Would You Hire Someone With a Side Business?

There still seems to be a slightly strange attitude towards employees having professional projects outside their day job. Not everywhere, obviously. Plenty of employers are perfectly comfortable with it. But I’ve also encountered the assumption that having a side business means you’re somehow less committed to your employer.

I’m not convinced.

Obviously, there are boundaries. Your side business shouldn’t compete directly with your employer, use confidential information, take place during working hours or interfere with the job you’re being paid to do. Employment contracts may also contain perfectly legitimate restrictions around conflicts of interest, intellectual property and outside work.

But once those boundaries are respected, I struggle to see why professional curiosity should automatically become a negative.

In fact, if I were hiring, I’d probably see it as a positive.

I’d rather hire the person who keeps experimenting

Imagine two equally qualified candidates.

One finishes work and doesn’t want to think about SEO again until the following morning. Perfectly reasonable. Work doesn’t have to be your entire personality.

The other finishes work and occasionally builds websites, experiments with AI, tests SEO theories, creates something, learns a new tool or tries to make a small business work.

I know which person I’d be curious to talk to.

Not because I expect employees to spend every waking hour working. Absolutely not. People should go to the pub, watch terrible television, lie on the sofa, travel, play games, stare at the ceiling or do whatever else makes them happy.

The interesting question is why doing more professionally in your own time can sometimes be viewed more suspiciously than doing nothing professionally at all.

If somebody spends Saturday experimenting with an LLM, building a website or trying to understand how a new search technology works, why would that automatically make them a less desirable employee?

Particularly in SEO and AI, I’d argue that it can make them a very interesting one.

SEO has always rewarded experimentation

You can learn SEO from courses, documentation, conferences and other people. But there’s a point where you simply need a website and permission to make mistakes.

Some of the most useful things I’ve learnt in SEO came from testing things myself.

What happens if I change this?

Can I rank that?

Will Google index this structure?

What happens if I automate this?

Can an AI workflow do something useful here?

What happens if I completely break it?

That last one is particularly educational.

Your employer’s website usually isn’t the ideal environment for satisfying every experimental impulse you have. “I wanted to see what would happen” is rarely an impressive explanation when somebody asks why production traffic has disappeared.

Your own projects are different.

They give you somewhere to experiment without putting somebody else’s business at risk.

That’s partly why I created Plain Arc Studio

I recently created Plain Arc Studio as a separate home for my independent work around SEO, AI, GEO and digital strategy.

It isn’t an attempt to secretly recreate my day job somewhere else. It gives me a place for projects and experiments that are mine: things I want to test, build or explore independently.

That distinction matters.

My employer has its business. I have my professional interests outside it. Those two things don’t inherently have to compete.

And having independent projects means I continue learning.

In fields such as SEO and AI, that matters enormously because neither waits patiently for your annual training programme.

Search changes. Platforms change. LLMs change. Tools appear and disappear. Something that sounded ridiculous twelve months ago can suddenly become part of your everyday work.

I’d rather keep playing with these things.

A side gig can tell you quite a lot about a person

If I were recruiting someone and discovered that they’d built their own little business on the side, my first reaction wouldn’t be, Oh dear, are they committed enough?

I’d want to know what they built.

Did they find clients? Build a website? Learn accounting? Make mistakes? Sell something? Deal with difficult customers? Figure out marketing? Automate something? Try something that failed spectacularly and then work out why?

Running even a tiny business teaches you things that are difficult to reproduce in a corporate environment.

Suddenly the money is real.

The customer is real.

The deadline is real.

And when something goes wrong, there isn’t necessarily another department to hand it to.

That experience can make someone better at understanding the commercial consequences of their decisions at work too.

Side businesses do need boundaries

I don’t think every side business is automatically fine.

If I worked for Company A and quietly started selling exactly the same service to Company A’s customers, that would obviously be a different conversation.

The same applies to using employer data, intellectual property, contacts, equipment or working hours for your own commercial benefit.

There are also contractual and legal considerations depending on the employer and country.

But having a side business and having a conflict of interest aren’t synonymous.

That distinction seems to get lost surprisingly often.

Someone can be fully committed to their employer during working hours and still have ambitions of their own.

Perhaps we should be more curious about curious people

I’ve always been drawn to people who make things.

It doesn’t necessarily have to be a business. It might be open-source software, a strange website, music, writing, research, a newsletter, an app, a YouTube channel or some wonderfully pointless technical experiment that exists purely because its creator wanted to know whether they could build it.

There’s something useful in that mentality.

Initiative is difficult to teach.

Curiosity is difficult to mandate in a quarterly objective.

And entrepreneurial thinking doesn’t suddenly disappear when somebody signs an employment contract.

Of course, I wouldn’t reject someone because they prefer to finish work at five and completely switch off. There’s nothing wrong with wanting a clear separation between work and private life.

But I certainly wouldn’t reject someone because they don’t.

If I had two excellent candidates in front of me and one of them had spent years independently building, experimenting, learning and occasionally failing at their own projects, I’d want to hear about it.

I wouldn’t immediately wonder whether their side gigs were a threat.

I’d wonder what they’d learnt from them.