Think Fast Talk Smart: Communication Techniques - 226. Reinvent Yourself: Turning Uncertainty Into Opportunity

Episode Date: September 2, 2025

Reinventing your life or career starts with reflection and conversation. Making the leap — to a new career, to the next stage of a relationship, or to a different version of yourself — requires honest communication. For Ilana Golan, being “leap-ready” requires that we answer three questions: Why me? Why this? And why now?Golan knows all about these leaps, as her career spans corporate executive roles, entrepreneurship, and even F-16 flight instruction. As the founder of Leap Academy and host of the Leap Academy Podcast, she helps equip others to navigate their own personal and professional reinventions. As she says, “It’s really about communicating from the vision,” which starts as an inside job. “Why is this the right thing for me right now? You convince yourself first, because when you're [at] peace with what you're trying to do, it's a lot easier to convince others.”In this episode of Think Fast, Talk Smart, Golan and host Matt Abrahams explore how honest communication shapes every stage of reinvention, whether that’s listening to the signals your mind and body are sending you — like “sleepwalking through life” and imagining something more — or articulating your pivot in ways that create understanding rather than resistance. Wherever you hope to leap, Golan’s insights show how to communicate through change with confidence and clarity.Episode Reference Links:Ilana GolanLeap Academy Podcast | Leap AcademyEp.187 Experimenting, Failing, and Finding Your Job Fit - Catalyze Your CareerEp.147 Disrupt Yourself: How to Innovate Who You Are and Become Who You Can Be  Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [e-mail] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedInChapters:(00:00) - Introduction (02:32) - Breaking Barriers & Career Patterns (03:11) - Waking Up to Change (04:35) - Signs It’s Time for a Pivot (07:38) - The Rise of Portfolio Careers (11:10) - Communicating Career Leaps (14:22) - Finding Clarity in Reinvention (19:39) - The Final Three Questions (22:34) - Conclusion ********Thank you to our sponsors.  These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be. 

Hi, Matt here. We have two days left before we close our listener viewer survey. A big thank you to all of you who have already provided feedback. Please take a few minutes to share your input on the show. We still have a few prizes left to give to lucky respondents. Go to FasterSmarter.com.com. To give us your input. That's FasterSmartter.com.io slash survey. And now a word from one of our sponsors.

Their support allows us to bring you quality content free of charge. If you've ever thought, I know I can do more, but something's holding me back. You're not alone. Whether you're navigating career growth, seeking better balance, or wanting to communicate with more confidence, coaching can help you bridge the gap between intention and action. At strawberry.comme, you'll get matched with a professional coach who's trained to help you clarify your goals, build lasting confidence, and make intentional choices professionally and personally. This is not therapy. It's not consult. It's a thought partnership designed to help you take action with more clarity and purpose. I strongly believe in the value of coaching. All of us can benefit from the help of a coach.

Visit strawberry.me slash smart to get matched up with your coach today. That's strawberry.combe slash smart and get 50% off your first coaching session. It's the most affordable time ever to see if coaching is right for you. Clarity comes from action. All of us need to be leap ready when it comes to our careers. My name is Matt Abrahams, and I teach strategic communication at Stanford Graduate School of Business. Welcome to Think Fast, Talk Smart, the podcast. Today I'm excited to speak with Alana Golland. Alana is a barrier-breaking leader and the founder of Leap Academy. She focuses on resilience, reinvention, and building portfolio careers. Alana also hosts the top-rated

Leap Academy podcast, where I have been a guest. Welcome, Alana. I look forward to our conversation. Thanks so much for being here. Oh, I love being here. Thank you for inviting me, Matt. All right. Shall we get started? Let's go. So you have quite an amazing, an eclectic career, including being a corporate executive, an entrepreneur, an F-16 flight instructor, and more. I'm curious, is there a through line across all that you've done in your career and what's motivated you for what you're doing and have done. I would say the only pattern that I can see is a little bit of breaking barriers.

