Learning from failures and setbacks

Let's make better mistakes tomorrow

I was standing at the top of a blue run on a sunny, late-season ski Sunday with tears rolling down my cheeks as I remembered my ACL tear 14 months ago, and fear gripped me as I contemplated if I’m going to ski down or get on the lift and go back to the lodge. I have done a year of physical therapy, have gotten all the medical clearances, have been running and doing weights and I knew logically that I was ready. I also could not get my legs to move as I looked out at my smiling family waiting for me right below the initial drop - who all skied effortlessly and were cheering me on. A few deep breaths later and a “we can do hard things” reminder from Glennon Doyle’s Untamed, I pointed my skies down and plunged ahead.

As I made my way down the run, I thought about the fact that triumphs only happen after setbacks. I also thought about how hard and vulnerable it is to reflect on things that don’t go well, openly and publicly. Inspired by my own story of perseverance with skiing, as well as a recent panel at Guild where our top leaders opened discussed their ups and downs, I’d like to share what I have learned from first-hand failures. Disclaimer: by no means is this the list of my biggest setbacks, but rather a sampling of experiences that have shaped me in ways I wasn’t expecting.

Setback lesson #1 - One closed door helps you notice another one

On my first day of moving into the dorms at UCLA, I knew I wanted to be a Resident Assistant. I could see myself guiding and coaching incoming students and I knew I could nurture them while also creating a community. I applied twice for a stepping stone position (Program Assistant) and then once for a Resident Assistant role - and I got rejected every time. To say I was devasted, does not do my feelings justice. To this day, I shudder when I remember the calls and emails informing me of the decision.

However, the thing that happened after my first two rejections, was that I applied for a different role - to represent my dorm in the “student government” of dorms. Yes, that’s a thing and it is just as it sounds: representatives of each residence hall get together to discuss policy, cafeteria food, and elevator permits. And as it turns out, I found my people there. I met Adam (who was representing his hall), my best friend, who was a former rep, and multiple friends I am still in touch with - almost 20 years later.

I’m grateful that I learned what rejection feels like and grateful that I tried multiple times until I was convinced that I should try something else. How I wish I could tell the 18-year-old back then, that what felt like the end of the world, will turn out just fine.

Setback lesson #2 - When things don’t go your way, keep hustling

I have recently been moved into action by the unjustified war that Russia is waging on Ukraine and have begun volunteering for the 1K Project (providing direct relief to families impacted by the war). My “job” is to help with corporate sponsorship - so basically fundraising. I came into this effort pretty confidently - with all my connections at Microsoft, my vast MBA network spanning big tech and startups in the Pacific Northwest, and my past experience of working with donors when I was in politics - certainly, I would get some easy wins and contribute to the cause.

Unfortunately, a few weeks in and I’ve had a slow start. Sponsorships at large companies are incredibly hard to secure, lots of folks I have reached out to are understandably busy and start-ups have other things to worry about. What is top of mind for me, is not necessarily true for my network.

But the upside of this, I have rekindled my network and have found other ways to spread the word - through internal grassroots campaigns, finding new opportunities via Snapchat and TikTok and bringing it up in various professonal forums, I know I am helping but it is taking a lot longer than I thought.

A lesson for me out of this - do not give up and keep trying. It would be easier to quit and look for another organization or another way to help, but I’m going to keep trying, keep hustling and keep learning.

Shameless plug - if you or your organization are interested in supporting Ukraine and providing the fastest direct relief to families, please reach out to me for more info.

Setback lesson #3 - Ask for help and look for the helpers

I was reading Busy Toddler’s guide the other day about what to do if you lose a child at Disneyland (or any crowd really). What struck me is the advice to get loud - tell everyone you have a missing kid, give a description and ask for help. As a parent, I know that if and when this happens to me, I will be mortified and swimming in my own shame of “how could I do something like this” - but at the end of the day, that’s not productive.

In parenting, this haunts us all the time - the sense of constant “perceived mistakes” and the eternal advice from books, the internet, parents, and strangers. Look for those around you who are helping, not judging. Whether or not it is people offering to just listen, to bring you food or to hold your baby while you are taking a shower - look for the helpers and also ask for help.

When I hurt myself skiing a year ago, our first call was to our neighbors who were able to step up and help - watch our youngest daughter and drive with Adam to come to pick me up.

Summing it up

Failure and mistakes are inevitable if we are going to lead full and interesting lives. It happens personally and professionally, in big and small ways. So avoiding it is impossible, but normalizing it by pivoting when needed, hustling when possible, and finding helpers in hard moments is what has helped me get through the hard stuff.

We have a poster hanging at home which serves as a good reminder:

As always, thank you for allowing me the forum and platform to share my journey.