We live in a society where changing direction in the face of insurmountable odds is seen as quitting or being a failure. But when you come to think about it, isn’t that a smart move? When everything is stacked up against you and there is no way you can succeed while following the same path, then it is time to pivot. As Casey Juanxi Li says, “There is no point in beating your head against a wall or going up the path of most resistance.” Continuing with this conversation, Samantha Postman elaborates on how pivoting has figured throughout her journey. Samantha and Casey also explore other interesting topics, including generational issues, finding your podcast niche, how to have good discussions and more. Listen in and treat yourself with an overflowing amount of bold perspectives that might just make your day.

Show Notes:

00:01 – Stereotypes About the Current Generation
07:19 – Cutting News Consumption
12:03 – Only Deal with a Problem You Understand
16:41 – On Pivoting and Motivation to Continue
26:21 – The Internet of Things
28:56 – Fear of Success More than Failure
31:40 – On Metrics and Analytics
34:30 – How to Merge Professional and Personal Life
43:29 – How to Thrive in Different Life Extremes?
48:00 – What is Your Podcast Going to be About?
52:38 – Why People Search for Simple Answers and Go to the Extremes?

⬅️ Part 1: The Whys of Podcasting, Challenges of Remote Work, and Bold Perspectives on Women, Careers, and Progress With Casey Juanxi Li

➡️ Part 3: Creative Vision And Connecting Podcast Creators With Casey Juanxi Li

Listen to the podcast here:

Stereotypes, Pivoting, Healthy Discussions, and More With Casey Li, Part 2 of 3

Stereotypes About the Current Generation

Casey: This is something that I hear a lot, “This generation is lazy, entitled, soft or snowflakes.” What do you think is causing that disconnect there?

Samantha: If you don’t mind, I’m going to use a story to illustrate this. I like to use stories to illustrate something. It’s a perception issue from the older generation. I challenge them on it. Anytime an older person comes and tells me this stuff, I challenge them. I’m like, “There’s hope for the future.” You just got to get to know the right ones and we should be fostering it, not criticizing. Everyone has a flaw, every single person. We can choose to focus on it or set it aside and focus on the great stuff.

When I’m with young adults, there are some things I could call out but you can call stuff out on me. I want to focus on the awesomeness of you. I’m going to give you an example of where I saw two generational issues. I was living in Costa Rica a couple of years ago. I took my daughter down there to teach English. We got to teach English as a foreign language certification. A little side note on that, everyone asked me, “Why did you go down there and do this?” She was thinking about becoming a teacher. I thought, “How do you know if you want to be a teacher and go into school for five years, spend $80,000 and then find out you don’t even know if you’re suited for it?”

I homeschooled her for a semester. I took her down to Costa Rica and she taught English with me for two months to find out if she loves it or not. That’s what we did. She was amazing at it. She’s sixteen years old. She went to school full-time. While we’re down there, we’re living in hostels. For two months, I lived in hostels in Costa Rica with 18 to 35-year-olds. I didn’t know this. When I got there, I’m like, “I’m living with my people for two months.” Do you have any idea what you learn from internationals all over the world in a hostel? It was amazing. I could tell you what the hotel industry should be doing right now based on what I learned from them. I got ideas about how the hotel industry should change based on what I saw down there.

There was a gentleman that came in at night. There’s some drinking that goes on and they get a little loose tongue sometimes when you’re there. We were all talking and this Australian guy was shirtless and had this massive tattoo covering his whole upper body. The best thing you can do when you meet somebody with a tattoo and you want to connect is asking them about their tattoo. If someone’s willing to put that on them, there’s a story. You’ll learn so much about that person by asking them about their tattoo. Even shy people will tell you about their tattoos. I love opening with this. I was like, “Tell me about your tattoo. What’s the story?” He was happy to tell me. He was up in Nepal and he did one of those magic mushroom journeys.

Casey: Ayahuasca.

Samantha: I don’t know if it was a different one that he did. It might have been Ayahuasca but it was by a special shaman. He did this journey up there. He’s telling me about the journey. At the time, I never talked to anyone who had done this journey. I was like, “World education.” My daughter sits there, world education at my side. He started telling us about this journey and during the journey he saw the Mother Creator. He had a profound experience as we hear sometimes with people who talk about those. The way he talked about the creator and how the creator connected with him was profound to watch and hear him talk about this story.

I then figured something out. He always used the feminine version of it. Usually, when we talk about God, it’s a male version because so many have been exposed to Christianity and Greek Mythology. I started to pick up something and I thought, “He might have some daddy issues.” I didn’t say anything to him. He was done talking about this and it was a Mother Creator. How Christians would describe God was exactly how he described his experience with a female creator, which I thought was fascinating. It was like he was a Christian and maybe he had some Christianity in him. I don’t remember having that conversation.

A further conversation goes on. I’m curious a little bit. I want to see if I’m right because I’ve sensed in him that he might have some daddy issues. We start talking some more and then I was like, “What do your parents feel about you backpacking all over the world?” He’s been in Nepal, China and all over the world, backpacking everywhere. He said, “My parents are disappointed in me.” I’m like, “Both of them?” I’m prodding a little bit. He’s like, “My dad especially.” I was like, “What’s going on there? You seemed like a great guy.”

Cutting News Consumption

He’s like, “My dad doesn’t think I care about the world.” I’m like, “What?” He’s like, “I don’t watch the news. I don’t read the newspaper. I’m not up on current events.” I’m like, “Do your parents watch the news twice a day?” He’s like, “Yes, they’re that kind.” I’m like, “What conversations do you have?” He’s like, “My dad would bring up political issues or different things that have happened locally. I don’t always know what all those things are. He thinks I’m selfish. I don’t care about the world and I don’t know anything about it. He thinks that I’m not a good citizen because I’m not listening to the news, taking part in it and not informed. He doesn’t think I should vote because I’m not informed about what’s going on.”

