The Problem With Being the Business

I am in an interesting conundrum with Tomedia at the moment.

It is not a bad conundrum to be in. In fact, it is probably the best kind of business problem to have. The business is working. People want the work. Clients trust me. The projects are coming in. Most of the business has grown through word of mouth, reputation, portfolio work, and me selling myself as the person who can actually figure things out and get things done.

That is a good thing.

It means I have done something right.

It means people respect the work. It means people trust the thinking behind the work. It means I have become good enough at what I do that people seek me out as an individual, which is exactly what you want when you are building something from nothing.

But it also creates a very annoying problem.

At some point, being good at the work becomes the thing that traps you inside the work.

That is the stage I am sitting in now. I have enough work to keep everything ticking along. I have retainers. I have projects. I have development work. I have marketing work. I have enough happening that the business is not just some fragile little thing anymore. But the core problem is still there.

If I stop working, money slows down.

If I get sick, money slows down.

If I go on holiday, money slows down.

If I eventually want to retire, take a break, change direction, or simply not be glued to the machine every single day, the whole thing risks falling over because too much of it still depends on me personally doing the work.

That is not really a business.

That is a highly skilled job wearing a business costume.

And I do not mean that in a depressing way. There is nothing wrong with freelancing. There is nothing wrong with being a sought-after individual. There is nothing wrong with being the person clients trust. That is how Tomedia got here. That is how most good service businesses start. You become useful, then you become trusted, then people keep coming back.

But at some point you have to ask a different question.

How do I build something that does not collapse the second I step away from it?

That question has been sitting in the back of my head for years, but it has become much louder recently. I have been running Tomedia since 2019, which means I am now around seven years into this thing. That is still early, but it is also long enough to have experienced some patterns.

I have experienced what happens when I take a holiday and the business does not really make money while I am away. I have experienced what happens when I get sick and suddenly everything slows down because I am the person everything depends on. I have experienced the stress of knowing that the income is only stable while I am physically able to keep producing.

I do not want that forever.

I recently came back from Europe, and this trip was different. For the first time, I had enough retainer work in place that the business did not feel like it stopped the moment I left Australia. The retainers covered a good portion of the base costs. Project work could still continue. I could work while overseas when I needed to. It was not a perfect “proper holiday where I do absolutely nothing” situation, but it was a lot better than previous holidays.

That was a sign.

Not a complete solution, but a sign of what the solution could eventually look like.

The retainer side of the business is the easiest part to understand. Retainers are scalable in a way that project work is not always scalable. With retainers, I can be the authority. I can set the direction, explain the strategy, guide the marketing decisions, and decide why we are doing what we are doing. Then the actual implementation can be handed to someone else.

That is already starting to happen.

For SEO work, for example, I can own the thinking. I can say, “This is the strategy. This is why we are doing it. This is what matters.” Then someone else can help with the delivery. That works. That makes sense. That is scalable.

Not infinitely scalable, and definitely not cheaply scalable, but structurally scalable.

Eventually, the retainer side of Tomedia could have an account manager handling client communication, expectations, and relationships. Then underneath that, there could be skilled people handling the actual implementation: SEO, social media, ads, content, reporting, whatever else fits into the machine.

That version of the business makes sense to me.

The problem is getting there costs money.

If I had a proper team of four people working on retainers, that could easily cost somewhere around half a million dollars a year once you include wages, overhead, management, and breathing room. That means you need enough retainer revenue to justify it. You need enough clients. You need enough margin. You need enough stability that you are not hiring people off hope.

That is the difficult part.

The model is clear. The path is clear. The timing is not.

Then there is the software engineering side, which is a different beast entirely.

The software development work is highly profitable. It is also the work I trust the least to hand off.

That probably sounds bad, but it is the truth. I have tried outsourcing development before. I have paid junior developers. I have paid dev teams. I have spent a lot of money trying to get other people to build things properly, only to end up fixing the work myself anyway.

Bad code is expensive. Bad architecture is expensive. Poor thinking is expensive. Cowboy development is expensive.

And I have a deep distaste for cowboys in this industry.

The issue with development is that it is not enough for something to technically work. It has to be built in a way that makes sense. It has to be explainable. It has to be maintainable. It has to be something I can stand behind when a client asks how it works or why it was made that way.

That is hard to delegate.

I know it is possible. Eventually, software engineering can scale too. But I think it scales differently. External client development work is much harder to scale because every client has different requirements, different systems, different expectations, and different levels of chaos. Internal software development is much easier to scale because the team is working on the same product, the same codebase, and the same long-term objective.

That is where things get interesting for Tomedia.

Because I do not really want Tomedia to just become a big agency.

Big agencies are not always stable. Big agencies can become bloated. Big agencies can lose their quality. Big agencies can become machines that exist to feed themselves. In Australia especially, I do not think simply becoming a big agency is the dream. It might work for some people, but it is not the version of the future that feels right to me.

I want Tomedia to be more than an agency.

I want it to become infrastructure.

I want it to become a marketing authority. I want it to become a software company. I want it to become a publishing engine. I want it to become a place where internal products, client services, research, media, education, and tools all feed into each other.

That is the real shape of it.

The retainer side gives stability.

The development side gives high-value project work.

The software-as-a-service side gives scale.

The articles, books, zines, videos, and research give authority.

And the authority feeds everything else.

That is why Brainwaves matters. That is why the zines matter. That is why the Big Book of SEO matters. That is why writing articles matters. That is why building tools matters. At first glance, all of these things can look like random side projects, but they are not random. They are all part of the same long-term structure.

I am trying to build authority around myself and around Tomedia.