I am very persistent. So I don't think I'm very talented, but I'm very persistent. So I think that's a pattern that I'm very proud of. And I think for me, a lot of it is pushing boundaries and seeing what's possible, which is what I've been doing all my life.

What advice and guidance do you provide to people looking to make a change in their career, whether small or big? The big thing for me was, I think that I was to some extent sleepwalking through life. To some extent, things were going okay and they're okay enough for you to just continue with that okay status. And again, for everybody on the outside, I had a perfect life. I had a good career, two kids, beautiful husband and a home, right? Like, theoretically, I should be happy, but it wasn't enough. Now, obviously, I needed like a big shove to my ego to really wake up. But I think,

you know, in hindsight, I wish more people would be more awake through their life. And I think this is the big thing for Leap Academy because it used to be a nice to have, but at the pace of change, it's not a nice to have anymore. It's a must have. And you need to be very intentional, very strategic, always be leap ready, right? Always know where you're trying to go. It could be in the same organization, by the way. I'm not saying always leave. But what's next for me? But what's next for What responsibilities do I want to take? What other technologies do I want to learn? What is my growth opportunity?

So you always want to be leap ready. You always want to be very awake of what's next. And to start being very strategic about how do I build my personal brand to take me there a lot faster, which is also a big thing that I wish I paid more attention to earlier in my career. You've said several things I want to dive into there. So I like this notion of being leap ready. We've done a few other episodes where people have said you want to hone your skills, be connected and build a social network so that when you are ready to move, that you have everything,

your bags are packed, you've got the connections that can help. So I like the idea of leap ready as a way of defining that. I'd like to pull on two different threads. First, I'd love for you to share what are the signs and signals that can help us become more awake in your terms, in other words, to say, hey, this is time to move on. And then I want to come back after that and talk a little bit more about personal branding because I believe the brand you build in advance of a leap can be really helpful. So let's start with the signals and signs. What should we be looking for when it's time for us to consider a pivot or a leap? It's a great question because I think sometimes, like you said, timing is everything and it doesn't mean that when you're leap ready, it doesn't mean that I need

to pack my bags and go. But I still remember a time when one of my big bosses came to me and said, what do you want to do next? Even within the organization, right? And I had no clue. Now, that was a beautiful opportunity. We were just acquired. I could probably have maneuvered anywhere if I only knew. Right. So for me, a big part is I want to get people into a habit of not necessarily looking for a leap, but always being intentional, strategic with their career and thinking, what's

next? Where am I trying to go? And I do believe that in this space of change, people will change careers, even within, again, responsibilities, titles, whatever it is, right? even within the same organization, but they will change it every year or two. So we will see a pace of change and we've never seen anything like it. So knowing what's next is the first thing. Now, unrelated, I think, yes, there are definitely signs that either you're more tired,

you're more burned out, you're not as happy as you could be. For me, a lot of it was waking up at three in the morning and saying, this should be more to me. What am I doing? Why am I pulling small? But it was good enough, right? So I think a lot of times listen to the signs of, is there more? And the other thing that I'll say is life is in phases. And in different phases, different things will be important for you. So the very first thing is to be okay with the fact that you're in a different phase. And it could be that you care more about money. It could be that you care more about growth and opportunity and possibilities and fame or you care about impact or balance. And you're not going to have it all. I don't believe in the myth. You're going to have it all just not at the same time. So you're going to pick a couple that are critical for you, knowing that the rest will be a little bit compartment, right? Like they're going to

take a backseat. And as long as you're intentional about what's really critical for me at that moment, now it's easier to make those leaps. But at the pace of change, we shouldn't be looking at a career direction because most of us are not going to be deciding on something for the next 20 years. We're deciding on something in a relatively short term. So if we're going to look at it as a career experiment, it's actually freeing up a lot of the anxiety of deciding something very big. I really like the idea of framing it as an experiment and the horizon is not 20, 30 year career. It's shorter. I do like this idea of constantly scanning and being aware of what's going on in your industry or in the areas that you're interested in so that, again, you can make a more

