Redraw Your Path as a Learning Opportunity, Not a Final Destination | Ep. 005 - Ali Greene

Join host Lynn Debilzen in this energizing interview with Ali Greene on Redraw Your Path!

In this interview, Lynn learns about Ali’s journey with change throughout her life–from middle school to being a published Author. Their conversation touches on:

💡How to create a values-driven lifestyle and use work as a puzzle piece to a bigger picture

💡The power of reflection and how it can help us reframe life’s experiences

💡The glamour of the digital nomad life–just kidding, we talked about the challenges of the digital nomad life behind the scenes of social media!

💡Navigating two seemingly conflicting pieces of your personality, and the beauty that comes from challenging those ideas and leaning in

Tune in for a dynamic discussion on life and growth!

About Ali:

Ali Greene is the Co-author of Remote Works: Managing for Freedom, Flexibility, and Focus (#1 New Release in Organizational Change and Business Management Science). Published by Berrett-Koehler Publishers and distributed via Penguin Random House internationally. With 9+ years of remote leadership experience, her mission is to empower people and companies, helping them thrive by making work (and life!) better. In 2022 and 2023, Ali was named a Top 50 "Remote Accelerator" as well as a "Must-Follow Remote Work Expert." Ali is passionate about intentional remote work, community building, lifestyle design, and the workplace experience. Her unique strength is understanding challenges and pain points at all levels of an organization, communicating best practices, and beta-testing solutions to improve distributed processes. Through her 13+ years of startup experience, she has succeeded in leading projects while being resilient enough to roll with the ambiguity of evolving priorities.

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Connect with Ali:

Book: Remote Works: Managing for Freedom, Flexibility, and Focus - https://amzn.to/3S6NSP5 

Website / URL: www.remoteworksbook.com

LinkedIn URL: https://www.linkedin.com/in/greeneali/

Connect with Lynn:

• www.redrawyourpath.com
• www.lynndebilzen.com
• https://www.linkedin.com/in/lynndebilzen/

Transcript

Lynn: 0:01

Hey friends, welcome to Redraw Your Path, a podcast where I share stories of people who have made big changes in their lives and forged their own unique paths. Guests talk about their moments of messiness, fear, and reframing on their way to where they are now. I'm Lynn Debilzen, and my goal is to inspire you about the shape your life could take. So let's get inspired. Hey y'all, I am really pumped to share a great conversation with you with Ali Greene. Ali dropped so many gems and words of wisdom, so I encourage you to listen with full attention. a little bit about Ali: she is the co-author of Remote Works: Managing for Freedom, Flexibility, and Focus, which is a number one new release in organizational change and business management science. It was published by Barrett Kohler Publishers and distributed via Penguin Random House internationally. With 9+ years of remote leadership experience, Ali Greene's mission is to empower people and companies helping them thrive by making work and life better. In 2022 and 2023, Ali was named a top 50"Remote Accelerator", as well as a must follow remote work expert. Ali is passionate about intentional remote work, community building, lifestyle design, and the workplace experience. Her unique strength is understanding challenges and pain points at all levels of an organization, communicating best practices, and beta testing solutions to improve distributed processes. Through her 13 plus years of startup experience, she has succeeded in leading projects while being resilient enough to roll with the ambiguity of evolving priorities. Ali and I connected a while ago when I was looking for remote work and I was really excited to hear about her book and learn a ton from it. So it's definitely a recommendation I give to anyone who is interested in remote work themselves or in creating a really positive remote work environment within their organization. I'm excited to share this with you and I hope you enjoy. Hey Ali, I am so excited to be talking with you today on Redraw Your Path. How are you?

Ali: 2:42

Hello, I'm so excited to be here. It's awesome to catch up on this recording again with you.

Lynn: 2:48

Yeah, absolutely. so let's dive right in. the first thing I like to ask guests is give me some context about where and how you grew up.

