What happens when the career you built no longer fits the leader you've become? And what do you do when the structures that once gave you certainty start to shift? In this conversation, Andrea Levinson sits down with Julie Fedele to explore the identity work that has to happen before the strategic work can begin. Julie shares the inside story of leaving a private equity career that had every box ticked but felt completely wrong — and what she learned through years of curiosity, experimentation, and career archaeology. They also explore the Hollywood model of work, why AI is expanding human need rather than replacing it, and why the smartest move for any leader right now is to get clear on the value they carry — before someone else decides what it's worth.

Five Things That Stayed With Me

1. Career archaeology

Most of us, when we face a career change, think we have to build everything from scratch. Julie's antidote is to excavate instead — map your industry domain, your human skills, your tech capability, and your energy. The goal is a clear picture of who you already are, so you can decide where to point it. Nothing is wasted. It just needs translating.

2. The translation problem

We've been in corporate speak for so long that we forget what we can actually do. Your ability to internally sell an idea is directly translatable to a market-facing skill. Your stakeholder management is relationship building. Your strategic thinking is consultancy. The knowledge was always there — it just needs to be named differently.

3. The Hollywood model

The OECD predicts that over 50% of people will have portfolio careers by 2030. Julie's framework for what that looks like: a producer sets the project, assembles a cast of specialists, they deliver together, then disband — each leaving with a career reel of outcomes rather than a list of job titles. The head of talent becomes a casting director. The workforce becomes fluid and project-led. Leadership clarity becomes non-negotiable.

4. Identity work before strategy

Before you can decide what to build, you have to know who you are — and be willing to let that evolve. Julie spent more than a year sitting with the discomfort of burnout before starting anything new. The question "what is the value I can extract and deliver to the world?" is a completely different question from the one most of us were taught to ask. And it's the one that matters most right now.

5. It's not binary

Corporate or portfolio. In or out. Employed or independent. Julie challenges the either/or framing entirely. The future is hybrid — individual contributors, fractional workers, and full-time staff working alongside non-human team members. The leaders who thrive will be those who can design their own architecture across multiple threads, rather than waiting for an organisation to define it for them.

Work feeling ‘fine’? Use the Leadership energy reset to gain clarity and a specific path forward.

Quotes Worth Holding

"I had every box ticked. I was completely unhappy, unfulfilled. And it actually wasn't challenging me or pushing me to be the leader I wanted to be." — Julie Fedele

"We really discount our skills from the past because we can't see them." — Julie Fedele

"It's not reducing human need — it's actually in some cases increasing it." — Julie Fedele

"I just don't feel like it's either or. There's a more expansive view of work and how we participate in it." — Julie Fedele

"Identity is one of the core pillars. We put our flag in the ground and then think we have to keep it there forever." — Andrea Levinson

What We Explored

0:00 Introduction & what "the future of work is personal" means

4:39 Julie's edge: leaving a ticked-box career that looked perfect on paper

10:19 Career archaeology: excavating your skills instead of starting from scratch

14:35 The translation problem — why we discount what we already know

16:36 AI, identity & what it means to be a knowledge worker

26:18 The Hollywood model — how portfolio careers & orgs will work together

36:40 Wrap-up: one thing to ponder this week

About Julie Fedele

Julie Fedele is a venture builder, coach, speaker, and founder of The Portfolio Career Club — where she helps talented women repackage their expertise, own their value, and build something of their own. She brings nearly two decades of experience across private equity, tech consulting, and business building, including time at ThoughtWorks, one of the pioneers of agile methodology. After leaving a ticked-box career that looked perfect on paper, Julie spent years excavating what work could look like on her own terms — and now helps others do the same. She has also built her own AI-powered career redesign platform, putting her to work in the tools she teaches.

If this conversation resonated, explore more insights and resources at andrealevinson.com.au

Full Transcript

Lightly edited for readability. The full timestamped version is available on YouTube.

ANDREA: Hello everybody and welcome to this latest Leadership at the Edge conversation. This series is all about exploring the ways that we are individually and collectively up against the edges of our knowledge, our certainty, our comfort zone in the way that we lead. Whether that's leading ourselves, our careers, an organisation.

