141 | Ilana Golan: Turning Setbacks into Success with Strategic Career Leaps
58 min
•Nov 9, 20257 months agoSummary
Ilana Golan shares her journey from Israeli Air Force officer training F-16 pilots to Silicon Valley executive, detailing her devastating ousting from her own startup after raising $800K and how that setback became the catalyst for founding Leap Academy, a platform helping professionals navigate career transitions and strategic leaps.
Insights
- High achievers often struggle most with identity loss after professional setbacks because their self-worth is deeply tied to titles and achievements, making the emotional recovery harder than the practical one
- Purpose storms—sudden loss of direction after major failures—can be more damaging than the failure itself; recovery requires intentional strategic thinking rather than reactive doing
- Career success now requires portfolio careers with multiple income streams and continuous reinvention every 1-2 years, not linear progression within a single company or role
- The hardest part of career leaps isn't recognizing the need to move—it's deciding when and having the courage to act despite fear, imposter syndrome, and social judgment
- Defining success requires choosing 2 of 4 must-haves (financial security, growth, impact, balance) and accepting seasonal trade-offs rather than pursuing all simultaneously
Trends
Portfolio careers becoming standard necessity rather than exception for high achievers seeking resilienceCareer transitions driven by AI disruption and rapid technological change requiring continuous skill reinventionRise of founder/operator-turned-coach model where entrepreneurs scale impact through education and mentorshipIncreased focus on personal branding and network cultivation as insurance against corporate instabilityMental health and identity crisis recognition as legitimate business challenges for high achievers post-setbackShift from linear career paths to intentional leap-based career architecture with strategic timingMentorship and advisory roles becoming primary income diversification strategy for executivesVulnerability and transparency in leadership becoming competitive advantage for building trust and community
Topics
Career Pivots and TransitionsStartup Founder Equity and Co-founder DisputesSilicon Valley Fundraising and Venture CapitalIdentity Crisis in High AchieversResilience and Setback RecoveryPortfolio Career DevelopmentPersonal Branding and Executive PresenceLeap-Based Career ArchitectureMentorship and Advisory RolesMultiple Income Streams StrategyImposter Syndrome in LeadershipCareer Readiness and PreparednessPurpose-Driven Work and Zone of GeniusWork-Life Balance and Seasonal PrioritiesAI Disruption and Career Reinvention
Companies
Intel
Mentioned as part of Ilana's career progression through major tech companies before entrepreneurship
Leap Academy
Ilana's company founded post-startup failure; named Startup of the Year 2023 by American Business Awards
Baylor University
Host Toby Brooks is a grad student and instructor in exercise physiology program at Baylor
AT Still University
Mentioned as institution where former guest Quincy Conley works and heard episode
People
Ilana Golan
Entrepreneur and founder of Leap Academy; Israeli Air Force officer turned Silicon Valley exec ousted from startup
Toby Brooks
Host of Becoming Undone podcast; athletic trainer, strength coach, and learning scientist at Baylor University
Gary Vee
Referenced as portfolio career example and contributor blurb for Ilana's upcoming book
Richard Branson
Mentioned as guest on Leap Academy podcast demonstrating portfolio career model
David Goggins
Referenced by Toby as example of grinder mentality in social media culture
Quincy Conley
Former guest on Becoming Undone podcast; connected with show through AT Still University
Quotes
"I needed to feel that regret. I'm the person, you know, training them on emergencies and all these things, like I should be able to do this, but I don't feel ready, right?"
Ilana Golan•Early career discussion
"You've been playing so small. Like, where are you, Ilana? Let's go back."
Ilana Golan•Cancer scare realization
"I don't think it's necessary. You wanna, I don't believe that you wanna burn the boats if you're not ready for it. I think you wanna be very strategic about where it is that you wanna go."
Ilana Golan•Career leap advice
"No career will give you all of them. You can have all of them just not at the same time."
Ilana Golan•Success definition discussion
"If it doesn't feed and fuel my purpose as a distraction, and that's a critical test for me to give something."
Toby Brooks•Opportunity evaluation
Full Transcript
This is becoming undone. The founder's story, right? We knew each other well. Both of us in tech, like it was just such a classic story. We raised three times more than we wanted to raise. They were evaluating our little baby at $5 million. Like the Silicon Valley love story. I was so proud and I told everybody about the startup. I told about the money we raised within the same day. It was amazing to be. Same day. I come back. I talk to my co-founder kind of thinking that we're celebrating. And I can see that something is wrong. It's like, what is going on? And he's like, well, you're not part of the company anymore. And I was like, wait, what? I actually had like a cancer scare at some point. And I remember at the lowest moment, you'd laying in bed and thinking, you know, kind of waiting for them to decide if this was cancer or not. And the truth at that point, I felt so much regret out my life and what I achieved and how somebody so high achievers. That was just the biggest stab in them. And the minute I got that it's not cancer, it was almost like, you've got to be kidding me. Like you've been playing so small. Like, where are you, Ilana? Let's go back. I needed to feel that regret. I'm Ilana Gollun. And I'm undone. Hey, friend, I'm glad you're here. Welcome to yet another episode of Becoming Undone, the podcast for those who dare bravely, risk mildly, and grow relentlessly. I'm Toby Brooks, Speaker, author, professor, and learning scientist. I spent much the last two decades working as an athletic trainer and a strength coach in the professional collegiate and high school sports settings. And over the years, I've grown more and more fascinated with what sets high achievers apart and how failures they can suck in the moment can end up being exactly what we needed to propel us along our paths to success. Each week on Becoming Undone, I invite a new guest to examine how high achievers can transform from falling apart to falling into place. I'd like to emphasize this show's entirely separate from my role at Baylor University, but it's my attempt to apply what I've learned and what I'm learning and to share with others about the mindsets of high achievers. It's a fall day here in Central Texas as we close in on a Thanksgiving holiday. The class I'm teaching is winding down and the two I'm taking are almost finished too. I'm managing to climb out of a deep midterm hole that I manage to put myself in for a less than stellar midterm performance. And with some hard work and a little look, my first semester as a grad student here at Baylor isn't pretty good shape. In other news, I can't leave well enough alone. I saw an ad this week for a prep course for the National Strength and Conditioning Associations certified performance and sports scientist exam. And I bought it. The CPSS, as it's known as a fairly new certification, and