Ali: 3:01

Yeah, so whenever I tell this story, I feel like people don't believe me because depending on who I talk to, I always have slightly different answers. That is because I grew up in different places moving around, and so that definitely impacted who I am as an adult, but I spent my early childhood years both in Michigan and South Florida, and so in terms of like local culture, the weather, what we did for fun, very different life experiences. And in that growing up, based on the ages I was when I moved around, had gone to four different middle schools, And so I always credit, like, this period of intense change in my formative years as to why I seek out change as an adult in my digital nomad life. And it was very interesting as an adult to sit back and reflect on the cadence of wanting new experiences, wanting to problem solve, wanting to learn like how to navigate new situations. And I was like, oh, that's because that's what I did when we moved from Michigan to Florida. And I went to all these different schools trying to find my place. And then when we moved from Florida back to Michigan in the middle of winter, and I was like, oh, now I have to learn how to adjust to this weather. And there's snow, and it's not as beautiful as it looks in Hallmark movies. And it is cold. But now I'm, your listeners can't see this, but I'm rocking a leather jacket today, because now I'm very into the cold, crisp weather.

Lynn: 4:30

I feel like cold weather fashion is a lot easier than hot weather fashion, in my opinion. So I'm, I'm with you. And I like, I welcome the cold weather when it comes around.

Ali: 4:43

I'm excited for it. I think it's really like shows the progress throughout the year and you're able to take time and reflect on, you know, who you are when. So I'm very sentimental in the seasons and how I live my life.

Lynn: 5:01

I love that. And I also want to just say, wow, four middle schools. That is so much change at such a pivotal time in childhood, which is often like a really hard time in childhood. So wow, that's amazing.

Ali: 5:18

Yeah, I don't think I like realized how intense it was until I had the time to reflect and each time didn't, I didn't know there was going to be that much change. And so, you know, when we moved to Florida, it was a family move and then there are situations like I ended up going to a magnet program in my school. And so I was really into math and sciences and the school was structured in a way where it was grades four through six. So everyone moved on at the end of sixth grade, um, instead of graduating at fifth grade, which is I think more common in a lot of schools, but then like the years that followed in seventh grade and eighth grade, and my family decided to move back to Michigan is where these like surprises happen. And I was like, okay, I gotta, gotta learn how to roll with the punches and how to start over. Um, Then realized that that starting over was going to happen again wasn't necessarily a planned thing.

Lynn: 6:11

Yeah. And I feel like kids are so much, honestly, so much better about like rolling with the punches, you know, especially when you have that foundation of doing that. I think adults have a harder time adapting to change sometimes.

Ali: 6:25

Yeah, what I've learned about myself and change now as an adult is I like to plan for change. So I can't be necessarily as spontaneous as I admire others in others. So I do things like, I want to know what the plan is, and I'm willing to change the plan rather than not having a plan and being spontaneous. And so things like, I did this road trip over the summer and I was camping. I was like, well, let's just like plan out like two potential places where we could end up when we get tired and like see what the camping selections are instead of just driving until we're tired and then deciding to camp. I wanted to know like, are we going to go east or are we going to go west? Like, what's the weather look like? Like, let's map it out and be planned flexible instead of totally spontaneous and I wonder if that is because of how I grew up that I want this security in having a plan but I'm also like very happy to change the plan because I know that life happens and now this is like a core part of my personality.

Lynn: 7:27

Yeah, well, and what powerful reflection you've clearly done on this and just realizing like, here are the factors in me feeling okay with this change and yeah, making a camping decision when you're tired and probably hangry is never a good decision. So,

Ali: 7:47

Don't make decisions when you're hangry. Life lessons.

Lynn: 7:51

never. I will always end up crying when I do that. so that leads me to, I like to bookend. All right. So where did you start? And where are you today? Where and how are you currently spending your time?

Ali: 8:04

Yeah, so I'm going to be very literal in answering this question today. Today, I'm in Tulsa, Oklahoma, for the first time in my life. And the reason I'm here is because of my propensity for change. I've been really attracted to this remote work lifestyle, and I've been remote working since 2014. I've been a digital nomad since 2017. In certain phases, way more extreme than others, there was a time where I was moving to a new country every single month. And now I go on very intentional trips to experience new things. So I'm in Tulsa, to experience what it is like for remote workers that decide to move to Oklahoma and be part of the community here. I'm really into spending my time learning about intentional communities, learning about the intersection of community and remote work, and trying to in a way like fight against this common media stereotype that remote workers are isolated and that they're sitting at home alone all the time and instead thinking about how do you create a values driven lifestyle and use work as a puzzle piece to a bigger picture. And so I'm a really big advocate for flexible work, not just because I love my digital nomad lifestyle, but because of what that means for everybody living according to their own values.

Lynn: 9:23

Awesome. I can really hear, the strength of your values coming through in that and deciding what you're doing and how you're spending your time, which I'm sure took a lot of reflection to get there.

