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Why I keep building things on the side

31 October 2026

My week is a bit full. By day I’m the Manager, Marketing & Technology at Big Dog Builds. Around that, I’m building Cushy Digital, co-hosting Slightly Over Par with a mate, running Off The Record, and getting my hands dirty with BCW Landscaping.

People ask why. The honest answer is that each one makes me better at the others.

I think anyone who gives advice for a living should be doing the thing themselves somewhere.

Advice gets soft without practice

It's easy to tell a client what they should do with their marketing. It's harder to do it with your own money and your own time.

When I'm running campaigns for Big Dog Builds, I'm the one looking at the results each week and deciding what to change. When I'm building Cushy, I'm the one working out pricing, and I'm the one who has to explain the offer to a business owner who's never heard of me. That keeps my advice grounded. I know which parts are hard because I'm doing them too.

Each project is a different classroom

They teach different things.

  • Big Dog Builds is the day job, and a real business with real customers. It’s where I see, week to week, what works for a specialist trade.

  • Cushy Digital is the startup. It's teaching me product, pricing and the humbling job of finding out whether people actually want what you've built.

  • The podcasts taught me how to listen, how to ask a better question and how to build an audience from zero.

  • BCW is the opposite of a screen. It's physical work for real customers, and it keeps me close to the kind of business I'm building tools for.

The connections are the best part

The ideas move between them. Something I learn about lead response for a landscaper shapes how I think about the sales process at Big Dog Builds. A question that works on the podcast becomes a better question in a meeting. A pricing mistake on one project stops me making it on the next.

Running one thing gives you depth. Running a few gives you patterns.

It only works with clear limits

I won't pretend it's easy. It needs structure, or everything gets a bit of attention and nothing gets enough.

What helps me:

  1. The day job comes first. Big Dog Builds gets my full attention in work hours.

  2. Each side project has a clear role. I know what I'm responsible for and what I'm not.

  3. Not everything grows at once. Some seasons one project gets more time and the others tick over.

  4. If something stops teaching me or stops being fun, it's allowed to stop.

Should you build something on the side?

If you work in marketing, sales or strategy, I'd say yes, in some form. It doesn't need to be a startup. It could be a newsletter, a small online shop, helping a family business, or a podcast with a friend.

The point isn't the side income. It's having somewhere you make the decisions and live with the results.

The take

I don't build on the side because I'm restless. I do it because practice keeps advice honest.

The best way to understand a business owner's problems is to have a few of your own.

Common questions

Is it worth having a side project alongside a full-time job?

For people in marketing, sales or strategy, yes. A side project gives you somewhere to make real decisions and live with the results, which keeps your advice grounded.

How do you manage side projects with a day job?

Clear limits help. The day job comes first, each project has a defined role, not everything grows at once, and anything that stops being useful is allowed to stop.

What makes a good side project?

It doesn't need to be a startup. A newsletter, a small online shop, helping a family business or a podcast with a friend all work, as long as you own the decisions.

Say hello

Got an idea, a question or a guest for Off The Record?

Send me a message. If it's help with your marketing you're after, that happens through Cushy Digital.

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I work across marketing and technology, based in Melbourne. Projects, writing and Off The Record.

© 2026 Jayden WilliamsMelbourne, Australia