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141 | Ilana Golan: Turning Setbacks into Success with Strategic Career Leaps - Becoming UnDone | Wave AI Podcast Notes

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141 | Ilana Golan: Turning Setbacks into Success with Strategic Career Leaps

Becoming UnDone

Sun Nov 09 2025

Summary

Becoming UnDone, Episode 141
Ilana Golan: Turning Setbacks Into Success With Strategic Career Leaps
Host: Dr. Toby Brooks
Date: November 9, 2025

Episode Overview

This episode features Ilana Golan—Air Force veteran, tech executive, serial entrepreneur, and founder of Leap Academy—who shares her powerful journey of resilience after facing major professional setbacks, including being ousted from her own startup. Dr. Toby Brooks and Ilana discuss how high achievers can transform painful endings into new beginnings by embracing intentional, strategic career leaps, building portfolio careers, and redefining success through every phase of life.

Key Discussion Points & Insights

1. Ilana's First Major Leap: From Israeli Air Force to Tech Leader

At age 18, Ilana became the first woman commander in an F16 pilot training squad, making life-and-death decisions far beyond her years ([08:48]).
- Quote: “I got to be the first woman to become a commander in the squad... it gives you a lot of confidence, but also a lot of teaching moments.” —Ilana ([08:48])
Early experience in breaking through barriers instilled resilience, grit, and the ability to act despite feeling unready—skills foundational to entrepreneurship and leadership ([09:53]).

2. The Ousting: Peak to Crash in a Day

After a successful career in tech (Intel, startups, executive roles), Ilana co-founded a Silicon Valley startup with a long-time friend. They raised three times more than their goal, valued at $5 million ([12:23]).
On the very day she celebrated with friends and family, her co-founder told her she was out. Suddenly: “No job, no startup, no investment, and my ego deeply crushed.” ([17:26])
- Quote: “My identity, Toby, was always attached to my title... suddenly I was a nobody.” —Ilana ([17:26])
The emotional fallout included shame, regret, and complete loss of direction ([18:31]).

3. Navigating the 'Purpose Storm'

Ilana describes the aftermath as overwhelming, lost, and sleep-deprived, physically and mentally unwell ([19:49]).
She tried to muscle through by overdoing: “throwing spaghetti on the wall,” but nothing was strategic or intentional.
Regret was a necessary, galvanizing emotion—solidified during a personal cancer scare:
- Quote: “I needed to feel that regret. That regret was something I never want to feel ever again.” —Ilana ([24:01])

4. Redirection Versus Failure

Ilana reframes all failures as redirections, not endings:
- Quote: "All the failures should be redirected... they’re teaching us something.” —Ilana ([25:23])
Her setback led directly to the founding of Leap Academy, a business helping others leap successfully.
Entrepreneurship is not always the answer for everyone—having intentionality and a personal strategy is more important than blindly chasing “success” ([25:23]).

5. Strategic Leaping & Portfolio Careers

Ilana warns that today, staying in a single corporate path is riskier than ever—everyone should be “leap ready,” building personal brands and multiple streams of income ([31:31]).
- 62% of top performers have more than three streams of income.
- “Even if you’re staying [in your job], you always want to know what’s next.” —Ilana ([31:31])
Importance of strategic, not reactive, choices—deliberately designing one’s next leap rather than just “throwing darts.”

6. Recognizing When to Leap

Ilana emphasizes always being prepared to transition—even if you aren’t planning to leave yet ([31:31]).
Key signs include misalignment with your values, desire for broader impact, or finding yourself on autopilot instead of being intentional about growth.
High achievers should cultivate advisory, board, speaking, and mentorship opportunities as “insurance” for inevitable change ([31:31]).

7. Helping the Driven, Not the Unmotivated

Leap Academy’s process isn’t for the complacent; it’s designed for high achievers who know they’re capable of more but need guidance and community ([36:09], [38:42]).
- “They all know there’s more they can achieve... they don’t want to feel regret. They want to create something incredible.” —Ilana ([38:42])

8. Redefining Success in Life's Phases

Success is not a static checklist; it evolves with life phases (financial goals, growth, impact, balance) ([42:17]).
Quote: “No career will give you all of them…you can have all of them, just not at the same time.” —Ilana ([42:17])
Allow yourself to focus on different ‘must-haves’ in different seasons—give yourself permission and grace to pivot, pause, or re-prioritize ([44:18]).