Ali: 9:36

Yeah, thank you.

Lynn: 9:38

Then let's back up a little bit again. so most of us grow up with these external pressures or expectations that are placed on us that we don't necessarily ask for. what do you think some of those were for you?

Ali: 9:56

It's so interesting. So I've, I've heard versions of this question being asked to me throughout my lifetime. And most people, I think their knee jerk reaction is to look at their family unit and say like, Oh, this is, you know, who put this pressure on me. And I really felt like the pressure came from myself. So I remember, you know, being a really high achiever all throughout like my elementary, middle school, high school days, and finally in University, like I think experiencing my first burnout, but we didn't have language for it then, but just studying to the point of being so overwhelmed that I wasn't sleeping well. I was making myself, sick because I, I wasn't, taking care of myself physically, like eating properly. And, and I was just all in on I want to get the best grade. And my parents actually were like, you don't need to push yourself that hard. this isn't good for you. It's not healthy. And so I had to do some more digging to be like, why do I feel this need to achieve, achieve, achieve? Like, where does this competitiveness come from? in, in my system. And for me, I think I was really socialized in the traditional school system to behave that way. And also the media that I watched growing up as a kid, I remember watching TV shows like Saved by the Bell and really identifying with people like Jessie Spano and wanting to be like the smartest kid in school and the most hardworking. And even her, like, it didn't work out well for in the, in the TV show. so, I think this pressure came from the time in the era in which I was growing up where There was an opportunity to feel like you could achieve things if you worked hard, if you were smart, but we didn't yet learn and have the vocabulary and have the conversations we're having today about taking care of yourself and balance and rest. And so. I wanted to go for it. Like I wanted to be the best. I wanted to get straight A's. I wanted to climb the corporate ladder. I had this vision of what a good life, what success looks like. And it was based off of these things I was seeing in my community. And I'm really happy that I think times are changing and people in communities are starting to realize the importance of talking about not just drive, but balance as well.

Lynn: 12:12

Yeah, and I think Gen Z is leading the way in many ways in that conversation. I, I find that I get a lot more inspired by looking generationally younger than me than generationally older than me in terms of that conversation.

Ali: 12:30

Yeah, I think it's really important what they're doing. I want a broader network of Gen Z people in my life, but from people that I've spoken with, they are seeing things and calling them out, whereas I saw those same things, but I felt more pressure to adapt and not speak out. And so I think that power of the voice of the next generation to say the things that we wanted to say is really special and I'm proud of people for doing that in the workplace, in school systems, and things of that nature. But I also have a lot of empathy for the generations of our past because it shows sort of the lineage of why I personally felt that pressure. And it's because, there was so much, I think, sacrifice and still like a very strong ability to work hard and have a good life in the generations before us. And now, You can work hard, but that doesn't guarantee you a good life anymore. And everyone has different definitions of what it means to live a good life. And finally, we're seeing divergence from that. It doesn't mean that you're going to own a house and own a car and get a promotion. Again, it goes back to that like values driven lifestyle. What is the values? And are you having enough time to spend time with your family, take care of your health, have hobbies? Um, how are you putting things into the bigger puzzle? And I think that's been the shift I felt throughout my kind of growing up years.

Lynn: 13:55

Absolutely. And I, I appreciate you naming all of that because I think it's so important to just untangle all of the things that are happening in society and, let's reflect on it collectively and come to, an understanding both collectively and individually for each of ourselves. And so what I'm hearing is like, there were very high expectations that you had, but it was, self driven. Did you do that reflection on that while you were going through that in college, because that's the time period you talked about. Or do you think that reflection has been more recent?

Ali: 14:36

No, I didn't reflect back then, and then I was still laser focused on the GPA, the things, that I wanted the, the gold stars for. that reflection was really recent. even to the point, I hate talking about this in conversations. I want us as a society to move past this, but I think the reflection happened to me during COVID. I went through a lot of life changes during that time period and I'm sure So many similar stories out there of people having the forcible time to reflect. when you stop making yourself so busy, you honor that time in yourself. And so, during COVID, there are a few reasons why my time and my calendar opened up and I started to feel a shift in my identity and it made me start to go back and question like, oh, why am I this way? Or why do I place such a high value or importance on X, Y, and Z thing? And so that reflection Is very recent and rough for me, which is why it makes me happy to talk about because I, I wish I could have been that reflective when I was 18, 19 years old, but at least now I can draw out those reasons of why my life took a certain pathway and why I've made changes and turned away from that path or leaned into that path, depending on what I was going through.

