Ep. 399 Why hitting your goals never feels like enough

First, it was getting the website up. Then it was the first paying client. Then a certain revenue figure, then enough clients to feel stable, then it was building the waiting list, the speaking gig, the TEDx talk, the book deal, the fee that finally felt like it reflects the work.

And each time you get there – each time – there’s a moment that feels amazing. Sometimes for hours. Sometimes a few days. And then something resets, and the next thing is already visible on the horizon.

I remember this happening so many times. When I published my second book, Outside of the Nine to Five, I pushed it through at the end of 2022 and I was ill on the day I’d planned the launch. I didn’t even do a launch party – it was just an announcement on Facebook, and hitting publish on Amazon. This one thing I’d worked towards for months (or years) – finally done. And then a couple of people go “yay” and then that’s it.

Even if you’re publishing with a proper publisher and doing a book tour, going on podcasts, having a launch event – we put a lot of pressure on this one thing. The book is going to finally help us charge the prices we want and get all those inbound leads and change the positioning. And don’t get me wrong, a book is an amazing thing to have. It’s a business card; it helps you say “hey, author of this, expert on that.” And it can open a lot of doors.

But it’s often a little disappointing. A little frustrating. That first book publication, the TEDx talk, the first media feature – you think, oh my gosh, now I’m going to get thousands of people coming to my website. And that’s often not the case.

I want to name this, not to be discouraging, because the work is real, the progress matters, and we should absolutely celebrate these milestones. But there is a gap between what we expect those milestones to deliver and what they actually deliver. And that gap is significant. People don’t talk about it enough.

What milestones are actually solving for

This pattern runs through almost every established independent I’ve worked with – across very different businesses, very different personalities, very different definitions of what success is supposed to look like. Because the goalpost keeps moving, the arrival keeps not quite arriving.

And the first thing I want to say about that is that this makes complete sense. We’re not ungrateful or endlessly dissatisfied or unable to enjoy what we’ve built. The reason is about what the milestone was actually supposed to be doing.

Because I don’t think it was ever really about the milestone.

What milestones are solving for is a feeling. And the feeling varies: settled, legitimate, credible, enough, arrived, safe. But it’s always a feeling.

The implicit deal we make with ourselves is: once I have X, I’ll feel Y. Once I have enough clients, I’ll stop worrying about the pipeline. Once I hit that revenue figure, I’ll stop feeling like I’m one bad month away from disaster. Once I have the TEDx talk or the book or the speaking fee, I’ll stop needing to prove this to myself.

But the feeling doesn’t come from the achievement and it never did. It was always going to have to come from somewhere more internal. Something slower. Something that doesn’t actually come with an announcement. Which means hitting the milestone doesn’t resolve the thing you were hoping to resolve – it just moves it. And then the goalpost moves with it to the next thing that might finally deliver that feeling.

The proof-of-concept pattern

There’s a second thing going on. The milestone isn’t just a goal. It’s often a proof of concept.

The question it’s trying to prove varies depending on who you are and what your particular history is. But it’s some version of: I am legitimate. I belong here. I’m not a fraud. I made the right choice. This is working. I am enough.

Think about how long that particular question has been running for you. For a lot of people who end up building their own business, the pattern started well before that. If you were the high achiever at school, success meant the grade, the place, the recognition. Each one proved something. Then came the corporate career and the same again – the promotion, the title, the salary, the performance review.

I won’t bore you with my own experience of this, but: the milestones at school, graduating top of my class, valedictorian, getting a place at Oxford to study PPE, becoming a top performer at Procter and Gamble. And what each of those milestones and achievements was supposed to prove. The solopreneur version is the same pattern, just with different milestones – the website, the client, the waiting list, the best-seller status on Amazon, the TEDx, the number of views.

But proof of concept doesn’t actually work that way. You can stack proof on proof on proof and still feel the question running underneath – because the question was never really about the evidence. There’s plenty of evidence that you’re already doing something real. It’s about the belief. And the belief doesn’t change just because you found more evidence for it. The TEDx talk doesn’t make you feel credible if the belief running underneath is “not quite credible yet.” It just moves the bar for what credible looks like.

