Ep. 397 Why solopreneurs procrastinate: the beliefs behind your to-do list

This is for you if you know exactly what you should be doing in your business and you’re still not doing it. Today, we’re going one layer underneath the to-do list to look at the beliefs that are older than any task on 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.

Why knowing what to do isn’t enough

Okay, so today I want to talk to you about something that nearly every client I’ve worked with has had some version of. I’ve said this myself as well. I know exactly what I need to do. I’ve got my list. I know the email I need to send – I should send. The post I should write. The conversation I should be having. The price I know I should be charging. And then I don’t do it.

And then I feel bad about not doing it. And then I do something else. Usually something productive enough to feel justified, but it’s not the thing.

And the first place people reach is discipline. So we look for better systems, a better tool. I moved from Asana to Notion. Maybe you’re using Cowork and Claude as holding you accountable now, some new productivity method, a hack, the 5am start, whatever. A new calendar is always a nice thing to do. A new accountability app. Sometimes this kind of thing does help, for maybe three weeks. But then the list starts winning again, because the problem isn’t on the surface. The problem isn’t productivity and discipline.

What success scripts are and where they come from

Underneath a to-do list, I see a set of beliefs that are very much older than any of the tasks – even the tasks that have been sitting there for weeks and months. There are beliefs that were formed at school. And I’m not going to go into the full detail of this, although I could very much go off on a tangent here, with teachers telling us certain things, or our first managers, the way they spoke to us, or the marketing advice we’ve absorbed from LinkedIn and webinars and other coaches. And just from the peer group we’ve spent time with, depending on what industry you come from.

I spoke to someone recently who comes from academia and realised that now, as a business owner, he needs to have a much more commercial perspective. Someone from a charity background or the heritage sector might carry a belief that there’s a ceiling to how much they can charge. A different way of operating that doesn’t serve you when you’re trying to make money and pay your bills as a solopreneur.

So there are these beliefs, and I call these success scripts. You have your own set, but I want to give you a few examples I hear. I’m oversimplifying to some extent, but I’d hazard a guess that some of these will resonate.

The “selling is sleazy” script

One example is: selling is sleazy. So every time you sit down to write a sales email, something recoils a little bit in you. You soften it, you add three more paragraphs of value to prove you’re worth it before the ask. Maybe you don’t even send the message.

You could attend all manner of sales trainings. I’m actually talking about this at a sales conference – hopefully, it hasn’t been confirmed yet, but I’m sure it’ll happen at some point. And you can learn all the sales strategies in the world. But if you believe that sales is icky, kind of the used-car-salesman cliché stereotype – I just went to see Matilda with my daughter, so I’ve got the shoddy cars sold to the Russian mafia in my head – if that’s your vision of selling, then of course you’re not going to want to do it. Because it’s icky, it’s not in line with your values, you have integrity. And I shouldn’t need to sell, right? Because people should just come to me and see the magic of the amazing work I do.

So it’s clear to me that it doesn’t matter how much I give you a script for a sales call, or a rhythm for how many messages to send each week. If you fundamentally believe you’re interrupting people, disturbing them, being annoying, being too pushy – then A, you probably won’t do it, you won’t send the message. And B, you’ll filter it through and be quite apologetic, you won’t articulate it as well as you could, your energy will be off. So not to blame yourself for this. These underlying stories and scripts mean that no amount of strategy or tactics or literal scripts (as in, the words to follow) is going to help.

The self-promotion block

Linked to that: oh, I don’t want to be too self-promotional. When you’re starting out, it might be I don’t even want to post on LinkedIn because it feels like showing off. So you rewrite it, you reread it, you decide it sounds too arrogant, you don’t post it. Or you soften it so it no longer has any of the credibility markers, it’s too apologetic, it doesn’t get the point across because it’s so diffuse. You’re doing the thing, you’re posting, but it’s not coming across in a compelling way, because you’re so reluctant to have even a hint of self-promotion in there.

What will people think?

Big one, especially when people leave corporate: what will people think? The old colleagues.

I had a client not so long ago who wanted to start posting on Instagram rather than LinkedIn, precisely because she was worried about what her colleagues would say on LinkedIn. She has, to her credit, now started posting amazing stuff on LinkedIn. Really showing up there. Showing up, not showing off.

The thing is, most of the people who knew you before aren’t paying attention. If they are, it’s because they’re interested, or maybe they’re a little envious of how you’ve taken the step and built something, when they don’t quite have the courage to do that. Or most of the time, they’re not paying attention, they won’t remember it, they’ll move on. If you’re posting something that isn’t relevant to them, the most they’ll think is: huh, that’s odd. And then they’ll forget all about you, I promise.

So this vague imagined audience that’s judging the version of you asking for clients – that’s a big cloud hanging over that stops you leaning in. And again, it makes you water down and dilute your messaging, hold back, and not step into your opinions and what you actually believe.

The over-deliverer identity

There are also some more reflective ones, like: I’m the one who always over-delivers. So if I’ve got an identity as the team player, the one who always delivers more and delights the client or the boss or the team – then anything that has even a little sniff of possible rejection or being difficult will feel like I’m breaking that contract with myself and with them.

Raising prices: oh, I can’t do that, because I need to first prove myself. I need them to really see how amazing I’ve been. Better to undercharge and have them think wow, this is so much more value. I won’t be able to say no, because I’m not the person who says no. I’m the person who always says yes and is easy to work with and easygoing. And this is an important relationship, so I’m going to keep saying yes even though it’s breaking me. I’m not going to end an engagement. Because I’m the one who always delivers. I’m the team player. The people pleaser. You can phrase it in all sorts of ways.