when I was back in Lubbock, I took it and I failed. The test requires a scaled score of 70 to pass, although my raw score was above that threshold, the scaled score wasn't. So I failed. And honestly, I was crushed. Up to that point, I'd never failed any type of licensure certification exam. And while I'd studied for it, I wouldn't say I studied hard for it. So what to do with a failure? Live what I preach, I guess. That setback was gonna be just part of my journey. I signed up for it again, and I'd show that test who was boss. I was strategic in my preparation that time. I spent weeks gearing up and getting ready. It was like 400 bucks to take it. So now I was in pretty deep. And after all that, some four months had passed. I went back, I retook it, and I scored exactly one point better. I still failed. Two of my subsection scores actually went down on the second try. At the first time I was crushed, second time I was ticked. I headed back to work with the knowledge I'd now failed this exam not once but twice. And to cap it all off, I'm away from the testing center where I'd failed to work. I got pulled over for speeding in a 40 mile an hour zone. It was not my best day. From there life got busy. NBA was in full swing. TAY Senior Year was going on. Then I moved to Waco and a new job. To be honest, I did my best to put the memory of that test out of my memory. Hopefully forever. Here's the thing though. I don't need it. I have no plans to ever work as a sports scientist. But it has now beaten me twice. And all together, I've spent over $1,000 and I have literally nothing to show for it other than the humiliating fact that I failed twice. So now I'm in a graduate exercise physiology program. It's first time I've had classes like this for decades. And to make things worse or better to be able to how you look at it, I have a class made in my ex-fizz class who's planning to take the CPSS himself. So when I got the notice that this prep course was on sale for the only time in the year of Buckles, I might not need this test professionally, but they're still part of me. It's a little embarrassed and ashamed and angry that I still haven't passed. Now I make no excuses for it, but I'm definitely older. My peak memory days may be behind me, but I don't think there's any reason why I cannot overcome this test. I've pulled out the book, sadly, in a petulant fit. I threw away the study guide I had created when we moved, you know, like a her team who scratches their exes pick out of their yearbook, I didn't even want to see it. But it turns out the CPSS hasn't seen the last of me. At least that's the plan. I was torn between keeping it to myself until I finally passed, if ever, and sharing it here, be invulnerable, letting you in on my struggle. And I'm still not quite sure that this is the right approach, but I'm choosing the latter, not for myself, but because I know that somewhere out there, someone listening to this show right now has either failed a license or certification exam, or you will. Trust me on this, it's not the end of the world, but it is time for a new strategy. So stay tuned. Hopefully, I can pass this, mother. This week's guest is a renowned entrepreneur and high achiever with an incredible story to share. While she didn't specifically mention my mountain of a CPSS exam, it's safe to say that there have been some tests she's faced along the way that maybe didn't turn out as she'd hoped, at least not in the moment. However, today, a CEO of Leap Academy, she continues to face down those obstacles with grit and determination that is nothing short of remarkable. Some of our guests build their stories step-by-step, others crash, burn, rebuild, and rise again. But this week's guest, she's done it all. A click Google search for Elana Golan popped up an image of a coffee mug she'd shared in an Instagram post a few days ago that says it all, quote, sometimes wrong turns are the very ones that lead to the right place, in quote. So imagine if you will be in just 18 years old, tasked with training fighter pilots in the Israeli Air Force. People making split second life or death decisions, before most of us have even figured out what we're going to do after high school. That was the beginning for Elana. From breaking barriers in the military to scaling the heights of Silicon Valley as a tech exec being ousted from her own startup after raising nearly a million dollars, Elana's path has been anything but linear. But through every twist, every setback, every leap, she's redefined what it means to be resilient. Today, she's a sought-after speaker in the founder of Leap Academy, where she helps professionals make bold career moves and navigate life's unexpected turns with clarity and with courage. Let's dive into her remarkable story. I hope you'll enjoy my conversation with the incomparable Elana Golan in episode 141. Let's get into it. Greetings and welcome back, becoming undone as the podcast for those who dare bravely risk mildly and grow relentlessly. Join me, Toby Brooks, design, invite a new guest each week, where we examine how high achievers transform from falling apart to falling into place. This week's guest, fantastic. I can't wait to get into this story. Elana Golan has come from Air Force Officer to exec, startup founder, being ousted from her own company. So she's got tons of stories, only to come back stronger. sought-after speaker today, founder of Leap Academy, we see the signage in the background, helping professionals make bold career leaps and define what's next. Elana, thank you so much for joining me today. Oh, thank you, Toby. It's great to be here. Yeah. I'll be coming undone. Let's go. Yeah, so looking forward to getting into the details of your story. One of the most nonlinear careers imaginable, Air Force Officer, engineer, tech exec, entrepreneur, investor speaker. What was the first big leap you ever remember taking? I mean, I think the big one is definitely Air Force. Again, I come from a place where we do have mandatory military service in Israel, but I think I got lucky. I guess there's a little combination here of luck and creating your own luck, but I got lucky and I did get probably one of the best roles you can have, which is training F-16 pilots on the F-16 flight simulator, which was the most advanced simulator. And I got to be the first woman to become a commander in this squad. So I got to see kind of how we break some ceilings, which is a really big deal. And so it gives you a lot of confidence. But also a lot of teaching moments, Toby, if you weren't. Yeah, for sure. Well, I've had several guests who were athletes, but also military and entrepreneurs executives. And you kind of check a lot of those boxes. When you look back and you kind of alluded to this just now, were there early experiences in the Air Force or even engineering that planted the seeds for resilience later on in your journey? Oh, so many, so many, so many. I think when you break barriers, this is such a beautiful question, Toby. When you break barriers, I think by definition, you're always out of your comfort zone. And you're going to get knocked down again and again and again. I think then you, you by definition have to create a lot of grit, a lot of tenacity, a lot of resilience. And again, like I found myself sometimes, you know, in the Air Force, only making decisions that are essentially life and death decisions, whether somebody can land or not. And, you know, and I remember catching my breath and saying, wait, I'm