Right away I knew exactly what was going on because I see this all the time. It’s a perception issue. The way his father’s brain works and the way he’s been brought up in school are current events and newspapers. That’s the gospel. When you meet somebody in a coffee shop, you talk about what you read in the paper. That’s your discussion. Your generation doesn’t think like that. They have the internet. I said to him, “You probably have your thumb on the pulse of the world more than your dad does.” He’s like, “What do you mean by that?” I’m like, “You’ve traveled and backpacked all over the world. I’ve listened to you for two hours and I learned more from you about what’s going on in different countries, some cultures and some things that you’ve seen.”

What I’m talking about is that his dad didn’t understand that backpacking and experiencing the world was world education. That was my long way of saying it’s a disconnect because their minds are in a completely different space. The son didn’t know how to say that to his dad either. He didn’t know how to say to his dad, “I am though. I just don’t know how to say it.” After discussing, I’m pretty sure he went back to Australia and told his dad, “I do care. If I didn’t care, I wouldn’t be visiting all these people all over the world to find out more about them.”

Casey: That’s a beautiful story. It reminds me of one of the atomic essays that you publish, the one about how you don’t read the news anymore. That one resonated with me because I gave up on reading the news a long time ago. People ask me, “How do you stay informed? How do you know anything?” What I want to say is that there’s a difference between being informed in the sense that you know about X people who got shot last week and engaging in the world to make it a better place. The reason I don’t read the news anymore is because I don’t like to take in information that I can’t do anything about. It depresses you and it makes you feel helpless. It’s cool that you can see this guy’s perspective. When you travel the world, meet all these people and see all these different cultures, you develop all this empathy and understanding. It makes you more skilled than every single interaction you have even if you don’t know exactly what happened on the news yesterday. That’s a great story.

Samantha: It’s funny about that news thing. When I tell people about that, they’re like, “What?” I’ve been doing it for years, probably before everybody did it with COVID. It took COVID for people to see how toxic it was. It’s partly why I’m creative. People say to you, “How are you so creative? How do you run two companies? How do you do this? How do you do that?” I’m like, “I cut the news out. I have no noise and my brain isn’t cycling that through.” Part of it is a little selfish. I get angry about people thinking they know what’s going on when they don’t because they read something in a newspaper. When I tell them that I don’t read the news, they pretty much won’t talk about it anymore. It cuts them down from talking about it further.

On a personal level, here’s something I hear a lot of people discuss. In my particular city, we had a safe injection site. It was a disaster. There are lots of opinions and a ton of them valid in both ways. What I had the hardest time was listening to people talk about the addicts themselves, “If only they would stop shooting themselves up. If only they would do this. Don’t they know they’re doing this to everyone?” It was the way they talked about the addicts that bothered me. Why it bothered me is because a few years ago, I lost my sister to drug addiction. It’s personal for me.

I don’t read the news but I know what’s going on because I picked up the phone and heard her talk to me about what she’s going to hawk because she needs to feed her addiction. I’ve taken her to a detox center. I’ve picked up the phone every millisecond when she’s in detox when she wants to run. I also know that there’s not that much support for addicts. If anyone wants some ideas about what cities can do, I have some seriously solid ideas about what we can do to help addicts long-term.

Here’s one example. My sister wanted to go into rehab. She goes into detox but she’s renting. What happens when she goes to rehab? Who’s going to pay her rent while she’s in rehab? Part of the reason why addicts don’t get the help they need is that they don’t have the resources. They have no one to pay their rent for two months. How hard is that? It would cost the government less to pay an addict’s rent while they’re in rehab than it would be for them to keep on having medical assistance and having to save on them all the time.

Here’s another one. Let’s say she gives up her apartment. Where is she going to put her things? Most addicts have burned through all their relationships and nobody wants to take their stuff, even storage lockers for people who want to go into rehab. I couldn’t even get my sister a bed. She wants to go on a detox. I had to phone six centers to find a place for her to go. I have a strong background and understanding of how government works and government organizations. I know who to call and what to do. What if addicts has someone like me helping them advocate for them?

Only Deal with a Problem You Understand

I’m going to put this out there. I have an app idea about how to get people to help with addicts getting help. I didn’t learn that from reading the news. Do you know who makes this stuff up? It’s the people who live it. I get my back up when people are like, “It’s this easy thing.” I’m like, “I don’t think you understand. There’s a lot of emotional stuff going on and they’re taking drugs to cover the pain. We need to deal with the pain and not the actual drugs.” I got my back up about that because people who read the news think they know everything. They start telling you how to handle it and they don’t know how to handle it.

Casey: I completely agree with you. One of my core beliefs, and I know there are a lot of people who agree with me on this, is that the only people who should be dealing with a problem are the ones who understand it. Everyone else should get out of the way if they don’t because otherwise, you’re just adding noise, distraction, animosity and judgment. It doesn’t help anyone.

“The only people who should be dealing with a problem are the ones who understand it. @sometimescasey @SamanthaPostman” Click To Tweet
BP 3 | Time To Pivot
Time To Pivot: There’s a difference between being informed in the sense that you know about X people who got shot last week and engaging in the world to make it a better place.

I would like to go a little further with that. It might even be the families of those who are affected who should be included in the conversations. When you are in your own shit, you can’t see very clearly. Somebody who can be a translator for both of them might be better than somebody who has a self-interest. For example, in churches, women are talking about women in leadership. It’s still an argument centuries later and we’re still discussing women in leadership. When women speak up, it comes across as a vested interest. If I speak up for women in leadership, I’m a woman. I’m trying to advocate for women. It has less value. If a male speaks up for females, that adds more value to it than a female advocating for herself. In our culture, men can advocate for men, men can advocate for women but women can’t advocate for men. We can’t even advocate for ourselves either because we’re screwed either way.

Casey: That’s weird that the people who are the most equipped to talk about a problem don’t get taken as seriously as when someone else who understands the problem less tries to talk about it.

Samantha: This thing I’m saying also applies to addicts. If an addict says, “I need this.” They’re like, “You’re blinded and you can only see it from this perspective.” People don’t take them that seriously. They are somewhat like tunnel vision. An addict probably won’t be able to tell you how a business can handle it because they’ve never run a business before. You do need people who can talk about what’s it like to be a business owner with addicts hanging around all the time. Many times that can be family. There are a lot of families who are lawyers, doctors, business owners and social workers. These are people who understand both sides of the story in a way that people on each side can’t.