ANDREA: Today we are with Julie Fedele — venture builder, coach, speaker, founder of the Portfolio Career Club, and someone who has experience inside corporate building and also building outside of corporate for herself and helping other people do that.

ANDREA: The broad theme today is the future of work is personal. As always, this is unscripted — we go where we want to go and follow the cues from you as well. For those watching live, if you have a particular curiosity or question, drop it into chat and we'll pick up those themes.

ANDREA: This idea that the future of work is personal — to me, part of what that really means is right now is the perfect time to get really clear on the value that we bring in work. Not the title or the label or the framework or the accreditation, but the value that we really bring and the way that we really want to relate to work. I think about ourselves in a relationship with work — and we want to love that relationship and feel loved in return.

ANDREA: So with that in mind, Julie — very keen to dive in. I've had a lot of conversations with executives, senior leaders, founders, both in coaching conversations and in my network generally. Some are in corporate and want to stay, but know things are moving around them. Some are very successful in corporate and know they want something different in the midterm but have zero idea how. There's a curiosity across the map right now.

ANDREA: So if you are watching, stick with that curiosity. Listen to what is being shared with that lens of inquisitiveness — how might this be challenging you? What might the invitation for you be? How might it apply to your world or your team or your organisation? Julie, let's kick it off with the usual opening question. Can you tell us about a time when you've been up against the edge in your own leadership? What did that look like? How did you navigate it?

JULIE: Thank you so much for having me, Andrea. I want to acknowledge the elephant in the room — yes, I am in the car. We had some technology issues this morning, so this has been an edge for me today. But in terms of my own career — for me, it was really the moment where I realised I had spent nearly two decades climbing this ladder. I was in private equity. I was in an executive role. And on paper, I had every box ticked. What I realised was that I was completely unhappy, unfulfilled. And it actually wasn't challenging me or pushing me to be the leader I wanted to be. So I had an incredible team, but because I was so unhappy in the context itself, I wasn't showing up in the best light.

JULIE: For me, that was really a moment where I had to think about what self-leadership looks like and what a different type of work looks like for me. Because I love working, but I couldn't figure out what context I wanted to show up in.

ANDREA: How did you figure out the answer to that?

JULIE: I went through quite a number of years. I always say, if people who read my Substack — this began for me in 2017. So it's been nearly a 10-year journey, which is shocking because I can't believe how time flies. It really started with reshaping what I called a breakdown into more of a curiosity. Instead of saying "I spent all this time climbing a ladder and it's leaning against the wrong wall," I decided to get really curious about — well, what wall do I want to be climbing, if I want to climb at all?

JULIE: What I found through a series of experimentation is that instead of trying to completely change our whole lives and say everything has to be perfect, what experiments can I conduct to get moments of evidence so I know whether I'm on the right track? So I started doing that. One of the first things I did was spend more than a year really understanding myself and working through burnout. I didn't try to start anything new. I just sat with the uncomfortable feeling of my engine not turning back on and gave myself time to pause.

JULIE: I resigned a really big role and took a step down — just to help myself recover but still earn money and still be in the game. Then I started to figure out what else I could do. I loved business building — that's what I'd done for 20 years — but I didn't want to do it in the context of an organisation. I wanted to support individuals, and women in particular, to reimagine their lives and build businesses. And that's where I landed.

ANDREA: I love hearing about the introspection and understanding-self element here. Putting who the human is in this equation front and centre is so powerful and a little countercultural — because generally speaking, we're in a consumerist machine which is all about the haves, all about the outcomes, all about whether it's the lifestyle or the label or the position or the title. We see those as very tangible indicators of success and latch on to them, especially early career. And then we forget — well, who am I? And is that actually something I will enjoy?

ANDREA: When we layer in the experimentation lens — the only way we're going to figure out what we actually enjoy is to run a series of experiments. Work life, to any particular point in career, is essentially a bunch of experiments. None of them are the wrong path. They're just different, and they give you insight and data that you can then make choices from.

