Fail Fast, Win Big: Why Risk-Takers Thrive feat. Sandra Possing

In this episode of Taking Back Monday, Alyssa sits down with Sandra Possing, coach and digital nomad, to explore what it takes to thrive by embracing risk and rejecting the conventional 9-to-5. Sandra shares her personal journey of redefining success, ditching the need for perfection, and leaning into failure as a path to growth. Together, they discuss why risk-taking can be a superpower, how to overcome analysis paralysis, and ways to create a career that aligns with who you really are. Whether you're looking to break free from the mold or just curious about what life outside the "safe" path looks like, this episode will inspire you to think bigger, take action, and maybe even redefine success for yourself.

Key Takeaways:

• Failure Fuels Growth: Taking imperfect action often reveals valuable insights faster than playing it safe.
• Redefine Success on Your Terms: Success isn’t one-size-fits-all; it’s about building a life that aligns with your values.
• Move Past Overthinking: Action is the antidote to analysis paralysis—taking steps forward builds clarity and confidence.

Key Moments:
00:00 Introduction and Welcome
00:14 Sandra's Journey to Becoming a Digital Nomad
03:13 Challenges of Leaving Traditional Work
05:55 Embracing Action and Overcoming Perfectionism
12:21 Living Authentically from the Inside Out
17:52 Finding and Honoring Your Passions
21:00 Spotlight on Inspirational Women
23:51 Conclusion and Where to Find Sandra

It's time to say "goodbye" to the Sunday Scaries.

Connect with Alyssa
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Transcript

Alyssa Nolte: 0:00

Hey everyone. Welcome back to taking back Monday. I am so excited that you decided to say goodbye to the Sunday scaries and hello to the future of meaningful work. And I'm even more excited to introduce you to my new friend, Sandra. Sandra, welcome to the show. Thank you so much for having me. I'm stoked to be here. So when I was reading your application to be on the podcast, one thing you mentioned was that you are a digital nomad. And I hear a lot of my friends who are like, let's just sell everything we own, buy an RV and live on the road. Tell us, what does that mean to you? What does it mean to be a digital nomad?

Sandra Possing: 0:30

I love this phrase so much because it could literally mean like 1 million different things. And if I think back to, so I might kind of like beginning of my career days were in back in San Francisco. And I was doing some work in person, but I, I was starting to have a leaning pretty early on to the idea of working remotely. And this is like way pre COVID days, my whole family. I'm from Scandinavia. Originally, my whole family is still back there. I grew up traveling and I, I kind of realized early on in my, like, soon as I graduated college, I'm like, I'm not cut out for the like normal 9 to 5, 2 weeks of vacation kind of thing. Took me a couple years to figure out that that meant I was going to be an entrepreneur and live a very unconventional life. But there was some workshop I went to where the workshop leader mentioned the phrase mobile world citizen. And I was like that, I was like, I don't even know what that means, but I want it. I want whatever that is. And the more I thought about it, I was like, to me, that means being able to work from anywhere in the world. While like living my life the way I want to live my life and then fast forward a couple of years and I'd launched my coaching business. I was meeting people in client or people in person like a coffee shops in San Francisco, which I love because I love hugging people and, you know, seeing them, but I was starting to realize like, wow, doing this virtually would be a lot more convenient, less Paying for parking, less driving, more, you know, this is like back before Zoom was even really a thing. I think we were doing like Google Hangouts and Skype and stuff. Right, Skype. Yeah. Oh my god. Oh my god. So it was a mix of the two. And then in 2016, my husband and I got married and we had been talking a lot about it. We're like, you know, it costs a living in San Francisco is pretty high. We could legit be paying less by traveling all over Southeast Asia and doing everything but like over there. And so we did. We got married instead of taking two weeks of vacation. We just sold everything. We bought one way tickets to Scandinavia so he could meet my family. And then we traveled for 10 months. Through 11 countries and I worked the whole time and it was kind of like a proof of concept. I wanted to prove to myself that I can indeed run this business from my laptop from anywhere in the world and it worked out even more easily than I expected it to. And then since then, it's just been like, all right, that's just part of my work in life and business and how I run things is even like, right now, I'm 7 months pregnant and we are in a new house and we're in a neighborhood that we love with great community. And we're like more subtle than we've been in a while. But I still identify so strongly as a digital nomad, because I know that I have the option to either pick up and leave and travel or to just, you know, even if it means working from a coffee shop or taking a couple months off for maternity leave. It's about the flexibility and the choice.

