Ep. 388 Why redesigning an established business is harder than starting a new one

Estimated reading time: 13 minutes

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 moments

[00:00] Introduction – Why redesigning an established business is the focus of this episode

[01:04] The solopreneur diagnostic – A new tool to help you assess what’s not working

[02:25] The house renovation analogy – Why working around an existing structure is harder than building fresh

[04:27] Reason one – Your past decisions have become your constraints

05:48] Reason two – You have more to lose, and the fear is rational

[07:19] Reason three – Your identity is more invested than you realise

[08:36] How people get stuck – Tweaking forever instead of addressing the structural issue

[09:37] The clean break that never comes – Why redesign has to happen alongside delivery

[10:38] Solving the wrong problem – When marketing spend masks a model problem

[11:41] Practical step one – Start with one room, not the whole house

[12:58] Practical step two – Distinguish load-bearing from cosmetic changes

[13:28] Practical step three – Accept the transition cost, financially and mentally

[14:02] The identity work – Why showing up differently requires more than a messaging refresh

Key resources

• Access the free diagnostic: onestepoutside.com/diagnostic
• Book a free call with Anna: onestepoutside.com/call

Redesigning an established business

In this week’s episode, I’m talking about why redesigning an established business is actually harder than building one from scratch. And what makes it so difficult to change something that’s already working, even when you know it needs to change. So this one’s for you if you’re a few years into your business, things are ticking along, but something about the model, the clients, or the direction isn’t quite right anymore, and you’re not sure where to start. Let’s get into it.

Welcome to Reimagining Success, the podcast that helps you build a profitable business as an independent expert, one that works for you and your lifestyle. I’m your host, Anna Lundberg, former corporate insider turned business mentor, executive coach, and mum of two. Whether you’re a solopreneur, a coach, speaker, consultant, I’m here to guide you in creating a business that gives you freedom, flexibility, and the fulfilment you’re looking for. Ready to redefine success and build a business that you love? Let’s get started.

Okay, actually, before I get started, I did want to mention that I’ve just revamped my solopreneur scorecard slash diagnostic. I’ve moved away from ChatGPT towards Claude, and I can talk about why I’ve done that in another episode. But as part of that, I’ve moved my diagnostic over into being embedded on my website and improved it. And I think it’s pretty snazzy right now. So if you’re considering some kind of change in your business, if you feel like something’s not quite working, you’re not really sure, or you’re just wanting a bit of a sounding board, then if you head on over to onestepoutside.com/diagnostic, you’ll be able to sign up there and get access to this very interactive little chat interface where it will walk you through some questions and then generate a report. If you’d like to, you can always send that to me and we can have a chat about your results. But I hope even if you don’t do that, it gives you plenty of insights and some tangible next steps. So that’s at onestepoutside.com/diagnostic.

But today, I wanted to also celebrate that we have recently finally got our curtains in our living room, in our open plan living room, and we also got blinds for our kitchen windows. White curtains – we even got a white sofa, so we were going all in on the Scandi coastal look, slightly risky with young children, but wish us luck. And then these lovely corally blinds for the windows. And I share this because this renovation has been quite a project. We moved down from London five years ago, believe it or not, pretty much this month. And initially we lived in the house, it was perfectly livable. And then we moved out while we did up the house, moved back in, scaffolding was still up and we only just finished the driveway a few months ago and now the curtains feel like the pièce de résistance. It’s very nice, although now it’s summer so we don’t really need the curtains as much – although the sun is pretty bright in there so actually it serves a dual purpose.

What I realised with this is we could have knocked down the existing structure and started from scratch – blank slate, every decision made once, no constraints at all. What we did was we decided to work around what’s already there because the house was perfectly fine. It wasn’t falling apart, it had a good structure. And because of that, there were certain constraints. There were load-bearing walls that you couldn’t move or it would be very expensive to knock down, pipes running through perhaps inconvenient places, and you fix one thing over there and something else looks wrong. What I’ve realised is that that’s really what redesigning an established business feels like.