only 18 or 19, probably at that point in time. Like I can't make that decision. And, you know, but then you're looking around and I'm like, yeah, I know why they called me. I'm the person, you know, training them on emergencies and all these things, like I should be able to do this, but I don't feel ready, right? And I think that is almost like that definition of entrepreneurship, like you're never ready, right? Or the definition of sports, you're never ready to be in that arena, right? But it's like you kind of have to be. And you have to create that almost alter ego for yourself to step in and to say, okay, I gonna have to make this. And God, it was sometimes so scary, but like I can't even stress it. So. Yeah, I think you hit the nail right on the head. There's so much about high achievement that involves, there's a self-awareness piece, like understanding what I know now and maybe what I need to acquire along the way to be successful with this. There's an ability to face your fear, understanding that I'm gonna step out in faith on this goal or this thing that I have in my future. And I might have to acquire skills I don't yet have in order to reach that successful completion. You've shared openly about the painful moment of being ousted from your own startup after raising close to a million dollars. And the theme of this show is that oftentimes it's the setback at see adversity. It's when we find ourselves in the rubble that we never would have chosen that actually lays the groundwork for our next level of success. Can you take us into that day? I really like to think about in that moment, when you're dealing with the despair and all the emotions surrounding that, how that can set you up for the next thing, what you felt, how you processed it. Yeah. And to give the listeners some context, so I was leaping again and again and again. And felt like I tick a lot of the boxes of success, quote unquote, right? Like what you kind of think of in body success, right? I studied here and here and I went to Intel and I went to startups and like to renegade you tick a lot of boxes of success. And I think that's important because in your mind that shouldn't happen to you, right? Right. So there's a little bit of like that piece, right? And after a leap again, again, and again, from engineering to technical sales and architect and all the way to vice president. And at that point, you kind of also get a little bit of that ego boost, you know? Like I'm vice president, I can do a lot. So no matter what I'm going to tackle, I'm going to be successful at it. So it does come with a little bit of maybe more ego than it should, Toby. And yeah, that's where our friend of mine came to say, hey, let's start a company together. I knew him for two decades. So it's not something I didn't know. Right. And we decided to work on this thing. We worked on it day and night. I was so excited, Toby. And yes, we were both in Silicon Valley. We had an incredible Silicon Valley, you know, kind of the founder's story, right? We knew each other well. Both of us in tech, like it was just such a classic story. We raised three times more than we wanted to raise. They were evaluating our little baby at $5 million. Like it's unbelievable. And, you know, and it wasn't from one small investor. It was three prominent Silicon Valley investors. It's like the Silicon Valley, you know, loving love story, right? And I was so proud, Toby, and we had this. So right after I actually parted ways from my VP role. And I wanted to make sure people don't run away after me. Right. So I wanted to come forward with a startup. Like I want them to know I'm not running away from the company. I'm running away from to chase a dream. And I told everybody about the startup. I told about the money we raised. Within the same day, it was amazing to be. Same day. I come back. I, you know, I talked to my co-founder kind of thinking that we're celebrating. And I can see that something is wrong. It's like, what is going on? And he's like, well, you're not part of the company anymore. So here's the thing about me. You're a faithful host and writer and producer and pretty much one-man show. Well, I'd venture a guest that most of your favorite podcasters just do their interviews and leave the rest to their team. Here, I am the team. After the interview, I go back in and I edit and clean up the conversation. In the process, I decide where to interject my monologue like this one. And then what I'm going to say, write it out, rehearse it. As a result, by the time this hits your ears, I've heard each episode at least two or three times. And I will say, I'm probably my own harshest critic. All that to say, I got to the meat of our conversation here too quickly. I didn't set this one up properly in order for you to be able to really feel the gravity of what actually happened to Elana. But that's the beauty of post-production and where I, as a writer and producer, get the chance to make up for me as the interviewer. J. Elana is an unmistakable force. As founder of Leap Academy, which we'll talk about in a minute, she's been honored as winner of Startup of the Year from the American Business Awards in 2023, and named to Inc. 5,000's fastest growing company in America. At just 18, she was responsible for training fighter pilots in the Israeli Army, soon after pursued a career in engineering and technology. Her ascent had been downright meteoric and marked with one success after another. That all changed in 2014. She had left her job as a VP in technical operations to launch a new Silicon Valley Startup with a long time friend. Not long after the pair and the team they disassembled, had raised more than $800,000 in seed funding to finance the new company. It was a pinnacle moment for Elana as she saw her wildest dreams coming true. But little did she know, she was heading straight into the teeth of a destruction level purpose store. In her own words, from a meeting article by Authority magazine published in 2020, she shared quote, right when we raised the money. He took the money and kicked me out of the business. I was left with no job, no startup, and my ego deeply crushed. I need to figure out what I want to do next with my career. And the downhill spiral wasn't easy. End quote. Friends, that is the very definition of a purpose store. And in the midst of one, it can seem impossible to find your way to safety, let alone success. But as Elana shares today, she no longer sees it as a hurricane sent to destroy all that she held dear, but rather a life giving thunderstorm that showed her where she was the strongest. While it undoubtedly cleared the way for the work she does today, in the worst of it, she found herself first stunned, then hurt, then angry. But in the aftermath, suddenly stripped of purpose and desperately searching for identity. And I was like, wait, what? We just, we just, we're just looking at the term sheets yesterday. What are you talking about? I made this big party. I told everybody, you must be kidding. And he's like, no, I took you out. And it was like 24 hours. I was out of a job, no salary, no startup, no investment. And to be really honest, the worst part is your ego. It's like, I don't even know who I am anymore. And I remember driving back home. I couldn't even, my family is like, how is the party? How is the party? And I'm like, I'm choking. I don't even know what to say. I'm hiding in the room. And I'm like, I don't even know how to face the world anymore. Because my identity to