JULIE: Exactly. And I collect different points of data. Some of it was what I call energetic data — what really expands me? Then I took that evidence and asked: do I have the capability and skill sets to actually do the thing I want to do? I have some what I call expansion areas that I need to fill, so how might I go and expand into those? And then I also look at market data — does what I really want to do match the capabilities I have, and is there market demand? If you think about that as a venn diagram, that's the perfect mix of where we have something we can actually be paid for.

JULIE: I basically turned all of my training in business building onto myself and said, how would I coach someone through this process? How would I mentor someone? And I followed my own process of how I supported founders when I was building businesses with them.

ANDREA: I hear in that a recognition of a transferable skill. Here's something I can do — what happens if I turn that skill or that strength and point it in a different direction? That can be useful in building our career and relationship with work, but also with any strength you have anywhere. If you're really great at building relationships with external stakeholders — well, maybe you can turn those skills to building relationships with your peers, or with your team.

JULIE: Yes. So I went through this process where I developed something I called career archaeology. I was inspired by a framework I experienced when I worked at a tech consultancy — a software engineering firm — where each of us had something called a honeycomb of capabilities. You would do an assessment and they would light up each hexagon and say, "Julie, if you wanted this to be a complete set, we'd need to get these types of skills into your honeycomb." What I think most of us do when we're looking to make a change is think we have to build everything new, versus excavating our skill set and putting it into different domains — what industry domain experience do I have, what human skills do I have, what technology and AI skills? Then you build out slowly to have a picture of who you are.

JULIE: Then it's about: how can I transmute these into a series of experiments where I can see if the market actually wants this? I feel like we really discount our skills from the past because we can't see them.

ANDREA: Say more about that.

JULIE: I actually call this the translation problem. It's not that we're not good at communicating — it's that we've been in corporate speak for so long, we forget all of the things we've actually done. Your ability to internally sell an idea is directly translatable to a market-facing skill. You can sell. That means you can sell something out to the market — but you've never phrased it like that in your mind, because you've never had to.

JULIE: I had a coaching conversation recently with an executive who had built a very successful career off the back of a particular framework and a set of human-centred skills. We were leaning into a new edge in her leadership, and she was saying, "Maybe I need to go and do this accreditation. Maybe there's a framework or a model you can give me." And the moment she realised she didn't need all of that — what she needed to do was show up and give people her attention and her presence and her understanding and her empathy, which isn't a head-based thing, it's a very human-based thing — she was actually crying in that moment. A quite cathartic realisation.

ANDREA: There's a connection here with what you're sharing around what we've been taught to value and the labels we're given — and how we take back ownership of some of that.

JULIE: Yes. And a lot of this work is identity work. And you'd be really familiar with this — even with AI. So many of us are thinking: what is going to happen to me as a knowledge worker, because AI can systematise and do things much better than I could? So where does that leave me? And a lot of that is identity work. Really understanding — if I don't do all of this busy work, what is the value I can actually extract and deliver to the world? That's a completely different question from what we were taught at university or in our corporate career. It totally flips that conversation on its head. And it's something that just doesn't happen overnight — we've all consumed this story of what success looks like, so it's going to take us a minute to reimagine a different path.

ANDREA: You've mentioned AI. We've got a question from Liam: do you think that with the rise of AI, there has been a pendulum swing back to a greater focus on the person, after the dehumanisation that AI caused initially?

JULIE: Personally, I never believed the AI hype around organisations saying they'd get rid of 20,000 people — firstly, the technology is far too early for us to know if it can deliver that return on investment. That was a pure play on pleasing shareholders, in my personal opinion.

JULIE: Also, back in 2005, I was part of a whole range of digital transformations where a very similar promise was sold to the market — that we're going to transform all of these organisations to digital organisations, have less workforce, streamline everything. And I was part of one of Australia's largest transformations where we got rid of all the software engineers and most of the marketing team, and within 18 months we'd hired them all back as contractors on super high day rates. This happened in 2005. I experienced it again in 2010, 2014, 2019. Similar patterns. So I always look at history. Accountants experienced this when the calculator was invented.