Lynn: 15:59

Yeah, I love that. I think we all wish we had that reflection ability in the moment and in the tough, tough times. And I think that's one of the reasons that motivated me around this podcast specifically was as I was going through a really tough transition in my life, the more people I talked to, that had inspiring stories about making big changes, the more I realized, oh, like that was really messy for that person. On the outside, especially in our day of social media, it looks really easy and linear and clean. And that's, Almost never the case. so I appreciate you. Absolutely.

Ali: 16:37

Social media is dangerous. Don't believe everything you see. I felt that so much, like, the digital nomad life can look so glamorous. And people are like, oh, like how could you have a care in the world? You're like in South Africa, you're in Vietnam, and behind the scenes it's like I'm trying to launch something new at work and I'm really struggling with learning this new skill set to achieve it. I'm, I'm feeling disconnected from my support system because I don't know how to cram into a certain time zone, both professional and personal things. Like I hurt myself abroad and, you know, have to get stitches and there's, there's all these like stories that I'm not always openly sharing. And instead you just see pictures of this, like, really beautiful dinner I had or this great view from a hike. And so, yeah, you know, we all are becoming more self aware of the dangers of social media. But just to reiterate that point, it's not, it's not always as shiny as it looks.

Lynn: 17:36

I, I experienced that as a Peace Corps volunteer. Everybody was like, your life is so cool and sexy. And I was like, I cry pretty regularly and, things are hard sometimes, but I'm also really loving it. So, it's a, real struggle with what to put out there and then what to believe. And I like your lens of try to dig into what's underneath there and don't believe everything that's going on. so Ali, tell me about, you know, like you're living this life, you're a high achieving student. let's talk about times where you redrew your path. what's the first time you redrew your path? Or what's the first way that you've redrawn your path?

Ali: 18:17

Yeah, so I'm gonna start in those formative years still. So I think, you know, you can start to paint this picture of me like real high achiever. I was a bit shy. I'm really just in my bubble trying to learn the things I needed to be studious to get those marks. And so the first time I really turned away from that path was, of course, at school. I was so into school as a concept that I wanted to soak up everything I could. And I joined a marketing club, when I was in high school, painfully shy, but I had to present in order to, to move forward in the competitions of this club. And so there are two core pieces of my personality now in direct conflict. One is, Compete, achieve, like win. And the other is don't do scary extroverted things. And so now I had to do both at the same time. And I was like, how do I navigate this situation? And I remember the first year doing this presentation, and all my note cards fell, and they got in the wrong order. And it was just very embarrassing. I put all this pressure on myself. And was very judgmental of my performance and I worked through it with my teacher and in the club and was like, but I still love this. Like, I love learning about marketing and business and how you can help people in a business. So I continued on with this marketing club to the point where, by the time I was a senior in high school, I was winning, national championships, like top 10 and getting to go on like field trips with them. And now I love doing podcasts and I love sharing my story and sometimes talk too much. And so it really like brought out this piece of me of being confident to use my voice in high school. And that was the first time I turned away from my path of labeling myself as a shy studious introvert and realizing that I could be multifaceted and I could love learning and I could love being in my bubble and having my alone time and I could love being on center stage and sharing stories that help others and connecting with people and both can be true at the same time.

Lynn: 20:30

Oh my gosh, I love that idea. Let's, let's hold both truths at the same time. I think I can only speak for myself, but I tend to be very black and white and I box things up all the time. And then I spend a lot of time trying to remember, oh wait, this label that I've just applied doesn't have to apply all the time. And how do we like navigate being multifaceted? Like you said, was that terrifying to you as you were going through that?

Ali: 21:03

Terrifying, exciting, like it felt like I was, you know, blossoming and like becoming that butterfly that we always talk about when, when that moment happens. So, um, it was a really special place in my heart. It's also what like, you know, kind of talking about another pathway, like turned me into the business world in it at a young age. before I was very math and science oriented and through finding confidence in business and marketing decided, Hey, You know, actually, maybe I don't want to study math and science. Maybe I want to study business because it gives me this new perspective of who I am as a person. And so, that's something that was sort of an accidental consequence of this experience as

Lynn: 21:46

I love that. Was that a realization in high school that you made because of your, marketing club experience?