Alyssa Nolte: 3:10

Yeah,

Sandra Possing: 3:11

absolutely.

Alyssa Nolte: 3:12

You mentioned. That you kind of jumped from more traditional work and then you realize that that's what not really what you wanted to do, but it can't have been that easy to go from, like, a traditional job that everyone expects you to have going to this new thing because that was way before digital nomading was like a thing that people did. That was way before van life on TikTok. So talk to us a little bit about how you made that choice to say no to traditional work and yes to something completely different.

Sandra Possing: 3:40

It, uh, it was not an easy choice and it was not a clear cut one by any means. I would say I probably spent the majority of my twenties kind of figuring stuff out. And that meant trying a lot of different jobs. I had some more traditional jobs. I had a lot of random side jobs. I called myself like the queen of the side hustle. Cause I just always figured things out, but I did a lot of unconventional things. And yet underneath it all, I was always searching for the thing. Like I knew I wanted to find a meaningful career that I like, that was like passion based and was having an impact. I just had no idea what it was going to be. And it was a lot of like trial and error, a lot of kind of process of elimination. Like I worked in finance for a while. I worked for startups for a while, worked in the service industry for a while. I was always kind of like drawn to entrepreneurs and entrepreneurship, but I didn't think that I would be. A founder or an entrepreneur. I was more like working with really smart friends who were computer programmers. And it took a while until probably almost my thirties when I finally found fitness and then that was close. And then fitness kind of led me to finding the coaching world. And then it was like, I finally came home to like my soul family and my calling, but it was all over the place. I mean, it took a lot of patience and resilience and like, You know, forgiveness, because I was beating myself up the whole time. Like I should have it figured out by now. All my peers were like well into their corporate careers. Like, what am I even doing with my life? And so that alone was like a huge personal development journey to just give myself the grace and the time to figure things out and to do things my own way. But I'm so glad that I did because I hear people, you know, in jobs that they hate, but they feel stuck.

Alyssa Nolte: 5:18

I was literally, like, I'm a big believer in serendipity, like, things happen for a reason. Literally not even an hour ago, before we were recording this, I was having this conversation with someone, and we were basically talking about how the career has happened to her. And none of it feels like it's been connected and that she's just been floating along from next thing to next thing, but none of it feels like it's been purposeful or a path. And we were having this conversation about, like, Do you, do you want to continue just kind of floating along or is it time to, to have a bias towards action is what we finally decided. We have a bias towards action. We're not going to sit here and talk about doing something great. We are going to do something great. And so that's really been my, my, my approach in the last couple of weeks is saying I have to have a bias towards action, towards execution. Let me stop talking about these cool things I want to do and start doing these cool things. And even if it doesn't work out, at least I did something.

Sandra Possing: 6:10

And that's how we learn is by kind of stumbling our way forward. I, in my practice, I work with so many clients who are, they're incredibly high achieving. They are, they have such high expectations for themselves, but they get in their own way because they have, you know, they're perfectionists. They're people pleasers. They like, they need to succeed and achieve. And so. A lot of times they don't actually take much action because they're paralyzed, you know, they're sitting on the couch stuck in analysis paralysis, or they're like, I literally can't go do the thing until I know I'm going to do it well, which is such a huge hurdle. And so one of my same thing, like one of my favorite things to do with clients is I think of it as kind of like metaphorically just pushing them off the cliff before they're ready, but it's just like getting them out the door to do something. And usually that something is like tiny baby steps because half the time we don't even really know what they're going for. They just know they don't like what they currently, they don't like their current place, their current destination. And so while we're trying to figure out the direction and like really what, who they are and what they want and what lights them up and what would be meaningful, but we're not just sitting around talking about it. We want them to get out there and try stuff because then they get more clarity. They get more confidence, they get more momentum, and then they get all sorts of little breadcrumbs and clues that they can actually work with. And then course correct versus just like sitting there and analyzing all the time,

Alyssa Nolte: 7:25

right? When I was in high school, I was taking advanced chemistry and I wasn't a great student. Like, I will totally admit that I was not. I didn't enjoy studying and I didn't want to, so therefore I didn't, but I was very good in the lab. So when we would do our theory stuff for. Advanced cam, I would be like very middle of the pack when we would do the lab stuff, I would get like the highest scores and my chem teacher once told me, I think it was. I don't know if it was supposed to be a compliment, kind of a backhanded compliment. He made a comment like, Alyssa, you're good at this because by the time everyone's finished reading through the instructions four or five times, you're already on your second try of trying to do the experiment. You messed it up the first time and then you just tried it again. He goes, That's why you're doing better in this is because you're just trying it. You're just going and everyone else is spending so much time reading the instructions. They, they get through it once and you've gotten through it four or five times. And I'm like, I think you just told me that I was reckless. But if it's working out for my grade, I suppose it's fine. And that's always kind of been my approaches. Try it, try it, try it, fail a couple of times and then maybe go read the instructions.

Sandra Possing: 8:28

That's I mean, if I could whisper that into the ear of my younger self and the years of like 90 percent of my clients that I work with, it's that it's like, dare to be a little reckless, dare to fail. Did like reframe failure is this massive, exciting learning experience because so many of us, we just, you know, we, we second guess ourselves and we need to, we need to get it right. So we don't even start. And we're totally caught in this fixed mindset of like, I can't even like show my face until I have it all right. And it's like. I have a friend who's basically the exact opposite of me. She's like, but I'm like the second guesser and I've really had to work hard to get to sort of the middle of the spectrum. She's like, kind of it. Slightly reckless. But I, I look at her and I study her because I'm like, she does all these things that I would never dare to do. And she fails a lot and she puts her foot in her mouth and she makes like kind of a hot mess sometimes, but she gets things done so much faster than anybody else. What's that? You know? Cause she just goes for it, you know, and then you feel stupid. And then she's like, well, learn from it. And then she just keeps going. And I was like that kind of, uh, just like not risk averse. What's the opposite of risk averse, like risk. Risk,

Alyssa Nolte: 9:30

um, risk,

Sandra Possing: 9:32

adventurous, you know, risk

Alyssa Nolte: 9:34

friendly. I don't know.

Sandra Possing: 9:35

Risk friendly. Yeah, exactly. I was like, we, so many of us could actually do with a lot more of that. And then maybe those folks can do with a little bit more like mindfulness and stuff to balance it out. But it really is. I'm like, man, it's so many of us, especially women who, you know, we're so conditioned to like, be careful and look good and be appropriate and play small and all that kind of stuff. Like a little bit more of that, just go for it, figure out face plant. And of course, correct.

Alyssa Nolte: 9:59

I feel like I, I used to be a lot more risk friendly, if you will. And then I got into like a stable kind of corporate environment. And then I, something about that environment really made it hard for me to go back to being risk friendly. I got much more risk adverse in a very corporate traditional setting. And I'm looking at that. I'm like, Oh my God, no, I lost my superpower, like my ability to just shove off and do things and go. And now I'm like actively working to get that back because it's hard. And it's, it's, You get comfortable in, well, we'll just go to a meeting and we'll talk about it instead of, well, I'm the only one here, so I guess I'm doing it, like, and have to be the one that makes it happen.

Sandra Possing: 10:41

Yeah, and that's I mean, that's a huge difference between someone who's living in more of like the employee context versus somebody who's in an entrepreneur context. But I think in no matter what kind of work we're doing, there's opportunities to to play with that. You know, it's like, you could be full on corporate employee and you have a lot of actual policies and rules that you need to play by so that you don't get fired. But within that, there's I think a lot of like, wiggle room to be kind of like, I have a colleague who, she started this whole like brand called corporate rebel because she was all about, you know, like people who, they work in corporate, but like, if they just, You know, like acquiesce and sort of conform to what everybody else is doing. They will lose themselves. They'll lose their spark, their creativity, their heart, their soul. So she was helping people like really find their, like their unique spunky flavor whilst still like existing in, you know, an ecosystem that certain things weren't allowed. Whereas as an entrepreneur, like. I can do whatever I want, basically. And if somebody doesn't like it, that's fine. No one's going to fire me.