I don’t know if you saw this. I wrote this on my Twitter. You’ve got extremes. Whenever you get extremes, there’s no discussion. Real discussion only happens in between the extremes unless you want people who are agreeing with you in saying what you want to say. That’s why I don’t like Facebook right now because it’s all your big cheerleading squad or it’s people who are super negative about it and don’t agree with you at all. There’s not a discussion either way on it. When we’re talking about societal issues, the ones that have exposure to both sometimes are the best advocates.

“Real discussion only happens in between the extremes. @SamanthaPostman” Click To Tweet

Casey: That’s necessarily true because many statements that get made on Twitter and Facebook are not very nuanced that they go viral. It gives you this little emotional jab of like, “Look how smart I am.” The reality is never that simple. Anyone who’s talking about the issue has to be in the middle because that’s where the problem is.

Samantha: Even if one party has a grand idea, if you don’t have buy-in from the other parties, you’re going to get nowhere. I can speak business talk but I can also sit there and talk to the people of my sister. I came from that world. From where I come from, people either end up dead or dead inside. That didn’t happen to me but I can go and sit with them and sit on the couch and have a conversation because I know how to talk to them. I’m one of them in lots of ways. Maybe I’m not going to dress like this that day but I’m one of them. I’m also a CEO, CFO and serial entrepreneur. I can do both across social and economic gaps. Those are the people you want advocating because they can talk both sides. We went off base. You got me all excited. You’re fun to talk to.

Casey: I’m glad. You’ve got all these amazing life experiences and all these opinions. I’m asking you to share what you know. I do have one final question about your podcast. I’d love to know your answer to this. I’ve been talking to a lot of podcasters from the Ship 30 cohort. There’s this common theme that people will start and get excited, but then they’ll fizzle out because it’s a lot of work to run a podcast. They’re not quite getting the reach in the audience that they want. I was wondering if you’ve thought about the risk of that happening and what you think will keep you motivated.

Samantha: That’s such a valid thing. Life gets in the way. Even if you have the best intentions, it’s not always because people fizzle out. It’s because life, all of a sudden, steps in front of you and says, “Your path is moving and you don’t have much of a choice.” I hate to judge people who don’t finish. We talked about failure and quitting. I had this conversation with my daughter. People who are reading this and I know there are some people out there who did quit or fail, it’s what people are going to label you. You might label yourself that. I may have that happen but I like to think of it a little bit differently.

For example, my daughter was at Simon Fraser University when COVID all happened. The first year, she wasn’t doing particularly well. The weather wasn’t great. The university is not organized. Sorry SFU but you need to know that. I help young adults all the time by figuring out what they’re going to take in school and how does curriculum works. I did my Master’s when I was 40. I’m pretty versed up on how everything works in a university and how you do your breath classes.

She wasn’t doing super great. She came back. She didn’t know what she wanted to do. She wants to edit books and help people publish. There are only two institutions in all of Canada that are offering an undergrad something in publishing and SFU was one of them. She decided to go there. COVID happens and they all of a sudden email out that they’re going virtual online again until December 2020. She’s homeschooled. She made the dean’s list even when COVID happened which is pretty significant. She’s homeschooled a few times because we travel. She’s probably a little more practiced in an online setting than most people. I’m like, “If you don’t need to go all the way to that university and pay a crazy amount of money, maybe we can do something different.”

I went looking online and we had looked at Ryerson University in the past. If you’re from Toronto, you probably know what Ryerson is. They’re pretty well-known for their publishing. They have a graduate certificate in publishing. When I had looked at it a couple of years ago and when she was looking at schools, it had said, “A prerequisite is that you had to have an undergrad or be 21 with industry experience.” I went back and looked at it and it said, “Recommended.”

I’ve got some lawyer background in me. To me, that’s a door that’s unlocked. It might be locked but they might give you a key to open it. I thought, “Let’s check it out.” She emailed the school and sent her resume. She edited all my Master’s papers. I also wrote a Federal budget proposal to the Canadian Federal Finance Committee. I came up with an idea about how to re-stimulate the economy using the tax system and help nonprofits at the same time and she edited that. She put all that in there and puts her portfolio in there. She has an interview and they’re like, “For sure. It’s COVID. Let’s try it.”

She’s nineteen. She’s in the Graduate Certificate Program at Ryerson. She’s probably the youngest to ever graduate. All of a sudden, she sits down and she’s like, “Mom, I’m a quitter now. I’m not going to finish my four-year degree.” She’s only finished one year of undergrad. She’s like, “I’m a quitter. I failed because it was hard. It wasn’t a fit for me. I’m a failure. I don’t want to be that. I’m going to finish my four-year degree. Maybe I’ll go do my Master’s.” I’m like, “You’re going to spend $80,000 just so you don’t have a failure as a label or be labeled a quitter?” She’s like, “If I fail or quit, maybe it’ll be easy for me to quit again. I don’t want to be that. I want to be the person who follows through. I want to be dependable but not so other people depend on me. I want to be able to depend on me that I follow through.”

On Pivoting and Motivation to Continue

I was like, “What if we change the word to pivot? You’re pivoting. You’re redirecting. You’re still going for publishing. You’re just doing it a different way.” I would prefer not to use the word quit or fail. Failure is a powerful word to use sometimes. It’s a good teacher. I would rather use stop, redirect or pivot because then there’s still this momentum that you’re moving in a different direction. It’s not a stop. As soon as you say fail, you visualize that. If I said I failed, I would see myself at the bottom of a dark well. I fell all the way to the bottom and then I have to figure out a way to get to the top again. That’s massive. That mental energy of that alone is crazy. Why would you even try anything again if you think you got to climb yourself back to the top again?

Imagine if you’re at the top of the well and I said, “Let’s pivot from here.” It’s a movement. Think about basketball like a guard. If you want to redirect, plant your foot down and you pivot. All you do is shift the direction of your body. Instead of going left or going right, you’re going in a different direction. That’s how I like to see it. Maybe I’m going to fizzle. It could be that Elon Musk calls me up and wants to work as a consultant.