Ali: 21:54

Yeah, so I ended up going straight away in undergrad to a business school. Instead of applying to universities where, I had to take gen ed classes first. So it was a very intentional decision after having this experience in high school that I wanted to study business and study it from the get go. And so because of that, like I ended up moving to Canada, studying undergraduate, in, in Canada, instead of staying in the U S and having the like non traditional university experience because of that. which was also really special and cool because I went and lived in, a big city for the first time. I, like, lived abroad. It really sparked my interest in traveling. so there are lots of components in a time period where you're already being influenced and shaping yourself in different

Lynn: 22:47

Yeah. Well, and even just that experience of I'm going to go out of the country for university is huge. And I imagine, did you have a ton of friends who were doing that at the time?

Ali: 23:00

No, I didn't, really think about it or consider it in any way. I didn't consider the social support network I would need when making that decision. I was just so driven on wanting to experience something new, forcing myself to get out of my safety zone and wanting to study business. And so I ended up going to McGill University, which is a great school in Montreal. I think Canada is a safe step for, Americans in a lot of way, because culturally it's similar, geographically it's close, but being in Montreal, you already have this influence of it being a bilingual city, having a bit of European culture. McGill is a very competitive school, and so again, it really nurtured my desire to achieve in a certain way. I got to study business from the get go, and so it fit all of these things, and I didn't necessarily consider the fact that oh I'm moving hours and hours away from my family and friends, and maybe I don't know anybody there. it felt like the right choice at the time, and I went with it, but I didn't consider the ways in which it would be difficult.

Lynn: 24:06

Well, and it sounds like you were really strong in listening to yourself and knowing what was right for you and, and just like leaning into that.

Ali: 24:17

Yeah, I think, a drive for new experiences is something that is a core piece of my value set. And so even though it was in a way a turn away from my path in the traditional setting, it was a turn towards these values that I had. I just didn't have the awareness to like label it at the time. Going back to your comment about labels, it's like in what ways are labels helpful, uh, to explain why you do things that you do and in what way are labels holding you back because you're limiting yourself to behave in a certain box. And I think the more I can label the reasons behind decisions and not so much, like how I show up in those decisions, that's like really empowering.

Lynn: 25:04

Yeah, and it sounds just like a really powerful tool and way to apply it to current challenges and, you know, current changes that you might be considering. Um, are there any other ways that you've redrawn your path in terms of like academically or educationally?

Ali: 25:23

I think academically, those are the biggest shifts I had. So like having these experiences in this club and then eventually moving away for school as well as studying abroad. So a second time studying abroad a little further away this time when I did a semester in Europe and then experienced travel for the first time. so those are all very special academic experiences in my life.

Lynn: 25:48

I love that. I think, one note I'll share with listeners is if you're a listener who is a young person in college or not in college, like going abroad, studying abroad is the best thing that you can do, for yourself and, and even like working through, you might go abroad and not enjoy it for the first week. And just like working through that, it's going to make a huge impact on your life.

Ali: 26:16

I love this advice. I almost think it should be, mandatory. Like, you learn so much, human empathy and humility and more than just intellectual skills. I think that it's a very, special, deep way to learn things about yourself and about the world. Um,

Lynn: 26:32

Absolutely.

Ali: 26:33

so I second that. Yeah.

Lynn: 26:34

Yay. And it's a unanimous vote here, So it'll be declared mandatory. And I think especially for Americans with how our culture views our own status in the world, I think that it's so important for us to build that humility and that intercultural skill set. what are other ways or what's another way you redrew your path, Ali?

