This year, I had the privilege of speaking with six incredible, courageous people who entrusted me with sharing the stories of their setbacks — and breaking them down to find the many jewels of wisdom in each one.
Every interview has left a mark on me, as we explored all kinds of subjects: from career confusion, to layoffs, to burnout, to health anxiety, to neurodiversity, to death of loved ones. I am grateful that this project could help even a few people realize that dealing with setbacks — of all sorts — is a shared, universal experience.
As Celebrating Setbacks turns nearly 1, I’m excited to share my favorite takeaways from each of my conversations this year.
Quick aside before we get started — in an effort to make this project as relevant as possible to readers, I’ve designed an extremely short (3 question!) survey. If you can spare 30 seconds, please take it by clicking the below button.
Now, let’s go!
#1: Joel Hoekstra: How To Move Past the Shame of Layoffs
Joel was my inaugural guest — and I’m thankful he agreed to chat, because it allowed this project to get started and set the tone for all future conversations. A former leader at Uber and Meta, Joel spoke bravely about his experience getting laid off two times, and how he used that as fuel to leave tech and start his own coaching business.
Main takeaway: It’s okay to be vulnerable, at any point in your journey. Joel admitted that he still felt nervous and had imposter syndrome as a coach sometimes, even after finding a career that was more aligned with him. It would have been easy for him to spin the narrative and say that his new job was a perfect antidote — as a contrast to the lows of getting layoffs. But it made me respect him even more that he was honest.
#2: Karen Chi: How to Let Go of the “Perfect” Career
A former executive at LinkedIn and Cameo, Karen faced a crossroads when she realized she wanted a career change - but didn’t know what to do next. In this wide-ranging interview, we discussed how “listening to your gut” is well-meaning but not helpful advice sometimes, and techniques to get clarity when you feel stuck.
Main takeaway: Collect the dots to connect the dots. Karen mentioned she had probably 100 informational interviews to get unstuck and decide her next move.
#3: Andrew Gorbaty: On Getting a New Job…And Cancer
Andrew is a former colleague of mine who was diagnosed with cancer at 28. Even while going through radiation and full-body surgery, he was still one of the kindest and most upbeat people I interacted with. We discuss how he processed getting the news of cancer, how to live for our dreams now, and generally how to go through a tremendously difficult experience — while remaining who you are.
Main takeaway: Death is less scary when we know what’s important to us.
I’m just going to requote from the reflection piece:
“It’s so easy to have a brush with mortality and freeze: to start freaking out and worrying about all the things we’d never get to accomplish. What I loved about Andrew’s approach is that it’s so simple, yet practical. He keeps a list of the things he wants to do in life, and tries to make sure he’s always making some kind of progress on it. It’s that simple. Instead of vaguely fretting about all the things he could miss out on, he clarifies what is really important to him, and works to move forward on it.
#4: Maddie Burton: Growing From Multiple Hardships At Once
This woman is amazing. Maddie Burton is the author of “On the Cusp,” a popular Substack newsletter, which she originally began when she experienced several losses at once: that of her mother, her job, and marriage, all in quick succession. She is graceful, kind, and unbelievably profound about how to deal with loss.
Main takeaway: Truly connect with people. Maddie said that before she lost her mother, she was generally good about connecting with people — but in retrospect, she was still keeping people at an arms’ length. Ever since our conversation, I have made an effort to really, truly connect with others — and it’s changed my life.
#5: Elizabeth Couch Naughton: How to Move On From Burnout
As a multiple-time startup sales leader, Elizabeth was living the life in her twenties: making more money than she knew what to do with, managing a ton of people. And yet she was battling severe burnout — that didn’t just disappear with quitting her job. In our interview, she discusses the nuances of burnout, and how the lessons she’s learned apply to her own career coaching clients, too.
Main takeaway: Quitting will not solve burnout or career misalignment on its own — you have to really, specifically understand what is not working for you.
#6: Sadie Shepard: How To Finally Embrace Who You Are
After ten years in tech and real estate, Sadie started her own business — but the journey wasn’t all easy. Dealing with multiple hardships at once — being a caregiver for her father, losing a friend, losing her job — helped her finally embrace who she was, without apology. We discuss neurodiversity, being a woman in business, and how watching our loved ones’ setbacks can make us grow stronger, too.
Main takeaway: Nothing bad will happen if we just show up as ourselves. During a particularly difficult period in Sadie’s life, she mentioned she didn’t have any more energy to indulge in people-pleasing — and what she found is that the people who loved and cared about her still supported her.
As always, thank you so much for reading throughout 2024. If you’d like to have your story featured, send me a message. And if you haven’t taken the survey, you can check it out here.
See you in your inboxes soon, and happy new year!
Cover Photo by Eyestetix Studio on Unsplash
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