JULIE: I think there's a lot of hype around AI and we're slowly starting to see what it actually means to partner with AI in an organisation to elevate the human. The research I'm doing is around how the human partners with AI to produce better work — and it's not reducing human need. It's actually in some cases increasing it. I'm excited to have more of that conversation, but for the moment I think the ROI-type conversation will start to dissipate, and we'll see more of: how can we really partner with this technology?

JULIE: There's a really great media company that shared a fantastic article recently, demonstrating how they're an AI-first organisation and they've actually said they need more humans, not less. What they're automating is the sludge — behavioural economists call it "meetings about meetings" work. It's automating the sludge and figuring out how we partner with intelligently trained systems to improve and enhance our human work and deliver even more exceptional outcomes. And that doesn't necessarily mean less humans.

ANDREA: What I love in that is essentially: how can we leverage the technology to dial down the noise so we can hone in on the signal? Protect our focus and elevate to the point where we're doing the work we're best placed to do, instead of being pulled down into this busy work that grinds our soul and triggers our nervous system and is the reason most people are unhappy in corporate.

JULIE: Exactly. I'll give myself as an example. I loved building businesses. I was in private equity and in venture for most of my career, building new products with software engineers. I loved the core content of my role. But as I progressed and became more senior and reached the c-suite, I didn't spend any time on the tools or actually building the thing. I just spent time managing the board, managing the executive team, managing my peers because they were upset at each other. Just sludge.

JULIE: When I stepped into working for myself full-time, I reconnected with my craft. And what I think is that if we partner correctly with this technology, we could start to see people hone in more on their craft and build more mastery. And I think that's what we're all craving — to build mastery and actually build something of value, versus being in back-to-back meetings for eight hours. No nervous system can deal with that.

ANDREA: And if we think about what it takes to have a really well-crafted role — one that gives us a sense of meaning and fulfilment — we want to feel like we're using our strengths, like we're actually contributing. AI is potentially one factor driving the necessity to consider that with more intentionality. Choosing to step outside of corporate and build in a different way is another. But either way, the question is: what does this experience of work actually need to look like? What do I want from my relationship with work?

ANDREA: And I think what a lot of my network and clients are starting to talk about is the legacy they're leaving behind. Not wanting to be here in this busy role in this big title doing these important things and feeling like they haven't contributed in a way that might exist beyond them.

JULIE: Absolutely. And this is where the individual contributor model becomes interesting — that's where the term "IC" comes from in tech. Being an individual contributor to a product team. And I think this is essentially what the model of the future of work could be. You talked about being in corporate or stepping out — but I'm also seeing a world where it's a hybrid.

JULIE: How might we reimagine the way we work so that we could have one thread of our portfolio working in an organisation — either as an individual contributor directly contributing our craft to an initiative, or leading a team on a fractional basis — and then in other threads of our portfolio we support individuals, teach, coach, speak, develop our own tech products? I'm a failed software engineer — I literally failed computer science in my first year of university and had to swap my degree. But I've been able to build my own platform and career redesign platform with AI. This is such a wonderful thread to a portfolio that I can leverage and bring into organisations. I just don't feel like it's either or.

ANDREA: I believe you've called this the Hollywood model — can you expand on that?

JULIE: I wasn't the first to coin it, but I have built on the concept. So I'll talk about how I see individuals participating in this new frame of work, and then how I see the organisation adapting to it.

JULIE: I'm not suggesting Hollywood is a perfect model — there's a lot of criticism I get on that. I'm suggesting it's an analogy for how I believe we're going to work in the future. If you think about how a Hollywood movie gets made: you have a producer who sets the terms of the project and says, "We want to make this movie" — they're like the CEO of the whole production. Then they bring in directors, cinematographers, makeup artists, and talent. They come together for a certain period of time, very focused, they have an outcome they all know they have to deliver. They deliver it, then they disband — and they disband with this new movie as part of their highlight reel. A career reel of outcomes, rather than a set of responsibilities.

