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. 2D AGO

    How I use AI as a solopreneur - and what I've learned so far

    After two-plus years of experimenting with AI tools - switching platforms, building custom tools, and making plenty of mistakes along the way - Anna Lundberg shares what she's actually learned about using AI as a solopreneur: what it's genuinely good for, where it falls short, and why the most valuable thing you bring to your business can't be outsourced to any tool. Key takeaways Your tool choice matters - and so do the ethics behind it. Anna shares why she moved from ChatGPT to Claude, and what she considered beyond just the feature set. The thinking partner use case is the most underrated. For solopreneurs without a team to sanity-check ideas, having a daily outlet for half-formed thoughts and strategic questions is genuinely valuable - if you use it right. AI-generated content erodes the thing that makes you worth following. Your voice, your perspective, your experience - these can't be replicated, and outsourcing them is a strategic mistake, not a time-saver. There's a useful three-tier framework: use AI generously for thinking and sense-checking, carefully for drafting, and thoughtfully for research - and verify anything that matters. You don't need a strategy to start. One small experiment with a task you find tedious is enough to begin, and it puts you ahead of most people who are still sitting on the sidelines. Try the free solopreneur diagnostic at onestepoutside.com/diagnostic - it's AI-powered, takes about 10 minutes, and gives you something genuinely specific to work with.

    13 min

  2. MAY 4

    Why your social media strategy isn't working (and what to fix first)

    Feeling guilty for not posting enough, anxious about your engagement dropping, or quietly relieved when you had an excuse to skip social media this week? This episode cuts through the noise around algorithms and reach to help you figure out what your content is actually supposed to do - and how to make it work for your business. The algorithm isn't the problem - Reach is down across platforms, but obsessing over impressions means optimising for the wrong metric. A post that reaches 200 people and prompts one DM is worth far more than one that reaches 10,000 people who will never buy from you. Passive consumption is costing you - If you're spending hours scrolling and comparing while barely posting, you're getting all the anxiety of social media with none of the benefit. The research is consistent: passive consumption damages well-being; active creation does the opposite. Tools don't fix clarity problems - No platform, AI tool or fancy CRM will compensate for fuzzy positioning. A tool amplifies what's already there - if what's there is unclear, you'll just produce unclear content faster and at greater expense. Content needs a job - Awareness, warm nurturing, direct inquiries and credibility-building all require different content. Most people try to do all four at once and do none of them well. Post less, think more - One post that takes a real position and says something you genuinely believe will outperform five filler posts. And the metric that matters isn't likes - it's the conversations that follow. Head to onestepoutside.com/diagnostic for a free 10-minute solopreneur diagnostic that gives you something specific and actionable to work with.

    12 min

  3. APR 27

    Wild and Wiser: Kelly Keating on portfolio working and designing a life with intention

    From a senior corporate career to coaching, festivals, and a master's degree - Kelly Keating's story is about what happens when you stop letting life happen to you and start designing it deliberately. Anna Lundberg talks with the founder of Wild and Wiser about building a portfolio life after 40, navigating the financial realities of leaving a stable career, and why "enough" looks very different when your values are finally doing the driving. Key takeaways: Success on your own terms takes time to define. Kelly's shift came not from burnout or crisis, but from a gradual deepening of self-awareness through coach training, parenthood, and a late ADHD diagnosis - all of which changed what she was willing to tolerate. The try-before-you-buy approach to leaving corporate. By building her coaching practice part-time over eight years while still employed, Kelly made the leap with far less financial and psychological risk than if she'd jumped cold. The financial case for leaving is often stronger than it looks. Most people never sit down and properly do the maths. Kelly found that stripping out the "emotional spending" that comes with an unfulfilling job made the numbers far more workable. Portfolio working is a season, not a system. Between coaching clients, associate work, a master's degree, and a festival she's launching, Kelly's week looks different to most - and that's entirely the point. Freedom and flexibility aren't the same thing. Kelly is arguably working more hours than ever, but the nature of those hours - the variety, the autonomy, the alignment with her values - is what makes the difference. If Kelly's story has you thinking about your own next chapter, a good first step is a conversation. Book a free clarity call with Anna at onestepoutside.com/call.

    38 min

  4. APR 20

    Why you're still taking on the wrong clients (and how to stop)

    A few years into your business, you have enough clients, enough experience, and enough reputation to be selective - and yet somehow you still end up working with people who aren't quite right, doing work that isn't quite what you want. Anna Lundberg unpacks exactly why this keeps happening and what to do about it. Key takeaways The filter problem - Your ideal client criteria was right for where you were three years ago. If your expertise and positioning have shifted but your filter hasn't, the business will keep pulling you in a direction you're trying to leave. Obligation masquerading as opportunity - A warm referral, a loyal long-term client, someone who genuinely wants to work with you. None of these are bad things. But they're not reasons to say yes to work that isn't right. The question to ask: if this came in cold from someone I didn't know, would I want it? The call is not a filter - By the time someone is on a call with you, you're already invested. Qualification needs to happen before that point - through an application form, a questionnaire, or at minimum a clear statement on your website about who this is and isn't for. Choose discomfort over resentment - Saying no has a short-term cost. Not saying no has a longer-term one. Most of us overestimate the first and systematically underestimate the second. Have the conversation earlier - If a client relationship has drifted, it only gets harder to address the longer you leave it. A simple, honest reset conversation is almost always better received than you'd expect. If you want to get clear on who you're actually best placed to work with right now, the Solopreneur Diagnostic at onestepoutside.com/diagnostic is a good place to start - 10 minutes, a personalised report, and specific next steps for where you actually are.

    14 min

  5. APR 13

    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

  6. APR 6

    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

  7. 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

  8. 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
See All (395)

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.

Information