be was always attached to my title. It was attached to the company. It was attached to the stream that I was after. And suddenly, I was an opening. I was like, how do I even start? Why do I want you want to do? Where do I want to go? And I think that's another thing for high achievers. You always expect to know what's next. And I have no clue. And that was driving me absolutely nuts. I didn't even know if I'm looking for a job. I'm starting a company or I'm looking for a venture. It was really that bad. Yeah. And it's something that I'm really starting to dig deeper on, the book I'm working on, several of the guests that I've talked to. I come from a medical background. And I came across this notion of a thyroid storm. And it's where your endocrine system just goes haywire. And in that moment, it's life threatening. But since your endocrine system is a communication network in your body, everything about your functioning is potentially at risk and doing the wrong thing. When we're hit, you're punched in the gut. And you go from one end of the emotional spectrum of being elated at the victory to the other end, where you are devastated by the defeat. We enter what I call a purpose storm, where you're wondering why you're here. Like I can't understand how this could have happened. This doesn't fit with the narrative of who I've built around myself. And in those initial moments, obviously, it's stunning. Like we've been hit, we've been dealt with a blow. How long did it take you to navigate that space of the not knowing in order to realize what was next? The truth is Toby, you nailed it, I think. I think maybe because I came from very high to very low, it took time. And again, I'm a doer. So I, to readically, and I think high achievers do that sometimes. I compensate by thinking I'm doing things, but I'm actually throwing spaghetti on the wall. See what sticks, nothing is intentional, nothing is strategic. I'm kind of in survival mode at that point. And I think that that kind of throwing darts and trying to figure out what on earth is next for me, I think I was lost for a while there. Like a good, good long time. And that is the basis of everything I do today. But at that point, I remember googling, like, what do I want to do? It was my life. How do I find my passion? Like, what's next for me? And I was watching TED Talks and YouTube and all the things. And it's like, why can't I figure this out? Like I'm a high achiever. I'm driven person. Why can I not figure this out? And that became the biggest mission in my life at that point. So I mean, fast forward, I did start a company and sold it. And I started leaping again. And we can talk about it. But that low moment, which you alluded to it, like I couldn't sleep at night. I could wake up in the morning. I was snappy at my kids. My health deteriorated. Like it's everything you talked about. Right. I've seen a visual depiction of this. And it really resonated with me. And the speaker had essentially a paint of glass. And they put several different colors of paint. And you remember as a kid thinking, oh, I have blue and gray. And I have all these beautiful colors. And you mix them together. And all this is this horrible brown, right? And so the speaker has this paint of glass with all this horrible brown, which to me is illustrative of, when I'm in the midst of a purpose storm, I'm waiting through some crap, right? And so the speaker has paper towels. And they're trying to wipe the glass. And the more he works, the more it smeared and the worse it got. And when we're in the midst of that, it's tempting to think I just need to do more. I need to buckle down. I need to sign up for a new degree or get a mentor. I mean, we're going to work our way out of the problem. And then he pulls out a paint of glass. He said, I did the same thing three days ago. And it's dry. And I'll let it sit. And he takes a razor blade and it just scrapes right off. And in that moment, I was just so taken with the notion that sometimes the best thing we can do is to just let things settle. And that's so counter to the way I'm wired, right? And it sounds like much the same. That experience impacted your career, but also your health, your sleep, your sense of self. At your lowest point, what would you pinpoint as the first sign that you could climb back out of that? Man, I think, to some extent, I don't know if there was a sign that I could climb back. I think eventually I found myself climbing back. And then you can always paint the dots. You can connect the dots backwards. And there was like, oh, I actually was starting to come back from this. But I think at the lowest moment, if I'm being really honest, I actually had a cancer scare at some point. And I remember laying in bed and thinking, kind of waiting for them to decide if this was cancer or not. And the truth at that point, I felt so much regret to be about my life and what I achieved and how somebody so high achievers so driven. This is all they achieved. And that was just the biggest stab in them. And the minute I got that it's not cancer, it was almost like, you've got to be kidding me. You've been playing so small. Like, where are you, Ilana? Let's go back. And I think that was the drive I needed. That was basically the boost that I needed to feel that regret. And that regret was something I never want to feel ever again. Here, Ilana shares candidly about a major health scare that altered her perception. And what strikes me is that last idea that she just shared, quote, I needed to feel that regret, end quote. So often, we can find ourselves slogging through life in survival mode. I know I have a to-do list every day, many times every week. But what we can sometimes lack in that approach, if we aren't careful, is vision. So often, we get sucked into what someone would call the tyranny of the now. All the small fires burning around us that need our attention. They can steal away our purpose. And our intentions to do the big things, and pursue the big dreams in our hearts. For Ilana, that cancer scare ended up being OK. But it brought her some much needed perspective. In her words, she'd been playing too safe, too small, choosing instead to address the needs of now, instead of a deeper, more impactful purpose for the future. That sting of regret proved to be like rocket fuel, helping to inspire her to make her leap, and eventually inspiring others to make theirs. Like that was it. And there's a clarity that can come from that. Not every storm comes just to destroy. Sometimes storms come to nourish and to redirect. And so that's kind of my next question is, how do you, maybe even today, differentiate between failure and being redirected? Hmm. I think all the failures should be redirected. So I do think that all of them are teaching us something. And the question is, what is it teaching us? And I think the more we're deliberate about asking ourselves the very hard questions, and really kind of looking backwards and reinventing ourselves and starting to be really intentional, strategic with our career, the more we're going to look at them as big lessons versus a thing that is a failure. It's not a failure. It's just something that, I mean, let's be real Toby. I would never have started leap academy. I was successful in the cloud data center space. I would have continued there. I would never have found this zone of genius. I would continue to being in my comfort zone, getting a nice paycheck and being a fraction of what it could be. Now, I'm not saying