JULIE: The OECD predicts that over 50% of people are going to have portfolio careers by 2030. As organisations shrink in size with full-time people, they're still going to need to execute projects. So they'll go out to the market, like a producer going to cast their talent — they'll go to different strategic networks and collectives and say "I need this product designer, this project manager, this software engineer," and they'll create a team to deliver a specific project for six or twelve months, then disband.

JULIE: For the organisation, this means reimagining how they manage talent. The head of talent will no longer be internally focused on succession plans and talent pipelines within the organisation. They'll be more outward-focused — a casting director who creates networks outside the organisation so that when a project is coming down the pipeline, they can get the right resources in to deliver it.

JULIE: And this is a really different way of thinking for a company too. If you want to work with the flexible workforce and the individual contributor, you have five months to onboard them the old way. They need to walk in working. They need to understand the culture on day one. They need to understand the outcomes they're delivering and figure out the system of work within days, not months.

ANDREA: What I love in that is: clear standards, a very clear deliverable, and communication that's structured and proactive rather than reactive and in-the-moment. These things might feel like heavy lifting upfront, but they make everything easier. And regardless of where we land from a structure point of view, these are leadership skills you're never going to regret building.

JULIE: Exactly. And where I actually experienced this was at ThoughtWorks — one of the best roles I've ever had, because they were some of the fathers of agile. When I was working with those engineers, they really taught me how important it is upfront to understand the ways of working and to have the same shape in your head of what product you're building. We used to spend five or six days with a client upfront in a room for eight hours figuring out exactly what we meant by things. We spent that time upfront, but then it just supercharged the work at the back end. It's like a slingshot — you pull it back to really catapult forward.

ANDREA: And what happens when your workforce is made up of full-time people, fractional people, individual contributors, and then non-human team members? That is a whole different leadership capability and skill set. The potential in that — yes, I can see it's a little more challenging for some. But the opportunity in it is significant.

ANDREA: We've explored a range of different angles here. Thinking about the threads we've hit in this conversation, Julie — what is one thing you'd encourage leaders to ponder or try this week?

JULIE: I always love to begin with curiosity. Is there a thread in your own leadership or in your own skill set or something you're looking to expand in that you want to investigate and experiment with? And if you've been sitting on it for a while — that's an interesting curiosity too. Why is that? I would encourage everyone to tune in to their bodies and ask: is it an edge of growth? Am I fearful about something? And start exploring from there. I really believe that life leaves you breadcrumbs, and all those little things that arise in your mind as an area you can expand in are there for a reason. Get curious and start experimenting.

ANDREA: Love that. Anyone talking about curiosity is speaking my language. To everyone watching live or the replay — thank you for leaning in with curiosity. I'm curious about what has stood out to you, what questions you might have, what might have resonated.

ANDREA: A couple of things sitting with me from this conversation. The Hollywood model analogy really resonates and lands — it gives us a schema, an example of what an alternative might look like, and that helps us follow the breadcrumbs and lean into different possibilities.

ANDREA: We started quite early talking about knowing yourself and this excavation, this archaeology of who am I, who do I want to be, what do I really enjoy, what lights me up, what am I actually genuinely good at? That is paramount. And if there's one thing I'd suggest anyone do in that space — go and think of five people who know you well and who you trust, and ask them: how would you describe me in five words? Or a slightly more value-oriented alternative: what are the two or three things that you just see I'm so good at? Collect all of that. Sometimes we can't see it ourselves. It's this unconscious competence, this genius we carry.

ANDREA: And then this identity work. You touched on this, Julie, at the outset — and I think there's a thread through the whole conversation. How we see ourselves, the role we see ourselves playing in our careers — that needs to continue to evolve if our relationship with work is to continue to evolve.

ANDREA: One of the disservices I think we do ourselves is put our flag in the ground and then think we need to keep it there forever — that we can't evolve or iterate beyond that without making that first thing wrong or a mistake. Please don't fall into that trail of thinking. Identity is one of the core pillars I see as essential here.

JULIE: Absolutely. I agree wholeheartedly.

ANDREA: Thank you, Julie, so much for joining us and for persisting with the tech. Thank you to everyone watching. Have a beautiful rest of your day.

JULIE: Thank you so much.