intelligent choice. And then finally, I think so important is listen to how you're feeling. right? And if you are waking up in the middle of the night or you're not feeling that level of fulfillment that you'd like to feel, those are good signs and signals. Before we get to the branding question, what if somebody feels like they've missed their chance or they're too far along in their careers to start over? What would you say to them? So we've talked about what can initiate a change, but some of us have been around a long time doing what we do. Have we missed the boat? In this era of change, we will see, I believe, a lot more of what we call portfolio careers. And I do believe that Leap Academy is probably the only one that really teaches that. And I do believe that

people will start, even if they have one stable job, which I do believe is actually really handy, but they're going to start, I don't know, advising and sitting on boards and doing some public speaking and maybe open this business and maybe investing a little bit. Like, they're going to start having these multiple income streams so that there's always a safety net. And it's just a lot more interesting. Life just gets more exciting. So I think there's a little bit of a combination, Matt. Can you briefly describe what a portfolio career is and how we can go about building one? So portfolio career is essentially just multiple streams of income. And I think in today's world, there's just a lot of options to create income these days. And again, sometimes it's more about

the income, but sometimes it's more about exposure to new things or volunteering or sitting on specific boards that you care about or like it's not necessarily income. It's like ventures, if you will. And what's really interesting in today's world, and we're going to tie it to personal branding because sometimes it is more about the personal branding than the actual money that comes with it. But if you get involved with certain things, it can actually create a really beautiful snowball on your personal brand, opportunities that come your way, how you're perceived, etc. This is probably one of the more powerful things that somebody can do is, you have a classic portfolio mat, right?

Like you're lecturing, you have a book, you have a podcast, like you have all these things that you're involved with. But the beautiful thing is they're all under the same umbrella of making you an even stronger communicator, more of a thought leader in your field, more invited to things, right? So now it creates this beautiful synergy. So if you can create this umbrella brand and tie these things together and create a snowball,

it's probably one of the strongest thing that you can do to your personal brand and to the opportunities and what kind of things will open your way. I think one of the things that has helped me, and I heard you mention it, is that having some clear through line or some guiding principle, I mean, everything I do is predicated on trying to help people hone and develop their communication skills. And the way I deploy that varies. Sometimes it's in the classroom.

Sometimes it's through a podcast, sometimes through writing. But all of it is really striving for the same thing. And for me, you know, income is important. Need to pay the bills. but for me, it's just the ability to impact an influence as well. And my newly named portfolio career, I hadn't thought of it that way, is really designed to help influence and impact people. And thank you for helping us understand that.

And this idea that we can all build a portfolio career is really important. So I want to bring this back to communication because we've flirted with branding a little bit. When I switched careers, when I made a leap from high tech to teaching high school, it was a big leap for me. And many people were like, why are you doing that? that seems strange or what's behind it? What advice do you have to help people communicate their pivots, their leaps, so that it tells a coherent story that helps others understand?

And I'm going to extend the question, not just to the actual leap, but as you build out your portfolio career, you have to be able to articulate that as well. How do you think about the communication and branding around those choices and are the best practices we can follow? That's just great question. And I think it will have a few components, Matt, because I think the very first one is internally, because you want to convince yourself first, right? Because when you're in peace with what you're trying to do,

it's a lot easier to convince others. I think usually the hard parts come when you're still trying to figure this out. And then there's people that are trying to help you and trying to prevent you from doing the mistakes. And it has a tendency to keep you stuck. But find your peace in what is. the right pattern for you. What do you want to be known for? Again, the more you think about it as an experiment, it's not as big of a decision to make, so it's not as scary. And then it's really about communicating it from the vision, but also the pattern of why you, why this, why now, which we talked about structures, right? Like, why is this the right thing for me right now? And why me, why this right now? And the more you can structure it in a very concise way,

it basically lets people understand, okay, she got this. And this is what we were trying to get. Because again, it's very rare that you all get a very solid advice. So somebody will say no to you if they've been where you're trying to go. Usually you're going to get it from the people who are trying to keep you safe. So for those people, we're not trying to get their advice. We're trying to show our peace in the idea and our vision and to explain to them. we're making decisions based on hope and dreams, not necessarily fear and doubt.