a paycheck is a bad thing. I actually think it's fantastic for the majority of people. I think we're creating entrepreneurship as if it's like the gold standard. And it's not right for a lot of people. Like I think where it's male practice to make it sound so. Right. Like pink and purple and it's all with those challenges. Like I think we're doing a lot of harm to a lot of people by driving them into entrepreneurship, if I'm being honest. But I think you need to figure out where are you, the best version of yourself. And I do believe that even incorporate in the world today, you have to create this portfolio career for yourself because nothing is for 40 years anymore. So you got to start being really intentional, very strategic and start being very deliberate about how you reinvent yourself every year too because the pace of change is absolutely mind blowing. Yeah. The alignment to me is key. And sometimes I will willingly choose whether it's the easier path. Sometimes it's just the path of least resistance and growth left unattended happens. If I look at the roots of my tree, it doesn't choose to go through concrete walls unless that's the path of least resistance. That's how growth tends to be for a lot of people. But you mentioned it being strategic in that growth, recognizing that zone of genius. And maybe I got complacent and maybe I've allowed what was easy to take the place of what was impactful. You didn't just rebuild. You sold another company, you invested in over 80 ventures. You become the sought after keynote speaker. How did you decide which opportunities to pursue during that comeback phase? I got to imagine that you were inundated with lots and lots of things. How did you plot your course? I had a good question, Toby. I think that initially I kind of threw spaghetti on the wall, which is exactly what I teach people not to do. Right? Like I feel like I teach a lot based on scars and wounds, not based on, you know, like successes. So from being really honest, like I think that initially I kind of let life, I almost let through life, you know, like I feel like I was sleeping through, I was doing my things and then it was like this moment of no, I need to start being deliberate, but you're right. I started a company, I sold the company. It's actually a beautiful story. I'm invested today. Probably it's way above 100 now, was probably some of the biggest startup, you know, investors in Silicon Valley. And I learned a lot on the way and I did do a lot of public speaking and what I realized, which is kind of interesting, Toby, is that as a geek engineer at the end, I'm a geek, right? Like I'm actually doing the same things again and again and again, I'm just getting better at them so that I can leap faster and higher. And at that point I realized, okay, if that it's so calculated, first of all, can it work, you know, can I leap on demand basically, right? And the other thing is like if I can, then can I start creating almost like a wish list and what do I want to do next? Oh, I want to join a board, great. Let me see how I do that. I want to do an advisory, great, hot. Let's see how I do that. I want to start a company, great. If we're going to be one of the fastest growing in just a few years, you know, I'm like, you suddenly realize that it's really just about taking these few steps. I'm not saying it's easy, but it's kind of for simple steps that I just need to do again, again, again, and now that I know that it helps, thousands of others, you know, I think like I wish I could get to millions and show them that it's really that simple. Yeah, that notion that it's not easy, but it's simple. Yeah. Execution can be difficult. It's not easy to execute, but once you plotted that course, it's just kind of, it's almost like a cookbook, like I just follow the instructions and reverse engineer the destination where I hope to end up. And you alluded to it to me because the hardest thing for people usually is the decision. Is that, you know, because it's scary. It's what will people say and what if I fail and what if, you know, people think it's not cool. Like it's all the things and these are all the things that scared the heck out of me of doing leap academy, right? Like I'm this business person, I'm investor, I'm this. Like who am I to start this thing, right? Yes. So I think a lot of times it's us. Yeah, who am I? The classic lament of the person struggling with, yeah. What will say, what if I fail? Yeah, that imposter syndrome is a thing. It's real. It is real. Yeah, you've described, and I've heard you even alluded to this, but definitely in the stuff that I prepped before the show, you talk about career as a series of leaps. And for me, I think the biggest question, and I've even encountered this with students, I've encountered this with folks that I've coached, and in my own life, it's not knowing that I need to leap, it's knowing when is the time for the next one. What advice would you give someone who is, maybe they're on board, they recognize that growth is a series of leaps, but I don't know when, you know, it doesn't feel safe to leave this paycheck. It, I don't wanna get rid of these benefits that I have and try this entrepreneur journey. Well, what are maybe some signs that it's time to leap? It's a beautiful question to me. I'll say a few things. The very first thing that I'm seeing in this world of this era of change, and maybe my answer would have been different five years ago, but in this specific era of change, we're moving faster than we've ever seen before, and even this one corporate career is not necessarily safe for you anymore. So the one thing that I'll say to anybody listening, you always wanna be leap ready. Even if you're staying there, you always wanna know what's next. How do I tell my story? I want my network to be my ambassadors. I want my personal brand to speak for me. I wanna get the relevant opportunities for myself according to what I wanna be known for. So first of all, just be intentional and deliberate about being leap ready. The other thing is that I will say that if you're gonna look at the top 0.1% of the people, they all have, it's actually interesting. The statistics say it's interesting. 62% of them have multiple streams of income, more than three. 62%. So what this means is that all of us need to start being very strategic about creating this portfolio career, even if we are in corporate. Now sometimes you can't visit issues, whatever I'm not going into the legal stuff here, but I would just say almost every single person needs to start looking at what are my multiple streams of income? How do I create a personal brand that I can leap again again? How do I make sure that I get the right opportunities for myself? And then it's really about, you know, I don't think it's necessary. You wanna, I don't believe that you wanna burn the boats if you're not ready for it. I think you wanna be very strategic about where it is that you wanna go. But again, maybe you just want the promotion. Maybe you just want a different industry. There's a ton of incredible opportunities that are really, really safe right now. So I think it's more about like what do you want? Is it even within the same corporate? You don't wanna be the person that always stays and does the same. You wanna be leap ready to the next role, to the next function, to the next responsibility. You wanna be the person that they're looking at to move you to put you in the right seat at the table and to bring you in and to, you