No, you’re not losing your mind (probably). Welcome to the messy middle.
- Jul 28
- 5 min read
Updated: Jul 30
You’ve asked someone on your team to do something. It’s relatively simple like answering a client query, setting up a new landing page, scheduling your social content, or designing the latest newsletter. You know, the kind of stuff you really shouldn’t be doing anymore.
But then it comes back to you and your heart sinks because, while it’s not exactly full of mistakes, it isn’t up to your expectations. The problem is, your expectations have never been explicitly communicated or documented, so your team doesn't know what ‘done well' or 'done correctly’ looks like. And instead of handing it back with clear instructions (because honestly, who has the time?), you quietly rage while fixing it yourself, and then you sigh and move on.
This isn’t a one-off though; it’s your life now. And this simple task, like all the others you’ve tried to delegate, is doomed to stay on your to-do list forever.
That loop is part of being in what we call the messy middle, and it means your business is growing up. But if you’ve been beating yourself up over all the ways you think it’s going sideways, I need you to know that it’s not you; it’s a phase your business is going through. Think of it like a moody teenager going through puberty. The bad news is that this phase can be really challenging and uncomfortable. But with the bad news comes the good, because you should take this as a sign that you’re ready to evolve into the next exciting version of your business.
The feelings are real and they’re heavy
When your business hits this phase, three things tend to show up together, and if you’re in it right now, you’re probably familiar with the symptoms.
The first is boredom, which can come as a surprise. I mean, this is your baby, your dream, and every day used to feel like a new adventure, so what gives? But yup, there it is. Boredom. The thing is, when you were starting out, everything was new, and there were so many milestones: the first client, the first hire, the first time you hit a revenue number that had you reaching for the champagne. But somewhere along the way the job of running your business became mundane, and every day started to feel like a slog.
The second is that growth has gone flat, or it at least feels that way even if the numbers are telling you something different. The big wins that used to be a regular thing now only come along every few months, if that. Which can leave you feeling like you’ve lost momentum, even though you're busier than you've ever been.
The third is self-doubt, and this one might catch you off guard because it pitches up late to the party, and it has you second-guessing everything. Results are taking longer to show up, so you feel like you’re stuck, even though you’ve been doing all the right things for weeks, even months. Making the hard calls on your own doesn’t help either. You don’t have anyone to share the weight of those decisions, so you’re left feeling isolated and questioning your judgement.
The challenges that are holding you back
And you know what they say about everything coming in 3s…
Decision-making is probably the first thing that gets harder. And that’s because you have too many priorities running all at once, and each one is vying to be at the top of the list. The problem is, when you make everything a priority, the stuff that really matters isn’t going to get your full attention. Fewer goals early on meant fewer problems, but now you've got a launch, you’re thinking about gaps in your team, you’re managing more clients, you’re working on a new offer, or you’ve got systems that are half-built.
Focus is the second one, and this one can have you believing you’re not disciplined enough or you're doing it all wrong. Because you’re not filtering the noise. Every podcast, coach, so-called guru, and founder in your group chat will have an opinion about what you should or shouldn’t be doing, and there’s a chance most of it isn’t even relevant to your business or your situation. Too many opinions and ideas will pull you in too many directions at once. And listen, I’m not saying you shouldn’t work with a coach or join any masterminds; I’m saying find the ones that are right for you and tune out the rest.
Letting go is the third. You probably think that you know your business better than anyone you could hand it to, and you may or may not be right, but that’s what’s keeping you in the ‘I’ll just do it myself’ loop. Letting go is hard because it’s tied to both fear and ego. But, at the end of the day, it's the results that matter, not the route someone takes to get there, and a perspective that's different to yours might actually be a better one. There is something called the delegation mindset, and it’s essential if you don’t want to stay stuck in the loop forever. (If you want to go deeper on the topic, I’ll share some resources below.)
Now, back to that loop
This is why that task lands back in your lap every time you try to hand it off, and it’s not because your team is underwhelming or that you’re just too much of a perfectionist. More often than not, it’s because the systems that take what’s in your head and make that knowledge accessible to the rest of your team are missing. It really is as straightforward as that.
And this is all part of being in the messy middle. You’ve got the offer that’s selling, you’ve got clients, and your revenue is finally consistent. But you just haven’t figured out the other parts yet—the parts that bring it all together and take the chaos out of running your business.
Where that leaves you
If you recognize any of this, just know that you’re not doing it wrong. Welcome to the messy middle, and there is a way to get through it. Plenty of founders running solid businesses are sitting in exactly this spot right now, wondering why the excitement's gone and the wins have slowed and their own gut feels less reliable than it used to. Including me! Because yes, I am, in fact, also a business owner.
And none of that means you need to work harder. It means something in your business has shifted, but the way you've been running things hasn't changed with it. That's not a reflection on you; it's just where you are.
If this is where you’re at right now, you need to book my free strategy session. This is a 45-minute call where we go deep, looking at what’s currently on your plate that shouldn’t be
and how you can hand it off.
If you’re struggling with letting go in your business, these books might rock your world:
