Redefining Success

Everyone wants to be successful. Does that mean having $1,000,000, obtaining your dream job, or buying your dream house? Cristina and Alex offer a different perspective than the material success we've been conditioned to believe we want.   This episode offers a discussion around what it means to be successful from the inside-out. They suggest having a more fluid definition of success. By using our internal compass, core values, and being present in our lives, we can redefine success on our own terms and in the present moment. "Success" might be difficult to answer for yourself, however you'll end up happier, more fulfilled, and more successful!

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Credits: Raechel Sherwood for Original Score Composition.

YouTube Channel: Uncover The Human







Alex Cullimore: Welcome to Uncover the Human where every conversation revolves around enhancing all the connections in our lives. 

Cristina Amigoni: Whether that's with our families, co-workers or even ourselves. 

Alex Cullimore: When we can be our authentic selves, magic happens.

Cristina Amigoni: This is Cristina Amigoni. 

Alex Cullimore: And this is Alex Cullimore. Let’s dive in.

Cristina Amigoni: Let’s dive in. 

Alex Cullimore: Let’s dive in. 

Authenticity means freedom.”

“Authenticity means going with your gut.”

“Authenticity is bringing 100% of yourself not just the parts you think people want to see, but all of you.”

“Being authentic means that you have integrity to yourself.”

“It's the way our intuition is whispering something deep-rooted and true.”

“Authenticity is when you truly know yourself. You remember and connect to who you were before others told you who you should be.”

“It's transparency, relatability. No frills. No makeup. Just being.”


Alex Cullimore: Hello and welcome back to this episode of Uncover the Human. Today, it’s just Cristina and I, and we are going to talk about something on everybody’s mind, success. What it means? What it doesn't mean? And how it stops us ironically from being successful? 

Cristina Amigoni: Yes. Yes, I’m sure that as the beginning of the year everybody's thinking about how to make this year successful, or their life successful based on this year. And so one of the things that I always find fascinating as a coach is to actually ask what your definition of success is.

Alex Cullimore: I’ve asked a few people that, and I don't think I’ve ever had somebody deliver an answer. There is lots of generic ideas. Lots of, "I’ll be successful when I have this job, or when I can go on a vacation or something." And there's some big ideas, but it's a weird implicit assumption. I think there's a lot of desire to be successful. I feel like I want to be successful. I also feel like I don't really know what that means even for myself. Like there are ideas. There are things. And I’ve done a lot to plumb that a little further than, "Well, I’d like a million dollars." But sometimes it does feel vague. And it's something that even when you ask people, it can be challenging to define even though we all think, "Well, I’ve wanted to be successful forever." But of course I want to be successful. Until you're actually asked that and you take that inventory. A lot of people I’ve asked that to don't have that answer. 

Cristina Amigoni: Yeah, I agree. I think it's a very difficult question. I think there's a lot of outside conditioning on what success is supposed to be like and what the definition of success is. And yet I find it fascinating that two things jumped out when you were talking. One was the tendency to look at success in the future, not the present. Meaning I will be successful when I make a million dollar, or I get this job title. I buy this house that it's 6000 square feet on one acre. Whatever. The very materialistic point of view of successes, which is very common and the most practical out there or conditioned out there. 

And so then my question is like, "Okay. So since you're not there yet, does that mean you've never been successful up until now? So you've reached no success because, well, you've just established what success is, which is when you will get to these things." And then also once you get to them, that's it. Is that the end of the line of success? Like are you just – That's it? You're successful for the rest of your life at that point. It seems like it's very point in time when it's tied to a materialistic reason. 

And the other thing that I was thinking, too, is when you were talking about being successful, is this – How being successful is not the definition of success. So the question is not when are you successful? The question is what's your definition of success? 

Alex Cullimore: And that's a really good distinction. It's kind of like saying I want to be happy. Because if you constantly think about being happy, you're not actually even spending time being happy, which is inherently an in-the-moment feeling. It's something that is just kind of ongoing. There is happiness that is and not usually because you thought I’m happy now. You're just experiencing it. I think that's very true. For me, I think that's why I conflate those in my head with success, is times when I am successful, or times when I’m just feeling I’m not even bothering to categorize feelings or think about what's happening. It's just I’m just so glad it's happening. 

Cristina Amigoni: Mm-hmm. Yeah, exactly. It's a little bit like a legacy, or the episode we talked about legacy. It's like if success and being successful is tied to these milestones, which we create for ourselves based on society, family, friends, colleagues, whatever is going on around us, then is that really what it is? I mean, then everybody's tombstone would literally have their – Whatever. Their bank account balance and the – 

Alex Cullimore: The last banking statement.

Cristina Amigoni: Yeah, the last banking statement, the square footage of their latest house, the title of their job. So I don't know that that's what we actually believe success is. It's just, as you said, we don't spend the time to actually define what success means to us. And so we adopt somebody else's. So while Jeff Bezos is successful. Well, is he successful according to his definition or your definition? 

Alex Cullimore: What do you do when you become successful? And if your definition – First, there's two things. If your definition is always in the future, you're chasing an inherently moving goal post. You're like holding the carrot out in front of yourself at a distance that you can never reach so that you can run towards it. And then people wonder why they feel tired and why they don't feel like they've achieved things.

Cristina Amigoni: And burnt out, and unfulfilled.

Alex Cullimore: And secondarily, if you got that carrot, what happens then? 

Cristina Amigoni: Yes. What happens then? They're very good question. I think there's a big difference between setting milestones and being successful. You can be successful at reaching your milestones. But does that mean you're successful – If by reaching your milestone you're going against your core values, was that really success? 

Alex Cullimore: I’m guessing it's not going to feel like it if you get it.

Cristina Amigoni: Yeah.

Alex Cullimore: I remember Brene Brown saying that there's two bad things that can happen when you release like issues talking about, I think, publishing her first book. She's like, "There's two bad things when you release a huge body of something like a book, like it's something that took a long time, some body of work. There's two bad outcomes. One is it's not well-received, and you feel like, "Oh no. Yeah, it just wasn't good. Nobody likes this." And she's like the second bad thing that can happen is it's well-received. And like now you've got the expectation. Now it's this: how do I keep up with that? Or you don't know what made it successful, and now you're guessing. Or it wasn't everything you thought it would be. But now it's successful. And what does that mean about what you thought it was going to be? 

And I remember, I’ve been reading a bunch of blogs recently and somebody was talking about having articles go viral. And they're like, "The ones that went viral for me were ones that I just felt like I had to write something. And so I just did it in like a day. So I got it out there. And then that one ended up exploding. And this one that I’d worked on for like four months, and I really loved the topic and got really into the research of it, finally released it. Nothing. Crickets. that one's just like barely received." 

It becomes a good lesson also in defining success externally when it's based on the reception from people. When it's based on some set of circumstances. It's not really following a lot of your values. And there's a good chance that becomes – Actually, I guess there's a slim chance that becomes happiness. You were really lucky it happened to also in kind of to something that made you happy.

Cristina Amigoni: Yeah. Well, that brings up a really good point. Like success is, it's an internal compass. It's not an external compass. And so when you look at success as what's the life I want to live? What's the legacy I want to leave behind? Then I can say that was a successful life, because I lived my why, whatever that why is, which goes back to values. It goes back to something much deeper than the job title I have for this company, or the salary I reach for this, or the vacation that I’m able to pay for. 

Alex Cullimore: What does that get you? 

Cristina Amigoni: Exactly. What does that get you? And maybe the vacation gets you to your why. But it's so successful because you've reached your why. Not because you were able to say I had that. Like I went to Fiji for a month.

Alex Cullimore: Actually, it's a pretty good similar metaphor to what we always – I’ve talked about this probably ten thousand times at this point, that there's so many like technology transformation projects in companies where they're like, "We're going to have a new CRM. We're going to move all our data to the cloud. We're going to implement this thing." And there's always that implicit, sometimes explicitly stated clause at the end of that that's like, "And that will solve all our problems and we'll be happy. And then we'll be successful as a company." 

And I think it's mistaking the tools for the outcome. And when you just treat technology as the outcome and we treat a vacation as the success, you're kind of passing by what that vacation gets you. Maybe that vacation is an expression of freedom. Maybe you've always wanted to try surfing and now you get to do that. Or it's just been a dream to check this off unless you really want to experience this food or something. That's more the why. That's your drive. That's your purpose. That's what that vacation gets you. It's not just because you had a vacation. And that vacation might just represent, "I’ve reached a place in my life where I felt comfortable doing this." And that means I have all these other things that kind of had to be built and that my life had to be in such circumstances that I could take this. And I’m thankful for that. I feel successful for. 

Which I guess is also then if you define it that way, is it actually not successful if you don't do that? What if those circumstances are no longer possible? What if, I don't know, a global pandemic happens? What if something like that strikes? Is this still not successful? 

Cristina Amigoni: Totally random. And I think that's why if you anchor your definition of success to something that's, first of all, fluid, because it may change throughout time, and also anchored in your core values. And even from a company perspective, on your mission and vision. So if your mission and vision are actually anchored into the future into creating something that's beyond this year's quarterly results, then that could be your measure of success. If the vision is to create a world where people can show up as their authentic selves, and you look back and you're like, "You know, we've provided a lot of opportunities to people to show up as their authentic self." Then you can say as a company, "We are successful, because we provide that opportunity." It can be really an anchoring thing even for tools and technology that you invest in. You're going to invest a million dollars, two million dollars, ten million dollars on this new technology. If you can't answer what's your measure of success from this, then maybe you should rethink the investment. 

Alex Cullimore: Even spend some of that 5 million defining that then if you need to, because otherwise what are you really aiming at? You're swinging in the dark and hoping that whatever you hit is this pinata of success where you feel just get rained little nuggets of happiness and whatever else you're looking for.

Cristina Amigoni: Yeah, exactly. And a measure of success can't be – Well, because we got to move to the cloud because everybody's on the cloud. That's not a measure of success. That can be a reason to invest in the technology. But what are you trying to achieve? I mean, if you're talking about a technology that people use once a year, well, okay, maybe you do need to move to the cloud, or maybe you know you're going to implement this and people are still going to use their local excel spreadsheets on their computers. So were you successful? 

Alex Cullimore: If the goal is like, well, we're going to move to the cloud because it's going to save us 30 percent. Like that's just fine. Also then that begs the question what are you going to do with that 30%? Why do you need that 30%? Is there a huge casual issue you need to cut back on? So now we're able to no longer lay off people because we have the cash flow down. Is it I have this money available to invest? And if you have that available to invest, what are you looking to do? What do you want to do with that? And I think that's an interesting way to think about our own personal success too, is what are we really looking to be able to do? 

We talk about values. Like I want to be able to have some freedom, which means having some flexibility, which means constantly making choices that don't always line up with material success. And sometimes you have to make choices to have enough material success to get to that freedom, whatever feeds the other. But if you're guided, like you said, by your personal why, then you have an actual direction. Rather than what often feels a little bit more like feeling around in the dark.

Cristina Amigoni: Yeah, definitely. So trying to figure out – And it takes time. I mean, figuring out what the definition of success is. It's not something that if you're used to doing the work, you may know. If not, it'll take some time. Because we never stop to think about it. We borrow the definition of success from whatever is around us at the moment, which also makes it a little bit hard to obtain. Because if your measure of success when you're 18 is to graduate college. And then you graduate college. Okay, then what does success look like when you're 25? And why does it change?

Alex Cullimore: I think about that with the Olympians every time the Olympics come up, because, obviously, there's ten thousand people that have commented on the fact that as you get older the athletes start to look like children not only because just half of them are children, but because just they look young. Some people like they're like winning Olympic gold medals in swimming at 16. You're like, "No. Okay. Wow! Wow! Okay." 

Cristina Amigoni: And you look like you're 12. That's better.

Alex Cullimore: It's not that that's not a huge accomplishment. It 100% is. There's so much work that would have to go into that. But I always wonder, is it even healthy for us to obsess over – And we rank countries where like, well, the US has this medal count. And that's measuring up against always like China and Russia [inaudible 00:14:28] is the only nation's big enough to field a team of athletes at that level. But why do we compare this and why are we that? And it's not fun to see that. It's not that you don't want to cheer for something. You don't want people to win. But I do worry about athletes sometimes who win these kinds of successes and then your entire career is still over by like 30 if you're really lucky to have a sport that lasts until 30. Half the sports do not. And even if they do, that's 30. Ends up being – Like Katie Ledecky absolutely destroyed at swimming like four years ago. And this time she still won a bunch. But now at like barely over 30, she's like old for the sport. It's insane. So is it good to like hyperbolize that? 

Cristina Amigoni: Yeah. And then you have huge existential crisis, and identity crisis, and depression. I mean, that's when mental health starts kicking in. And Michael Phelps was very open about it in the last Olympics of when he stopped competing because of age. That took a huge dive into his mental health, because your entire identity is tied to, “You're successful because you win these many gold medals.” That's what success means. Which, again, if we bring it back to the rest of the 8 billion people in the world, so does that mean that if I swim in the swimming pool every week because it keeps me healthy and it gives me energy, it means that I’m not successful because I’m not winning eight gold medals every time I get in the pool? 

Alex Cullimore: That's exactly it. I mean, where do you draw the line of success? And it's not to say that it's not worth finding discipline or finding something you want to do and really honing a skill. Those are both valuable and worthwhile endeavors. I think that it's worth doing some of those things, but it has to be done with some knowledge of what success is and isn't and being very careful to define that for yourself, because otherwise I 100% would believe that. I mean, the world knew who Michael Phelps was. His identity to all of us was an Olympic-winning swimmer. And then you can't swim anymore. I mean, what do you do for your own identity at that point? I mean, it's no wonder we have like child pop stars that have a really hard time at – Especially because you have such a young malleable brain at the time and you reached that kind of success. And what happens afterwards is that identity changes as the world starts to change.

Cristina Amigoni: Yeah, it's very fascinating. It's depressing at the same time how much we've tied success to outside external materialistic accomplishments, when really the definition of success should really be personal. My definition of success can't be the same as yours because my why is different than yours.

Alex Cullimore: Yeah, which makes it excruciatingly painful when we spend our time measuring up to somebody else's definition of success, especially because it tends to feed itself if you do reach that level. So it's like you're saying like my goal is to graduate college. When I’ve graduated college, you've joined the ranks of people who graduated college. And I don't know how that would become like a personal why other than getting to something. Again, like that college, why would you go to college unless you want to do something with that degree? So it still would be a stepping stone. So even if it wasn't though, it becomes very easy to then just try and grasp for whatever the next thing must be, which people will give you ten thousand messages on what that is. You can go on Instagram and it will look like it's the private jet lifestyle. You can go on Forbes and it'll look like it's the billion-dollar evaluation cutting the ribbon or ringing the bell in the Nasdaq. And it's not that that's not an achievement, but is that success? And if you weren't happy with this one, why would you be happy with that one? Unless you personally understand why that would fulfill you.

Cristina Amigoni: It's very true. So what's your definition of success? 

Alex Cullimore: I think this is going to sound so rooted in everything we talk about with Siamo. But it's about being able to live out values. And that is getting the chance to live a life of deep-seated curiosity, being able to help other people. Because I think there's so many – And this is why I love doing this podcast. That's why I love doing Siamo. Just it's hard to stop long enough in life to ask questions like what is success for me. And I’ve tripped over that many times – Even in the last year, I’ll trip myself over these things. And I’ll fall back into traps that I already know about. And being able to identify these things and help illuminate that for other people so they can live that better life, that is much more successful. That feels more fulfilling. And then the more personality of that is getting freedom to do things like that, which requires sacrifice in other realms. That means making sure having enough money coming in so that I have that freedom to do that. And that means taking the hours to build that money to do whatever else. So there are all these other factors that build into that. But it's really about the life you get to live and the things you get to do because it feels moving to me. And those are the things that feel moving to me. And maybe that'll change over time and I’m going to have to keep on top of continuing to ask myself that. But that is where success starts to come out for me. And what about for you? 

Cristina Amigoni: For me, it's very similar, in the sense that it's completely tied to my values and my why. And it took me a long time to define both. And the values are still a work in progress. I think the core are defined. The words around them are a work in progress. I found that my measure of success is to end the end of each day feeling that I have made someone, feel like someone. So I very much like to quote be someone that makes everybody feel like somebody. So if I have done that in some level every day, then that's been a successful day. Establishing deep human connections to then, again, with the goal of have I been able to elevate someone in a way where they didn't feel like they were alone or they didn't feel like they didn't exist? If I have, then that's success. And I can take that into work. I can take that into personal lives. 

Sometimes the titles of my jobs have allowed me to do that more or less. And it's very much of a compass in the sense, and a guideline, in the sense of saying, "Hey, with this role, will this project, will this opportunity allow me to live my why?” Because if it doesn't, then there's definitely guarantee that I will not be successful.

Alex Cullimore: I think that's a perfect example. And I love the way you said it, too, that some titles have allowed me to do that more, because that's exactly it. You can choose to move towards what other people still define as material success. It's not wrong to pursue these things. It's just has to be in service of a larger why, otherwise you're very unlikely to find satisfaction with that. It’d be a stroke of absolute lightning in luck if you manage to just happenstance pursue seemingly material wealth and then fall your way into something, fall backwards into something that also is very personally fulfilling. 

And I was recently also introduced to this concept, which I’m embarrassed to say is recent to me. Somebody looked at me and they gave me that look that look like your dog gives you when they're like, “What are you saying?” It's just touching your head. Like did you say we’re going to walk? Or did I just hear that – Who are you?” And they gave me that look and they were like, “You do know life isn't a problem to be solved, right?” It’s like I just got floored, because I kind of continually moved this way of like, “Oh, I got to fix this. Oh, I got to do these things. Oh, I got to move this. If I do this, then life will be happier. It’d be more successful.” Whatever. Like it was always – And I’ve read a few articles recently, too, talking about – And it's very common this time of year to kind of reflect on the just nature of self-help because we're all in the new year's resolution time. There's a lot of articles of like you can't keep treating life like there's always something at fault without burning yourself down. You can't keep treating it like there's a problem to be solved. Life is an experience to be had. And so in that way success is also having the freedom to choose to enlarge my experience, enlarge and experience. Enlarge the experience that we all get to have of life. 

Cristina Amigoni: What do you mean life is not a problem to be solved? 

Alex Cullimore: That's what I said. 

Cristina Amigoni: What have I been doing with my life this whole time? 

Alex Cullimore: That's what I said. So like there's things to do. Like, yeah, there's – And like there's things to do at work. There are problems to be solved in life. I have to decide how to feed the six cats I’m currently fostering without having them like walk all over each other, and that's a problem to be solved, yeah. Right back up there. We'll eventually tone it down. We'll find out. By the way, those are problems to be solved. 

Cristina Amigoni: Your cat residence is like a harmonica. Every time I – I think it's like shrinking. It re-expends automatically. 

Alex Cullimore: Yeah. If you've got that kind of space available, you just fill it with another cat. Apparently, we just have a bunch of sick cats we're trying to help. 

Cristina Amigoni: Exactly. Part of your why is to take care of cats that need shelter. 

Alex Cullimore: Yeah. And you get some satisfaction out of it. Even though there's also sometimes you're like, “Oh my God. I have six cats. I’m constantly wearing cat slippers because they're always on my ankles.” 

Cristina Amigoni: There's such a thing as cat slippers? I think if you could pass there, life is not a problem to be solved. But cat slippers, really? They exist? 

Alex Cullimore: Yeah, they live and they breathe and they walk all over you. It's great. 

Cristina Amigoni: Yeah. I think I have finally figured out the key to solving life. Cat slippers. 

Alex Cullimore: That is the secret, and I didn't want to give it away. But I am glad that everybody has stuck around to this part of this podcast, because it’s a sneak peek. Douglas Adams thought it was 42. But it's not the life. Life of the universe and everything is all down to cat slippers. 

Cristina Amigoni: Indeed. It is interesting to shift the perspective to experiencing life as opposed to solving life. 

Alex Cullimore: I think it's worth asking ourselves repeatedly at the end of the year, the beginning of the year, great times to reflect on something like this, why – If I continue doing the same efforts and I’m just not feeling like I’ve gotten anywhere or it's not feeling satisfying, it’s time to dig into more of the why. And it's worth digging in even if you're not feeling stuck. It's just usually harder to get yourself to do it. Like we always say, change doesn't happen unless you're disturbed. So you get to the point of being like, “[inaudible 00:25:04 ] for me.” And then it's time to reevaluate that. And best to re-evaluate that, I think, if you're doing it without the external lens. And it's easy, because to do the external lens, everybody will give you ten thousand definitions for success if you look around. But you have to know what's going to fit you. And that's a much harder question to answer, but way more worthwhile.

Cristina Amigoni: It is. It is a much harder question to answer. And again, would love to hear your answers on what your definition of success is. 

Alex Cullimore: Yeah, yeah.

Cristina Amigoni: And then we'll rank them and figure out which one is the best. 

Alex Cullimore: Yeah. And we’ll rank them. We’ll tell you who's right. 

Cristina Amigoni: Just kidding. That defeats the purpose. This is not an Olympic medal count.

Alex Cullimore: But it is worth seeing other people. So if we get some responses, we'll happily post these. We can keep them anonymous. But it sometimes helps just to know what other people are also seeing as successful, because it gives us ideas. It's like you one of those sayings. It's like you can't do what you don't see. And you can't start to invent what you don't have an inkling of. So having those kind of just kick starts can sometimes help us think and brainstorm in a new way that we haven't done before. So we will happily share those. So please share with us. Feel free to email at

Cristina Amigoni: And thank you for listening.

Alex Cullimore: Thank you.


Cristina Amigoni: Thank you for listening to Uncover the Human, a Siamo podcast. 

Alex Cullimore: Special thanks to our podcast operations wizard, Jake Lara; and our score creator, Rachel Sherwood. 

Cristina Amigoni: If you have enjoyed this episode, please share, review and subscribe. You can find our episodes wherever you listen to podcasts. 

Alex Cullimore: We would love to hear from you with feedback, topic ideas or questions. You can reach us at podcast, or at our website,, LinkedIn, Instagram or Facebook. We Are Siamo is spelled W-E A-R-E S-I-A-M-O.

Cristina Amigoni: Until next time, listen to yourself, listen to others and always uncover the human.