Ali: 27:02

I would say the like biggest other way, and this has happened multiple times, so like listeners out there, you can like redraw your path and then redraw it again the same way with different results, is like pivotal moments. Pivotal moments in my life has always been quitting a job. And every time I've quit a job, it seems like a chapter's ending, but in reality, a chapter's beginning, and, and you don't realize it till you do it, and I feel extremely lucky and aware of, like, the economic climate that every time I've quit a job without something lined up has been a very unique and special experience to me where I've allowed myself to be able to explore something new and both times the results in how it's led me to something else have been has been quite dramatic. So the first time I quit my job, I was living in New York City. I was doing that thing, like, eight to six, working in Manhattan. I talk about this a lot as it relates to, the catalyst behind why I'm such an advocate for remote work. it was the rat race. Like, people know this about New York. It's, it's not a secret to anybody, but until you experience it firsthand, you're cut out for it or you're not. I Was not cut out for it. I wanted to be, because it seems like that was what the definition of success was for me back in the day. And then I realized that I could be successful, but it wasn't making me happy. And I came to a crossroads where I had a decision around, do I want traditional success? Do I want to climb the corporate ladder? Do I want to achieve professionally? Or do I want to be happy? And I couldn't find a way to have both in that current situation. And so ultimately I left my job and I left New York City to backpack and I started doing HR consulting and it really opened my eyes to. different ways of living life. Like you can travel and work at the same time. You can be a consultant or a freelancer. You don't have to be a full time employee. You can choose to not live in these cities that have prestige just because it doesn't fit your vibe and that doesn't make you a failure. And Those lessons were really important for me to learn because I had to question what do I want to define success as not do not what do I want to follow other people's definition as. And so that that was a huge pivotal moment for me and going on a new path path that ultimately led me to being a digital nomad the path that ultimately led me to be a remote work advocate for really honing in and boundaries around like time flexibility with work. So people talk so much these days about location flexibility but for me it's always been about autonomy over your time and how you spend your time and what energy you give to your work and what energy you give back to yourself. And, and that first time quitting the job was huge for that. Um, you know, pause before I share my second quitting of the job story.

Lynn: 30:15

well, I love that and I appreciate and I appreciate that you're like, yeah, I quit a job twice without things lined up, which I think is like pretty unheard of I have found in terms of going through my own experience with that and also sometimes the best decision you can make for yourself and I'm curious so the point at which you realized oh I'm using someone else's definition of success, was there like an aha moment there or do you remember a moment that kind of woke you up to that realization?

Ali: 30:53

I don't think there was one moment. There was one, there was one or two moments where I was like, I cannot do this anymore. But there wasn't a specifically an aha moment. It was just sort of this building of constant dread around decision making. And so I felt like the decisions I had to make was okay, I can't control how I'm spending my time or where I'm spending my time because from 8am till 6pm I'm expected to be in this office doing this thing. I have an hour commute on both sides. So what do I want to do with my free time? I'm, I'm, you know, living in New York City. I'm, have some friends here, but I'm also building a social network. Do I want to spend time making and cultivating friendships? Do I want to go to the gym and try to like, be healthy and do things that make me physically feel good? Do I want to go grocery shopping at the same time of day that everybody else in New York City is going grocery shopping after work? Do I want to have a night in by myself to, like, watch a movie or read a book, um, take a long shower? Do I want to try to go on dates? Like, I felt like I could never do more than one thing. a day,

Lynn: 31:59

Mm

Ali: 32:00

sometimes even two or three things a week would be like a spectacular week. And I was like, why can't I do more of these things? Like, why can't I, live this life? And it just felt like every time I had to say no to things I really wanted, I got more and more confused by why I was spending all of this time, energy, and money to live in a city where I wasn't allowed to do all of the things I wanted to do. Um, and then, and then the final straw was, um, just having, like, a really not great living situation. And, um, in the winter, like, the heat stopped working and just having to live through these, like, very traditional, like, sort of classic New York in your 20s living examples. And I was like, everyone goes through it, but why? Like, it was every time I sat down, it was like asking myself the question why. I was like, is this really what I want? you know, I grew up in the era of, like, sex in the city and it seems really, cool and glamorous. Like, yeah, you're gonna live that life. But then you're sitting in an apartment, wrapped in blankets with a space heater and you're like, is this really what I want? And so I think there are a lot of moments like that.

Lynn: 33:12

Yeah, I love that. And always bringing the question back to like, is this what I want? And what you said before was like, if it's not what you want, that doesn't make you a failure, right? And, um, and I just spent some time in New York City and I was, and maybe it's because I'm turning 40 and I'm like, getting up there and I just don't, you know, want to do all the things, but I'm like, Oh, like, this can be a really hard life. Like, it can be amazing in many ways, but in many ways, everything just seems a lot harder. so it goes back to priorities and really getting true to your values and knowing like what's most important for

Ali: 33:54

Exactly. Yeah. And I was, I was recently back in New York for the first time in a while and had opportunities to go to like really amazing lunch and learns and build my professional network in person. I went to a really cool concert. I went shopping, like, of course, there's great things about being there, but it comes down, you know, to just being really aware of every situation in life has pros and cons. Do you want the pros so much that you're happy enough with the cons? And if ever that situation's reversed, it's a time to reflect.

