Please Advise: How Do I Chase a Big Dream Without Losing Everything?

Becoming You with Suzy Welch

Suzy Welch interviews Lily, a 68-year-old retiree looking to embark on a new, meaningful venture that challenges her. While Lily possesses a

Key takeaways

• Lily's career history includes news anchoring, medical claims, and running 'Crafternoons'.
• The primary barrier to Lily's new venture is a very low tolerance for financial risk.

Main topics

• Retirement transitions
• Pursuing ambitious dreams

Notable quotes

I want to do something so scary it keeps me awakes at night and makes me doubt myself.

Conclusion

The episode serves as a practical guide for anyone feeling stuck by la

Transcript preview

Speaker 4 (0:00) I want to do something so scary it keeps me awake at night and makes me doubt myself. This is someone I want to talk to right now, the person saying that. And I'm telling you, Lily, our caller today is someone you want to hear from right now. Hello, I am Suzy Welch, and this is Please Advise, the companion podcast to Becoming You, where each week I take questions from real live listeners and walk alongside them trying to figure out something big and important about their lives. Our guest today is a woman named Lily. She's my vintage. She's 68 years young. She's just retired after a long and really interesting career, which has included everything from traveling with a band through Canada to settling medical insurance claims to wool felting, which happens to be actually an amazing art form. I'm aware of it, but not a lot of people are, I suppose. She's done all that and more. But now she's retired and she wants to do something that makes her uncomfortable. Something that's, you know, out of her comfort zone or something that's big and meaningful. But here is the complicating factor and it's not insignificant. She has very little comfort with financial risk. Riddle me that, will you? Well, guess what? Lily and I in the podcast today go on a journey together and we get there. We excavate our values and our aptitudes and our interests and we dig and we dig and we talk and we talk and eventually we get to a place that works for her, a place that feels scary and safe at the same time. Yes, we do that. And you don't have to believe me. You can listen in and hear Lily say it herself. So let us get going. I'm really glad you're here and you're along for the ride. Welcome again. I'm Susie Welch, and this is Please Advise. Speaker 3 (1:49) So I've had a number of traditional jobs and a number of creative jobs throughout my life. I retired about 18 months ago from the VA hospital. I loved the job. It was time to retire. And I had a bunch of things lined up that I was going to do. And within a week, I'm like, I don't want to do any of those things. So I am bored. Not ready to lay down the briefcase or whatever. I still have time left. And I want to do something so scary that it keeps me awake at night and makes me. doubt myself. This Speaker 4 (2:23) is going to be a very short podcast because the answer is come sit right next to me. I'm scared out of my mind with my life and I am don't sleep at night and you could just hang out with me. This is going to be the most fun and interesting conversation. I love you, by the way, because I am such a kindred spirit with you. And I think actually we are at the age where you're like, the clock is not ticking backward. Let's do the big swing. Let's do something super exciting. Let's do something scary. Because you know what? We've fallen down. so many times. Look, I don't want to speak for you, but I'm just saying like women of our age, we've fallen down and gotten the stuff kicked out of us enough times that we realize, you know what? Nothing's going to get me. I got this. So I want to hear a little bit more about what you want. You want to be scared. You want to be out of your comfort zone. Say more. Okay. So I've owned a number of businesses. Speaker 3 (3:13) Right before I retired, I was also running a thing called Crafternoons. Once a month, I'd teach an art class or what have you. I closed that down at this right around the same time I was retiring. I like organizing. I like planning. I mean, show me a spreadsheet, show me whatever. I don't work with committees well. It's like, what is the end result you want? Let Speaker 4 (3:38) me go do it. I want to start a little bit at the beginning here. Where were you born? Buffalo, Speaker 3 (3:42) New York. Speaker 4 (3:43) And tell me a little bit about your childhood, like just, you know, what kind of family and what, like, did you go to college? What'd you study? Give me a little, tell me the story of your life. So my Speaker 3 (3:53) dad Speaker 4 (3:53) was a Speaker 3 (3:54) salesman. He traveled, he sold wholesale shoes to stores. Mom was a homemaker. She basically raised me. My dad came in on Thursdays Speaker 4 (4:05) and Speaker 3 (4:05) Fridays and the weekends from traveling. And I had a really good childhood. I... Went to college. I started going to school for radio and TV and was going to go on and get my master's. But I got hired while I was still in college to be a news anchor. And I did that for a while. And I got bored, honestly, reading other people's stories. So I took a step down to be a reporter. And I loved it. I could go out. I could interview people, find out the story, whatever. Did that for actually five years at the same station. And then moved on, I needed more stable income. So I started working in medical claims, medical billing. Speaker 4 (4:48) Wait, wait, wait, wait, wait, wait. Let's just stop right here. You moved from reporting, which I happen to know is the most interesting job you can ever have, right? Every day different and exciting, meeting new people. Some days you're covering a fire. Another day you're covering something really beautiful, blah, blah, blah. And you went into medical claims? Speaker 3 (5:05) Yeah. because the money was great. At that point, I needed to be able to support myself. In between there, I had traveled with a band in Quebec. Didn't speak French, but, you know, fake it till you make it. So this was a good way for me to support myself. Wait, wait, Speaker 4 (5:22) wait, wait, wait, wait. I'm sorry. Like a Speaker 3 (5:23) rock and Speaker 4 (5:24) roll band? Speaker 3 (5:25) It depended. If we needed a place to sleep and food, we would play at a church and pretend to be, you know, a church band. Speaker 4 (5:35) Okay, so you left reporting to go like be in a band, which does sound incredibly fun. Then you went into medical claims. The money was fantastic. This reminds me of when I went into consulting after business school and I was like, I have more money than I actually know what to do with. It was the craziest feeling having been in reporting. All Speaker 1 (5:52) right. Speaker 3 (5:52) So what happened after that? I got married and didn't need the income as much. And so I started working as a full-time artist. And I had my own business selling wearable art, new, no felting, making scarves, making capes, that kind of thing. And that was exhausting. Okay. I actually made a piece that went to Stevie Nicks, which Speaker 4 (6:19) really, I know. I mean, so. Hello. So you, when did you know you were an artist? Did you always know you were an artist and that you were just waiting to express your artistry or did you suddenly say, hey, I think I'm going to try being an artist? Speaker 3 (6:32) I kind of was always doing something, even when I was a little kid, you know, drawing things or, you know, construction paper, whatever. Yeah. Speaker 4 (6:41) When Speaker 3 (6:41) I was probably 20, I started looking at it a little more seriously, not as a business, but. learning more. And then when I was in my 30s is when I really started saying,