
In this episode of This Is Woman’s Work, Nicole and career reinvention expert Ilana Golan unpack how to reinvent your career and life at any age, build a portfolio career, and boost your adaptability quotient (AQ) so you can thrive in the future of work. You’ll learn practical frameworks, mindset shifts, and real-talk strategies to turn setbacks, burnout, and “WTF now?” moments into intentional, exciting next chapters.
Loading summary
Alana Golan
This episode is brought to you by State Farm. Listening to this podcast Smart move Being.
Nicole Khalil
Financially savvy Smart move Another smart move Having State Farm help you create a competitive price when you choose to bundle home and auto bundling.
Alana Golan
Just another way to save with a personal price plan. Like a good neighbor, State Farm is there.
Nicole Khalil
Prices are based on rating plans that vary by state. Coverage options are selected by the customer. Availability, amount of discounts and savings and.
Alana Golan
Eligibility vary by state.
Nicole Khalil
The holidays mean more travel, more shopping, more time online and more personal info in more places that could expose you more to identity theft. But LifeLock monitors millions of data points per second. If your identity is stolen, our US based restoration specialists will fix it, guaranteed your money back. Don't face drained accounts, fraudulent loans or financial losses alone. Get more holiday fun and less holiday worry with LifeLock. Save up to 40% your first year. Visit LifeLock.com podcast terms apply if this show adds something to your life, I'm asking for your help so it finds its way to the next woman who needs it. The three best ways to do that Rate, share and support the Sponsors. I am Nicole Khalil and you're listening to the this Is Woman's Work podcast, where together we're redefining. We're reinventing what it what it looks and feels like to be doing woman's work in the world today. And that reinvention part? Let's face it, it can be overwhelming. It's a huge part of adulthood that no one ever warned us about when we were kids. I don't know about you, but I thought the hard work would be figuring things out in the first place. The career, the relationship, the family, the life's purpose. I figured by my 30s I'd have a blueprint and from there it would just be about living the life that I'd carefully mapped out. Clear plan, steady path, all systems go. But the truth is, life doesn't work that way. It turns out life isn't about figuring it out once. It's in reinventing yourself over and over again. Because careers shift, relationships change, dreams evolve, and sometimes life blows up in ways we never expected. I'm approaching 50 and I'm still reinventing. My mom is over 70, recently divorced after 50 years of marriage, and she's reinventing too, in bold and inspiring ways that fill me with pride and admiration. And my guess is you're reinventing too, which doesn't necessarily mean throwing everything out and starting from scratch. We collect breadcrumbs along the way, experiences, wins and losses, joys and pain, success and failure. And those give us hints about who we're becoming and where we're headed next. But this reinvention shit, it ain't easy. It isn't for the faint of heart. It requires us to dig deep into our intuition, our courage, our confidence. It demands boldness, bravery, determination. So today we're going to talk about it and listen. There are countless directions we could go with today's guests, and we'll probably wander into a few different things. But what I'm most excited to explore is this thing we've all done and we're likely doing right now the work of reinventing ourselves. Because if I know anything, it's that none of us were put here to stay the same. Alana Golan has turned reinvention into a superpower. From F16 flight instructor in the Air Force and the first female commander in her squad, to becoming the youngest hire at intel, to tech executive to founder of Leap Academy, one of the fastest growing companies in America. Leap Academy is disrupting professional education and is the only platform in the world helping individuals build portfolio careers and prepare for the future of work. Alana is also the host of her own podcast where she's interviewed leaders like Richard Branson, Gary Vee, the president of Starbucks, the founder of Zillow. She's a mountaineer, ironman, triathlete, award winning entrepreneur, keynote speaker, and has shared the stage with some of the most powerful leaders in the world. Let's talk about reinvention and let's start with yours, Alana. How do you go from F16 flight instructor to tech entrepreneur to founder of one of the fastest growing companies? I mean, talk about reinvention. How do we do that?
Alana Golan
Oh, Nicole, it's so great to be here. And for those listening, look, reinventing is everywhere. Like we do this all the time. And in fact, at this pace of change, we're going to do it every year or two. So we better get really, really good at it. Right? And you're right, like these are very or they seem very different, but there's always like transferable skills. There's always a path. Success leaves clues. And if you can start looking for those clues, you actually going to start understanding what is your zone of genius. Where is that superpower? What lights you up, what gets you fulfilled. And then it's about like experimenting and trying different things and we can definitely go into that. But I think it's really about finding the patterns, figuring out what is my pattern and where do I really, really want to shine.