Lynn: 34:28

Oh, I love that. That's like a gem, like mic drop right now. So, um, so are there other ways that you have redrawn your path? Along that like professional journey.

Ali: 34:41

Yeah, so the second time I quit my job was not as fun or exciting, I would say. so at the end of February 2020, I left a role that I actually really did love. And I, I was really passionate about the company. I still really care about the mission of the company and the people that work there. I just knew that my time in that role as it was designed was coming to a close and I wanted to take a personal sabbatical and I had been living this digital nomad life for a while, I wanted to travel again for the sake of just travel and not travel and work. what I didn't know and like the rest of the world didn't know was that like two weeks later the world shut down and I had this kind of oh shit moment where I was like, oh. On one hand, I know in my heart I made the right choice, like, I, I needed to take time to reflect, but also, now, the world is not what it once was, and there are two things that happened to me in that experience. One, I felt, I don't know if the word grief is too strong of a word, but grief for two identities, two labels, external labels, that were really important to me and I needed to figure out why they were so important to me. And one was being a digital nomad during, COVID in 2020, I stopped traveling. And traveling and traveling as fast as I was traveling was such a thing for me. It was like how I described myself. And I was like, well, I can't call myself that anymore. Like nobody's doing that these days. who am I, if not the person that's constantly planning their next trip? So that combined with, then I stepped down from a role at a company that I felt like my job was very prestigious and I felt like I was successful in a way that aligned with my values.'cause it was at a remote company. I had flexibility, I was working towards a mission I really cared about. And I was sitting on the leadership team of this company and, and I was really proud of that. And I, and I stepped down from that. I was like, I lost two labels working for the startup company, which made me feel intellectually challenged and stimulated and that I was doing things for a mission that I cared about and losing this like adventurous streak of myself at the same time. And so the grief that came with that loss of identity during COVID was really eye opening and we're having this conversation about like not using labels in that way. I think the first time that I started to ask myself questions, questions that I don't have the answers to even today around like If I'm not using these things to describe myself, like, how would I describe myself? And what does it mean to me to, like, be a digital nomad? What does it mean to me to be a remote worker? What does it mean to me to, like, want to work for a tech startup? And then the other thing that happened was I saw a lot of companies start trying to work from home during COVID. And I realized that my passion for remote work was a lot stronger than I realized, and that I wanted to educate. with no real clear sight of like what I would get out of it or like what it would mean for like my business. Just felt very like compelled to help change behaviors because I had this fear that remote work would become a scapegoat and people wouldn't get the same opportunities that I had to make their own choices in life and be flexible and this immense like work privilege that I've experienced that has allowed me to redraw my personal path because I was allowed the autonomy at work. And so I felt like equally motivated and questioning myself at the same time. and that was a big turn in a path that I, I'm still going through that turn, I would say, three years later is how do I reconcile my professional values. how I want to give back to the world and how I want to spend my time.

Lynn: 38:27

Yeah. Well, and sometimes those turns more often, those turns are not like 90 degree turns. Like I'm going to do this thing. It's like one degree this way and one degree, you know, over and over and over again, until three years later, you're kind of around this curve. And what I'm hearing, too, is you were grieving two identities, one of which you were ready to transition out of, your work identity, and one of which you were not. And that identity was basically taken from you in COVID. And then out of that, you blossomed a new identity. And still the question is what does this mean to be applying these identities to me? And who am I at my core? If it's not about what am I doing?

Ali: 39:15

Yeah, exactly. it's like I, I turned a path and I went into this open field and now I'm just frolicking in this open field and exploring all of life's possibilities. That's like, I would say current what, what's up with, with Ali. And in the meantime, of course, there's like new labels. Like I, I wrote a book, around remote work, but even the label, and I know you're going to use this to describe me in your intro, author is like kind of weird. Um, honestly, like, what does it mean to be an author? you know, remote work advocate. I think everyone who has a knowledge job should have full autonomy and flexibility in how they spend their time and where they get their work done from. I think it's just better for business and it's better for people. But what does it mean to like champion remote work? Like, what is that label? so there's all these things that I'm still exploring deep down. The, the why beneath the words. And it's a really fun time.