And as long as you can make those decisions, everything changes. Lots of really insightful tidbits there. So the first and foremost, you need to get clear with yourself. You have to understand why this, why now, what's motivating me. So it's hard to communicate something that you haven't clearly articulated to yourself. And this notion of reminding yourself that the people you're communicating to care for you and they really want to keep you safe. And so helping them understand that the pivot, the change, the leap that you're making

is part of your hopes and your dreams, I think, is a wonderful way to initiate the communication. And of course, your music to my ears when you talk about a way to structure it. And I like this, why this, why me, why now. And that's a beautiful way to package up your story of the pivot, the change, the leap, but also to help you position your brand. So thank you for sharing so many insightful. bits of information in such a concise way. I've listened and learned a lot from you. And one of the things you talk about that really hit home for me is this notion of clarity in reinvention. What's your

approach to helping someone figure out what they really want to do next? We've talked about how to figure out when the time is ready for that next thing. But how do you really find that clarity about how you want to reinvent yourself? Do you have some specific advice? First of all, I will just say, that not having my clarity was probably one of the hardest times in my life. And it sounds like weird because you've already been successful. Why would that take you down? And I have to say that for high achievers and driven people that kind of always knew what's next, this was a very alarming time for me.

And I was actually in that soapbox for a while. And I think that was a big calling for Leap Academy and to try to help more people to figure out what's next, a lot faster and a lot more engineered way. But in the general sense, what I would say is success leaves clues. And if you're willing to look at the different clues in your life, and that can be all the way from childhood and adulthood, it's many times not necessarily the skills, the learnable skills in school, but it's more the patterns. You talk about patterns, right? It's more the patterns. Is the transitions, when did you get awards? What are the people intrigued by you? Where did you feel so happy and energized and excited? And so we look at these clues and start creating, again,

experiments. And when you look at these things as little experiments, they're not heavy on a decision because you don't need to make a big decision. You need to make, we call it the five days, five weeks, five months. You just need to decide if this worst five days of my life to think about it. Right? That's all you need to decide. And then is this worst five weeks of experiment a little bit, et cetera? So it's a lot easier to make those decision. Really listen to what other people are telling you in many cases. These are the best clues that you have. They wrote a review about you. They sent you a thank you text. Sometimes ask them. Like what's the most intriguing piece for you to work with me? And you'll hear things that you didn't even think of. And I think there's a lot of clues there as well. And so for me, a lot of the ideas

came from mentoring and some of the biggest startup accelerators in the world, like Google and Singularity University and Carnegie Lamella and et cetera. And what's interesting when you look at startups, they need to do the same thing. There's a plateau of opportunities and it's endless. Which direction should I go after? And it's really more about these very engineered, structured experiments that will give that clarity. But I will also say, Matt, which is really important, the clarity comes from action,

not just thinking about it. And I think we try to engineered a way or decide ahead of moving forward. and that's actually really scary and it creates almost like a prison and we can't move forward. So the clarity actually comes from the momentum and I think the big thing in Leap Academy is we give people momentum

and suddenly the clarity kicks in because sometimes you don't even know. I'm sure you didn't know you're going to have a podcast and a book and a thing and the TEDx that has millions of people. You don't have all the recipe but with the clarity things click in. I really like the idea that

a way to learn about reinvention and what you should be focusing on is through the feedback the world gives you. So your peers, your accolades. We can become very internal focused when we're thinking about reinventing ourselves and letting the external world what people are saying about us, how they're honoring our work, be a guide is really important. And this notion that clarity comes from action, comes from the experiments. And the experiments don't have to be super long. that can be very short. I totally hear you when you say we actually can prevent ourselves from taking action because of all of our thinking and really you have to do to get some clear ideas. Thank you for that. We'll be right back to finish our conversation. But first, a quick word from one of our sponsors.