Or Mercedes-Benz to work with their heartbeat technology with their new Avatar car. I got some ideas about what they could do with that. Sorry crowd. I’m not going to be podcasting.

Mercedes-Benz VISION AVTRAS VEGAS – The Mercedes-Benz Vision AVTR, as in Avatar the movie (and director James Cameron showed up on stage), made an earth-friendly debut Monday night at CES 2020. It is the automaker’s view of a battery electric vehicle / autonomous vehicle ready for a sustainable future. AVTR stands for Advanced Vehicle Transformation.  The AVTR recognizes the driver from his or her heartbeat and breathing, and gives an affirmational pulse on the seatback, as passenger and vehicle become a single “symbiotic organism.”

 Those sound like pivots worth taking. I don’t think anyone would hold that against you.

Samantha: It might be that I decided that I need to spend my energy somewhere else, maybe it’s with family. There are lots of reasons. It could happen. If you worry too much about that happening, you’ll never start. It’s like getting a prenup. The statistic is higher for divorce with the prenup than without. It’s like saying upfront, “We don’t trust that this is going to happen. We’re going to put up all these little in-case things.” At some point, I will quit podcasting but I’m not going to quit unless I pivot into something else.

Casey: I liked that reframe. It’s an empathetic reframe. What you said at the end about that fear of failure preventing you from ever starting, we want to get rid of that. Reframing this to, “I’ll pivot my energy to wherever it’s most rewarding,” if that’s what makes someone feel better and gets them to make that first episode, then that’s a great thing.

Samantha: What you said gave me the visual of basketball. I don’t know if you played basketball. If there are too many people blocking you on one side, it would be stupid to keep on going that way because you’re going to lose the ball. That makes no sense. When you’ve pivoted to the clear area to get to the net, that’s a smart move. Life-wise, if you’re going in this direction and then you stopped as you failed. No. You made a smart move. Football is the same thing. Why would you take the ball and run into the crowd? You were running away and then the crowd came and started to stop or beat you. It’s time to pivot. In basketball, you have to keep your foot on the ground when you’ve got the ball because otherwise, you’ve traveled and that’s an illegal move. You pivot to the area where you have the best path to score.

It’s hard to hone and sharpen your skill when you have to keep so many people happy simultaneously. - Samantha Postman
Time To Pivot: It’s hard to hone and sharpen your skill when you have to keep so many people happy simultaneously. – Samantha

 No point beating your head against a wall or going up the path of most resistance. I’ve run through my list of questions. Was there anything else you wanted to mention or something you’ve remembered from before?

The Internet of Things

Samantha: Elon Musk again I did sign up for Starlink the second they opened up. I don’t have it yet but I’m on the list. I’m probably one of the first people who went on. I want to be on the beta list. The second I got the email to be on the beta program in my area, I was on it. I’m supposed to be a beta tester for Starlink.

Casey: That’s amazing. You’re going to have to tell me about it. I’m pumped. That’s incredible.

Samantha: If you think about the internet, it was created for consumption and not for contribution. You think it’s for contribution because how could you consume something if somebody didn’t put anything on it? Mass internet was meant to download and not to upload. Now you look at Cloud storage and all these creators. The need to upload is significant. Mine is like a 1.5 megabytes upload. I call the company every four months, “Is there anything we can do? I will pay for the equipment. Can we get a better upload?” They’re like, “No.” I live in the middle of nowhere and I got a dish on the top of my head that jumps off other dishes. I’m hoping the upload will be worth it with Starlink. That’s the one I’m hoping for.

Casey: I’d love to see that happen. In Toronto, I take it for granted. I’ve never had an issue with upload speed. It’s always slower than download but I’ve never thought about it.

Samantha: It will take me three days probably for it to go up all the way.

Casey: I feel like once this is up and going, there will be this huge influx of content from all these places where it didn’t make sense to do this before because no one wants to upload something for three days. That’s awesome.

Fear of Success More than Failure

Samantha: One of the things that you would ask me about is what would be successful for me. I was half-joking about Elon Musk. Do you know what they say about a joke? There’s a seed of truth in every joke. Otherwise, it wouldn’t be funny. I would be super impressed if he does that. What encouraged me is that when I was talking to Podetize and they’re interviewing me to see if they’ll take my podcast on, I was validating the idea of my podcast like what I wanted to talk about which is something we didn’t talk about what my podcasts are going to be about.

He said to me, “You’re going to be infectious in a good way because when people listen to you, they don’t know what you’re going to say next. They just want to hear it.” He’s like, “Listeners like that unpredictability.” I was like, “Okay.” He said to me, “I honestly think that you could hit at least 10,000 downloads within three months of launching.” I was like, “What?” First, the ego kicks in. It was like, “Yeah.” The fear kicks in and I’m like, “Are you kidding me? Why am I doing a Podcast? That’s Insane.” I fear success more than failure.

Casey: What’s scary about it?

Samantha: Even if you look at J.K. Rowling, she has all these publicity events and then she says, “I can’t create if I’m constantly doing publicity.” If you think about Einstein, could you imagine if Einstein would be in today’s world? People would think that he’d be much more creative. Honestly, I don’t know if he would be. If he’s at a university, he’d be put on all these committees and boards that he’s got to be on. He’d have to be on YouTube, Twitter and all these things. How could he hone in and sharpen his skill when he would have to keep many people happy simultaneously? That’s the tension that I’m nervous about because part of the reason why I’ve been able to grow my super skills is because I haven’t had to do any of that. I worry that it will keep me from continuing to develop. Although my husband tells me I’m a superhuman already. He’s like, “I don’t understand what more do you want to do?” When I signed up for Ship 30, he’s like, “Are you trying to be a superhuman?” I was like, “I don’t know, maybe, I guess.” I didn’t think about it.

“It’s hard to hone and sharpen your skill when you have to keep so many people happy simultaneously. @SamanthaPostman” Click To Tweet

Casey: You said this thing about having to keep all these people happy. Who are all these people? Why do you have to keep them happy?