Nicole Khalil
Yeah, I'm so glad that you said that because I think sometimes when it's happening, we feel like whatever we were doing before was a waste. And in my experience, as you said, there are breadcrumbs, clues through lines, whatever you want to call them. Could you give us an example of maybe some of the clues you picked up along the way as you've reinvented yourself? I'm sure in countless ways, but at least professionally.
Alana Golan
Yeah. Yeah. So even professionally, it was fascinating. So I started at intel and just writing code, right? And in fact I realized that, yeah, I'm a, I'm an okay coder, but really what I loved is when I got to speak with clients and, and do things that are interacting with humans, with people, not just computers. And it's like, wow, like, can this be a job? Can I figure out a way to be more in front of people? Right? And that's when I started looking for a job. It was actually a funny story, Nicole. Maybe some, some people will like to hear this. So it was 2000, right? Or 1999. Like if you had a resume that said anything about engineering, you would find a job in two seconds. And here I was wanting to find my first client facing role. And I'm going with my resume from intel with all the engineering lingo and algorithm, guess how many opportunities for a customer facing role I got? 0. Because my story, right, because my story was based on who I was, not who I want to become. And it's not because I didn't have a story. It was emphasizing the wrong thing. So when you want to start telling your story, you want to start thinking of what do I want? How do I emphasize the right points? Again with complete integrity. But how do I emphasize the right points towards where I want to be? And at that point I started basically experimenting with different career facing or client facing roles and technical sales and product management. And, you know, and I started climbing up the ladder. And if you think about it, at the end of the day, this was all experimentation. Like, I loved every one of them, but they were different types of experimentation, trying to figure out where is my sweet spot. And I kind of moved all the way to vice president, technical operation in charge of like. So I, I moved up the ladder. But what I realized is as I was leap, you know, kind of moving between roles. And if you really think about where my sweet spot was, it was really the moving between the roles, not necessarily the specific skill. And I think this is another interesting reminder to people. The zone of genius is not necessarily the exact skill or the thing that you studied in the university or the thing that you work right now, it's sometimes in between. It's the things that, you know, kind of like in between the leafs or in between that makes you different. And one of the things that I would also say to people is really listen to what people are intrigued by you. Because at some point, Nicole, this was so interesting. At some point people were starting. At that point I was, I think I already started a company and I sold a company and I started investing in companies and. And I could see people come to me not for the business related stuff, but they would come to me for asking me about their careers. And to me these were two different things. Like I would help them with their careers and then I would continue and do my work. Right. And I wasn't seeing that as a, you know, they were actually telling me something that I wasn't listening to. And I think this is another thing is like, look at, like sometimes our ecosystem and our people around us will already hint us about our zone of genius and we're just not attentive enough to see the clues. So. And I think that's just really beautiful because that's where, you know, everything comes together. It's beautiful.
Nicole Khalil
Okay, so I have this thought that I'm going to try to formulate into a cohesive thought. What I heard is a lot of times we define ourselves by our history or what we've done. And that actually can be problematic in both seeing outside the box or alternative or really seeing what actually is our gifts or our genius. And also this feeling of being willing to experiment and test and be curious about. Because I think so many of us, especially women, feel like we're supposed to be certain. So I guess how do we take on this spirit of experimenting, of testing? Because experimenting and testing implies potential failure, right? It implies potential it not going well. And I just find so much of the time we're so afraid of that.
Alana Golan
Right.
Nicole Khalil
How do we take on more of this spirit of curiosity? I guess. Yeah.
