5 Things I Learned from Trying (and Failing at) Something New


Do you replay embarrassing moments in your head? I do and no matter how much time has passed I STILL shudder. My cringe-worthy memories center about a handful of character flaws, with my competitiveness set firmly at the center of my most embarrassing moments. Like that time I stormed out of a bowling alley because my sister was beating me. (Classy).

You see, I hate losing. Always have. My parents say I was born with the competitive streak (I don’t know which family member to thank for this— probably my dad!) and there are VHS tapes to prove it. Five-year-old Kate, on her big wheel, racing around the track with her head down as other 5-year-olds peddled leisurely, waving to their parents. I’m pretty much hard-wired to want to win at whatever it is I’m doing. That makes me a really great partner at cards and a really bad sport when forced to participate in any activity where hand/eye coordination is necessary.

With every weakness, there are strengths and vice versa. My competitiveness has helped me power through setbacks brought on by ADHD, it has given me the grit and sheer brute force needed to keep going when things got tough. It is true that as you get older the stark contrast between the positive and negative aspects of your character traits become a bit more gray. You learn to manage the extremes and regulate when you tip too far towards the pitfalls.

In my case, competitiveness has led me to abandon things I wanted to do just because I wasn’t good at them after a few tries. You might never know it, but most of what I do for a living every day used to live on my list of things I was bad at. Writing, illustration, social media, public speaking. I have failed spectacularly in ALL of these areas. I like to joke that Wit & Delight was the most sadistic of career paths considering the things I have to do every day have never come easily to me. And we all know now how much I HATE that. But what I’ve learned from having to set aside my ego in order to build a business that fulfills my purpose— helping people figure out who they are and how they want to live— wouldn’t be possible if I didn’t continue to learn new things.

Now, failing when learning something new is something I actually MAKE TIME to do. It is part of my weekly routine. I wind down by taking a class on illustration, on delivering a better story, on figuring out how the HECK to interpret analytics (which I am still SO BAD AT DOING). The act of being a student each week has taught me more than what was covered in each course. It has taught me lessons in humility, self-awareness, and most importantly, the importance of listening.

Lesson One: Doing something you are terrible at can be liberating. Gone is the pressure to make something amazing. There are literally no expectations, which means you can focus on the act of just doing, rather than excelling. This leads me to lesson two…

Lesson Two: There is always room for improvement. Once I started dabbling in Skillshare as a way to learn new skills, I checked out what other designers were teaching. It turns out I had A LOT to learn within my area of expertise! This was at first humbling, then scary. Making learning a part of growing your expertise is a must. What we decide to make our career requires looking outside ourselves at what others are doing better than we are.

Lesson Three: I kicked creative envy to the curb. I used to look at what other people could create with total envy. If only I knew how to take photos like her! If only I could illustrate like he does! After taking courses from the people I admired and envied I had a whole new appreciation for their process and humility. It turns out every expert is afraid of failing and has days, weeks, months, and even years when they are insecure about their work.

Lesson Four: Learning from other experts made me more open to sharing my knowledge. After taking courses from people who were eager to share their tricks of the trade, I felt inspired and driven to share MY secrets to help others who want to learn from my success. I’m currently trying to figure out how to take my years consulting for brands and putting it out into the world for others to utilize. (If you have thoughts on this– please e-mail me. I’d love to chat one-on-one with you!)

Lesson Five: You can learn something new from just about anyone. After taking 32.2 hours of Skillshare classes (!!!), I now make sure everyone on our team is in a role where they can totally own one aspect of our business. I turn to them when I have questions about their area of expertise. I ask them to go off and spend time honing in that skill. Even when they don’t think they’re teaching me, there are nuggets of inspiration, lessons, or new ways of thinking that they each contribute through collaborative work. I’ve learned that even when someone doesn’t think they’re teaching you, one simple prompt can help bring their knowledge to the surface. My go-to question? “I don’t know, what do you think?” I try to say this at least once in every meeting now.

I have had countless conversations with people who—after years of friendship—confess a creative dream to me as if it was something to be ashamed of. They think that because they don’t have the skills to make their dream a reality, that they are a fraud. That thinking is the biggest hurdle you need to get over in order to start investing in taking that first step towards learning something new.

So get out there! Fail at something you are terrible at! You might just learn something along the way.

Resources for you!

9 Skillshare Classes Definitely Worth Watching
Try one of my Skillshare classes: Building Your Online Presence: Personal Branding Through Social Media // Personal and Lifestyle Branding: Building Your Story
5 Ways to Harness Your Ambition + Powerful Tools to Help Get You on Your Way!
My First Podcast: What I’ve Learned From Failing

  • “I have had countless conversations with people who—after years of friendship—confess a creative dream to me as if it was something to be ashamed of. They think that because they don’t have the skills to make their dream a reality, that they are a fraud. That thinking is the biggest hurdle you need to get over in order to start investing in taking that first step towards learning something new.” – This very last part speaks to me the most. I am almost 50 and dreaming of a more creative life but scared shitless to jump!! Thank you for this post, it is just what my competitive self was needing.