know, so you wanna even within the same corporate role, like you still wanna create a bigger impression of yourself, more executive presence, more opportunities. And unrelated, I would start looking at mentorship advisory, public speaking, investment, like whatever it is right for you, but I would start creating these things on the side that A, their incredible gets ageism, their your, you know, insurance policy, you know, if something God forbid does happen, this is what's gonna help you leap again again. So I'm a huge believer now that I've seen, now that I almost lost everything in my life, you'll be, I'm a big believer that you need to do things very different. And again, when you're kind of looking now that I have this podcast, you know, leap academy with Zilana Goran, and I get to speak with the Richard Branson and the Gary Vs and the president of Starbucks, they all have portfolio careers. Why is nobody teaching this? Right, yeah. Why should, I mean, everybody's talking about diversity and financial and investment, why should we not do this in our career? So that kind of why leap academy became, you know, it became a passion to teach others how to create these multiple streams and how to leverage them to leap again. Right. I love that. And to me, I've worked in higher education most of my career. And if you find someone who is too upwardly focused, they're more worried about the next job than their current job, that can really be stigmatized. Like, you know, this person's not a team player or they're not really all in on what they need to do. That's true by the way. Well, it is, but I also recognize that high achievers are always looking for what's the next step. And as a leader, I want to cultivate that in my team. I want people that are being actively recruited by other places because that means they have something of value that is marketable, you know, that is not something that I shy away from. So you've mentioned leap academy born from your own 25-year journey, helping others through transitions. And that's really kind of, I mean, I love the alignment between your message and mine, even though we're coming at it, maybe you're more entrepreneurial and me from sports. The idea is pivots and transitions can be fraught with fear, they can be frayed with shame, there's so many emotions that can pollute an idea. What patterns do you see in people who are stuck and really ready for leap? Oh, it's a great question. And, you know, and we do see it, I mean, I love that you see it in sport, right? Because again, I, you know, I listen to your show. I mean, in sport, we see it a lot. We've had, you know, people who been before in like Olympians, et cetera, like, and suddenly they're in this like pivotal moment in their career, they kind of checked all the boxes of success to some extent, right? And now they're coming into this, but oh my God, what's next? Right? And, and that, you know, reflection point of, I never really needed to think about it because from a very young age, everything was scripted. I knew exactly what I need to do. And for the first time, I need to actually reflect back and think about what is that combination of things that I want to do? What is my passion? What is my zone of genius? What are people intrigued by me? What, who even needs this? Like, who can I, you know, how can I monetize this thing? And I think that is definitely a common thread between, you know, what we're both seeing. And I think, you know, what, what, what, the common theme though, like you're asking me about a pattern, the one thing that I'll say is, both what you're doing, and especially what we're doing in the Academy, it's not gonna work for somebody who's not driven. You know, I think what, if you're looking at what is the common path, they're all driven. They all want more for themselves. They all know that they're a fraction of what it can be. I absolutely must jump in here and enthusiastically agree with this idea and give you your roses. Right now, my listener, my friend, my companion on this journey from where we are to where we want to go. A lot of says that the one thing all her clients have in common is a desire to get better. And all of a she says they, I want you to hear this truth. Refraze it, you, the same is true for you. Every last one of you, you know, we are now 141 episodes deep. And you've got my word here that I've gone all in to get better at this journey each and every episode. So I felt like now, as good a time as any to say, thank you. I see you. But if you aren't yet where you want to be, that's okay too. Just be patient, trust the process. Your door is coming. The fact that you're here tells me all I need to know. I know and you know that there's more. And you gotta believe me on this, your more is coming. They all know that there's more that they can achieve in life. And they want to, like they, they don't want to feel that I regret. They want to create something incredible. They know they can and then it's like, but how? And how do I monetize it? And how do I become a full potential? And I think that that that driven part, that because again, I don't, I don't think that I can, if somebody's never been successful ever in their life and they reached the age of 60, I can't suddenly create magic. You know what I'm saying? Like I need them to really want something out of life. I want them to eventually have that fire in them that once they find it, they're like, let's go, right? And Olympians sometimes are sport figures or, you know, Ellen Fell, whatever, like sometimes they're like the biggest because they're so driven, because they're so wired since, you know, childhood, once they get that new focus, they're like all in. It's incredible to watch. So that's why I love working with that. Yeah, it's navigating the what now to the, and I talk about, I go from being undone, feeling like I'm in pieces to realizing I've got a purpose left to achieve in that I'm undone. That's beautiful. I love what you said about how so many times folks who are in that what's next. And from your story, I gather this as well. But in my book, I talk about how there was a time in my life when sport was over, I wanted to play longer and it wasn't an option. It was, I was pushed out of sport. It wasn't that I was jumping toward. I wasn't leaping into my life after athletics. I was, I was being forced out of it. And I had a what next moment. And I can remember sitting in that locker room and audibly saying to myself, what next? But what a lot of people don't recognize, I think, is that you aren't immune to that same emotion even when you succeed. There are times when you will reach that goal that you set that was so high, that that's so audacious goal and you got there and you're just as purposeless. Where they're... I'll push back on you Toby. I think it's even harder because you've been in that peak, because you've been in that peak. It's incredibly hard to ask for help because we're used to be the person that people are coming to us for help. Like for me to ask for help, you're kidding me. Like that's not where my ego goes. Like I can't ask people that I need a job or that I'm lost or that I don't know what I wanna do next. Like that is weakness that I can't show. So I think to some extent, because you got to that peak, it's almost harder. Like it's, you feel so alone on this and you're actually not alone. Like I think the reason Lee Pakadami has succeeded is because suddenly people are meeting thousands of others in the same