Entrepreneurial angst: When your industry doesn’t feel like it fits

An entirely self-indulgent post about the angst of finding an industry that is a poor fit, like a bad bra. I’m calling it Entrepreneurial Angst, and thinking about whether or not industry fit even matters.

Lately I’ve had a nagging feeling that the industry I’m backing myself into isn’t right. And that, in fact, there isn’t an existing industry that my company fits neatly into, or that the work it provides fits into either. It’s difficult, for a bunch of reasons. In this article I am going to explore some of these issues, because as an entrepreneur there is something about breaking new ground that is lonely, uncertain, and risky.

And who better to share this stuff with than you guys, right? We’ve been here before. You’re sighing, god more entrepreneurial angst, and we all know that a cup of tea will mostly set us to rights.

We hope, anyway. The truth is, poor industry fit is like a bad bra: Annoying, uncomfortable, feels unfixable. And yet, it might not even matter. Let’s go exploring.

So, to go back to the beginning: Lately I’ve had a nagging feeling that the industry I’ve backed my company into isn’t the right fit. Or rather, to clarify, it doesn’t feel like it’s a great fit. It’s the closest fit, yes, that is undoubtedly right.

But there are some things about it that put me on edge. They are:

  1. That the clients I’ve gained this year are at the bottom end of the rung, in terms of offerings, knowledge put to use, and zazz
  2. That I feel like marketing is a rip tide that is determined to suck my company in and destroy it
  3. That (without sounding arrogant) my peers in the industry appear to be focused on areas that seem, well, insignificant at best, and downright incorrect at worst.

To clarify, my company is a content strategy company. Most content strategists who write and publish and stride conference stages worldwide talk about things that are not strategic, really. They talk about planning. (Planning is not strategy.) They talk about resource allocation (again, not strategic). They talk about content modelling (which is information architecture, not strategy).

I find myself reading articles and learning some things. And reading articles and having this conversation with myself.

This isn’t strategy.

Plans aren’t strategy.

Tactical implementation is not strategic.

Have any of these people even studied strategy?

Why am I so concerned with strategic things instead of awesome delivery?

Is it really so bad that I write things and am at the beck-and-call of other people who build other people’s products?

How do I get involved in projects at the last second when all the stuff I add value to is already done, except the words?

And so on.

It’s a consistent, interminable monologue about things that just don’t fit.

In my frustration, I study strategy and strategic management. I study strategic paradoxes. I study economics, to better understand the relationships that business, capitalism, and society have with each other. I study user experience, business systems, quality management. I’m learning to audit to ISO 9000:2015 (and will soon be qualified).

Yes, I’m a writer (a good one), and I understand editorial strategy like few others do.

But the things that apparently make content strategy are not things that I do.

So what, then, do I do? Do I work in strategy? Or in content? And is there a way to resolve this weird problem: That content strategy isn’t strategic, doesn’t learn from strategy, doesn’t apply strategy? And, more importantly, is my abhorrence for being plonked with marketers just goddamned pigheaded bullshit?

You see, I’m in a pickle.

In the past few days, this rumination, study, reflection, and general angst about my daily work, has culminated in model that is more about strategy than it is about content itself. It is about positioning, process, and accountability. It’s about as far away from content modelling and user experience studies as you can get.

It’s about half-way to a point where I feel like it’s where it needs to be. Once I mapped the spiral structure of the framework, I sat down to allocate its parts. The frustrating thing was that I almost came back to where I began.

And then it hit me that I’m doing too many things. In a bid to fit into some arbitrary industry box, I’ve added everything in the arsenal. But I don’t need to: What I can do is play to my strengths, give the work a fancy new name, and keep marching forwards.

The risk is that then the content strategy fraternity will turn around and say: Well, you’re not a content strategist’s arsehole, because you don’t do X, Y, or Z. You’re just a [insert word here that’s an alternative for fraud].

And thus, I come back to the beginning. I have a nagging feeling that the industry I’ve chosen isn’t right; and that the industry I am most closely aligned with is unforgiving in its inability to define itself.

To some extent, it’s a heartening place to be. If I were doing the same thing as everyone else, I wouldn’t have the edge that they don’t have. And while my existing customers are the samey copywriting, do-the-marketing-administration-I-can’t-afford-to-employ kind of customers, my company is only in its third year. Reorienting to face and specialise in new areas and new markets takes time.

The challenge in the interim is defining a product set that doesn’t rely on me to sell or run, and indicating that in sales copy. It’s a challenge, because it’s evolutionary; there’s no fixed product or thing, because this entire process is one of discovery, of evolutionary change. I know what I need to do to sell product that I don’t have to deliver. That part is easy. The difficult thing is working out the nuances of the sale, the elements, how they fit together. Creating product that seems to change every three months.

And ultimately, I get hung up on names and titles. That question: What’s your business? is fucking hard to answer. You can’t really say, I’m a content strategist but really I don’t fit that industry very well. Or pure strategy. Or anything really. I just make your life more amazing.

So, here I sit, writing blog posts. Surrounded by books about strategic management, decision support, business intelligence, ISO 9000 systems, entrepreneurialism, economics, strategy, and content. Daily, I am beseiged by the idea that I don’t know enough about My Thing; that I don’t know enough to Do What I Want To Do; that I don’t know enough to know what That Thing I Want To Do even is.

Floating takes courage. It requires you to become the Flow, and find out by doing. This is truly why the entrepreneurial lifestyle terrifies people: There’s no structure, no answer, no way to find out except by dint of work, trying stuff, and thinking. Letting go of labels and definitions is difficult.

And yet, it’s why I don’t gel with all of the standard definitions, structures, and job tasks that I can see that this emerging field is going to be swallowed whole by something else. Probably soon. Kind of like editing was, yeah? I’ve seen the patterns in this industry before. The only difference is that because content strategy is so heavily tech related it has a bigger splash.

There are few who question the industries that we are part of. I’m not a disruptive entrepreneur; I don’t engage in creative destruction. I don’t believe in violent business analogies. But my inability just to persist with the status quo means that I’m sitting here on the edges, and wondering WTF I’m doing… just like I have done my whole life. Ok not my entire life: The music industry felt like home. Few other places have done.

It’s exciting, and terrifying, and kind of makes me feel sick. So if you have an answer or a comment, let me know. I’m all ears.


My company has a well-defined strategy, intention, purpose, vision, mission, and trajectory. What it doesn’t have is a label that fits. Just to be clear. 😉

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