Lisa Guan's Innovation World

There’s a quote by John Bergman that stuck with me the moment I read it:

“There is never enough time to do it right, but there is always enough time to do it over.”

The more I think about it, the more I realize how true—and how frustrating—this is in the way we often approach work, projects, and even life decisions.

Why does this happen?

1. “Do it over” feels easier than “do it right”

When you’re redoing something, the steps are clear: fix, patch, repeat, ship. It’s mechanical labor. But “doing it right” requires mental labor—reflection, iteration, cross-checking, thinking through second- and third-order consequences. That’s hard work. And hard work upfront often doesn’t have visible payoff until much later.

Further more, there is a dopamine hit when you cross out a task. It feels like progress. In fact, ticking boxes might be one of the biggest productivity illusions. We look busy, we feel accomplished, but we may not actually be advancing toward the right outcome.

Finding the right problem, defining it clearly, and setting up the right solution path doesn’t give you that quick dopamine hit. It’s slow satisfaction. And that delay often discourages people from taking the “do it right” path.

2. We don’t reward discovery time

Discovery requires patience. It requires sitting in ambiguity. It requires saying, “I don’t know yet.” And honestly, our work cultures don’t always reward that. There’s constant pressure to deliver fast. “Agile” gets misinterpreted as “ship it yesterday.” But true agility is about adaptability and learning, not speed at all costs. When we skip “doing it right” in favor of “just get it out,” we often buy ourselves speed today at the expense of time tomorrow.

Sometimes people know deep down they’re skipping critical thinking, but they’re afraid of being seen as “slowing things down.” So they keep quiet, follow the momentum, and let problems accumulate. Ironically, this silence ends up delaying the project even more down the road.

3. “Doing it over” usually costs more than we think

Sure, it feels like a quick patch. But hidden costs add up: wasted hours, team frustration, customer dissatisfaction, lost credibility. Rarely do we actually calculate the cost of rework. If we did, we’d see that “doing it right” upfront isn’t a luxury—it’s a cost-saving measure.

4. Doing it right requires courage

It’s not just about patience—it’s about courage. It takes guts to raise the uncomfortable questions early. To challenge assumptions when everyone else is charging ahead. To insist on clarity when ambiguity feels “good enough.” That courage is often what separates great leaders and teams from mediocre ones.

What can we do differently?

I don’t think this is about perfectionism. “Doing it right” doesn’t mean polishing endlessly or delaying forever. It means making sure we’re solving the right problem, with the right approach, at the right level of depth.

Here are some practical shifts I’ve seen help:

1. Celebrate questions, not just answers. In meetings, give recognition to people who slow things down with thoughtful questions. It signals that discovery is valuable.
   
2. Separate “deciding” from “doing.” Build explicit checkpoints where the team pauses to validate assumptions before moving forward.
   
3. Reward long-term outcomes. Metrics that only track short-term deliverables encourage “do it over.” Metrics that track long-term impact encourage “do it right.”
   
4. Shift the culture of speed. Redefine speed as “fast learning” instead of “fast delivery.” Encourage small experiments early rather than large corrections later.
   
5. Normalize discomfort. Remind teams that sitting in limbo—when things feel uncertain—is not wasted time. It’s part of doing the deep work that prevents rework later.

A personal reflection

When I think back on the times I rushed, I see exactly what Bergman meant. I got the immediate satisfaction of finishing a task, only to face the disappointment of redoing it later. But the times I slowed down, asked the uncomfortable questions, and allowed myself to sit in uncertainty—those are the times that produced the most enduring results.

It makes me wonder: what if we measured productivity not by how much we do, but by how little we redo?

In the end, it’s not about never making mistakes—mistakes are inevitable. It’s about having the discipline and courage to invest in “doing it right” often enough that our mistakes become stepping stones, not sinkholes.

Because while there may always be enough time to do it over, imagine what we could to do it right.