boat. They're also high achievers. They're also motivated and they're also stuck and it's okay, right? And it's also part of that hidden market and people are bringing each other's to opportunities and it's beautiful to see. But guess what? Nobody's, everybody has a hard time asking for help. Like that is like the one comment or if they're all driven and they all have a hard time. Yeah, asking for help. So what you said, I'm just like, oh my God, Toby, yes. Yeah. Yeah. Okay, and we're talking with Ilan and Belan, the host of the Lee Pakadami podcast, noted entrepreneur and speaker and coach. How do you define success now compared to when you started? Ooh, that's so good. That's a great question, I think, because I think my definition of success changes. And I think we also need to understand that life is in phases and different phases will bring different levels of success and different definitions of success, if you will. And I think this is something I didn't understand because I think I kind of thought that if I'm gonna tick a lot of the boxes, that it's all about boxes, right? And once I ticked a lot of these boxes, like I've been a VP, I've been a CEO, I've been in it. They're like, okay, the boxes are ticked. What now? Can I die peacefully? And the answer is no. Right, so now it's really more about what is the space in your life? What's critical for you? And this is a big piece that we work with people, speaking of what's next, because I think the hardest thing is to also admit to yourself more than anything is what's really critical for you right now? What is your must have? And sometimes it's financial, whether because we need the money or it gives us confidence, or we want the second home, or we want the first class. It doesn't matter why, but we need the financial. Sometimes it's gross. We need to feel like, it's a responsibility, that reputation, that fame, whatever it is, right? And sometimes it's impact. Like I just need to feel like I move the needle on the company or society, the world, or whatever, right? And sometimes it's balance, because I want to do sports, or I want to have kids, or whatever I want to have hobbies, it doesn't matter. But no career will give you all of them. You can have all of them just not at the same time. So the hardest thing is to choose the two that absolutely must have for you. And to be okay with compromising, at least for a little bit on the other two. But the beautiful thing is because you're going to reinvent yourself every year or two, you're going to change, your face will change. And as your face will change, suddenly you can start creating a little more for yourself, or another stream of income, or less streams of income, et cetera. So you're going to start navigating through this based on what's critical for you. And I think the hardest thing is to admit it. Yeah, I love the liberty that is baked into that approach, because for so many high achievers, we think we have to hit all those boxes all at the same time immediately. And to give yourself a little bit of grace to say that this season is about this. And I'm going to really drill down and focus on my physical health. Or I'm going to grow in this particular skill set. It's coding or it's writing or it's speaking, whatever that is. It's so heavy to carry the expectation and unrealistic. But I don't know about you, but I'm looking at my to-do list that I had for the weekend. And there is no possible way a human could have knocked out all of these things. And so what happens? I got a lot done. But when I look at the list and realize what I didn't get done, I walk away from the weekend feeling guilty. That's crazy. I underperformed, right? But what I love about the approach that you're saying, and on a macro scale, that you're kind of giving yourself permission to have a mental approach that's sustainable. It's not going to grind me into the ground. I love David Goggins. I love the rock. And in my last episode, I quoted both of them and this kind of grinder mentality that has really taken over social media so I was like, you should be working 27 hours a day, eight days a week. And that's the only way you get ahead. You mentioned Gary Vee. He does talk about things like that too. That's great for a time. But rest is an important part of the growth process as work. And I find with high achievers, the challenges isn't kicking them in the rear to get them going. It's kind of peeling them back and realizing that your work needs to be directed. Yeah, no, I love what you just said, because I think it's so, so, so important, because I think, first of all, it is about creating somewhat of a freedom of choice. And that freedom of choice doesn't mean that I'll slip certain fajitos on the beach all day. Like, I'm probably told to be one of the hardest workers you've ever seen. But I can work on my own term. And I can decide when I'm going on vacation. And I can decide when I'm out. And I can decide if I'm taking the weekend or I'm working on the weekend. So first of all, it is on your term. But I think that so, so again, life is in faces. And sometimes the hardest thing is to say, you know what, this phase, I don't want to fly. I want to be there for my kids, or I want to be there for my family. And it's okay to say that. And I think for us is high achievers. I think sometimes the guilt is the hardest thing. And I think if you can look at it as phases, it's something a lot more in peace with yourself that you can kind of be in peace with yourself and to say, you know what, it's just a phase. It's a year that I want to be closer to them. And then I can fly again. But you define, and guess what? If the phase changes and suddenly you need to fly again, then you fly again, right? But you get to decide. You are intentional. And the one thing that I'll say is that as high achievers, because we sometimes compensate, and I'm not saying entrepreneurship is different, Toby. So I think it is a lot about throwing a lot of things, right? But I think a lot of times high achievers, we work really, really hard, but we don't necessarily work smart. Yeah. And I think we sometimes the grind is a compensation for starting to be a lot more deliberate and saying no to things that we should have said no to. Yeah, right. And, you know, and again, this is kind of where when you have your must-abs and you have your zone of genius, this is where you start saying no to a lot of things and you're saying, you know what, this is not, if I want to 10x myself, this is not where I should focus. Yeah, one of my mentors says, if it doesn't feed and fuel my purpose as a distraction, and that's a critical test for me to give something. Like it may be a great opportunity, but if it's not fueling and feeding my purpose, then it's distracting me. It's keeping me from things that would. And I love to kind of weigh things in light of that. I got two laughs. I want to be aware of your time. I certainly appreciate it. When I ask of all my guests, if we were to watch a montage of your life, what song would you pick to play in the background and why? Ooh, some top-gun song probably. Ha. Ha. Ha. Ha. Ha. Music Ah! Your aviation background is showing. Yeah. Probably, probably. And I think because it created, it opened up possibilities that I probably didn't even realize and it built me in a way that I don't think I knew back when I was 18, 19, 20 that it was building me to such an incredible way. So definitely that would be a love it. I put together a mixtape of all my guests and