Luck & Opportunity with Katie Dill


Katie Dill, Head of User Experience Design at Airbnb, grew up with a creative background that was far from typical. So how did she land her dream job at a company centered around creating unique experiences for their users?

Katie shares all about her journey, which often required her to step outside her comfort zone, and how she found her niche. Learn specific ingredients designers have that are useful to leaders, how she handles growing pains and tough feedback, and her wisdom on the relationship between luck and creating opportunities.

You have to make the scene ripe for luck to happen.
— Katie Dill

Highlighted Excerpt:

Majo: I’m curious about your time in Italy. What do you feel you really got from that experience? What did going into another culture do for you?

Katie: Yeah, it was the first time I had lived outside of the country, essentially on my own. This was in college, going to Florence, so yeah there were probably eight of my good friends in the city at the same time so it wasn’t exactly going out on a limb by myself, but it was baby steps to that and it definitely got me more open to the idea. It was actually quite transformative for me in a number of ways. So one– before I went my family used to make fun of me and say that I was a vampire because I would only eat white food. Like french fries and grilled cheese…basically I barely ate anything and when I did it was very bland. But when I went to Italy, and of course, Italian food is amazing, I got introduced to paninis and all sorts of wonderful things, because often times when you’re traveling you’re kind of forced to eat things you wouldn’t normally, maybe because you can’t understand the menu or whatever it is, and because of that I just fell in love with food. I realized how great it was and I realized that I was missing out on things.

So I think that’s just one example. When I travelled in that way, I realized I was missing out on things. And I realized that you can actually gain a lot by going outside your comfort zone and exploring new places. So I do think that changed me in a number of ways, including the fact that I continued traveling… and eating.

Majo: Which is fitting now that you’re at Airbnb.

Katie: Oh yeah, absolutely. I mean, it’s one of the reasons I wanted to go there. From that experience and subsequent ones of traveling and living in other parts of the world, I realized the value of going to another place and really being there, not just visiting. This might sound grandiose, especially ’cause I work at Airbnb, but I do feel that’s what Airbnb is doing. They’re helping people travel in a very different way, where you can live like a local. It’s actually breaking down cultural barriers, helping open people’s eyes and minds to other people in the world and see that there’s really less difference than they thought. There’s more commonality. And there’s more value in getting to know each other better. And so I’ve enjoyed Airbnb because of that, and I think it was my experience traveling that helped me see that.

Linda: It sounds like you might have been a little scared at first to go outside your comfort zone, what made you just actually do it?

Katie: I think it just goes back to remembering those things I was scared about once upon a time that ended up working out really well. A more recent example of something like that is, like when you’re asked to go and speak at something, something like that, and you run through all the reasons with yourself for why you shouldn’t do it. Like, I don’t have time to prepareI won’t say anything interesting, or I could screw up. You start to convince yourself out of it. One of the things I’ve been doing recently whenever I’m asked to do something like that is remembering the fact that I’ve been in that situation before and I was able to talk myself out of that negative voice. I did whatever it was, and it ended up paying off really well. In fact, I wouldn’t be working at Airbnb today if I hadn’t said “yes” in a situation like that.

Listen to the full episode here.

Show Notes:

  • Katie’s outdoorsy upbringing as a talented problem-solver and trouble-maker. [4:30]
  • How she discovered her niche and figured out how to make a career out of it (despite feeling out of her element). [10:58]
  • On her transformative trip to Italy, where she learned how much there is to gain by going outside your comfort zone. Plus, how to talk yourself out of talking yourself out of things. [15:58]
  • Creating opportunity vs. Luck (and the relationship between them). [20:17]
  • The different types of designers at Airbnb, Katie’s own creative vision as a designer, and how being creative makes her a better leader. [24:48]
  • Do women have a secret superpower they need to unlock? Katie, Majo, and Linda discuss. [29:19]
  • Dealing with transition: How Katie used positive self-talk, self-reliance, and self-confidence to adapt. [34:43]
  • Her biggest career challenges. [41:44]
  • How Katie handles growing pains and critical feedback (including the toughest pieces of feedback she’s ever received). [46:35]

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