Reimagining Success® with Anna Lundberg

Anna Lundberg
  • 5.0 (19)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

In a world where traditional work no longer fits how we actually want to live, the Reimagining Success podcast helps you design a business that works for you - not the other way around. Hosted by Anna Lundberg, solopreneur business coach, strategist, and former Fortune 500 leader, the show is for independent experts and founders who have outgrown the old model and want more clarity, capacity, and calm in their business. Each week, Anna shares practical tools and thoughtful perspectives to help you redesign the way your business runs - from your business model and operating rhythm to your pricing, positioning, and delivery. No hustle culture, no pressure - just grounded, strategic support. What you'll learn inside the show: • How to create a business model that truly fits your life and capacity • How to simplify your offers, pricing, and delivery without losing revenue • How to build a visibility rhythm that brings clients consistently (without more hours online) • Tools for managing time, energy, and attention as a solopreneur • Real stories from experts who redesigned their business for sustainability and success If you're ready for more clarity, cleaner margins, and a way of working that feels spacious rather than overwhelming, Reimagining Success will help you build a solopreneur business you can grow - sustainably. Start listening, and explore more at ReimaginingSuccessPodcast.com.

  1. 1D AGO

    Is your business infrastructure running you?

    You set up the systems, hired the support, and made the commitments - all sensible decisions at the time. But there's a point in many established businesses where the infrastructure quietly takes over, and you find yourself reactive, stretched, and not quite sure why. Anna Lundberg walks through four common examples - team members, open calendars, content commitments, and long-term clients - and shows you how to reclaim control without blowing everything up. Key takeaways When your team sets your priorities - The person you hired to handle something can gradually start deciding what matters most in your week - without either of you noticing it's happening. The open calendar problem - An unfiltered booking link made sense in year one. Leaving it unchanged into year four means you're still making early-stage decisions in a business that has grown well beyond that point. Content commitments that outlive their purpose - Posting every day or sending a weekly email builds momentum when you're starting out. But if that commitment is now driving your week regardless of results or relevance, it's worth questioning. Long-term clients and unspoken scope - When a working relationship becomes comfortable, it can quietly expand in ways that were never agreed. You're the expert - and you still get to set the terms. Take ten minutes to get a clearer picture of what's actually driving your business right now. The free solopreneur diagnostic is at onestepoutside.com/diagnostic - personalised report, specific next steps.

    14 min

  2. APR 6

    RS388 - Why redesigning an established business is harder than starting a new one

    A few years into your business, something shifts. The model that got you here starts to feel like it's holding you back - but changing it feels far riskier than building it ever did. In this episode, Anna Lundberg unpacks exactly why redesigning an established business is harder than starting one from scratch, and what to do about it. Key takeaways Past decisions become constraints - The offers and structures that built your reputation can trap you in a model that no longer fits, even when walking away feels too risky. More at stake means more resistance - The fear of disrupting income, client commitments, and a hard-won reputation isn't irrational. But letting it freeze the redesign entirely is where the real risk lies. Identity is the hidden blocker - A few years in, the business isn't just something you do - it's become part of who you are. Real redesign requires separating your identity from your business model before you can change either. Tweaking is not redesigning - Adjusting prices, redoing the website, and shifting messaging can all feel like progress without ever touching the structural issue underneath. Start with one room, not the whole house - Pick the single change that would make the biggest difference - who you work with, what you charge, or how you deliver - and work on that before touching anything else. Book a free call with Anna at onestepoutside.com/call to explore what a redesign could look like for your business.