Alana Golan
And Nicole, first of all, you summarize it beautifully, right? Because I think the difference in the mentality of where we used to grow up, as, you know, you learn a certain topic, you get a grade and this is how good you are. Right? Like that was kind of how we grew up. And in fact, and I'll say a few things about this, the pace of change and what we want to do, we actually need to flip this around. So what we want to start thinking is what do I want to be known for what is it that I want to do? And if I'm not too sure, how can I experiment to figure this out? And the interesting thing is the way I found this, it was interesting. I was mentoring in some of the biggest startup accelerators in the world, like Google and Singularity University and Carnegie Mellon and a bunch of others. And it was fascinating because in the world of startups, we experiment all the time. This is what we do. We find the market fit, we find the thing. And for some reason, and I remember catching myself in the middle of one of these conversations where they needed to experiment. I was like, why are we not doing this for careers? Like, it's actually the same. There's like this massive land of opportunities. There's so many options these days. Why in my career, I'm thinking that I need to find the thing that will fulfill me for the rest of my life. And, you know, when I'm looking at a startup, we can experiment, we can do things, we can. We can move fast. And that's where everything shifted. Um, and it actually created a big, you know, a big portion of Leap Academy is how do you experiment with your career? How do you decide that, Joan of Genius? How do you kind of experiment to figure out, like, that this is it? And then how do I start creating a little more of the story around it and my brand around it so that opportunities will come my way? So everything shifted, but it was at that moment that I was like, why are we doing this differently? Because our career will not be there for 40 years. It's just a different thing. And. And maybe I'll add one more thing, Nicole, with your permission, because I think it's just really interesting and it's something that I found out kind of relatively recent, and I think your listeners will enjoy it. So at least my age, I don't know, I might revealing here a little too much, but back in the days, like, IQ was everything. Like, you would do, like these IQ tests, and if you had a high iq, you would be successful if you. Right. Like there was like, iq, right? And then a few decades ago, it was morphed into eq. So emotional intelligence became the thing. And I think Richard Branson was one of the first that said emotional intelligence is actually more important than iq. And, you know, that kind of gave a green light to a lot of leaders and a lot of entrepreneurs that just kind of felt like, you know, I didn't tick all the IQ boxes. But, hey, I'm really good. And right now, Nicole, really, really interesting. It is Actually aq, and if you look it up, it's adaptability quotient. What it means that in today's world, with the pace of change, with the pace of AI, with, you know, everything moving so, so fast, adaptability, reinventing, leaping is actually becoming the most important skill for the future of work. So not only that, you know, we want to master it. We want to master it and do it again and again and again. So I think this is where it becomes really interesting.
Nicole Khalil
That is fascinating. And it makes sense, right? At the pace of change, the rate of change that we're at, being comfortable with change seems like a pretty important skill. And maybe not comfortable, that might not be the right word, but being willing to. And I just had the thought and I actually oddly got a little emotional about it is like, what would life and career look like? What would be different if we just saw it as experiment, if we just let go of the shoulds and the supposed tos and the outcomes and then it was just like, this is just one crazy experiment. And I know I would have probably done a lot differently. Maybe I'm a slow learner, but I have found more often than not that my biggest reinventions came out of some of my hardest, most challenging, most painful experiences. I don't think that it has to be that way, but I do find that that is true for lot of us. How do we reinvent ourselves after rejection, failure, pain, trauma? And how do we, and I'm just going to put in air quotes, use it in a way to propel us forward. Any thoughts on that?
Alana Golan
Oh, it's a beautiful question. So unfortunately it's true so many, many times we, you know, like, we need to learn. Yeah, we learn the hard way. And you know, you can't really tell your story, you know, when, when the wound is, is really bleeding, but you can tell your story from the scars, right. And, and, and it sometimes takes a little bit of healing. So if there's something very traumatic, you know, Nicole, like it's, you know, about a decade ago, I was kicked out of my own company, right. And it, and I can tell you it's a devast. Like it's one of those things that are just mind blowing hurting.
Nicole Khalil
Right.
