions. You don’t need to predict the future; you need to stay adaptable to it. Flexibility outperforms foresight.

The Evolving Compass

Clarity isn’t about seeing the whole map. It’s about trusting that your next step will reveal the next clue. Each decision teaches you something about who you are and what you value.

The map keeps changing. The compass doesn’t. It points forward, but only when you’re moving.