    15 min

  3. MAR 30

    The FIRE movement and building a life by design with Jake Wysocki

    What would it look like to design your life the way you'd design a great product - starting with the why, testing before you commit, and building towards a shared vision with the people you love? Design thinking strategist Jake Wysocki shares how intentional decision-making, the FIRE movement, and honest conversations with your partner can help you stop living by default and start living by design. Key takeaways: Stop living on autopilot: Most of us follow a paved path - school, job, ladder, retirement - without ever asking why. Jake's Intentioncraft philosophy starts with one question: what are you actually doing this for? The FIRE movement demystified: Financial independence isn't about retiring early - it's about building enough of a financial foundation that you have real choices. Jake explains the 4% rule, coast FIRE, and the concept of memory dividends from Die With Zero. State of the union sessions: Jake and his wife run structured half-day workshops three times a year to check in on life across eight pillars, align on shared goals, and make intentional decisions together - before resentment or drift sets in. Bullets before cannonballs: Inspired by Jim Collins, Jake's approach to business pivots is to test small before committing big - a principle that led him from helping millennial parents live regret-free to building five-star workshops for established experts. Excellence over perfectionism: Perfectionism assumes you'll reach a finish line that doesn't exist. Excellence is the ongoing pursuit of better - and it's what lets you ship, serve clients well, and keep improving without waiting for perfect. Book a free call to explore what building your business with more intention could look like for you - onestepoutside.com/call

    46 min

  4. MAR 23

    "Is this it?" - Reframing success before your next chapter

    Voted most likely to succeed at 17, Anna Lundberg has spent years asking what that actually meant - and whether it still matters. This episode traces the quiet question so many high-achievers carry but rarely say out loud: is this it? And reframes it not as a sign that something's gone wrong, but as evidence that something's ready to shift. "Is this it?" is a signal, not a crisis - When the life or business you've worked hard to build starts to feel like friction, that's not failure. It's evidence you've outgrown something, and it's asking you to grow in a different direction. Conventional success has a hidden cost - From Elon Musk to Arianna Huffington, the pattern holds: external achievement is rarely measured against what it costs in health, relationships, and presence. Our relationship with work is a design choice, not a natural law - From Ancient Rome to hustle culture, the way we've been taught to measure success has a history - and it can be redesigned. Success changes with the seasons of your life - Each chapter calls for a different definition. Running an old script past its sell-by date isn't loyalty, it's avoidance. The third way exists - Between pushing through and blowing everything up, there's a quieter option: pausing, examining the inherited scripts, and redesigning deliberately rather than reactively. If this episode prompted something - a quiet question you've been carrying, a chapter that no longer quite fits - book a free clarity call at onestepoutside.com/call.

    20 min

  5. MAR 16

    How to design a portfolio career that actually works for you

    Forty percent of professionals under 35 now earn from multiple income streams - and yet most people who end up with a portfolio career stumble into it by accident rather than by design. Anna Lundberg explores what a portfolio career really is, why it's rising so fast, and how to build one with the intentional architecture it needs to be both sustainable and fulfilling. Portfolio careers have a name now - and momentum: Over 63% of UK adults already have or plan to have multiple roles, but most people arrive at a portfolio by accident rather than conscious design, which is where the overwhelm starts. There's a real difference between a portfolio and just having multiple jobs: A genuine portfolio requires a coherent umbrella, deliberate architecture, and an honest view of which strands are anchoring your income, which are building your future, and which are feeding your passion. Context switching has a cost: Moving between different client worlds and problems is cognitively demanding - the solution isn't to do less, but to structure your time and identity around the portfolio model intentionally. The identity shift matters as much as the practical structure: Introducing yourself as someone with a portfolio career - not someone who "does a bit of this and a bit of that" - changes how you show up, how you make decisions, and how others see you. An audit is the place to start: Before adding anything new, label what you already have - anchor, growth, or passion layer - and decide what needs to drop to make space. Ready to bring more intention to how your work is designed? Book a free call with Anna at onestepoutside.com/call.