9. The Power of Community and Asking for Help

High achievers often struggle to ask for help or admit vulnerability after big wins, but community is critical for rediscovery and next steps ([40:51], [41:21]).
Finding peers in similar situations at Leap Academy was liberating for many, including Ilana herself.

10. Saying No & Working Smarter

Success isn’t just working harder, but being intentional about what aligns with your purpose. If it doesn't "feed and fuel" your purpose, it's a distraction ([48:05]).
- Prioritize what’s truly impactful and learn to say no.

Notable Quotes & Memorable Moments

“I needed to feel that regret. That regret was something I never want to feel ever again.” —Ilana ([24:01])
“All the failures should be redirected... they’re teaching us something.” —Ilana ([25:23])
“Even within the same corporate role, you still want to create a bigger impression of yourself... you want to be leap ready to the next role.” —Ilana ([31:31])
“They all know there’s more they can achieve in life, and they want to...they don’t want to feel that regret.” —Ilana ([38:42])
“No career will give you all of them...You can have all of them, just not at the same time.” —Ilana ([42:17])
“If it doesn’t feed and fuel my purpose, it’s a distraction.” —Toby ([48:05])

Timestamps for Key Segments

Ilana’s Air Force story and first leap: [08:48]
Being ousted from her startup: [12:23], [17:26]
Navigating despair and rediscovering self: [18:31] – [21:11]
Cancer scare and epiphany: [22:44] – [24:01]
Reframing failure and the birth of Leap Academy: [25:23]
Strategic approach to career changes: [27:54], [31:31]
Building portfolio careers/multi-income streams: [31:31], [34:41]
Patterns among high-achieving clients: [36:09], [38:42]
Challenges with vulnerability & community: [40:51], [41:21]
Redefining success and life’s phases: [42:17] – [46:02]
Saying no and being intentional: [48:05]
Ilana's future: the next leap (upcoming book, scaling Leap Academy): [50:08]

Lighthearted and Personal Moments

Song for Ilana’s life montage: "Some Top Gun song, probably. … It opened possibilities I didn’t even realize." ([48:39])
Host Toby’s support: “Consider me in because I am all in on Leap Academy.” ([52:48])
Ilana’s parting humility: “Toby, you are an incredible interviewer … incredibly talented at what you do.” ([53:05])

Where to Find Ilana and Leap Academy

Leap Academy: leapacademy.com
LinkedIn/Instagram: Ilana is active and welcomes genuine connection ([53:30]).

Takeaways

Setbacks hurt, but reframed intentionally, they provide the fuel for future impact.
Be deliberate about your career and growth—prepare for the next leap before you truly need it.
Remain open to reinvention; success can and should look different as you grow.
Build a community; high achievers struggle alone, but thrive together.
Define what matters to you in your current life phase and organize your goals accordingly.
Above all: resiliency, reinvention, and leaping strategically are not just possible, but necessary in turbulent times.

Summary by Podcast Summarizer AI

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Transcript

Ilana Golan (0:03)

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. Toby. Same day I come back, I talked to my co founder, kind of thinking that we're celebrating, and I can see that something is wrong. And it's like, what is going on? 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, laying in bed and thinking, you know, kind of waiting for them to decide if this was cancer or not. And the truth is, at that point, I felt so much regret about my life and what I've achieved and how somebody so high achievers, that was just the biggest stab. And the minute I got that it's not cancer, it was almost like, you gotta be kidding me. Yeah, 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 Golan, and I am Undone.

Toby Brooks (1:28)

Hey, friend.

Toby Brooks (Producer/Host Voiceover) (1:29)

I'm glad you're here. Welcome to yet another episode of Becoming Undone, the podcast for those who dare bravely risk mightily and grow relentlessly. I'm Toby Brooks, speaker, author, professor, and learning scientist. I've spent much of 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 that can suck in the moment can end up being exactly what we needed to propel us along our path 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 is 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 managed to put myself in for a less than stellar midterm performance. And with some hard work and a little luck, my first semester as a grad student here at Baylor is in 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 Association's Certified Performance and Sports Scientist exam, and I bought it. The cpss, as it's known, is 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 or 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 going to be just part of my journey. I'd sign 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. If the first time I was crushed, the 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, on my way 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. MBA was in full swing. Tay's 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 altogether, 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 the first time I've had classes.

