It was the beginning of 2018 and I believed that I was on the cusp of “the next big thing.”

After nine months of hard work, I had built a platform called Educo with TED Talk speakers to help them turn their content into step-by-step applications that people could use to take action on the advice from their talks.

The idea of helping individuals take action on expert advice had been a dream of mine for years – and finally it was about to become a reality.

It was not long, however, before my dream turned into a nightmare.

We didn’t hit our sales projections for the quarter.

Our applications were full of bugs and the customer complaints continued to pile up.

There was no question that I had created more problems than I had solved.

I had failed.

I let my investors down, I let the TED speakers down, I let our customers down, I let myself down.

But the company wasn’t out of cash yet. And this was no time to feel sorry for myself.


Resonding to Failure

Rather than wallow in guilt, I needed to take a cold hard look at my situation.

How much runway did I have left?
How could I use that time to keep the company from folding?
What services could I provide to keep the company alive in the long-term?

I only had a month of runway left, so I needed to act fast.

Luckily, I lived in Florida at the time and could rent my apartment out on Airbnb at a hefty profit.

Although this would buy me some time, it also forced me to confront one of my greatest weaknesses as an entrepreneur – a lack of attention to detail.

My building frowned upon renting out your place on Airbnb. So I needed to get every detail of the check in process right in order to pull it off without them finding out.

This increased pressure helped me hone my organizational skills. It exposed me to new automation tools and processes. It helped me realize that I’m actually quite good at operations when I set my mind to it.

The Airbnb was a success. I bought myself some time.

Next, I needed to start selling my services.

Although we didn’t have success with the end-users of our applications, I found that I was very good at selling to the TED Talk speakers.

I learned that selling isn’t about trying to convince people to buy your product. It’s really about asking good questions, understanding the person’s needs, and working together to find a solution.

I created such a strong bond with the TED Talk speakers that I felt completely comfortable telling them the hard truth of the situation and asking if they knew of any opportunities for someone with my skill set.

One of the speakers, Bill Eckstrom, connected me with Josh and Econic.

Josh told me he needed someone to head up a new project his company was working on to help rural communities develop entrepreneurial ecosystems.

I was just at as passionate about taking on that opportunity as I was with Educo and I have been working here in my dream job ever since.

I made it through the hardest time of my life – and became a better person because of it.

That doesn’t change the fact that I still let a lot of people down. However, if I had beat myself up with guilt, I would’ve only made things worse.

Rather than embrace guilt, here are three better ways to respond to failure:


1. What Would You Tell Your Best Friend?

Imagine your best friend took a risk like I did and failed.

What advice would you give them?

Would you try to make them feel guilty about their poor decision-making skills?

Would you call them stupid and hopeless for taking a chance?

Of course not! You know intuitively that making them feel bad won’t help. Right now, they need your support to rebound from this failure and learn from it.

Are you any different? What would your best friend tell you if you failed?

When you treat yourself like a best friend, you gain perspective on the reality of your situation.

You can see that you can’t dig yourself out of a hole by simply beating yourself up. You can see that this isn’t the time to mope. This is the time for action.

The next time you start to feel guilty about a failure, pause.

Think about what you would tell your best friend if they were in your situation. The advice you give him or her may be the difference between getting out of a hole – or digging deeper.


2. Withhold Judgment

We live in volatile and uncertain times.

You have no idea how a failure may end up actually helping you over the long-term.

I had no idea that facing a failure would reveal my operational skills. I had no idea that failing would lead to finding the best job of my life. I had no idea that, despite the failure, 2018 would still turn into the best year of my life.

When you allow yourself to embrace guilt over a failure, you judge the situation for how it appears today. However, you have no idea how failure is going to look in hindsight.

Instead of being quick to judge, be quick to seek the whole truth of your situation.


3. Seek the Whole Truth

Feeling guilty makes you feel emotional. And when you have failed, an emotional, judgmental, response is not what you want.

Instead, you want to take a calm, cool, levelheaded approach to understand the truth of what really happened here.

Why did things not work out the way you wanted?

Was it the wrong goal?

Was it the wrong behavior?

Finding the answers to these questions helps you learn from failure. However, the more guilty you feel, the harder it is to find those answers.

Feeling guilty about a failure feels bad enough. Searching for all the reasons why you failed feels even worse.

So when you feel guilty, you don’t want to find a truth that will make you feel even worse than you already do.

Instead, you want to push away all of your feelings of guilt and find the things that make you feel better.

Bring on the Ben & Jerry’s.

It may feel noble to feel guilty when you fail. But a far more noble act is to look the truth about your failure in the eye and learn from it.



Failure is inevitable. Beating yourself up about that failure, isn’t.

Our brains are always worried about how others may judge our success and failures. That judgment was once the difference between the safety and security of the tribe, and facing the wild alone.

Thus, we all have an internal judge who makes us feel guilty whenever we don’t live up to the story we want others to believe about us.

Defeating this internal judge is no easy task. I doubt anyone ever silences it completely. But understand that you are not imprisoned by your guilt. You have a choice.

You can choose to think about what you would tell your best friend.

You can choose to withhold your judgment and see how this failure looks in hindsight.

You can choose to look past your guilt in search of the truth.

Rather than beat yourself up, you can choose to get up.