Why Some Failures are Worth Chasing?

I’ve been thinking a lot about failure, and I think we often talk about it in ways that are either too romantic or too vague.

There are a few ideas about failure that have shaped how I think about risk and growth.

1. Fail faster.
If something is going to fail, you want to know as quickly as possible.
The most expensive failures aren’t dramatic—they’re slow. Years invested, energy drained, momentum lost, all to arrive at the same outcome you could have reached much earlier. Fast failure isn’t recklessness; it’s respect for time.

2. Growth requires discomfort.
If you never feel uncomfortable, you’re probably not taking meaningful risks.
And if you’re not risking failure, you’re likely choosing safety over growth. Most of the opportunities that matter feel a little (or a lot) unsettling when you step into them.

3. Not all failures are equal.
There’s a big difference between failure from doing and failure from inaction.

A friend’s son recently did a college project modeled after Shark Tank. His idea—an AI platform—was compelling enough that the judges gave him a small amount of funding to pursue it. Since then, he’s changed the focus, adjusted the target customer, reworked the product, and poured real effort into trying to make it work.

It might fail.
Honestly, it probably will.

But what an incredible failure.

In the process, he’s learning how to:

• Start something from scratch

• Work with partners

• Engage with investors

• Navigate ambiguity and pressure

• Understand what he’s capable of

He’s building skills, confidence, and relationships that will compound long after this specific idea lives or dies.

That’s what I think of as a good failure.

Failure driven by effort, curiosity, and courage—not by apathy or fear.
Failure that leaves you better equipped for whatever comes next.

The goal isn’t to fail for the sake of failing.
The goal is to take real swings, learn quickly, and avoid the quiet failure of never trying at all.

I’d take a good failure over a safe regret every time.

About Carter Cathey

Carter Cathey is a sales and revenue leader with more than 20 years of experience helping market research, technology, and private-equity-backed businesses scale revenue, improve operations, and build predictable growth systems.

Throughout his career, he has led sales transformation initiatives, pricing strategy projects, subscription business model transitions, operational redesign efforts, and commercial growth programs.

He writes about leadership, organizational design, business systems, data-driven decision making, and the challenges companies face as they scale.

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