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Failing Flawlessly: How to be a Graceful Small Business Owner

Updated: Feb 12, 2023

No one likes to fail. No one talks about their failures in great excitement or pride. If anything, failure is something we all keep a secret, ashamed of what we didn't accomplish, instead only sharing our successes. However, talking about our failures shouldn't be one of shame, it should be one of reflection and appreciation.

Husband helping his wife back up after she slipped on some ice
We all fall down sometimes.

That's because we took a chance, we leapt when we didn't know what might be on the other side. So what if it didn't work out, we eliminated one more what-if in a world of unknowns. That should be something to celebrate, especially if we didn't give up!

Navigating your business is a constant struggle for most.  Like using a compass, a business advisor can help.
Navigate your failure
"Failure is simply the opportunity to begin again, this time more intelligently." - Henry Ford

Chances are, if you're a small business owner, you've achieved a great success in your life; however, there is an equal chance that you also have a lot of failure behind and around you OR you want to take a chance, but are afraid you might jeopardize it all.

We, as the entrepreneurs and business owners of the world, should talk about failure and how to learn from it instead of keeping it a secret. We should avoid it as best we can, but we should also celebrate the positives when it shows its face.


As small business owners, we take failures a bit more harsh than the average person. It's just part of the culture of entrepreneurship. How we handle failure can have a massive impact on the moment but also on your ability to succeed on your next venture.

We put together a few tips on how you can best handle failures when they come along. Hopefully we can also put to bed the stigma surrounding failure so you can thrive.

1. Lend a Helping Hand When You See Failure

We all know from experience that failing is hard. And it never gets any easier, does it? So, when you see others experiencing a failure or getting dangerously close, be sure to offer your help and guidance. Not only is this right thing to do whenever someone is suffering, but it can have lasting benefits on your end as well.

Girl helping up a boy off the ground after he fell down
We have all fallen at some point.

By entrenching yourself within the issue at hand you will gain both knowledge and perspective that could help you avoid whatever downfall befell this other person. You can learn and understand what led them to the failure and use that to contrast with your own business decisions.

You'll also gain a bit of perspective. On how someone else dealt with their own failure, good or bad. This experiential perspective will give you a basis to rely upon if failure falls in your own backyard. You can now know, at least on some level, some of the do's and don'ts of handling failure.

In the end, more often than not, they will thank you for stepping up to help. And who knows, maybe they will be the ones that's there for you one day when you're facing failure yourself.

2. Celebrate the Benefits of Failure

In a world that punishes failure, be different. Be the someone that celebrates it!

Woman jumping for joy in the middle of a road in a remote location.
Always Celebrate! Even Failure

During a "normal" failure, there are all sorts of penalties, I-told-you-so's, and sly looks from both enemies and allies alike. We won't dive into the sociology of it all, but we all know that people cannot help themselves from reveling in disaster. Think of all the rubberneckers on the highway when there's an accident, for example.

Instead of focusing on those negatives, focus on the fact that you TRIED, which is a lot more than most can say. In fact, it is almost guaranteed those most of those trying to cast a penalty upon haven't even attempted anything near what you have.

Take a moment for yourself and look back on what you have accomplished. Even if the business ultimately failed, what did you learn or create along the way. We would even argue that you should formalize the celebration in form of a party of sorts.

Celebrating what you accomplished or even what you attempted to accomplish is one of the best ways to take the sting out of any failure. Celebrate the destruction of the "what if?"

3. Discuss, Chat, or Speak About Failures

Going off of the last tip, don't just celebrate failure. Discuss the failure with others within your sphere. Make sure you talk about it with your business partners, your team, or a business advisor. If needed, chat with someone who can also help with the emotional side.

business meeting where they are discussing the failure of a program
Discuss Your Failures

Discuss what went wrong, what you could have done differently, what worked, what ultimately fell short. Use these chats to deconstruct the map of decisions that led to the failure. It'll not only help you avoid those choices in the future. You may learn that it was an external factor beyond your control.

Consider a speaking engagement on the subject of your failure. This can bee a means of both helping others avoid clear mistakes, but also normalizing the failure in your mind. By confronting it regularly and logically you can nix its ability to become a stigma or wound in your entrepreneurial psyche.

This step is probably the most important component of overcoming failure, because without this step, how do you get better and try again. If you don't discuss your failures, you are more apt to make the same mistakes over and over again, and that's no fun!

4. Truly LEARN From the Failure

Learning goes hand-in-hand with talking about your upsets, because without discussing and analyzing the problems, you can't learn how to fix them.

Obviously (read with sarcasm) you should learn from your failures. But what we mean is to truly learn and understand your failure. From start to finish and every detail in between.

Business owner sitting on the best with a bunch of work items studying a failure
Studying isn't just for school

How you accomplish this step really comes down to each individual. But one thing we often suggest to our clients is to craft a detailed powerpoint presentation. The process of creating the information for the slides will be a subtle way of studying the issue.

Once you've created the presentation find a group of persons that you trust to take an interest in an give advice on the failure. Deliver your presentation to them and receive any questions or feedback. The presentation itself is a minor focus, the real goal is to get you comfortable with talking about it and more importantly, you gain comfort in discussing your failure.

Doing exercises like this gives you a method of study. This study helps engrain the failure in your mind to both handle the failure itself, but prevent future mistakes.

5. Be Courageous and Try again

Finally, my personal favorite - TRY AGAIN.

This one is easily the hardest to accomplish, but is easily the most effective. All the other items had a task to do, whereas this one is purely about self motivation.

As small business owners, we were all motivated by some drive to create. Sometimes failure can hit us in different ways, such as our ego. That wound can limit our drive.

However, this is the critical moment where you need to step up, dust yourself off, and try again.

It can help to look back on what motivated you to take a chance on business in the first place. If that younger, more naive version of you can do it, then there is no excuse for your current self.

Remember the quote from Henry Ford above and don't give up so easily. Stand back up, figure out what to change, and GO FOR IT!


Remember, if you're experiencing a failure or fear of failure with your small business, make sure to talk to someone. If you're unsure about who can help you, a business advisor, like Out of the Box Advisors, is a great place to start.

Having a business coach on board is a great way to minimize your chances of failure to begin with, but they are absolutely capable of helping you through one too. In fact, most have experienced failure along their path already and are poised to help you through yours.

If you've ever thought about bringing on a business coach for your small business don't forget to schedule a free consultation with one of our coaches today!

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