The term “failure” is scary.
Most of us were taught to stay away from it, be afraid of it, or be ashamed of it. We think that if we fail, it indicates we weren’t smart, good, or dedicated enough.
In the realm of side hustles, though, failure—especially failing quickly—can be one of the best ways to succeed in the long run.
Chris Guillebeau says in Side Hustle and The $100 Startup that you don’t need to plan for years or spend a lot of money to try out an idea. You only need a simple framework that lets you act quickly, learn quickly, and, if you need to, fail quickly.
This is why accepting controlled failure can be the key to finally getting your side business off the ground.
What Does It Really Mean to “Fail Fast”?
Failing quickly doesn’t mean being careless or giving up easily. It means:
- Trying out your idea early
- Getting feedback from the actual world
- Letting rid of things that don’t work
- Changing course or making changes based on data, not ego
You can save time, money, and energy by not committing too much to a lousy concept.
You could spend six months making a product that no one wants, or you could spend six days testing to see if people are interested.
Failing quickly is a strategy to keep your momentum going and boost your chances of finding something that works.
Why People Don’t Do This (And What It Costs Them)
There are two main traps that most side hustlers fall into:
- They take too long to start because they’re stuck in planning, researching, and overthinking.
- They stick with a bad concept for too long because they’re scared to leave or start over.
Both ways will take up your time, energy, and confidence.
If you don’t deal with minor, quick failures, they can turn into bigger, slower ones that make you give up and leave for good.
It’s not just sensible to fail quickly; it’s also a way to respect yourself. You mean: “My time is important to me. I have faith in my ability to learn and act rapidly.”
How to Prepare for Controlled Failure
Here’s how to accept failure without losing your mind.
1. Begin With a Small, Testable Idea
Choose a version of your hustle that you can try out for 7 to 10 days at a low cost. Please ask:
- How can I get something in front of someone the quickest?
- Can I sell it before I create anything?
- Is it okay if I provide a basic version instead of the whole package?
Guillebeau calls this the MVP, or Minimum Viable Product, in Side Hustle. It’s not about being perfect. It’s about evidence.
2. Set a Clear Picture of What Failure Looks Like Ahead of Time
Set your own standards for success and failure before you start. For instance:
- “I’ll change my mind if I don’t get 5 sign-ups in 7 days.”
- “If no one answers my outreach emails, I’ll try a different group of people.”
- “If I get interest but no sales, I’ll change the price or the message.”
This makes failure into information, not drama.
3. Start Before You Feel Ready
If you wait until you feel completely ready, you will only get one thing: a delay.
Instead, launch when you’re 70% ready, because you can only get the last 30% of input from real life.
The earlier you launch, the sooner you learn. And that learning is what gives you clarity, traction, and confidence.
4. Use Feedback as Fuel, Not Fire
You can learn a lot from things that didn’t succeed. After each test or launch:
- Look over what people said (or didn’t say)
- See where the procedure went wrong
- Just ask a few folks, “What didn’t you like about this?” or “What would have made you buy?”
You don’t want applause; you want the truth.
And honesty is the key to any great hustle.
5. Do It Again. Don’t Get Too Worked Up.
Your first concept doesn’t have to be perfect. It only has to be good enough to be tested.
Then, use what you learn to get better. Try a different group of people. Change the deal. Change the way it looks.
The objective isn’t to escape failure; it’s to keep getting better through it.
In the Real World: T-Shirts and Templates
You opened a t-shirt store on Etsy, for example. You spent weeks making, uploading, and promoting. No sales after a month.
That failure happened quickly, and it hurts.
You don’t give up completely, though; instead, you look back and see that your best post was on how you made your designs.
You change course: instead of selling shirts, you now sell design templates to other people who make things. They begin to buy.
Same abilities. Different offer. Same drive, but a new path.
That’s what failing fast looks like.
The Psychology of Failing Quickly (And How It Helps You Win)
You get locked in fear when you try to escape failure. You lose faith in yourself. You put off doing things. You wait for the “perfect idea,” but it never comes.
But when you let failure happen on a tiny scale, you:
- Gain confidence by building up speed
- Make yourself more emotionally strong
- Look at mistakes as feedback now
- Move on without any emotional baggage
It changes the way your brain works so that you can be flexible instead of scared.
And in the world of hustle, being able to change is always a good thing.
The Quickest Way to Find Out What Works
To people who aren’t in the know, it looks like anarchy, but it’s really a system:
- Check
- Fail
- Learn
- Change
- Grow
This is the same technique that has helped thousands of people across the world convert little ideas into full enterprises, like the ones in The $100 Startup.
It’s not a matter of luck. It’s quick failure with smart recovery.
Use Speed as a Strategy
You don’t have to fail large to learn.
You need to fail on purpose, early, and often so that you can fix your mistakes quickly, make something better, and attain your goals with minimal waste.
Just because you fail quickly doesn’t mean you’re not good at this.
It signifies you’re a pro at the game.
So stop trying to be flawless. Set your sights on the genuine thing. Try something little this week, and if it doesn’t work out, be ready to walk away.
That’s not giving up.
That’s what strategic entrepreneurship is.