3 Real Life Super Embarrassing Failures

After reading lots of articles, blogs, and books about failure I've realized that a lot of writers talk about "Failures" as if it is a metaphor. Like some kind of low stake trial more than big, flat out, embarrassing failure. Because I didn't want you to get the wrong impression about what I meant here are 3 real life, super embarrassing, failures from my own life. 

See how young and hip I look.

See how young and hip I look.

#1 Being The Cool Hip Young Pastor

Right out of grad school I was hired by a fantastic church to be the cool hip young pastor. You know the type. The guy you hire to start a new worship service and bring in all the "young people". Six months in I started it up and boom we had 250 people at the first service. Six months later we had 100 people. Six months after that 50. By the time I left 30 or less. Based on the terms I was hired on....this was a failure. A big, public, embarrassing failure. 

Here is what I learned:

People are gracious. Even though we didn't start the next megachurch (thank God) a lot of people experienced a lot of really great joy, growth, and friendship as a result of our work. Turns out "success" wasn't required for good stuff to still happen. 

I am resilient. Even though I didn't hit the goals set out for me at the beginning I persevered and continued to find ways to do good work. I learned that my value is not my work and that people will give you second chances if you just keep showing up.

#2 The Big Fish Donor

When we started Neighboring Movement.org by SoCe Life it was my job to be the fundraiser. Within the first month I had a donor on the hook for a large, game changing, donation! I couldn't believe how awesome I was at this fundraising stuff!  Long story short; after 4 months of negotiating, dreaming, and acting like the money would come through the gift did not materialize. 

Here is what I learned:

Don't count money until it is in the bank! Because we were planning on a big gift we also were planning on big expenses including salaries, rent, and programs. Not having the gift come through meant decreasing and delaying most of those things. Which leads me to the second lesson.

You have to ask people for help when you need it. Remember the line from Lean on Me, 

Please swallow your pride
If I have things you need to borrow
For no one can fill those of your needs
That you won't let show

This was my moment to share my need. My big fat embarrassing need. On one Tuesday I spent the day making 21 phone calls to family, friends, and supporters. I shared about the donor and that we were on the brink of closing the non-profit before it even began. By the end of the day I raised enough money to cushion the blow until we could craft a new plan. It was the most humbling and grateful day of my entire life. 

#3 The Delayed Thank You

After months of nurturing a relationship with a donor we received a $10,000 check! I was blown away at the generosity and could not have been happier. The timing was weird. I was on vacation when it came in, there was a holiday, and we were transitioning responsibilities internally. Everyone thought someone else had completed our thank you process, and the donor went without contact for a month! It was horrible I felt like an incredible heel. 

Here is what I learned:

Don't rely on a process to relay gratitude. We did review our process for saying thank you, and I no longer wait for the process alone. From now on if I feel especially grateful then I'll just call right away. 

Apologies suck and are important. I did the only thing I could I called and apologized. Using the skills I learned from Nate Regier and Next Element I apologized my heart out. The donor was gracious and continued to give. 

So there you have it! These are some of my most embarrassing failures and they are now on the internet for everyone to see. These big ones and the little ones have helped shape who I am and I am sure that there will be more to come! 

Over the next couple months I am going to share several post all under the category: Free to Fail. Failing is one of the fears I am struggling with while launching this website; so I figured I would head it off early by obsessively reading and writing about it. Here is what you can expect


  1. August 1: Fighting with Dragons.
  2. August 8: Success is My Biggest Failure
  3. August 16: 3 Real Life Super Embarrassing Failures
  4. August 23: Apologies Don’t have to Suck
  5. August 30: Crushing the Second Attempt
  6. Sept. 6: Snappy Quotes about Failure
  7. Sept. 13: Shame Shame Go Away, Come Again...Never
  8. Sept. 20: Never Too Late for Now
  9. Sept. 27: The Irregular Webinar; Free To Fail

Each post will show up on Wednesdays. On Friday the post will be followed by a Tune In Tip. These weekly tips will share a practice you can try in real life. Finally the whole series will end with a webinar where we can discuss the topic in real time.

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