how to stop feeling like a failure
by choosing who you're willing to disappoint.
“I’m trying my best 😭”
In my 20’s, I was working in our creative department and everyone was mad at me. At least, that’s how I felt. If you’ve ever worked with clients, at an agency, or in the creative field on any level, you know this feeling of abject failure. You have 50 projects. All of them have different deliverables. All 50 of your clients consider their project the most important undertaking that you have. Unless you work 24/7, you won’t be able to accomplish all of this work. Feels like a recipe for disaster.
My mom - who also happened to be my boss’s boss - and I were talking one day and I was describing my predicament to her. My closing statement was something like this: “I have all these projects, I’m failing at all of them, and everyone is disappointed in me. I’M TRYING MY BEST AND I’M FAILING.”
What my mom said next felt like a stream full of cold water to a man dying of thirst. It felt like a warm blanket in the winter. It felt like the feeling you feel when you take your socks off after a long day. It changed my life.
My mom said, “well, you just have to choose who you’re willing to disappoint.”
Wait. It can’t be that easy can it?
Trying to hide my joy at this revelation, I asked “what do you mean?”
She said, “who are you not willing to disappoint? You won’t fail if you know who you can’t disappoint.”
I said, “You, my dad (also my boss’s boss) and Tad (my boss).”
She said, “great, now you know who you can disappoint if you need to.”
From that day on, my relationship to the people I worked with changed. It wasn’t that I became belligerent, but I became more willing to “give up to go up.” To embrace the conflict of disappointing someone for the sake of pleasing someone who I care more about.
Now, the list is a little longer for me. But not that long.
To the best of my ability, I’m not willing to disappoint:
My wife
My children
My parents (I still work for them)
My team (I lead the leadership team at our church, and have a team of guys I coach with)
My closest friends
Everyone else is optional for me based on a lot of factors. And those people know it. Mostly because I disappoint them…😂
I don’t aim to do so, they’re just not more important to me than the other people on this list.
When considering your options, who are you willing to disappoint?
Every day, we are confronted with choices and opportunities as well as disappointments. When you make a choice there is always a trade off. The word decision means “cut off” in latin. So you cut off other options when you decide.
When you make someone happy, you often disappoint another. When you decide to take advantage of one opportunity, you miss out on the one you could have had. Choices are what life is made of.
Are you willing to disappoint your clients or your children? Your boss or your team? Your friends or your family? Yourself or the crowd? There’s a lot of layers to this.
Most of us burn out, get frustrated and otherwise “lose it” because we can’t please everyone and we feel like we have to. You don’t have to make everyone happy, just the people that matter most to you.
That doesn’t mean that we should intentionally disappoint people. But when weighing our options, we need to choose the people we are least willing to disappoint. In different seasons, we may be able to please more people than others.
you’ve had this power the whole time.
For a long time, you’ve been able and responsible for choosing who you are willing to disappoint. It’s ok. You can start giving yourself permission to do so.
PS
This is one of the greatest leadership lessons I’ve ever learned and it’s a short one. Some of yours probably are too. I’ve often found myself wrestling with a problem until the answer becomes as clear as one sentence or thought. That’s why coaching matters. When you have a coach, they help you distill your life into lessons, and your lessons into progress.
The greatest lessons in my life have come because I have sought coaching. Yours can too. It might be your parents, or a network or a mastermind group. But find someone to talk to who can help you realize what you’ve known all along.