Samantha: Even for Ship 30 for 30, it’s like, “See what your viewers like and then write about that.” We’ve got thirteen of them. We look through which ones had the best engagement and then continue to write about that. There’s a tension in that. I can write about what people want to hear but then at what point do I not get to talk about what excites me anymore? I have a tribe built up from Roam Research. I love my research Roam Research tribe. They are the most amazing people on the earth. They are giving and kind. It’s an amazing community, and now I have Ship 30.

They would want me to talk about Roam Research or essay writing but that’s not going to fulfill me. If my Twitter group is giving me engagement, it’s not necessarily a good indication of what I should be writing about. They want to hear that because that’s the tribe I’m in right now. I feel I have more to offer the world than talking about Roam Research or essay writing. I fear success because success is going to push me to keep them happy and then maybe talk about things that make them happy instead of things that are going to make me happy.

Casey: I’m sure you’ve heard the classic quote that Henry Ford one about, “If you were to ask people what they wanted, they would say a faster horse.” You strike me as the kind of person who has enough strong thoughts of your own and certainly enough life experiences and worldviews. You don’t strike me as a person who’s particularly vulnerable to trying to gain the approval of others. Am I wrong about that?

On Metrics and Analytics

Samantha: You’re right about that. Where we come in is when you start getting into podcasting, specifically advertisers, because they’re about numbers. My one company makes enough that I wouldn’t be dependent on a podcast to make an income. That gives me quite a bit of freedom that other podcasters wouldn’t have. I’ve heard so many times that you can take something that you’re passionate about and turns not too passionate when it’s all driven by numbers and metrics. Even like what you’re doing is with metrics. Maybe that’s something to consider. At what point am I willing to let go of some metrics so that I have a happy factor? Can you create a happy factor? If I’m talking about this, am I happy? If I’m not, then those metrics shouldn’t be as strong. Maybe I’m willing to take fewer metrics if it makes me happy.

Casey: I like what you said there. I know it’s what our website says right now. Tom and I have no idea what Podding is going to become yet. Part of the reason why we’re talking to all these podcasters is because we want to get as wide of a view as possible. He and I have this debate all the time. He likes analytics and metrics. He’s a product person. If you’ve ever heard of Hotjar, it’s tracking where you click on a site. He’s a big fan of having hard data to slice.

I’ve learned this from the Ship 30 community. There are a lot of other ways that people can get fulfillment from podcasting besides seeing the download numbers. Its connections with awesome people that they otherwise wouldn’t have met, or hearing feedback from a particular fan that you change their life in some way. All of the things that you mentioned are possible through podcasting. There are no tools focused on those things. All the tools are focused on analytics, advertising and numbers. I don’t want it to seem like we’re just focused on metrics. We want to make the experience more rewarding. If there are more humane ways to do that, that’s where we want to go.

Samantha: Is there a way to do in your formula that allows the user to measure how they felt when they did a specific podcast? What you’re doing is combining qualitative with quantitative. In general, metrics are all about quantitative when we’re talking about hard data, but there’s a qualitative factor. The podcaster should be allowed and permitted to add a qualitative factor to the metrics. There got to be a way to find a magic sweet spot where the podcasters are happy but the metrics measure enough to make that sweet spot for both parties.

Casey: At the end of the day, all the numbers are completely useless. I’ve released this episode and I’m seeing people engage with it. If all of that doesn’t feel right for you, the rest of it is completely irrelevant. I agree with that.

Samantha: I struggle with even my content a bit. I have a strong background in leadership development. Do you know what the Global Leadership Summit is?

BP 3 | Time To Pivot
Time To Pivot: There are a lot of other ways that people can get fulfillment from podcasting besides seeing the download numbers.

Casey: I don’t.

Samantha: It’s a global movement from this Willow Creek Church out in Chicago and it’s an amazing opportunity for people. It’s a two-day summit. It’s live broadcasted around the world twice. It’s all up my alley. I took a Management degree. I’m all about business and leadership development so I love it. That’s where people want to hear me talk. I was in a leadership impact group a little while ago with other executives in the city and I love that. That’s what people want to hear me talk about because it gives them value. It’s what they can monetize. They see the quantitative value of being a better leader.

How to Merge Professional and Personal Life

I’m still in the business world but I don’t have a team under me anymore. I want to talk about cultural things. They do ripple into management and leadership even in parenting. Even at the Global Leadership Summit, I was telling all my friends who had kids, I’m like, “You should come to the Leadership Summit.” They’re like, “Are you kidding? I don’t lead anybody. I’m not a manager. I don’t work in an office. I’m a mom.” I was like, “You need to go.” I heard this one mom who had three kids talking to another girl and she’s like, “This is a big waste of my time. I didn’t learn anything at this Leadership Summit. How does this apply to me as a mom raising three kids?” I was like, “I think they were talking about the multiplier effect.”

Some multiplier effect is when you let your team go and they grow. You can do that with your kids. You can empower your kids to grow with something and look at what you can accomplish as a family if you all take on something or grow this. What we would use in management works in parenting. What I did is I talked to the emcee and I said, “You need to help connect those dots for people. When you’re done with the next segment, maybe say, ‘That was cool. This is a takeaway.’ Use something that’s cross-sector or cross-professional like personal and professional.” The listeners will go, “I can take this learning and cross learn it over here.”

When I’m talking to people about the stroller idea I have, it’s cultural and behavioral. It would fall into Psychology and Behavioral Science. However, some of the theory of what I’m talking about would apply in the management or business world. How do you cross those over for people who struggle with that? You can’t be everything to all people but I don’t just want to talk about it in leadership.

What we’re finding is people don’t talk about the professional world and they want to talk about the personal world. I don’t know what La La Land you’re from if you think that those are two separate things. They’re not. They’re both connected. That’s what I talk about. I’m like, “Talk about stuff that happens between all of them.” If your personal life informs your professional life and your professional life informs your personal life, then they’re not separate entities.