It’s much easier – and this might seem odd, but I think you as someone who are experienced like me will recognise – that it is much harder to change something that’s already there than it is to start out from scratch. And I think most people underestimate it because from the outside, it might look like you’re just tweaking things, but it’s just so much heavier and more complicated. There’s so much more at stake when you’re redesigning, renovating, if you will, around an existing structure instead of just being able to make it up from that blank piece of paper however you want.

And there are a few reasons for this – three reasons, if I can remember them. The first one is that your past decisions are now your constraints. The offer you created in year one made sense back then. It got you clients, it built your reputation, it taught you what you were doing – so my initial career coaching, or in fact before that, even my digital marketing consulting. But it also created expectations in your clients, in your market, in yourself. So for example, and this might sound familiar, a consultant might build a done-for-you service early on because that’s what clients would pay for. Now she’s known for it, she’s dependent on it financially, and she’s exhausted by it. So moving to a different model – let’s say more of an advisory role – feels risky because her whole pipeline, all her income now that’s paying her mortgage and for her family and so on, is built around that old model. She’s not trapped by the market conditions, she’s trapped by her own history. And in that sense, the build was easier when she started because there were no prior decisions to unpick. You can go wherever the pull is right now – your particular life circumstances, the need in the market and so on. But now you have something that’s working, and that becomes a constraint to changing to something that might work better, but it’s unproven.

So that’s the first thing – your past decisions are now your constraints.

The second thing is, and it’s connected, is that you have more to lose. And man, don’t you know it. Early on when you’re starting out, I was a bit naive, but I kind of expected uncertainty. You’re figuring it out. That’s what’s exciting. Nobody is surprised when things change because you’re completely new to it and it’s the first stages and nobody expects you to even make money at the beginning, etc, etc. Fast forward, three years in, five years in, whatever it is, 12 years in for me – you have clients who depend on you, you have income you’ve come to rely on, and you have a reputation that took time to build. So change feels like a risk in a way it just didn’t feel like a risk at all at the start.

So let’s say a coach knows her group programme isn’t working anymore. It’s the wrong clients, it’s the wrong format, it’s the wrong price point, but 12 people are currently inside it. She can’t just shut it down. They’re committed. They’ve paid her to deliver this programme. So she keeps running it. And because she keeps running it, she keeps filling it, keeps not fixing the underlying problem. The fear – look, it isn’t irrational. There genuinely is more at stake. But the mistake is that we let that fear and that risk of losing freeze the redesign entirely. We need to recognise the fear and the uncertainty, and that fear notwithstanding, make the decision that we want to change – and ask how we can make that change without risking everything. Sounds easy, right?

Now the third reason why the redesign is harder is that your identity is more invested. And this is the one I think no one talks about. When you’re starting out, the business is something you’re building. But a few years in, it’s become something that you are. I was very much like, oh, I’m trying this, I’m trying that – and there was a different lightness to it when I started out. Now you’ve become anchored in identity. I’m an executive coach, I’m a this, I’m a that. It’s become your identity in the same way that your corporate title used to be your identity. And that means that changing the business starts to feel like changing yourself. And that in turn triggers a different kind of resistance than just a tactical decision.

So I don’t know – a founder who built his entire platform around one area of expertise. He’s known for it, his audience expects it, his book is on it. And then moving into adjacent territory feels like betrayal – of his audience, of the thing that made him successful, of the version of himself that he’s been presenting to the world for years. And that’s why redesign actually requires identity work. It’s not just business strategy. You have to separate what you do from who you are before you can change what you do.

Okay, so it’s harder to redesign because your past decisions are your constraints, you have more to lose, and your identity is more invested. And this is where people get stuck. We end up just tweaking forever – changing the offer slightly, adjusting the price, redoing the website – without ever actually addressing the structural issue underneath. And it feels like progress. It isn’t. So we need to ask – coming back to my renovation analogy – am I changing the wallpaper here, or am I moving a wall? Am I actually changing how this works in my business, or am I just changing something superficial, putting on a lick of paint while the cracks are still there?

