Ep. 184 Are You Using Defeat to Win or Quit? Failing Vs. Experimenting in Business

Failing versus experimenting might seem subtle, but this reframe can be a pivotal mindset shift for retail business owners! Let’s look at how choosing to reframe your thoughts around your business’s success (and failures) can help you be a happier, more resilient, and more successful indie shopkeeper.

Your brain might tell you that every other business immediately succeeds—and that you’re a failure when yours doesn’t. But what if you could reframe your failures as experiments instead? 

Entrepreneurship Is An Experiment

The truth is that entrepreneurship is a journey of pivoting, testing, experimenting, trying, attempting, and constant learning. Entrepreneurs don’t always hit it out of the ballpark with an idea or a newly opened business. Your mind may want to tell you this is the case, but it isn’t! 

I’ve heard many interviews with entrepreneurs on podcasts, at virtual summits, and at live events talk about how they’d worked on their business for 7, 10, or 15 years before they found success. 

Again and again, these stories include how people often assume they’re overnight sensations! People make these assumptions because they didn’t see how the business evolved—they only became aware of the business once they saw tons of success.

Failing versus experimenting

How We Think About Our Failures is Exhausting

Of course, some businesses succeed more quickly than others, but immediate success is NOT the norm. 

Instead, most of us are running marathons (probably with leg braces, smears of icy hot, and extra Advil in our running belt!), not sprinting with smiles on our faces and gold medals around our necks in year one of business. 

The marathon can be exhausting, I know. And when we’re failing to keep up the pace and wondering why we even started running, it can be extra frustrating to get a well-intentioned text from a friend with a platitude like… 

  • “Don’t fear failure, fear regret”
  • “It’s not a loss, it’s a lesson”
  • “Don’t give meaning to failure. It didn’t work. Move on.”

We might appreciate the gesture, but when we hear these things in the middle of feeling miserable, we can’t possibly embrace that type of positive thinking. We want to wallow in our anger, frustration, self-pity, and fatigue. Trust me, I’ve been there! 

But let me be clear: 

What truly makes owning a business exhausting is how we THINK about our failures.

And one of the quickest mindset shifts we can make to help us feel less fatigued? It lies in the idea of failing versus experimenting. 

Failing usually results in giving up. But if you’re experimenting, then you’re going to try again and again until the experiment works. Some might say this is splitting hairs, but reframing your failures as experiments can make a massive difference in how you feel about your business.

Let’s look at the three-step thought process that has helped me no longer hate myself for failing and instead view my failures as experiments. 

Step One: Identify Your Thoughts

The mentally draining thoughts are the ones where we beat ourselves up, ridicule ourselves for not getting something to work, and listen to the criticism of people around us. These thoughts can be about anything from a failed product line with a thousand bucks of extra merchandise crowding your back room to a failed business and shuttered store.

When you’re stuck thinking about failing (versus experimenting), your negative thoughts might tell you…

  • This is way too hard.
  • This was all a waste of my time.
  • Things never go my way.
  • I was never smart enough to do this.
  • I’m not good enough to do this!
  • I’m going to let everyone who counts on me down.
  • If only I tried harder.
  • I should have known better.
  • I never do things right.
  • All my employees think I’m stupid.

Instead of holding space for all those thoughts inside your head, I want you to dump them all on paper. Then, you can see and release them once they’re out of your brain. 

Step Two: Learn That Failure Can Be GOOD

Until I became a full-time entrepreneur, no one ever taught me that what we all know as “failure” is actually “experimenting”—and that experimenting is a GOOD thing! 

I still have people in my life who look down on pivoting or “quitting” when something isn’t working for me. But I embrace this part of me! The part of me that not only LOVES change, but the part of me that’s willing to test something without the result defining me. It’s so liberating. 

Winston Churchill once said, “To improve is to change; to be perfect is to change often.” 

In other words, if you want to get better at anything, you have to accept change. Change is a natural and beautiful process that leads to internal and external growth. Without that change, you would become stagnant and stale.

I’m not a fan of holding myself to a “perfect” standard, so my version of Churchill’s saying is this:

To improve is to experiment; to evolve is to experiment often.

If you feel a tug to stop beating yourself up and sitting in negativity about something that didn’t work, then you’re willing to or ready to embrace a shift in your thinking.

And that’s where thought work comes into play. Yep, you’re going to work on reframing your thoughts so that when you think about failing versus experimenting, you know you’re on the experimenting side.  

Failing versus experimenting

Step Three: Shift Your Thinking

Use the following as internal counter-arguments whenever your brain brings up mean thoughts about how you’re a failure, can’t do anything right, and shouldn’t even bother to continue.

  • Failure doesn’t slow me down. It propels me forward.
  • Failures are what you collect towards winning. 
  • Experimentation leads to success.
  • The great thing about experimenting is that I get to try again and figure out what will work. 
  • Everything is working. Even if this didn’t work out, I’m learning! 

Failing versus Experimenting Is How You Keep Going

There was recently a brief convo about failing versus experimenting in Master Shopkeepers. A group member posted the following: 

“I know that trial-and-error is a very costly, time-consuming, exhausting strategy at times, but I gotta tell ya….sometimes it leads to the greatest outcome. I think it’s important for us retailers to set ourselves up for surprises every now and then. Keeps the wheels turning!”

I responded with, “Yep! I have a podcast episode coming out soon on this topic. So many entrepreneurs let all the small and big failures define them. They don’t realize that THIS is what’s going to bring them success!”

I genuinely feel that one of the main reasons entrepreneurs “give up” on their businesses is that no one ever told them or modeled for them that experimenting leads to success. 

The next time you’re in the middle of a failed launch, a failed business, a failed revenue stream, or a failed project, you’ll probably find yourself drowning in negative thinking and weighed down by negative thoughts. If that happens, listen to this episode again! 

Instead of avoiding negative thoughts or shoving them into a dark corner of your brain…feel them. Process them with the three steps I’ve outlined in this post. And then thank your brain for trying to protect you. 

From one entrepreneur to another: Are you willing to be uncomfortable trying? 

Are you willing to let other people make comments and judge your journey? 

Are you willing to have fun experimenting? 

Failing versus experimenting might not seem like a big difference. But choosing to see your business as an experiment where you can try again without beating yourself up about failing? That thought process will help you become a resilient, happy, and ultimately successful entrepreneur.



  • [01:22] Entrepreneurship Is An Experiment
  • [02:17] How We Think About Our Failures is Exhausting
  • [04:09] Step One: Identify Your Thoughts
  • [06:22] Step Two: Learn That Failure Can Be GOOD
  • [08:23] Step Three: Shift Your Thinking
  • [09:30] Failing versus Experimenting Is How You Keep Going

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