Their support allows us to bring you this show free of charge. If you've ever felt like you're trying to do everything yourself, especially when the stakes are high, you're not alone. One of the biggest shifts I see in effective leaders growing their organizations comes from focusing on the right things. But that's hard to do when you're stretched thin. You need to be able to delegate some tasks to competent professionals. That's where Upwork can really help. Upwork is a one-stop platform to find, hire and pay expert freelancers across areas like marketing, development, data and analytics, and more. It gives you fast access to specialized talent so you can move quickly, fill key gaps, and scale your work without taking on

full-time overhead. You can browse profiles, review past work and get support scoping your project so you can hire with confidence. It's a simple way to focus your time where it matters most. Visit upwork.com right now and post your job for free. That's upwork.com to connect with top talent ready to help your business grow. That's upwork.org.com. And now back to our conversation. So, Ilana, this has been fantastic.

Before we end, I like to ask three questions. one I create just for you and then the other two I asked to everybody. Are you ready for that? Of course. So as the expert of pivoting, leaping, changing careers, I'm curious, what do you see next for you? Do you have some ideas about what the next leap will be? I do just because my book is in the making and it's the final stages. So there's a leave, the art of leaping book that is like we're in the book proposal phase. So it is coming. I truly believe that in today's world, we're in front of a cliff of millions of people that will need to reinvent themselves. And I think there are a lot of re-skill schools, but not a lot of companies that teach reinvention and creating portfolio

career. And we just need to grow fast enough to be able to help the millions of people that will need us. I love that idea of helping people reinvent rather than just re-skill. And congratulations. Writing a book is a big deal. And it can be a lot of fun and it's certainly a lot of work. Question number two, who is a communicator that you admire? and why? I do love Simon Sinek and how he communicates in the sense that he's very soft, articulate, and I think I have a lot to learn from that too. I agree that Simon Seneca is a very effective communicator. And I like that you are appreciating the things he brings, but also noting the things that the ways in which you're different. And we all have to find our own style.

All right. Final question. What are the first three ingredients that go into a successful communication recipe. I will say peace of mind, knowing what you want to say basically and being okay with saying it, knowing your audience, very critical. I mean, kind of I'm repeating you because structuring the way you're saying it. Like I feel embarrassed because I was like, why can I say different? But these are like, totally agree. So I think I'm repeating what you're saying. There are some truisms and I think structure knowing your audience, et cetera. The piece you added that I think is really important for everyone to consider is there's confidence in how you deliver information, but there's also confidence in what you are delivering.

And you highlighted that in one of your ingredients saying, you have to be comfortable with what you're saying. And that's important. That's important to feel confident in what you're saying. Now, that's not to say that you can't change it and make adjustments, but I appreciate you adding that little nuance to what we say. We have to be confident in it. Well, Alana, you shared so many valuable tips.

You helped us to realize that the leaps that we make, are experiments, that clarity comes through the actions and experiments that we run, and ultimately that we all need to be helping ourselves by being leap ready and being ready to communicate what it is we do or are planning to do to those around us. Thank you so much for your time. Thank you, Matt. This was so fun, and you're such a great interviewer. Thank you so much. Thank you for joining us for another episode of Think Fast, Talk Smart, the podcast. To learn more about careers and pivoting, please listen to episode 187, with Dory Clark and episode 147 with Whitney Johnson.

This episode was produced by Catherine Reed, Ryan Campos, and me, Matt Abrams. Our music is from Floyd Wonder, with thanks to Podium Podcast Company. Please find us on YouTube and wherever you get your podcasts. Be sure to subscribe and rate us. Also follow us on LinkedIn and Instagram. And check out FasterSmartter.io for deep dive videos, English language learning content, and our newsletters. Please consider our premium offering for extended deep thanks episodes,

Ask Matt anythings, and much more at FasterSmartter.io slash premium. Before we wrap up, I just want to say thank you for listening. It really means a lot to hear how people all over the world are using these ideas in their own lives. It inspires me and the whole team that brings you this show. If you want more episodes and resources, feel free to follow, subscribe, and explore past conversations. We're grateful for your support of that. think fast, talk smart.