If we’re just tweaking, we avoid the big redesign yes, but we also don’t get the results that we actually want. Maybe, and this is a common one, we’re waiting for a clean break – oh, I’ll fix this when this client contract ends, or I’ll reposition after this launch, I’ll raise my prices in January because that’s the new year energy. But the clean break rarely comes because the business keeps generating the conditions that make change feel impossible. Redesign has to happen alongside delivery, not instead of it. There’s never going to be a perfect moment when all the programmes are finished and ta-da, we can stop it and start again as if it was a new business.

And then I also think we tend to be solving the wrong problem. We might come to redesign thinking, oh, I’ve got a marketing problem, or I’ve got a pricing problem. But that’s not it. My lens is that often it’s a model problem. It’s a fundamental structure of how the business works, and that structure isn’t right anymore. So someone’s spending money on ads to get more clients for a service that’s already burning you out – not a great solution. More clients is not the solution. Fewer, better-priced, better-scoped clients is – but that requires a redesign, not a marketing campaign.

So those are some of the areas where I see people getting stuck. Now, how can you actually go about doing this redesign, knowing that you’re not going to knock the whole thing down, knowing that you are still reliant on some of these things working in the meantime?

A few practical ideas. The first is to start with one room, not the whole house. Pick the single thing that would make the biggest difference in your business if you changed it. It might be who you work with. It might be what you charge. It might be how you deliver. Don’t do all three at once. Start with one of these aspects – who you work with, what you charge, how you deliver – and don’t try to change everything at the same time, unless you love uncertainty and chaos and you’re not dependent on the money coming in.

Secondly – sticking with the metaphor – distinguish load-bearing from cosmetic changes. What genuinely cannot change in your business, at least in the short term? Your core expertise, your values, your family situation, your best existing client relationships. Versus what can change but just feels a bit risky – maybe your positioning, your formats, your price point. Those are totally movable, it’s just a bit uncomfortable to make those changes.

And then – an important reality to face – accept the transition cost. There will be a period where the old model is winding down and the new one isn’t fully running yet. And that’s quite scary. So we need to budget for it both financially and mentally, because if we are steering the ship in a new direction, there might be a moment where we shut an old offer down or we’re turning away a certain type of client and we haven’t quite got the new client and the new machine working. That’s something to be aware of and manage quite sensitively.

And then, as I said before, the most important foundational work is the identity work. We need to be doing that in parallel. If the redesign requires you to show up differently, talk about your work differently, attract different clients – that is not just a simple messaging exercise. It’s a genuine shift in how you see yourself in relation to your work. And you need to give it the time that that shift needs.

So, recognising in summary that it is harder to redesign – a beginner might not understand that, but they will find out when they get years into their business. It’s much harder to change the course of a moving vehicle. And you know, it’s harder to change direction when you’re already heading for this particular place, and you suddenly realise that that email funnel is talking about this and your book is talking about that offer and there’s that video and your YouTube channel and what about these clients – it’s a knock-on effect where one change over here changes everything over there.

But there is a point at which more tweaking isn’t going to do it. Another lick of paint, new wallpaper, even new curtains or a new sofa isn’t going to do it. And that’s when you really need to take some time to reflect – where do we want to move to? What got us here might not be what gets us there. And as I said, starting with that one change, getting clear on what really can’t change and what can, and accepting that there will be some teething issues as we start that redesign.

But if this resonates, I’d love to hear from you. There are a couple of ways in which I can support you with this kind of redesign, either in a group container or as more of a one-to-one thinking partner. You can always book a call with me at onestepoutside.com/call. And hopefully there’ll be more episodes in a similar vein over the next few weeks if it is resonating. I’d love to hear from you what you take away and what change you might be considering in your business. Thanks so much for listening and I’ll see you next week. Bye for now.

If any of this resonates, if you’re in that renovation phase right now working out what stays and what needs to change, the best place to start is with an honest diagnostic of where you actually are. I’ve built a free solopreneur diagnostic at onestepoutside.com/diagnostic. It takes about 10 minutes, covers the five areas that matter most in your business right now, and gives you a personalised report with clear next steps. I’ll put the link in the show notes – that’s onestepoutside.com/diagnostic. See you next week.