Ambition vs being driven

There’s a distinction I want to draw between pursuing because you want to pursue something and pursuing because you’re running from something.

Ambition is good. Wanting to do more, to reach more people, build something meaningful – all of that is good. But what I’m talking about is the person who’s always just one more thing away from feeling settled. Where the pursuit isn’t expansive – it’s driven. There’s a quality of running rather than moving towards. Where if we stop, even briefly, that feels dangerous rather than “ah, this is nice, I’m taking rest.” That distinction matters because one is energising, the other is exhausting.

The TEDx thing is quite fresh for me – and we’ll see where I am in this process as you listen to this podcast.

The first TEDx I applied to, I got to audition and then didn’t get the actual talk. And in that audition I shared that initially, years ago, I had colleagues who did TEDx. And I kind of told myself I shouldn’t chase it, ironically. It became something I rejected because I didn’t want to jump on it just because everyone else was doing it. And I’ve come full circle.

Now I go: no, actually, this is the right thing for me at this stage of my business. I want to increase my reach. I want to anchor my positioning in the IP I have. I want to challenge myself to really articulate the message clearly. So I’m using it as a way to sharpen my thinking – as one piece of a broader puzzle alongside the book and talks and other things.

The question to ask yourself is this: what am I hoping the next milestone will finally prove? If you can name that, you’ll get closer to the actual thing that’s going to change things for you.

What the journey actually looks like

Life is not a series of arrivals. It’s more like: a leap up, then a plateau. A consolidation. A few steps back, a few steps forward, another plateau.

And the plateau is the other bit that no one prepares you for – because from inside a plateau, it feels like you’re stagnating. Like nothing is happening. Like everyone else is moving and you’ve got stuck.

They rarely are what they feel like. We forget all the progress we’ve made – how, one year ago, we’d have been thrilled to be where we are today. But because we’re constantly chasing the next thing, we’ve forgotten that we already have the very thing we were desperately chasing before.

Staying in the plateau long enough

The plateau is usually where the work of the previous leap gets integrated. Where the clients you want start referring others. Where the reputation you’ve been building starts to become visible to people who weren’t watching before. Where the confidence that comes from having done the hard thing – not just planned to do the hard thing – starts bedding in.

The danger is spending the plateau planning for the next peak. Launching the next thing, announcing the next thing, starting the next project – not because it’s time, but because it feels completely intolerable to stay where you are, and movement, however manic, feels like proof that something’s happening.

Sometimes the most important thing you can do in a plateau is to stay in it long enough to notice what’s actually building.

The journey is harder than you probably expected. Slower than you hoped. And it’s more meaningful than it looks from the outside. But it’s definitely nowhere near as linear as anyone’s LinkedIn feed suggests.

The work that changes the pattern

What starts to shift this pattern isn’t hitting more milestones, or deciding to want less (that’s rarely the answer either). It’s getting outside of the pattern far enough to see it. And that’s really hard to do alone.

Most people doing this work are extremely self-aware. But you’re inside it. So you can describe the pattern. Maybe you can even name it. But you still find yourself moving the goalpost again because the belief underneath it hasn’t been examined. And that’s your identity. That’s just what you do.

The belief – and the identity especially – is so much older than the business. It predates that first milestone. It probably predates your corporate career. And it may have been running for a long time and become invisible because it just feels like the way things are.

When I work with clients one-to-one, we get underneath that goalpost to the belief that keeps driving towards it and ultimately moving it. It’s establishing: why is that? What is the belief? Where does it come from? Would you still choose it today, consciously? And what would have to shift for the next milestone to feel genuinely different?

Not because you’ve lowered your standards or reduced your ambition. But because you’ve examined what the milestone was actually supposed to be proving.

And that is, honestly, slow work. It’s not a one-hour strategy conversation. It’s not going to produce a clear to-do list at the end of the session. But it’s the work that actually changes the pattern rather than working around it. And that’s where things start to feel different in your business.

If today resonated, this pattern – the goalpost that keeps moving, the feeling that the arrival never quite arrives – is often the thing I work on most closely with people in Atelier, my one-to-one coaching. Read more at onestepoutside.com/atelier.