[Our Team] The Freedom I Found In A $462 Mistake

I have to confess, I am thrifty. Ask my wife.

She might say I’m a penny-pincher; I say ‘frugal’ and ‘penny-wise.’ If there’s a deal or a promotion, I’m in! If there’s not, you bet I’m going to ask for one. I like quality stuff too, and I believe you-get-what-you-pay-for, but that doesn’t mean you have to overpay, right?

Naturally, this finance-savvy trait follows me in my personal and professional life too. So when I made a $462 blunder at work, my heart sank. But when I took the leap to share that blunder with our staff, I was surprised how it felt. This mistake felt like…freedom. (Right back at you, George Michael.) This post isn’t about how to avoid mistakes at work, although I hope you learn from mine. This post is about the freedom you find in a healthy work environment, and what I learned through my mistake—my $462 mistake.

A few weeks ago, I was busy planning our Annual GreenArrow Get-Together. It’s an event where all of our team members, far and wide, are flown into the Chicago area for a week of work meetings, coffee, socializing and getting to know each other more. My responsibilities include arranging flights, transportation to-and-from the various airports, hotel accommodations, meeting spaces, dinner reservations, social activities… you get the idea.

I was almost done when I started the usual double-check of my todos (thank you, Basecamp). And that’s when I saw it glaring at me: I had just booked a flight for Michael at 12:50 AM when it was supposed to be 12:50 PM. All my thrifty mind could hear were two words screaming in my head: CHANGE FEE?!

I jumped online, hopeful I made another mistake. Maybe I also accidentally paid for a fully refundable ticket? Granted, I never do, but that would be awesome, right? Nope. This was a legit mistake. A few points and clicks later, I updated the reservation. There it was: $462.00 to change the flight. But this post is about freedom, not about airline change fees (although that might be coming soon).

As I clicked ‘update’ and used my company card to pay for the change fee, I noticed something. Something I didn’t have at my previous employers. Something I couldn’t quite articulate. I noticed, I never once thought, “Oh man, management is going to ream me out, they’ll call HR, and this will come out of my next check.”

Below is what I emailed our management team, including David, our CEO:

The_Freedom_I_Found_In_A_Mistake-01.png And here was David’s reply:


Isn’t that refreshing? I knew telling David would get a fair response. He’s a fair guy. But how often does your CEO acknowledge mistakes are ‘easy’? My previous employers sure didn’t. With one mistake, I found a kind of freedom I’m not sure many people have at work.

Freedom? Yes, freedom. That ‘something’ I couldn’t articulate? It’s mental, physical, even spiritual freedom. My mind was free; I didn’t have to hide the truth or feel guilty or worry about what would come next. Physically, I no longer carried the weight of my mistake. (Studies show work stress or guilt can leave you in physical pain.) And spiritually, I was free; my conscience was acquitted and set at liberty. A freedom that was validated with the words “an easy mistake to make.”

Don’t get me wrong: make too many $462 mistakes, and the reply might not be so gentle. But David’s response reminded me that our management team is up to something big. We’re committed to a healthy work environment where our team members are free to do their best work, ask questions, and challenge the status quo. We’re committed to create great email software, laugh along the way, and yes, occasionally even make mistakes. (Sometimes, we willingly admit those mistakes on our blog!)

It wasn’t until I heard the team’s response at the Get Together that I realized making this mistake was a gift! Not one to repeat, but it served as a clear example of how far we’ve come in creating the environment we want for our team members—not to mention how far I’ve come in my own career (I’ve worked in some pretty unhealthy environments during my 15-year career).

Ours is a culture with high standards, high expectations, and yet the freedom to make mistakes. And I’m proud to be a part of it.


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