“If your personal life informs your professional life and vice versa, then they’re not separate entities. @SamanthaPostman” Click To Tweet

Casey: A theme that I’ve heard throughout this conversation based on the things you’ve talked about is your ability to be in the middle and translate ideas from one world to another, especially when they wouldn’t otherwise touch. You were talking about being able to talk to your sister and the things that she struggles with versus the government agencies that are putting in the policies that might make a difference. You’re talking about this guy and his father who didn’t understand and that you met on this trip. You’re talking about these leadership summits that you go to and these mothers who don’t see these lessons. They might be in some specific business jargon wording but the lessons apply to what they’re doing. I agree with you that that’s hard work. To me, that seems worth doing. There are a million and one business podcasts out there that are business for business people. I’m sure there are a million and one podcasts that are motherhood for mothers. There’s little that crosses between the two. I see a lot of value there.

Samantha: I struggle doing that on my own. I’ve recorded five podcasts. They’re all just me talking. This is the first time I’m talking with somebody. I find that easier to be like, “It’s this and this story,” instead of going out and talk to them. Talking to myself is difficult because you don’t know that you’re trying to connect. You’re talking in a space and it’s not relevant to anyone party. I hadn’t thought that much about being an interpreter. In my first life, I was a tax expert. For many years, I’ve prepared probably over 7,500 tax returns in my lifetime. Some of them are corporate and some are personal. There wasn’t a walk of life I didn’t get to meet in that capacity. Imagine what your accountant or your finance person knows about you. It is the most vulnerable place we can be as humans.

People say to me, “They’re medicalized,” but no. People will tell you about their medical issues way more descriptive than we all need to know but they won’t tell you about their finances like that. I used to have spouses that didn’t even know each other’s finance. There was the Chinese wall when talking about finances even between spouses. When you do a person’s finance and they know all that about them, there’s nothing that you can’t know after that, even medical. I would see all their finances. I’d see how they spend their money, what kind of money they make, what kind of education they have, how they spend their money, if they’re saving or not, if they’re in debt. Because I’m doing their tax return, I also see where do they live. I also see all their medications because your medical expenses all go on there. I know more about you than your doctor does.

I have a lot of questions about medical sometimes because there are certain deductions. What it did is it gave me a special view into people’s lives in a way that you wouldn’t get in any other occupation. In one minute, I could have a CEO in front of me. The next minute, I’m talking to somebody who’s a custodian at McDonald’s or something like that. Huge difference. You’re switching constantly. I got to switch the way I talk a little bit. I’m taking complex concepts and explaining it to them in a way that they understand. I got to listen. I’m dealing with all the employees. The employees are telling me what’s going on at work. Not the stuff that you read in the news. The business owners are telling me what’s going on too.

People have no idea. Restaurants, for example, have one of the narrowest margins there is. Everyone’s like, “You’re a business owner. You must be rich.” If you had any clue how many restaurants I saw that had two mortgages on their home because they either re-mortgage their home to go and start the restaurant or it got tight that they needed to do it to pay their staff. If it was a male owner, their wives would go and get a second job so that they could pay the staff and keep the restaurant open. People don’t see that. They’re like, “My restaurant is not paying me good enough money and they’re peaking off.” I’m like, “I know your owner. They’re working two jobs to make sure that you don’t lose your job.”

I would see both perspectives. Also, because I did it for many years, I got to see the same person, same couple or same family over a twenty-year span. You get to see where they were when they were 20 and where they were in their 40 or where somebody at 40 and 60 is, and 60 and 80. I learned a lot about the world and organizations. I’ve seen pretty much every T4 there is. I write for government agencies, political campaigns, universities, any job that you could have in Canada. I’ve seen that person has probably sat in front of me at one point. I’ve seen every investment there possibly is. I’ve seen every mutual fund. For insurance policies, I could tell you the difference between a term policy that would pay an annuity in the end or one that’s an insurance policy. I saw everything that you could even possibly imagine. You get pretty educated on what’s going on in the world. That’s part of the reason why I can talk about so many things because I’ve talked to so many people.

How to Thrive in Different Life Extremes

Casey: Not only do you seem to have this ability to bridge these extremes but it also seems to me that you thrive in it. Whereas it seems it’s a thing that a lot of people back away from. This is a personal question, what do you think has made you this way?

Samantha: I do thrive in that. I haven’t thought of it like that. I love the challenge. I love connecting with people and finding ways to connect with them as a person. I love helping people. You have no idea how much joy I’d get when I hear somebody say, “I can finally get that computer so my kid can do their schoolwork at home.” I would get flowers and all kinds of lovely things sometimes from people. There are some pretty cool magic tricks you can do when you’re a tax repairer. Anytime that you thrive in something, it’s probably because you hurt yourself in a way.

“Anytime that you thrive in something, it’s probably because you hurt yourself in some way. @SamanthaPostman” Click To Tweet

I’m going to get a little triggered here. You probably hit the spot there. I was born to a teenage girl and raised by a teenage mom. I’m not going to get into all of it here. When you see me, you would never guess it. I’m always talking about my sister. From where I come from, people are dead or they’re dead inside. I came from the wrong side of the tracks. I was the misfit. My best friend in elementary was a girl that no one talked to. She had this ear condition in which some fluid came out that had an odor that people didn’t like. They wouldn’t talk to her. She was my best friend. I had no other friends. No one talked to me. I got bullied unbelievably. The girls were ruthless to me. I had crazy acne that started when I was young. My breast started to develop young before all the other girls. The boys are pulling my bra strap.

I don’t know why my mom tells me this, she comes back and she’s like, “The teacher told me all the kids say about you behind your back.” After parent-teacher interviews. They were calling me Dolly Parton behind my back. It hurt my self-esteem. I used to play the violin. I would go like this. My teacher was like, “You can’t play the violin like this.” I wore stupid amounts of makeup to cover my face because I thought I was hideous and ugly. I think like the ugly duckling story. I started as the ugly duckling and then later turned out not to be the ugly duckling. It was harsh being the ugly duckling with all the other swans.