Alana Golan
Like we started the company, we raised capital and I, you know, and within 24 hours I left. I lost my job, my salary, my company, my, you know, like I lost everything in my life. And the truth is, you know, the downhill spiral can be really, really hard. So, and, and I would say to people, if you're in the downhill spiral, if you're, you know, trying to breathe, first of all, yes, there is a little bit of space for grace. Right. Like, sometimes you need some healing because you just can't. And for me, my healing was actually to throw spaghetti on the walls and see what sticks. Instead of being intentional and strategic, like, I was doing things, but I was actually becoming a red flag. So I think sometimes it's better to just take a step back, heal for a second, and then really see it as an, you know, experimentation. And if you think about it as experimentation is not as something that you have to decide for the next 40 years. It's actually not suffocating, Right. Like, the whole idea of deciding on something for, like, for so long, like, it was suffocating for me. Like, I couldn't do it, and suddenly I wasn't fulfilled about anything, and I lost my sen of worth, and I was failing, you know, feeling like a feat failure. But, you know, it's really not about that. It's really about, okay, so let me try to experiment this, and let me try to experiment this. So I would say a few things. So first of all, yes, looking at as an experimentation will really, really help you. The way I look at it is five days, five weeks, five months, Right? Five days. I'm just gonna learn about it as much as I can. Five weeks. And what's beautiful then, Nicole, is all you need to decide is, is it worth five more weeks or I want to switch to something else. Right. So you just look at it in chunks. And when you just look at it in chunks, you know, it's just, sure, I'll try it for four, five more weeks. You know, it's not a big deal. It's not a big commitment or, you know, I'll try it for a few months and see if I want to actually leap there. Right. Like, it's just not as suffocating. The other thing that I would say is surround yourself with people that are willing to leap faster and higher. I think one of the biggest thing in Leap Academy is that you are surrounded with a lot of people that are forcing you to leap honestly. Right? And the beautiful thing that, you know, once you master it and you do it once, the interesting thing is it is an art. And when you can do it once, you can actually start ticking the boxes and creating the life that you want. Because I'm a big believer in portfolio career. I'm a big believer in multiple streams of ventures and things that you can be involved with that will start ticking more of the boxes, right? Because it's not like there's no way one thing will tick all your boxes, but when you can start looking at it as, you know, kind of like multiple ventures and some with income and some is fulfillment and some is for fun and some is for, you know, volunteering and the impact and suddenly you create this incredible life that is just now I just have a list of things that I want to achieve and every single time I'm like, cool, so I want to start a podcast. This is what I got to do. I want to start getting on a board. This is what I going to do. I want to write a book. This is what I got to do. And suddenly it becomes more of a let me just, you know, tick the boxes. I going to surround myself with the right people and I will get help. So I do surround myself with a lot of help. I do believe in that shortcut. But it's something I didn't believe in for many, many years. And so I learned the hard way.
Nicole Khalil
Sex is a skill. And like any skill, it can be learned, practiced and mastered. Bet you never thought about it like that, right? Because somehow somewhere women were told we're supposed to magically know everything about sex, intimacy, desire and pleasure. All of course, while looking goddess like. Meanwhile, nobody expects us to pick up a violin and play without a single lesson. And that's why Beducated exists. Think of it as the masterclass library your sex ed should have been over 150 courses created by top experts on everything from building real intimacy to exploring new territory. Whether you're thinking I want more connection or I want to change things up or I just want to stop second guessing what I'm doing. Beducated has you covered. And because it's December and it's so freaking cold, here's your chance to turn up the heat in the best way. Sign up for Beducated at Beducate Me and use code WomansWork to get 50% off the yearly pass. Locked in for life? Yes, forever. It also comes with a 14 day money back guarantee, so it's completely risk free. Click the link in show notes, get beducated and make this winter your hottest one yet. I don't know who else needs to hear this, but drinking coffee doesn't count as hydration. I learned this the hard way the other morning when I stood up too fast and briefly visited another dimension. So if you too want to decrease the coffee intake and increase your water cure, makes it actually enjoyable. Their hydration packs are plant based have no added sugar and I get their variety pack because I like to change things up and I like all the flavors. I use Cure in the morning when I'm trying to remember how to function after workouts, when I'm questioning my life choices during holiday travel. Don't even get me started on airplane air and on slower mornings after holiday festivities because the Cure formula is proven to hydrate as effectively as an IV drip. And staying hydrated isn't just about water. You also need electrolytes, which is why I love Cure. It's clean, tastes great, and actually works. And here's a bonus Cure is FSAHSA approved so you can use your FSA or HSA funds to stay hydrated. The smart way for this is Woman's Work listeners. You can get 20% off your first order at curehydration.com womanswork with code womanswork and if you get a post purchase survey, make sure to let them know you heard about Cure for right here. It really helps support the show. So don't just drink more water, upgrade it with Cure. Shopping is hard, right? But I found a better way. Stitch Fix Online Personal styling makes it easy. I just give my stylist my size, style and budget preferences. I order boxes when I want and how I want. No subscription required. And he sends just for me pieces plus outfit recommendations and styling tips. I keep what works and send back the rest. It's so easy. Make style easy. Get started today@stitchfix.com Spotify that's stitchfix.com Spotify A few things that you said because I thought were so good. So first, I think we've all had that experience in our lives where we've had something where we're not sure we can recover from it. Whether it's losing a company or a relationship or a law. I mean we that feeling of like, I don't know if I can make it through this. And I'm so glad that you reminded us to give ourselves space and grace to the extent that you can because it's so important to begin the healing journey before you move right onto the next. I love the 5 days, 5 weeks, 5 months. Great concept and thank you for the reminder again of surrounding ourselves with really good people. The visual came into my head of like standing on a cliff and jumping. When you talk about leaping and like having people around you where maybe somebody goes first and you like, okay, we are. We can make it. We're not going to die, right? Or people who can cheer you on or maybe even somebody who gives you that final push. It's so, so, so important to surround ourselves with good people. You've said a few times, portfolio career. I know this is a big part of your work. Tell us what that means and how do we build one? Yeah.