    17 min

  6. MAR 9

    Beyond stay or go: the full menu of career options after corporate

    Most people frame leaving corporate as a binary choice - and that's exactly what keeps them stuck. This episode maps the full range of career and business models available to independent experts and career changers, from flexible employment variations to fractional work, portfolio careers, and solopreneur paths - with honest trade-offs for each so you can find the model that actually fits your life right now. The binary framing of "stay or go" is what keeps most people stuck - there's a full spectrum of options between and beyond traditional employment, and most people don't know half of them exist Freelance, independent expert, and fractional are genuinely different models with different pricing ceilings, lifestyle implications, and sustainability profiles - understanding the distinction matters for how you position and build Portfolio careers have gone mainstream, but they require active management and a coherent umbrella message to avoid creating two businesses worth of workload on top of each other The most clarifying question isn't "what do I want to do?" but "am I building something to sell one day, or building a container for my work and my life?" - the answer shapes every decision that follows You don't have to know the whole path. The next right move, given who you are and what your life looks like right now, is enough If you're mapping your options, Anna's first book Leaving the Corporate 9 to 5 is a practical starting point - and if you want support working out the model that fits your life, book a free clarity call at onestepoutside.com/call.

    21 min

  7. MAR 2

    Why Women Are Leaving Corporate - and What They're Building Instead

    The conversation around women leaving corporate careers has reached a tipping point - and the numbers back it up. This International Women's Day episode unpacks the real structural reasons behind the exodus, why it isn't an ambition gap, and what women are quietly building on the other side. •       The data is clear: women aren't opting out of ambition - they're opting out of a system that consistently extracts more than it gives back, with caregiving pressures, lack of flexibility, and burnout all cited as primary drivers. •       Lower interest in promotion, as McKinsey's 2025 report flagged, is a rational response to structurally unfair conditions - not evidence of an ambition gap. •       Women are quietly building - founding businesses at record rates, designing portfolio careers, and creating models that give them genuine agency over time, income, and energy. •       Leaving corporate is only step one. The real work is building differently - not recreating the same overwork, undercharging, and boundaryless patterns in your own business. •       For those still inside organisations, the question isn't how to get women to lean back in - it's what leadership teams are genuinely willing to redesign. If you're at the beginning of this journey, Anna's book Leaving the Corporate 9 to 5 - available on Amazon - is a brilliant starting point. And if you're already building independently and want to do it with more intention, keep an eye out for something new coming very soon.

    13 min

  8. FEB 23

    How to turn a restructure at work into opportunity with Michelle Schafer

    A restructure at work can feel like failure — until you use it to reset on your terms. Anna Lundberg talks with Michelle Schafer about turning restructures into opportunity by getting clear on non-negotiables, value, and what you want next. Key takeaways A restructure at work can become a reset point when you define your non-negotiables first (family, health, flexibility). Underpricing is often a confidence issue, not a competence issue — especially when you already bring decades of experience. Visibility is more sustainable (and more human) when it's rooted in contribution, relationships and conversation. Picking a lane can make it easier for the right people to find you — and trust what you're known for. A resilient business model is built around boundaries, rhythms, and proper time off — not constant availability. If this resonated, share it with someone navigating change right now.

    39 min
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5
out of 5
19 Ratings

About

In a world where traditional work no longer fits how we actually want to live, the Reimagining Success podcast helps you design a business that works for you - not the other way around. Hosted by Anna Lundberg, solopreneur business coach, strategist, and former Fortune 500 leader, the show is for independent experts and founders who have outgrown the old model and want more clarity, capacity, and calm in their business. Each week, Anna shares practical tools and thoughtful perspectives to help you redesign the way your business runs - from your business model and operating rhythm to your pricing, positioning, and delivery. No hustle culture, no pressure - just grounded, strategic support. What you'll learn inside the show: • How to create a business model that truly fits your life and capacity • How to simplify your offers, pricing, and delivery without losing revenue • How to build a visibility rhythm that brings clients consistently (without more hours online) • Tools for managing time, energy, and attention as a solopreneur • Real stories from experts who redesigned their business for sustainability and success If you're ready for more clarity, cleaner margins, and a way of working that feels spacious rather than overwhelming, Reimagining Success will help you build a solopreneur business you can grow - sustainably. Start listening, and explore more at ReimaginingSuccessPodcast.com.

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