I had death threats in my lockers. I had a horrid experience growing up. I wouldn’t wish that on anyone. I did okay. I have no idea how sometimes. I don’t want other people to feel like they’re not valuable. I want them to feel that people see them like, “I see you.” We need to be seen. I see who you are. I see all the beautiful things. I see your potential. I don’t want people to be hurt like that. I don’t want people to struggle as much as I did. That’s partly what made me strong but not many people are that strong

My sister was so much like my personality and she didn’t make it out. She’s similar to me. We’re half-sisters. We didn’t grow up together. I’m slightly motivated by that. I didn’t have an opportunity. I worked at McDonald’s for four years when I was a teenager. I had no networking, no name, no connection. I was a welfare kid. I had to do it all myself. My kids, they’re Dutch. They got a Dutch heritage father. They live on a farm. They walk up and say, “I want a job,” and people are handing them jobs because they know they come from a good family that works hard. I didn’t have any of that. I want other people to have opportunities.

I love helping young adults get an opportunity. They need to prove themselves because it’s there. Someone just got to hand them an opportunity. I see that with taxes too. The government doesn’t spend our money particularly well. I took it upon myself to make sure they get the least amount possible within the legal framework. That was my goal. I love explaining things to people where they’re like, “I get what you’re saying.” It’s a challenge. I didn’t realize I love that so much but I do.

What is Your Podcast Going to be About?

Casey: It shows in everything you say. Now might be a good time for me to ask the question that I didn’t realize I didn’t ask because we’ve been talking about many things. What is your podcast going to be about?

Samantha: To be honest, I should have called this Samantha Postman Show but that’s super narcissistic and people don’t love it. You’re not supposed to do it. I didn’t want to call it that for narcissistic reasons. I didn’t want to be put in a box. Once you put a label on it, now you got to talk about this one thing. I’m struggling with everything in me. I feel claustrophobic talking about what’s my one thing. My brain is going, “Stop. Get out of the coffin. There’s no room to breathe in the coffin once you put a label on yourself.”

“There’s no room to breathe in the coffin once you put a label on yourself. @SamanthaPostman” Click To Tweet

My one friend calls it potpourri. It’s going to be a bit of anything that I feel needs to be said. Sometimes it’s going to be about leadership. It’s mostly cultural. It’s a bit of a Seth Godin go at the world. That’s been the culture like I’m talking about Santa Claus and strollers. I want to talk about things like what my client said to me. I did an essay on that. My clients are telling me what they would want the younger generation to know. A lot of times when you read these things, “Nobody died in their deathbed wishing they worked more.” Who did you ask that question to, males? I’m sure a woman wouldn’t have said that. You’re not representing the population when you make that comment.

What do women say on their deathbed? I want to know that. Do they wish they would have pursued their career more? Probably more women say, “I wish I would have also pursued my career when my kids moved out or went back to school.” It’s going to be mostly cultural growth. When I talk about Santa Claus, when the next-gen has their kids, they’re going to think about that and go, “Do I want to make my kids believe this lie and keep faking it for them? Later, I’m wondering why they don’t trust me or they don’t respect me.” We don’t connect those dots.

Maybe my podcast has been helping people connect the dots in the middle. I don’t know. Maybe you’re helping me figure out how to say it. I honestly don’t even know what to say it’s about. It’s about life, doing life and anything that could happen in your life. Nobody grows up, goes to school and does one thing. Maybe a few but that’s not happening anymore. If what I can say can prepare somebody for something that’s coming ahead, I’ll consider that as an accomplishment. Everyone won’t get there if they don’t have a big category that says, “Here’s this category.” It’s probably going to be psychology. More or less psychology unless you have an idea for me because that’s one of my feedback requests. Tell me what niche I am in.

Casey: This conversation has gone to so many different places and they were all great. It’ll change over time and you’ll iterate. The consistent theme I’ve heard in everything that you’ve said is this idea of connecting in the middle and the magic that can happen there. The fact that conversations aren’t happening there because it’s hard and there’s not a lot of people who can do it. If you keep digging in that middle, you’ll find a lot of good stuff.

“The magic happens when we all connect in the middle. @sometimescasey @SamanthaPostman” Click To Tweet

Samantha: You reminded me of a picture before COVID. I had some young adults together and we did a theme together. Part of the discussion with the young adults is we were talking about black and white. We try to be this black and white world taxes that people think are black and white. There can be some less gray. I like Math because I didn’t like gray growing up. I like a right or wrong answer growing up. Surprisingly, I’m in the middle so much now.

My mom always says I’m a black or white person. My husband tells me, “There’s either on or off. There’s no in-between with you.” It’s funny. People always tell me there’s no in-between with me but I talk in-between. You reminded me of something that I would want people to take away. I’m not going to use black and white. I’m going to use dark and light. We’ve got daytime and nighttime. What is the most beautiful time of day? When do we get the most light? When do we get the most color? When do we get the vibrancy? When is it?

Casey: Do you want me to say dawn or dusk?

Samantha: The sunrise. It’s when it’s not all the way dark and it’s not all the way light. That’s where the beautiful part is. Culture is always like, “It’s either this way or this way.” It’s not like that. It’s not meant to be an either-or. It’s meant to be a sunrise or a sunset where you get beautiful when it’s not all the way one or it’s not all the way the other. That’s where the beauty is.

The sky is most beautiful during sunrise or sunset. It’s when it’s not all the way dark and it’s not all the way light. Beauty is where it’s not all the way one or it’s not all the way the other. - Samantha Postman
Time To Pivot: The sky is most beautiful during sunrise or sunset. It’s when it’s not all the way dark and it’s not all the way light. Beauty is where it’s not all the way one or it’s not all the way the other. – Samantha
“Time To Pivot: The sky is most beautiful during sunrise or sunset. It’s when it’s not all the way dark and it’s not all the way light. Beauty is where it’s not all the way one or it’s not all the way the other. @SamanthaPostman” Click To Tweet

Why People Search for Simple Answers and Go to the Extremes?

Casey: Why do you think people search for these simple answers? Why do we go to the extremes?