Alana Golan
So, Nicole, it is part of reinvention. So I think that's what's beautiful about it and part of the experimentation because I think there's one career if you, you know, gone are the days that you'll usually land one thing, be there for 40 years and retire with a golden watch and a party. Like these days are kind of gone. Like they exist from time to time, but they're really rare and they're going to be less and less of them. So the truth is, we going to reinvent ourselves every year or two. Like, it's actually moving really fast. If you're going to look at a stuff, you know, kind of a what happens to our skills. There's actually a fascinating graph of looking what happens to our skills. So it used to be about 30 years ago that a skill would actually survive for 30 years. Now it's two years. It's fascinating. So we're actually losing relevant at a speed we've never seen before. So if that's the case, you're going to need to reinvent ourselves anyway. Now, the gist of it is that one career is probably not enough if you actually want more from your life. So if you want fun and travel and experiences and impact and to do something that matters and status and generational wealth, like, if you're going to start looking at all the things that we actually want from a career and from life overall, one will probably not tick every single one of the boxes. And when you can start creating kind of multiple streams and multiple ventures, and it's not all going to be about money because sometimes it's about fulfillment and sometimes it's about fun and sometimes about you. If you're going to look at the top 1% of the millionaires, billionaires in the world, it's actually fascinating. 50% of them will have more than four income streams. And the more you're going to go up to the billionaires, it's actually a bigger amount. So. So what's interesting is they already have it. The question for me was then why is nobody teaching this right? If it's, if it's so common and it's. But you need to do it right. So the problem with portfolio career is done wrong. It's a disaster because you just look Conf. Right? So, and then you throw spaghetti on the wall and nothing sticks. So in order to create a portfolio career, you do want one stream of income that is relatively stable, whether it's a job, whether it's your own business, but it needs to be relatively stable in the best portfolio careers is when you can actually create ripple effects, right? So if you're employed right now, you know, you can have. You add, I don't know, some speaking opportunities and maybe some advisory and take some equity here and there and maybe, you know, whatever. And then now you're starting to be known as somebody that is even more at the leadership or more at the helm or more at the C suite. And now you're getting more promotions, better pay, that more respect, more seat at the table. Like it creates ripple effect. Or if you're an entrepreneur, you add, I don't know, mentorship and startup accelerators or advisory or board seats or whatever, right? And now you're starting again to be seen in a different way so you can raise more capital. So whatever it is that you're after, you can start creating. It's almost like a chess game. And if you can actually start looking at that as a chess game, mind blowing.
Nicole Khalil
Yeah. Okay. So I again feel like I figured some of this out for myself the hard way, in that there is comfort or stability in having something that is consistent or something that you can count on or rely on. So in my work, coaching has always been the thing that provides the baseline, right. It's something I love doing. It's high impact. I think I do it really well for the right people. But it just provides that stability that I need, that my business needs, that my everything needs in order for me to go and experiment and explore and try. And I've tried and failed at many different potential revenue streams or ways, directions my business could go or work that I could do. But in that I've narrowed down closer and closer those few other things that I am passionate about or that I love doing and don't care about income or that generate income and things like that. So again, back to this reinvention and experimenting. But I'm so glad that you talked about having something that provides some sort of security, stability, safety. Is that what you're saying? Or did I make?