Lynn: 40:07

Yeah, well, and you'll get there, right? I think that's what I've kind of had to remind myself is, okay, I'll get there. And it just takes time to explore. I do have a question because you brought up the frolicking in the field metaphor. And I love that. And so I'm picturing this Really just like joyous, happy Ali, just like frolicking around. Is it always a joyous, happy Ali? Or like what are some of the Kind of thoughts and emotions that are coming up as you're frolicking around.

Ali: 40:37

No, of course not. Sometimes it's like frolic where you fall down and you skin your knee and you're like, oh, that hurt. Um, how do I pick myself back up? So, you know, I'm human, like everybody else navigating the ups and downs of life. And that's, that comes with the package.

Lynn: 40:54

Yeah, I, I love that. I think it's a good reminder to listeners like, it's just not always going to be clean. Like, it's just never going to be completely frolicking. Um,

Ali: 41:05

No, sometimes you fall in the mud. Like, yeah, sometimes you get mosquito bites because mosquitoes really like the fields too. Like, things happen in life. I think what's important also is there's so many things happening in the world to so many people that, if you're experiencing something, let yourself experience it. Don't feel like you're not allowed to have. the negative times because they're not as negative as somebody else and I think that's a really important reminder for people too is like everything that you're experiencing is your life experience and there's things to learn from it. There's things to feel from it and just let yourself be in your field.

Lynn: 41:43

love that. And it's a reminder. I mean, it's not a suffering Olympics and just really getting into okay, this is true for me. And what am I going through? And how is that making me feel? And that's a really great reminder. Is there other advice you would give Because you just dropped a ton of wisdom, but any

Ali: 42:02

Thank you.

Lynn: 42:03

to listeners considering redrawing their paths?

Ali: 42:06

I think just like the more you can have empathy towards yourself and others and look at redrawing your path as a learning opportunity not like a final destination. better it will be. And so questions like what can I understand more about my core values? How can I use the choices I've made in my life or my desires or my fears or my passions as a guiding light for how I make my decisions? And how can I safely take more chances on decisions that can be reversed? how do I want to show up and experiment with? I mean, not saying everyone should go and quit their job. That's unrealistic for a lot of people, but how can you make more chances in a way that will push you out of your comfort zone while still creating the safety net that you need in your life, to learn how to navigate your own path and redraw it if needed?

Lynn: 42:58

Wow, I love that. I'm hearing like a couple themes come out in there. It's self reflect, self reflect, self reflect, and be willing to take chances where you have the space to take chances.

Ali: 43:13

Thank you for that summary. I love it.

Lynn: 43:15

Yeah. this is so full of wisdom. I'm so excited to share it with listeners. and thank you, Ali, for being here today and just sharing about your experience really authentically and in a way that is, just like really concise for people to hear about, like, what was that like for you?

Ali: 43:35

Thank you?

Lynn: 43:35

so where can people find you and is there anything you'd want to share?

Ali: 43:40

Yeah, so people can find me on LinkedIn. it's my platform of choice. And so I, I really blurred the lines there of, not just talking about work and tech and remote work, but also just, how we show up in the endeavors that make us us. And so I love connecting with people on that platform. And for those specifically interested in remote work and want to check out the label of Ali as author, I wrote a book with a dear friend of mine and it's now available called Remote Works and so you can find that on Amazon.

Lynn: 44:12

Awesome. And I highly recommend the book. That is how Ali and I connected. I was in a career transition looking for remote work, and I was like, this is really cool. And some of the exercises in there, were just really helpful for me. And I specifically will shout out some of the, resources you share around energy management and leaning into your natural energy cycles. they really gave me the permission to realize, oh, my best energy is at this time of day, even if that's not when the rest of corporate America's best energy is and how do I take advantage of that?

Ali: 44:48

I love it. That's my favorite section too.

Lynn: 44:50

yay. Yeah, it's, it's so helpful. And, I think like reduces a lot of shame from my life around when I'm awake and when I'm not awake. Ali, I appreciate you being here and I can't wait to stay connected and I can't wait for listeners to find you.

Ali: 45:08

Thank you so much for the work that you're doing. I appreciate you.

Lynn: 45:12

Hey, thanks for listening to Redraw Your Path with me Lynn Debilzen, If you liked the episode, please share and subscribe. That helps more listeners find me. And don't be shy, reach out and connect with me on LinkedIn. I would love to know what resonated with you. Can't wait to share more inspiring stories with you. See you next week.