Ilana Golan (12:23)

Yeah. And to give the listeners some context. So I was leaping again and again and again and, and felt like I tick a lot of the boxes of success, quote, unquote. Right. Like what you kind of think of embody success. Right. I studied here and here and I went to intel and I went to startups and like theoretically tick a lot of boxes of success. And I think that's important because in your mind that shouldn't happen to you. Right. So that there's a little bit of like that piece. Right. And after a leap, again, again and again to it from engineering to technical sales and architect and all the vice president and at that point you kind of also get a little bit of that, you know, ego boost. You know, like I'm vice president, I can do a lot. So no matter what I 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 to me. And, and yeah, that's where a friend of mine came to say, hey, let's start a company together. I knew him for two decades, so it's not somebody I didn't know. And we decided to work on this thing. We worked on a day and night. I was so, so excited to be. And yes, I. We were both in Silicon Valley. We had an incredible Silicon Valley, you know, kind of the founder 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, the Silicon Valley, you know, loving love story. Right. And I was so proud to be. And we had this. So right after I actually parted ways from my VP role and, and I wanted to make sure people don't run away after me. Right. So I wanted to come forward with the 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. Toby. Same day I come back, I talked to my co founder, kind of thinking that we're celebrating and I can see that something is wrong and it's like, what is going on? And he's like, well, you're not part of the company anymore.

Toby Brooks (Producer/Host Voiceover) (14:57)

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 Alana. 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 Today, Alana 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. 5000, 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'd left her job as a VP in technical operations to launch a new Silicon Valley startup with a longtime friend. Not long after, the pair and the team they'd assembled had raised more than $800,000 in seed funding to finance the new company. It was a pinnacle moment for Alana 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 storm. In her own words, from a Medium 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 needed to figure out what I want to do next with my career, and the downhill spiral wasn't easy. Friends, that is the very definition of a purpose storm. And in the midst of one, it can seem impossible to find your way to safety, let alone success. But as Alana shares today, she no longer sees it as a hurricane sent to destroy all that she held deer, 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.

Ilana Golan (31:31)

It's a beautiful question, Toby. I will 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 want to be leap ready. Even if you're staying there, you always want to 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 want to get the relevant opportunities for myself according to what I want to 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 going to 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 3, 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. Visa 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 necessarily you want to. I don't believe that you want to burn the boats if you're not ready for it. I think you want to be very strategic about where it is that you want to 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 want to be the person that always stays and does the same. Like you want to be leap ready to the next role, to the next function, to the next responsibility. You want to be the person that they're looking at to move you, to be put you in the right seat at the table and to bring you in and to you know, so you want to, even within the same corporate role, like you still want to 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, they're incredible against ageism. They're your, you know, insurance policy. You know, if something God forbid does happen, this is what's going to 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, Toby. 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 Ilana Golan and I get to speak with the Richard Branson and the Gary Vee's and the president of Starbucks or whatever. They all have portfolio careers. Why is nobody teaching this?

Ilana Golan (42:17)

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 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 there like, okay, the boxes are ticked. What, what now? Can I die peacefully? And the answer is no. Right? So the. Right. So now it's really more about what is this phase in your life, what's critical for you? And this is a big piece that we work with people, you know, 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 financials. Sometimes it's growth. We need to feel like, you know, it's a responsibility, that reputation, the fame, like 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 are 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 phase will change, and as your face will change, suddenly you can start creating a little more for yourself or another, you know, 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 though, to admit it.

Ilana Golan (46:02)

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 on the beach all day. Like, I'm probably 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 my, the weekend. So first of all, it is on your term. But I think it's also, again, life is in phases. 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 as high achievers, I think sometimes the guilt is the hardest thing. And I think if you can look at it as phases, there's something a lot more in peace with yourself, that you can kind of be in peace 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, 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. And you know, and again, this is kind of where, when you have your must haves 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.