I need people to trust me online the same way they trust me in person. When people speak to me directly, they understand that I know what I am talking about. The challenge is expanding that trust beyond conversations, meetings, referrals, and existing clients.

Articles do that.

Books do that.

Videos do that.

Software does that.

Research does that.

Products do that.

They create proof. They create presence. They create ways for people to discover the thinking before they ever speak to me. And if that works, it can lead to more agency clients, more software users, more retainers, more product sales, and more opportunities that do not rely purely on me chasing work.

That is also where passive income enters the picture.

I do not think passive income is ever truly passive, at least not at the start. Everything requires work. Software requires building. Books require writing. Zines require production. Articles require editing. Products require marketing. Even a supposedly passive system needs maintenance, improvement, and attention.

But passive income, to me, is not really about doing nothing.

It is about building things where the money is not directly tied to the hour I just worked.

That is the goal.

If I write a book, it can keep selling after I finish writing it. If I build a software product, it can keep creating value after the first version is made. If I create a library of useful articles, they can keep attracting people long after the day I publish them. If I build a magazine or zine system, each issue becomes another asset in the ecosystem.

That matters.

The Big Book of SEO is a good example. It ended up being enormous. Around 400 pages. That is great because it means the thing has substance, but it also creates a practical problem: print-on-demand becomes expensive. A huge book costs a lot to print and ship. If the final price is too high, fewer people will buy it. So now there is another layer to figure out: pricing, markup, format, perceived value, and whether the book should exist as a premium physical object, a digital product, a smaller series, or all of the above.

That is the kind of problem I like, though.

It is a product problem.

It is not just “how do I get more client work?”

It is “how do I package what I know into something people can buy, use, learn from, and trust?”

That is a better problem.

The same thing applies to Brainwaves. I can talk endlessly. I can talk to a phone, a screen, a camera, or a microphone all day. This entire article started as a voice note. That is the easy part for me. The harder part is editing, packaging, distributing, and turning that thinking into something consistent.

That is why the video side has slowed down. I like making videos. I like talking. I do not like editing. Editing is the bottleneck. So eventually, that might be something I hand off. If I can talk and someone else can turn that into polished videos, then Brainwaves can become more than articles. It can become a YouTube channel, a podcast, a publication, a content engine, or whatever shape makes the most sense.

Again, the pattern is the same.

I own the thinking.

Someone else can help with the implementation.

That might be the actual business model hiding underneath everything.

Tomedia scales when I stop trying to personally do every task and instead build systems where my thinking guides the work.

That applies to retainers.

It applies to content.

It applies to publishing.

It applies to software.

It may eventually apply to development too, but only once the systems, standards, and internal quality control are strong enough that I can trust the output.

The long-term version of this is even more interesting.

In my head, the endgame is not just Tomedia serving external clients forever. The endgame is owning multiple businesses that all connect back into Tomedia. Those businesses generate their own revenue, then they use Tomedia for marketing, software, strategy, infrastructure, and growth.

The money starts flowing in a loop.

One business feeds another. Tomedia supports the businesses. The businesses fund Tomedia. The software supports the operations. The media builds the authority. The authority brings in more opportunities. The whole thing becomes less dependent on any one client, any one service, or any one version of me working nonstop.

That is the dream.

Not a giant agency.

Not a fragile freelance business.

An ecosystem.

A family-owned infrastructure company with media, software, services, products, and authority all supporting each other.

That will take time. Probably a lot of time. I know that. The retainer side needs more clients before it can support a proper team. The development side needs better internal systems before it can scale safely. The software-as-a-service side needs more marketing, and I need to get better at sales or eventually bring in someone who is good at sales.

That is another uncomfortable truth.

I am not naturally good at asking for money. I do not like sales. I do not like pushing. I do not like feeling like I am convincing someone to pay me, even when I know the work is valuable. I have undercharged in the past, and if I had not undercharged, I would probably be much further ahead than I am now.

But that is part of learning.

Pricing is a skill.

Sales is a skill.

Delegation is a skill.

Authority is a skill.

Building a business that does not depend entirely on you is also a skill.

That is where I am right now. I am not at the finished version of Tomedia. I am at the version where the shape is finally becoming clear.

The retainers are starting to show me what stability can look like.

The software projects are showing me where the high-value work is.

The publishing projects are showing me how much knowledge I have sitting in my head that can be turned into assets.

The zines, books, articles, and research are showing me how authority can be built slowly, one piece at a time.

And the holiday showed me what I want more of.

I want to be able to leave without the business collapsing.

I want to be able to get sick without everything stopping.

I want to be able to take a proper holiday eventually and know that money is still coming in, clients are still looked after, systems are still working, and the business is still alive without me having to manually hold every piece together.

Will I actually stop working one day?

Probably not.

I know myself well enough to know that I will likely be doing something until I die because I cannot sit still. I like building things. I like thinking through problems. I like making stuff. I like the chaos of it, even when it annoys me.

But I want the choice.

That is the real point.

I do not want to stop because I am forced to stop. I do not want to keep working because the entire structure collapses without me. I want to keep working because I enjoy it, because I am useful, because there are interesting things to build, and because Tomedia has become strong enough that my work is no longer the only thing holding it up.

That is the transition I am trying to make.

From worker to owner.

From freelancer to infrastructure.

From agency to ecosystem.

From “Tom does the work” to “Tomedia creates the machine that makes the work possible.”

And honestly, in theory, everything is going pretty well.

The zines are coming. The books are forming. The articles are continuing. The software is there. The retainers are becoming more stable. The bigger picture is starting to make sense.

Now I just have to keep building it.

One system at a time.