Samantha: It’s crocodile brain. We’re meant to survive. “Am I going to survive or not survive?” That’s who we are. We’ve evolved a lot from caveman days. It’s not okay to just be in survival mode all the time. It’s okay to stop your brain and say, “I’m not a caveman anymore.” Take some time to be comfortable with thinking things through for yourself and not being worried about what everyone’s going to think about it. What do you think about it? Also, what do you think about it right now? When I’m mentoring young adults, they’ll make these comments that make it sound it’s going to be something forever. I’m like, “No. That’s how you feel right now.”

Once you put a line in the sand and you say, “This is how I feel about this.” You’ve now put a line in the sand and you aren’t going to make yourself lie to yourself. It’s called cognitive dissonance. You’re not going to lie to yourself. You probably know what that is. You’re not going to make a liar out of yourself. Once you put a line in the sand, it’s hard to change. We do this all the time. We put restrictions on ourselves by putting all these lines in the sand. It’s black and white or, “Either I agree or disagree.” We have this one friend and she says, “I can’t talk to anyone who can’t choose a side.” I was like, “That’s terrible.” It’s survival. She needs to know, “Are you with me? Are you against me? I need to know that.” Why?

We can support a side but we don’t have to choose a side. Supporting a side doesn’t always mean you’re choosing it by the way. If I have two friends that have divorced, people are going, “It’s black or white. I’m going to choose him or I’m going to choose her.” That’s the simple answer. No. I can love them both. I can support her because she needs it. I’m a female and that’s healthier support. It doesn’t mean that I’m choosing her side. People oversimplify it. They’re like, “You support her. You’re choosing her side.” No. I’m supporting a side. I’m not choosing a side. There’s a difference.

Casey: There is this tendency to search for simple answers.

Samantha: There is a place for that. Someone told me that I think way too much. It was done in a not nice way. They’re like, “You think way too much.” I remember thinking, “You don’t think enough.” This person was oversimplifying things. I was like, “Things aren’t as simple as you say they are.”

Casey: It’s not a nice thing to say to someone. That’s quite a judgment.

Samantha: They were being judgemental. I also got to see a little bit of ugly in my own self. When somebody challenges us, we get to learn about ourselves. There’s value in that. When a person said, “You don’t think enough.” I learned something about myself that I wouldn’t have learned had he not said that to me. I learned that it’s valuable for me to be around people who think a lot. I wouldn’t have necessarily come to that conclusion had I not been challenged to it. It helped me go, “You’re not my people. I like you as a person but you’re not somebody I want to intellectually engage with.” That helps you.

It reminds me of when my son went to do a ministry in Chicago. It was a horrible experience for him. He went down there and wanted to save the world and do some good for the homeless down there, which was great but he had a terrible experience. He was upset because he didn’t have a great experience. He wanted this wonderful experience of his lifetime. He had given up a lot to go, a lot of Sundays. He had done fundraising and missed out on a lot of family things. I said to him, “You learned who you’re not. That is valuable.” When you can say, “This isn’t who I am,” then you can focus on who you are. Anytime we get those opportunities and they hurt, we get to learn who we are and who we’re not. That’s valuable. When someone gives you a life lesson, we can still thank them inside and be like, “I learned something super valuable from the interaction.”

Casey: This reminds me of someone’s essay that I read. The headline was so good. It was, “Your values aren’t your values until you’ve sacrificed something for them.”

Samantha: With young adults, I get that a lot. They’re like, “I value this.” I’m like, “What are you doing for that?” They’re like, “What do you mean?” They’re like, “I value authentic relationships.” I’ll be like, “What are you doing?” I might ask more questions. Maybe that wasn’t a good example because it’s a harder one to do. Once we start talking, they’re not being authentic at all. They’re not engaging with the community. They’re watching Netflix all the time or Minecrafting or video gaming all the time. There can be authentic relationships in that but not the way they’re thinking. I’m like, “Do you value it or is it wishful thinking?” It’s important for us to understand the difference between value and wishful thinking. We usually think they’re the same thing.

BP 3 | Time To Pivot
Time To Pivot: It’s important for us to understand the difference between value and wishful thinking.

Casey: A lot of it is aspirational. There are values that we wish we had or maybe wished we live by.

Samantha: If you’re not living it, then it’s not of value to you. I come across a full-time working mom and she’s like, “I want to be with my kids at home right now.” If I have any moms or any parent reading this, an important time to be around a lot is about the 14 to 16 years of age. They always say the start and the beginning are the most important in anything. It’s the only thing they’ll remember.

When you think about your childhood, what do you remember? Most people will say they’ll remember their last few years more than anything else. If it was a terrible experience in your home, that is going to set your relationship with your family and your parents. It could even be for a lifetime based on how those last years ended. That’s why I recommend 14 to 16 years of age. Around sixteen, you’re pretty much doing stuff with your friends. You’re not around your family a whole lot anymore. At fourteen, most kids will still listen to their parents to a degree. At sixteen, they’re not listening very much. It’s important to be around.

I was talking to this girl and she had kids around that age. She was saying to me, “I want to be home for them. It’s important to me.” She was taking on extra work at work. I was like, “I thought you said you value spending more time with your kids. It’s important to you.” She said, “It is.” I said, “You took on more work.” She’s like, “What do you mean?” I was probably a little too bold. I was like, “It’s admirable that you want to do this. You say you value wanting to put this last investment in your kids but everything you’re doing is the opposite of that. That’s wishful thinking.” She went, “Oh.” I was like, “I said too much.” To be honest, in my brain, I was like, “These kids at home are screaming for you. They want you and you took out an extra job.” I’m thinking about the kids. I felt I was trying to advocate for them and tell the mom to shake a little bit, but then she didn’t take it well.

Casey: Sometimes people know deep down that they’re not living by their values. It hurts to have that pointed out. You’re absolutely right.

⬅️ Part 1: The Whys of Podcasting, Challenges of Remote Work, and Bold Perspectives on Women, Careers, and Progress With Casey Juanxi Li

➡️ Part 3: Creative Vision And Connecting Podcast Creators With Casey Juanxi Li

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About Casey Juanxi Li

BP 2 | Why PodcastingCo-founder and CTO of Podding Labs
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