Alyssa Nolte: 11:43

If then it's all on me, it just means I maybe don't, don't win your business, right? Yeah, exactly.

Sandra Possing: 11:48

But I think no matter what our situation, we can play with that a little bit.

Alyssa Nolte: 11:51

A hundred percent. You got to be your authentic self, no matter if you're in a corporate environment or if you're your own leader, right? So you mentioned that you, you talked to high achievers and you really helped them break out of that analysis paralysis. What, What would you say is the number one thing that really makes a difference? If I'm, if I'm one of those people, I'm a high achiever and I, I'm in and out sprouts right now, what would you say to me?

Sandra Possing: 12:16

I would say the biggest shift. Can one of the biggest shifts happens when we switch from living from the outside in to living from the inside out. And what I mean by that is when we're living from the outside in, we're letting external reality dictate who we are. So we're letting, you know, I have to dress a certain way to fit in at work, or I have to, Act this way because that's how I grew up or you know, I'm I want to fit in with my colleagues. So I need to also, you know, do this on the weekends. It's like we let the world, our conditioning, our family, our media, our peers, all of that. Tell us who to be, how to be, where to work, how to work, what success looks like, all of that. Which like that can work out for some people who just kind of get lucky where their external reality matches what they actually want. But for so many, at least the people I work with and so many people in my world, the external reality is like maybe a part way match, but it's not a full match to who you really are inside because we're all so unique and so different and have preferences and all this stuff. But it's hard to make that flip when there's a lot of pressure from the outside. And so my work with people usually is about flipping the whole paradigm on its head. I mean like, let's get you living from the inside out, where the outside reality is whatever it is, but you determine who you are, how you are, You know, what are your values? What are your passions and designing a life? That's like your external reality becomes a reflection of who you are on the inside versus your insides becoming a reflection of whatever environment you're in, which is when we lose ourselves, which is when, you know, I guess probably one of the most common themes I see in my business. And I've been doing this for 12 years is like, These really, especially, you know, I'm in the San Francisco Bay area. I get a lot of high achievers, like very successful people who come from successful families with a lot of pressure. And they've created these, you know, lives and careers that are beautiful on paper. But internally, they're miserable, or they're so burnt out, or they're so stressed. Like, I mean, it's a wild to the, the, the amount of imposter syndrome, especially from people who are like, they're actually crushing it in their fields. You know, anyone else in their sphere would say they're doing so well. They're at the top of their game, but inside they're crippled by this deep belief that they're an absolute fraud.

Alyssa Nolte: 14:39

When it can't be like you talk about. You know, the way that they're feeling, but I would imagine there's actual physical health effects on the body. Like, my husband and I are both very high achievers, right? And every once in a while, I'll be like, I just need to go lay in a room and not have anybody talk to me because I've got like, so much going on. I need to go lay under a weighted blanket and have no one talk to me. And he's like, you good? I'm like, I will be just give me a second. But like, I can't imagine that that's, you know, where I want to be in 10, 20, 30 years. In my work life. I don't want to be laying in bed being like so stressed out.