Alana Golan
Yeah, exactly. Yeah, exactly. And if I'm looking at somebody, you know, I mean, again, Nicole, you already have some portfolio career, right? Like you're doing the coaching, you're doing a podcast. Like, that's exactly probably career, you know, for people who you Know, are coaches, consultants, advice, you know, you can add, you know, maybe being paid to speak, maybe you can, you know, or, you know, or maybe you go to speak and you get more clients with it, and then it's more about the media and the podcast and whatever, and the awards and, like, there's other things that you can start kind of creating for yourself and write a book. You could write, whatever. Right. You know, there's like, multiple things that you can start doing in order to create those ripple effects. And again, Nicole, you're doing them. But I think it's important for the listeners to kind of start thinking about it. Where. Where in my, you know, world can I start creating ripple effects that will actually change my trajectory? And I think that's what's beautiful about it, because you reinvent yourself, but you just leap again and again and again, and it just becomes a norm. It becomes part of. I, you know, I want something new. Let's go.
Nicole Khalil
I wonder, too, if the same concept can be applied to so many other things. Like, I think of, like, relationships and friendships. We want that, you know, maybe have gone the distance or that there's a high level of trust or that we're really connected with. But having those people, that allows us to experiment a little bit more, meet new people, have some, you know, relationships that it's not meant for the long haul, and that's okay. My last question is a doozy. I think for many of us, reinvention can feel impossible, intimidating, scary as shit. I don't care what you call it, but the idea of it feel sometimes too big, too insurmountable. What advice do you have for people who are like, I don't know if I can do it.
Alana Golan
So first of all, I love the question, Nicole, because the truth is, at the moment when I was at the bottom of my barrel, I didn't think anything or anyone can get me out of the. The. The. The heck that I was in. You know what I'm saying? Like, it was like, a very hard moment. So first of all, if you're listening to this and you're feeling like you're drowning or you're feeling like. Like it's hard in the middle of the night. You're tossing and turning. First of all, I want you to know, like, that it's normal, right? And usually that means you're also, you know, in the beginning of something big because it's always darkest before the dawn. And so the first thing that I will say is, you know, a big part of it is your mental Game around it and are you letting. Because it's never the challenges that stop us. It's always our belief around the challenges and the meaning that we're giving it. Right. So I think the very first thing is to understand that that's usually a hint that you're in front of a big thing. And the only question is if you continue when all the rest stop, that's where you get a life that you know, the rest will only dream of. Right. So it's really more about that stuff now in order to continue. Really some of the best steps that I can see, it's like I'm very engineering so I need, you know, somebody to spell it out for me. So one, do this, two do that. So the one thing that I'll say to the listeners, the first thing is kind of really understand your must haves, like what is really critical for you. Again, we can have it all, just not at the same time. So release the need of trying to have it all because again, sometimes it's more finance, sometimes it's more growth or title or function or fame or whatever it is. Sometimes it's impact. I just need to feel like I have a seat at the table, I move the needle, whatever. Sometimes it's balance because, you know, I need more time for family, for whatever. And again, no job will give you all of this or no career will give you all of it at the same time. So what I would say, first of all, just be honest with yourself and think what are the two that are really, really critical for you? And when you start distilling it one by one and then you know, and really honest about what it is that you have to have, the rest kind of piles up together. And I think the hardest thing in a goal is to let go of what society expects from us. What's cool, what other will think. What if I fail? Like, the hardest thing is the emotional part of it. But once you can spell it out, you can start, you know, really figuring this out and doing some massive, you know, changes and it's. It feels incredible.
Nicole Khalil
Yeah, I think you're dead on. Especially when things are hard or haven't worked or you feel like something is just ended or you've lost something. I think that's. I'll speak for myself. Those are the times where my instinct to care about what other people think goes way higher. It's when I am hurting where I'm like I should or I supposed to or whatever. And I liked what you said earlier, it's not the challenge, it's the belief around our challenge. And having people who can support us by thinking about it differently can be really helpful. But something you've said over and over is that reinvention is an ongoing thing. Right? We're talking every couple years, and maybe that's just even in your career. But I would say reinvention is no longer a detour. It's the road we're on. We are constantly reinventing. So maybe the belief around the challenges is that it is the beginning of something next or it's the path on the road you're on, as opposed to thinking about it as an ending or a detour, blockage or something like that. I know that's hard when you're in it, but I just. I just wonder if there's something to it.