post that on Spotify so I think I'm going to hide away to the danger zone. Exactly. I'm a huge fan also of just top gunning at them. When I put that on the headphones and head into the jam, I feel like I'm getting ready to do some work. You hear me, exactly. Right. Well, I usually ask this one like this. I usually say what for my guest name, Elana Golan is left undone. But I'm actually going to change the phraseology for the first time in the history of this show because of your platform and say what's the next leap that Elana Golan is preparing to take? Oh, I love that Toby. So first of all, I have a book that is upcoming. So we're writing the proposal now. I'm really proud that Gary Vee is blurbing the book and we have incredible people like the president of Starbucks, the previous president of Starbucks, that word and Tim's story. And other incredible individuals are blurring the book. So that's really exciting. So my aim is for New York time bestsellers, so fingers crossed. And I can, I'm in a mission to be really honest. I think we're right in front of a cliff where millions or tens of millions will need to reinvent themselves. And my biggest worry is how do I grow leap academy to impact the life's not having right now. We're in thousands a year, which is beautiful. And we're one of the fastest growing private companies in America. But for me, the biggest question is how do I bring this to millions and to tens of millions. And to me, that's what keeps me up at night. So Toby, I'm glad you're here to help me. And I hope I hope these listeners had a lot of value. Absolutely. You know, I can't really imagine a closer, better alignment than the platform that I've worked to build. And the thing I love about this podcasting journey, I mean, I can remember just muddling through episode one, love the guest. I didn't have any idea what I'm doing. I have a little bit more idea what I'm doing. If I'm not growing, hopefully, a year from now, I'll realize that, oh, wow, like last year, I really botched that interview. I mean, that's what growth is about. It is recognizing how horrible we were back when, right? But the thing I love about it is it is cause for conversation with people that I never would have had a chance to connect with before. And there's an alignment with that. There's a tribe. They're just the notion and the idea that you are looking to scale this to millions. And I hadn't really thought about it. I mean, I've pitched this as I'm helping people in transition. But as we're on the threshold of this AI age and maybe not even on the threshold, like we're squarely in the doorway, you're right. People are going to have to pivot. They cannot continue to do their role the way they did before. And I'm in higher ed. So I see this all the time. I'm not scared that AI is going to take my job. I'm recognizing what AI can do to help me do my job more efficiently and faster and broader. I always talk about augmented intelligence, not artificially. That allows me to have a much greater impact than I had before. And if I'm a laggard on this, I'm going to get left in the dust. And the thought that chat GPT is not yet crossed its third birthday, like it blows me away. How differently my world is operating just due to generative AI being in the workplace. So I love the alignment with what you're doing. And I will say for everyone that's listening that if you have anywhere that you can use me in the work that you are doing, consider me in because I am all in on leap academy. Let's go Toby. And so I'll give you something back into the listeners. Like Toby, you are an incredible interviewer. And again, I sit on a lot of interviews and I see on both sides, you're incredible talented at what you do. I appreciate that. And I just want to say that. How can listeners connect with the work you do and drop your socials? I'll be sure to drop those in the show description. But let us know where you can find the work that you're doing. And of course, leapacademy.com. We have a lot of free resources. We have sometimes free day challenges. We have free trainings. We have a lot of free conversations if we think it's a right fit. So we're really, really, we love giving back. So just reach out and I linked in Instagram. Like I actually see these things myself and I would love to talk to any person that would like to. So it makes them my day. A lot of thank you so much. It's been my pleasure to connect with you. I really appreciate your insights. Again, a lot of good on entrepreneur founder of leapacademy and any number of other things I could add to that by how you are a treat and a tremendous guest. And I thank you for being on becoming a done. I am Elana Golan and I am a done. From the cockpit of an F-16 simulator to the board rooms of Silicon Valley and beyond, Elana Golan's journey reminds us that falling apart isn't the end of your story. It's often where the real story begins. Whether you're contemplating a bold leap, reeling from a professional setback or simply searching for your next move. I hope Elana's story offers truth that resilience is built in the rubble and reinvention is possible and even powerful when you're brave enough to begin again. Big thanks to Elana for sharing her incredible insights into you for joining us on this episode of Becoming Undone. Thanks a lot Elana for dropping in and I hope you enjoyed our conversation. For more info on today's episode, be sure to check it out on the web. Simply go to undenpodcast.com, backslash EP141 to see the notes, links and images related to today's guest Elana Golan. Coming up on the show, I've got film or college and professional athletic trainer turned sports scientists Dr. Josh Boema who shares his story of finding yourself in the midst of what you thought were your dreams, only to discover that they're nothing like you'd hoped and what to do next. Then I've got athletic trainer Morgan Dietri who bravely shares her powerful story of recovery and redemption and her fight without call addiction. This and more coming up on Becoming Undone. Do me a favor, head on over to undenpodcast.com. You can click that subscribe tab at the top, sign up for my free newsletter that I produce almost every week. Yet, too, is always free and built to help you pursue better every day. In other news, my brand new personal website launches this week as well, Toby Brooks at THD.com. And I have an exciting new mobile app to tell you about in another week or so. So be sure to stay tuned for that. Also quickly wanted to share, I connect monthly with former guest and friend Quincy Conley out at AT Still University who mentioned this week as he was chatting with someone who'd heard his episode and he's a friend of the show. So whoever you are friend, virtual fist bump and thank you for being part of this undenmoving movement. I'd love to connect. I know there are great stories out there to be told and I'm always on the lookout. So if you or someone you know has a story that we can all be inspired by, tell me about it. Again, go to undenpodcast.com, click that contact tab at the top and drop me a note. Becoming unden is an I-Trop creative production written and produced by me, Toby Brooks. Tell a friend about the show and follow along on Facebook, Instagram and LinkedIn at Becoming Undenpod and follow me at my new socials handle at Toby Brooks PhD. On Facebook, Instagram, X, LinkedIn, TikTok, anywhere else. Check out my link tree at link tr.ge backslash.toby Brooks PhD. Listen, subscribe and leave me a review at AT