Sandra Possing: 15:14

And that's exactly why, to me, it's so important to help people, especially women flip that paradigm and get to the place where they're, they can still be high achieving, they can still create these beautiful lives and careers and have a huge impact, but they're doing it in a way that's an integrity with who they are. They're doing it in a way that reflects their core values. They're doing it in a way where they get to like, you know, be whatever identity they're working on being, let's say professionally. But it's still an authentic version. They can still express themselves in a way that's true for them. They can create alignment in their lives. And like, you know, some people I work with, like we look at what they've created and then they start doing the inner work and they're like, Oh boy. Like I might literally need to burn it all down to start over. So I've had people who, you know, get divorced, quit jobs, start businesses, move to a different country, like big, big life changes. Shifts, but most of the time, honestly, it's like tiny little shifts. You know, it's somebody who is so stressed, so burned out. They hate their job. They think they need to quit. They think they need to move to a totally different industry or something. Turns out they just needed to like paint on the weekends. You know, they just needed to honor a passion. They do need to do more of what lights them up and less of what drains their life force for other people. It's like, wow. Yeah. No, this is actually, everything's out of alignment. So it's a big shift, but a lot of time, just like identifying a little bit of these things, like the quirky little things that make each of us who we are and honoring those things. Like I had several women who are these, like, Badass corporate, you know, high achieving gals who same thing were really, they thought they needed to like change their job or do something drastic. And then they realized that they loved, had like three separate people who all realized they love flower arranging. And I'm like, I can't relate to that. I'm like, I love flowers, but like, it does not light me up. Like, you know, yay. But like, but they were so pumped. about flower arranging, but they weren't doing anything about it. So it basically like insisted that they carve out time for flower arranging. One gal even like quit her job and started a flower arranging business on the site. Like, and one guy just like did it for herself. Another one started like a little side business where she would put them out, like in a cart with a Venmo code, you know, like little farmers market

Alyssa Nolte: 17:22

type concept. Yeah.

Sandra Possing: 17:23

Cool. Yeah. It was like, they just lit up like light bulbs once they started doing that one simple thing. And I was like, Wow, did we just like, crack the code to life and happiness, at least for these people, you know? Flowers. Flowers is the hack. Turns out that's a

Alyssa Nolte: 17:35

secret, y'all. That's awesome. So, I mean, that's kind of hard though, because like, I feel like, I'm an adult, right? I'm a grown up. I'm not in college anymore. I have kids. And finding those hobbies, I think, can be really difficult. Like, how do you find that passion, that thing that lights you up? How do I find out that flower arranging is that for me? How do you go about that?

Sandra Possing: 17:59

It really can be hard and I'm laughing because I have like so many great stories about this. One of my favorite ones was a client who she was in a group program of mine and we were specifically working that week on like, identifying and honoring your passions and you know, everyone's like working away and having discussions and she comes to me. She's like, Bro, she's like Sondra. Not only like, I can't even relate to the word passions. Like that does, it just falls, like it doesn't even mean anything. She's like, I can't even, I don't even know what I like. Cause she had spent her last 15 years in a very toxic relationship with a, you know, somewhat abusive person. So she was just surviving. Yeah, she had like zero access to passion, you know, so the place that it's like kind of depends where we each are, but I think actually just recorded a podcast on this last week, I think an easy place to start for people who feel really blocked is like, what do you hate? And then what's the opposite of that, you know, like, look at your life or look at your day to day and anything that you're like, Oh, gross. I hate it. Or you don't like it. Like, that's a clue. That's contrast, appreciate the contrast and look at underneath that. Like, what is the thing that I do like then? And then just look at things like, I don't know, list off a bunch of random hobbies or a bunch of random things that, you know, what, what is a typical human potentially into? I don't know. A lot of people like music or like hiking or, you know, yeah. Hanging with friends and family or whatever, but then you can get specific and you're like, okay, music. Do I like, yeah, okay. I like music, but like, what kind of, do you like, you know, listening to Mozart quietly at home, or do you like going to like a concert where people are basically like beating each other up in the mosh pit or something? And then you start to identify, well, I like this more than that. So we just start to like have leanings. And then I think we can dig much deeper and ask ourselves things like, why do I like that thing? Right. A lot of us are like, Oh, yeah, I'm really into, you know, going to see live music, but then you realize you're just tagging along with your friends who like this one band who you don't really like. But then you're like, Ooh, but if I was to choose the band, I would like this. Or actually what I really want to do is just like, go take a pottery class. So the more I can get into the details.