Alana Golan
I think you're absolutely spot on. And I think. I love that you said, you know, it's not a detour, it's some. This is the road, like, you will need. And I think the, the faster that you claim it and understand it that, like, you will need to reinvent yourself every year or two, and the more you understand that this is your career, like your career is to learn to reinvent as fast as possible to whatever it is that you want at will, to any direction that makes you fit. And it just creates an incredible life. Once you let go of that, oh, my God, I need this one thing that will be sustainable for the rest of my life. So the minute you understand that this is it, this is the new norm, this is the new thing, and it just creates a beautiful, beautiful wish list of life that you can just do whatever you want. It's. It's. It's the most brilliant, exhilarating thing ever.
Nicole Khalil
Yeah, I am. I describe myself as a realist, which is what most pessimists say about themselves. But I have a feeling when people hear that, that we're going to be reinventing ourselves every couple years, that there are some of our listeners who are like, like, it. It sounds scary and overwhelming. And I invite us all, myself included, to think about how exciting that is, this idea that we get to. That we can become better and better, that there is nothing that we're just locked in on or stuck on. I mean, I think that as you're saying it, there's this excitement that comes up. Like, what's possible?
Alana Golan
Yes, it's the new possible, Nicole. And I think, again, don't scare yourself in the sense of, like, reinventing doesn't mean you're going to leave a job every Year or two. Right. Like you could reinvent yourself within the same corporation but to a new function or to a little more responsibility or to a new title or to whatever. Because again, it's about, you know, it's not enough to stay. There is no stuck anymore. It's like stuck is actually moving backwards at a pace that we've never seen. Like it's losing relevance. But the beautiful thing is, like you said, there's a land of opportunities now. There's a new possible that is mesmerizing. And the more we can lean into that, it just creates such a beautiful, beautiful life. You just start creating that wish list and oh, I want advisory and some equity and companies.
Nicole Khalil
Great.
Alana Golan
I know how to do it. I want a board seat.
Nicole Khalil
Great.
Alana Golan
I know how to do it. I want a C suite. Great. I know how to do it. I want to be paid to speak.
Nicole Khalil
Great.
Alana Golan
I know how to do it. Like it just create this like incredible life that you know, it just. And you just follow the same steps, which is beautiful. Yeah.
Nicole Khalil
Yes. Amazing. Thank you, Alana. I know our listeners are going to want to learn more. So Alana's website is alanagolan.com we'll put the link and all the ways to find and follow Alana and as well as her socials you can go to Leap Academy. But we'll put it all in show notes. And Alana, I know you have a gift for our listeners. So if you want to just explain that real quick.
Alana Golan
Yeah, so I, we love hearing from you first of all. So if you hear this and you got some good nuggets, please reach out. Like we would love it. We're in leapacademy.com or ilanaleapacademy.com and yes, we have a gift for you. So basically on leapacademy.com, what we'll give you is a free a little assessment of kind of where your career can go. And you know, it's really fun because it's really short. You also have a free training about, you know how to leap your career was a lot more elaborated than what I give you now. And you can apply to a 15 minute really strategy, career strategy call to have one of my experts sit with you and kind of understand where you can reinvent yourself. And then I just want you to feel the new possib possible and it's really fun.
Nicole Khalil
And do people go to Leap Academy for that? LeapAcademy.com Yep. Yes.
Alana Golan
Free.
Nicole Khalil
True. Okay, great. Awesome. Alana, thank you on behalf of my listeners for that free gift and for your exceptional conversation and wisdom today.
Alana Golan
Ah, thank you, Nicole.
Nicole Khalil
My pleasure. Okay, here's the deal, friend. Reinvention isn't optional. It's not a backup plan. And it sure as hell isn't a sign that you failed. Reinvention is the work of the brave. The people who refuse to see stay stuck, who collect the breadcrumbs of their lives and decide to make something bolder, truer, and worth reinventing for. So stop waiting until it feels easy, because it never will. Stop buying into the lie that you only get one shot at figuring it all out. You get as many shots as you're willing to take. Reinvention is messy, it's uncomfortable, and it will demand every ounce of your courage. But it's also where freedom lives, where fulfillment lives, where you live. Reinvent as many times as it takes. Because staying the same, well, that was never the assignment. Be more you. That is and will always be woman's work. The Uniswap wallet makes crypto easier and.
Alana Golan
Safer to own and use. Discover new tokens, research confidently, swap instantly.
Nicole Khalil
And manage it all securely in one place. The Uniswap trading protocol has powered over.
Alana Golan
$3 trillion in volume, and it's trusted by millions worldwide.