“Real experts don’t need to market themselves”

Or even – and this one’s interesting, it’s almost a bit arrogant – real experts don’t need to market themselves. The work should speak for itself. It’s the Nice Girls Don’t Get the Corner Office book that I never actually read, but I saw the title years ago. And it feels like: if I’ve got to market myself, if I’ve got to message people, then I’m admitting the work isn’t enough. That I’m not good enough. I’m not fully booked.

And that’s really damaging. Because unless you’re Simon Sinek or Brené Brown – and even then, they have teams marketing them, selling them, putting them on podcasts – it’s quite naive to think there will be a point when we no longer need to do this. Obviously when we’re further along, there’s more inbound. I have years of podcast episodes and articles and relationships that weren’t there when I first started. But positioning will only get you so far, and there’s always going to be an element of marketing and selling.

How to name your script and question it

So I’m not blaming myself, and I’m certainly not blaming you. These aren’t personality flaws. They’re scripts, stories we’ve absorbed from early jobs, first managers, corporate cultures, families, and the peer group we’ve spent time with. And over time, they stop feeling like beliefs and just start feeling like the way things are. So we don’t challenge them.

The example I always share: I was the good girl at school. I followed the rules. I got the gold star and the tick. And sadly, that doesn’t happen in entrepreneurial life. If I become totally dependent on a great testimonial, or engagement on a post, or being chosen for something, I’ll always have an emotional roller coaster. Always outsourcing my worth. Never feeling quite good enough because I’m always waiting for other people to tell me. And I’ll be diluting what I actually believe, because I’m constantly trying to contort myself into what I think other people want. Working away in the corner, hoping someone will notice and give me that gold star. That’s not how it works, my friend.

So it’s important to recognise the script. Recognise the behaviour first: oh, I’m not selling. Why is that? Is it because I don’t have enough discipline and I just need someone to tell me to send those messages? Or is it because I fundamentally don’t believe I’m someone who can sell, should sell, that people will buy from me when I sell?

And that is why putting things on the to-do list won’t fix it. You can totally understand intellectually that you need to send the email and still not send it. Because underneath there’s something saying, probably subconsciously: people like me don’t do that. Or: this is going to seem desperate. Or: if I do this and it doesn’t work, then I’ll have to confront something I’m not ready to face. This isn’t a case of willpower. It’s that belief doing its job, which is to keep you consistent with who it thinks you are – to keep you in that same identity you’ve had for however many years.

Rewriting your success scripts

But I do think this is genuinely empowering. Because once you can name the script, you have a choice. Still not easy – I’ll tell you that. But it is a choice.

So: I don’t want to be self-promotional. First, ask where that comes from. Was it a manager, or someone you’ve seen on LinkedIn being super self-promotional that felt really icky and cringey? Was it a culture that rewarded modesty? And then the question is: is that still true for you now? Is it still serving you as a solopreneur trying to promote your services? Maybe not.

And the work isn’t to have more discipline, to try to override that script through more effort. It’s to examine it, decide whether it’s one you still choose today. Sometimes that can be enough – just to see it and go, actually, no, that’s not helpful right now. And then to try to rewrite it. To become the person who does show up and who does sell. Because selling, ultimately, is just having conversations with people. I believe I have a way I can help people, and the best way to help them is through my service, through them working with me as a coach, a speaker, whatever it is. And for that to happen, I need to tell people what I do, invite them for a call, tell them what it costs to work with me. Then, dot dot dot, it’s pretty simple when you take the emotion out of it.

Why you can’t always spot your own scripts

One of the things that makes this genuinely hard to do alone is that you can’t always see your own scripts from inside them. You’re too close to it. Plus maybe your peer group reinforces them – and that can actually be dangerous. I’ve caught it myself in our Offscript calls and in other communities. If everyone’s saying, oh, this is what’s happening and I don’t want to do this, and our LinkedIn is so off – that can become a reinforcing, self-enforcing story in itself. Which is quite dangerous.

So what we need is people around us who will name that pattern rather than just reflect back what we’re saying. In our Offscript call a few weeks ago, we went through exactly this – asked what selling means to you, thought about times you’ve bought something, what the person did, whether that felt icky or not. Just examining and exploring it a little bit, seeing if we can challenge our thinking and reframe in a way that would be more helpful.

That’s part of what Offscript is built around: a group of people who will tell you what they notice, because they’re close enough to your world to see it, but removed enough from your day-to-day to be able to say it. If that sounds interesting, you can go to offscript.club to apply. Doors are open now in June to join us next month. We’d love to have you – link in the show notes.

I appreciate this was a bit intellectual in a way, but also very simple. I’d really encourage you to sit with it, because it’s so easy to go, yeah, I know, that’s what I think, but I’ll just change. And then you’re back to the to-do list and the accountability and the discipline. So sit with it. Spend some time thinking about what you believe about business. It’s not possible to have work-life balance. I can’t both have financial success and follow my passion. I can’t earn six figures working 20 hours a week or 3 days a week, whatever it is. I can’t, etc, etc. What are those stories you’re telling yourself? Are they actually helping you at this stage? And what might be a way to reframe in a way that does serve you?

Thanks so much for listening and I’ll see you next week.

One more thing before you go: if today landed, Offscript might be worth a look. It’s a community I’ve built for established independents who want people around them who will name what they actually see – not just validate what you’re already thinking. Doors are now open for the July intake. Apply at offscript.club.

What is the peer gap for solopreneurs?