Alyssa Nolte: 20:07

Yeah, giving yourself permission to, to, to like those things, right? Like I, when I, when it was COVID, I played a lot of like, like Animal Crossing, like those little cozy games on the Switch that we all played when we couldn't go outside. Um, and I'm like, it's okay to like, enjoy sitting down and playing a video game for an hour. You know, I'm, I'm in my thirties, but it's fine. Like I can enjoy those things without having to worry about like, Oh, you know, this isn't something that helps me be a better person. I'm not, you know, listening to a TED talk. Like it's okay to not enjoy TED talks and to not enjoy reading nonfiction books. Like I can just read a romance novel for the weekend and that's okay.

Sandra Possing: 20:46

A great journaling prompt is like, what would you love to do if you knew that nobody would judge you for it?

Alyssa Nolte: 20:51

Yeah, I love that. Yeah, still that one. So tell us, Sandra, who do you think is taking back Monday? Who would you put into the hot seat?

Sandra Possing: 21:03

Oh, man, there are so many, um, especially women who I look up to who I think are just changing the world and the way we do things and the way we show up as humans and as women, but especially in our careers, it's like across so many different categories. The one that happens to be top of mind right now, just because I've been binging some of her content is, uh, this woman, her name is Amy Tallestrude. She on Instagram is the lazy millionaire. It's her. Okay. I already love that lazy millionaire. She's a, she's an entrepreneur. I, most of the people at being an entrepreneur, I that's mostly like, you know, those are the, my expanders, the people I look up to a lot, even though most of my clients are not entrepreneurs, but I'm like learning from these, these, especially I really resonate I'm 44. So I'm like an elder millennial border Gen X, but I resonate so much more with millennials and especially younger millennials, like really speak to me. I don't know. I think I just like. Like I'm a, I'm an old soul trapped or I'm like a young soul trapped and I don't know. Anyway, but like this woman, she is a course creator and she makes millions of dollars a year being basically like her whole brand is Lazy Millionaire because her whole thing is like. The, it's kind of the antidote to like the bro hustle hustle mentality and like work, you know, sleep when you're dead, work hard, right. That tech bro culture, bro culture. Exactly. Which is so in so many start like startups and founders are like that. And she, I mean, she works hard and she creates a tremendous value with her free content and all her courses, but she demonstrates this life where she, it's so authentic, like most of her stuff is just like, she's at the beach club and. Paris or somewhere in Italy and she's just getting spa treatments all day long and stuff. So it's like she's embracing who she really is, which is this kind of like, she's like, I'm ADHD. I'm kind of lazy. And so she's doing things her way, which, and you know, that obviously wouldn't work for a lot of us. Some of us would be grateful, but the point is like, there's so many ways to do your career, whether it be as an employee or as an entrepreneur or as a creative or a performer, whatever it is, there's so many ways to do it in your own way, your own unique flavor, but like, in order to do that, if we're going to design a life and a career that is a reflection of who we are, we've got to know who we are. So again, it's that coming back to authenticity is coming back to just being, like you said, giving ourselves permission and daring to be a little bold and a little unapologetic about who we are and getting excited about it. And then like the more loudly we live our lives. And I think the more that we model for other women, especially like younger generations and show them what's possible when we're true to who we are, versus just like, you know, following the roadmap to how you're supposed to live your life. Because this is what success looks like, like, well, like, that's like makes me want to both like go to sleep out of boredom and like break a window at the same time. It makes me so mad. It just doesn't have to be that way. It can look so unique and so authentic.

Alyssa Nolte: 23:50

I, I love that. If someone is really connecting with you, they want to, they want to get more Sandra. Where should they find you online?

Sandra Possing: 23:57

I'm very easy to find. I'm the only one of me. So you can, I always just say, just Google my name and you'll find all the things, but it's also Sondra passing. com. I'm at Sondra passing on all the social medias. And then I also have a podcast called, Oh, hi self, which is all about bringing you back home to your authentic self. Just like everything we've been talking about here.

Alyssa Nolte: 24:14

I love it. Well, thank you so much for taking back Monday with me. I can't wait to have this podcast air air.

Sandra Possing: 24:19

Such a pleasure being here. Thank you.