Nicole Khalil
Buy your first crypto assets in a few taps and experience the freedom of decentralized finance with Uniswap Tap the banner to get started.
Alana Golan
There's phishing, and then there's phishing. Out here, you're after dinner. Online hackers are after your data. They'll bait you with fake emails, lookalike sites, anything to lure you in. But with Cisco Duo's end to end phishing, resistant access control, every login, every device, every user stays protected. Looks like no one's biting today. Cisco Duo fishing season is over. Learn more@duo.com.
Podcast: This Is Woman's Work with Nicole Kalil
Host: Nicole Kalil
Guest: Ilana Golan (Founder, Leap Academy)
Date: December 29, 2025
Episode: 374
In this episode, Nicole Kalil invites Ilana Golan—tech entrepreneur, mountaineer, podcast host, and founder of Leap Academy—to unpack the complex, ever-present theme of career and life reinvention. Together, they challenge old paradigms around "woman’s work," offer actionable advice on navigating transitions, and celebrate the courage it takes to reinvent over and over again. With candor and humor, they reframe reinvention as not just an option, but the new norm.
00:55–04:28
"It turns out life isn't about figuring it out once. It's in reinventing yourself over and over again." (02:00)
"We do this all the time. In fact, at this pace of change, we're going to do it every year or two, so we better get really, really good at it." (04:30)
04:28–09:02
"There's always like transferable skills. There's always a path. Success leaves clues. And if you can start looking for those clues, you actually are going to start understanding what is your zone of genius." (04:40)
09:02–13:18
"In the world of startups, we experiment all the time... Why are we not doing this for careers? It's actually the same." (10:39)
"It is actually AQ... Adaptability quotient. With the pace of AI...reinventing, leaping is actually becoming the most important skill for the future of work." (11:54)
13:18–18:37
"My biggest reinventions came out of some of my hardest, most challenging, most painful experiences." (13:41)
"You can't really tell your story when the wound is really bleeding, but you can tell your story from the scars." (14:41) "Think about it as experimentation... It's not suffocating. All you need to decide is, is it worth five more weeks or do I want to switch to something else?" (16:20)
22:48–28:09
"One career is probably not enough if you want more from your life." (23:15)
28:54–34:53
"It's never the challenges that stop us. It's always our belief around the challenges and the meaning that we're giving it." (29:46)
31:27–34:53
"Reinvention is no longer a detour. It's the road we're on." (32:04)
"We collect breadcrumbs along the way, experiences, wins and losses, joys and pain, success and failure. And those give us hints about who we're becoming and where we're headed next."
—Nicole Khalil (03:10)
"At some point people were starting to come to me, not for business-related stuff, but for asking me about their careers... Our ecosystem will already hint us about our zone of genius and we're just not attentive enough to see the clues."
—Ilana Golan (08:00–08:56)
"Adaptability, reinventing, leaping is actually becoming the most important skill for the future of work."
—Ilana Golan (11:54)
"You can't really tell your story when the wound is really bleeding, but you can tell your story from the scars."
—Ilana Golan (14:41)
"The hardest thing in a goal is to let go of what society expects from us...the hardest thing is the emotional part of it."
—Ilana Golan (30:42)
"Reinvention is the work of the brave. The people who refuse to see stay stuck, who collect the breadcrumbs of their lives and decide to make something bolder, truer, and worth reinventing for."
—Nicole Khalil (36:34)
| Timestamp | Segment | |:-------------:|:------------------------------------------------| | 00:55–04:28 | Framing reinvention as an ongoing necessity | | 04:28–09:02 | Finding your zone of genius, telling a new story| | 09:02–13:18 | Embracing experimentation, AQ over IQ | | 13:18–18:37 | Moving forward from failure, 5/5/5 framework | | 22:48–28:09 | Building a portfolio career | | 28:54–34:53 | Advice for reinvention when feeling stuck | | 31:27–34:53 | Reinvention as the new normal | | 36:33–36:59 | Nicole’s closing reflection on courage & reinvention |
The conversation is candid, empowering, and honest, mixing humor and hope with actionable strategy. Both Nicole and Ilana use personal examples to make reinvention less intimidating and more accessible, encouraging the audience to embrace change as both normal and exciting.
For new listeners:
This episode is a handbook for anyone feeling “stuck” or craving change. Expect inspiration, practical frameworks, and permission to rewrite your life’s script—however many times you need.