The One Question to Ask When Things Go Wrong


I was talking to 2 different friends this week about 2 completely different situations: 1 had some important recording sessions that had been in the books for months get postponed for weeks due to the recording engineer getting sick, and the other had come back from having dinner with friends and was feeling bad about not being “the fun friend.” 

One situation was caused by external forces, and the other was an internal force. 

But I had the same thought about both of them: 

What if it’s a gift? 




I’m sure you’ve found yourself in that kind of moment, when all of your hard work, planning, practicing, scheduling, etc. gets thwarted by something out of your control. The venue floods, the engineer gets sick, there’s a blizzard that night, or the world shuts down because of a global pandemic. 

We’ve all been there. 

“Oh no!” is our first thought. We feel demoralized. Like all of our hard work has just been flushed down the drain. It’s just so unfair! 

Somehow, we always focus on what was lost. The plan, the date, the expected outcome. We become so attached to them that we feel the loss deeply, and wonder how to move forward. Surely, we had set out the best possible plan, and, well, now what? Any other plan will be subpar, right? 


But what if it’s a gift? 

I asked my client how this delay in her recording sessions could actually benefit her, and she was able to list 1 good thing. Then another, and another. Soon, she had a list of about 6 reasons it was better to do the sessions later and was convinced this new plan was far superior to the old one.  


Photo by Brooke Lark by


As for my “unfun” friend? I actually laughed when she said it. This friend of mine is warm, generous, funny, kind, and loyal. Even though she is far away, I know I can depend on her, and she is my go-to person for bouncing ideas off of. 

I have other friends who I would describe as our “fun friends” and they serve other purposes. I go to them when I want to get out of my world and have an adventure, laugh, and forget my worries. Not be serious. 

But I wouldn’t necessarily think to go to them with a problem I was trying to work through. 

So I posed the question to my friend:

“What if the fact that you’re not super fun is your biggest gift?”



Her serious nature makes her calm, focused, and able to read people. She excels at one-on-one conversations, making the other person feel completely heard, understood, and appreciated. 

We all need a healthy mix of all kinds of friends: fun ones, serious ones, ones who know about the hip new wine bar that just opened, and ones who know how to keep a houseplant alive. 

We can’t as individuals be all of those things to all people, all the time. 

Instead of seeing a perceived lack as a flaw, what if we saw it as a gift? 



Are you “overly sensitive”? How can the fact that you are extremely sensitive be the most wonderful thing? Can you read people better than others, and pick up on subtle nuances in their moods?

Are you a terrible cook? How might that be the most wonderful thing? Are you the go-to expert on all of the best restaurants and food trucks in town?

Even “failures” can be a gift. Knowing what doesn’t work can be just as important as knowing what does, and you probably made new friends and contacts along the way that you can continue to partner with in other ways down the line. 

So my friend, the next time circumstances SEEM less than ideal–whether because of a perceived failure, an external smash-up of your well-laid plan, or something you see as a character flaw, ask yourself that one little question: 

“How might this be the most amazing gift?” 



P.S. Interested in a 2nd weekly dose of creative motivation and inspiration? Grab a copy of my free workbook “10 Habits of Successful Artists” and sign up for my weekly Friday newsletter: The Weekend List. See you soon!

2 Comments on “The One Question to Ask When Things Go Wrong

  1. We used to tell our kids, “expectations can kick your butt” and “try to shift your perspective”; I’m hoping one day to be able to internalize that for myself. Thanks for the pep talk!

  2. Lol. Thanks David, and yes-we’re all just works in progress when it comes to this. It’s as much a reminder for myself!

Leave a Reply

%d bloggers like this: