How to use your side-hustle to propel your career, not crash it.

Stephen Pratley
4 min readSep 21, 2022
image by Andy Hermawan

There’s an idea that having a side-hustle, a second income source is always in conflict with your day job.

There are plenty of stories about people getting fired for expressing public opinions about issues that are in conflict with their employers, and somehow this had been blown up into the idea that anything you do outside work is a conflict.

But your employer would have to be seriously short-sighted to cut off every learning opportunity like that.

There might be a few of the terrible middle-manager types who are jealous that you’re not reliant on them for a paycheque to survive, that their grip over you is weakened, but even if that’s the case, picking the right thing to work on can get you promoted ahead of these individuals, or find you a way out form under them.

Because picking a side-hustle isn’t about the money, it’s about growth.

As an employer, I would actively look for people who used their skills outside the workplace.

I had an ecommerce designer with a sideline in creating album covers, a developer who ran the technology for a dog shelter, another designer who illustrated gift cards.

None of these competed with the work they did for me. All of them showed an obsession with their craft, and brought new ideas into our business.

The best ideas happen when different fields clash together.

Music & design, charity & technology, art & celebration.

Relying on your day job to get you to the next level is a slow slow process. Taking your learning outside your current role can be a far better way to grow.

Your side-hustle should teach you the skills you want for your next career step.

In each instance my team had found something they wanted to do, and instead of trying to persuade someone to give them a job doing it, they’d turned to friends & charities to get some experience.

Now i’m not a big fan of working for free to get experience. You won’t usually find good clients this way, but here’s one advantage — you’ll have to focus on a real problem and see it through to the end.

Making up your own portfolio pieces is a pretty good way to get started, but it’s easy to dodge the hard parts. When you’re accountable to someone else, even just for a testimonial, you have to tackle real problems in real world situations.

With just one good piece in their portfolio, they were able to approach other people and say “I know how to do this. I have a process. Here’s the proof.”

Here’s a few tips about how to choose your market which will help, whether you’re learning the skill for your day job or for a career move.

Tip #1: Make it about something your employer hasn’t taught you. This isn’t just about avoiding conflict, it’s about growth and motivation. If all you do is the same as you do at work all day it’ll exhaust you. A side-hustle should energise you with the new learning.

Tip #2: Keep it separate from your employer’s audience. This one IS about avoiding conflict. Unless you’re very careful about staying anonymous (and there’s only a few platforms you can get away with that), keep your work and your job separate.

Tip #3: Keep the audience broad. When you’re learning a new skill, picking one that can be used outside of your current employer is a good way to bullet-proof your job-security AND find a wide market for it.

For example, when I wanted to get in to email marketing, I worked on learning automated email campaigns. A very specific skill, but one that can be used for ecommerce, information products, services and probably plenty of others as well.

Great side-hustles are about growth as much as money

I built my own list and ran my own email campaigns for several years before I quit my job and started my first agency. I made job moves that multiplied my salary, giving me the cash runway to eventually quit altogether. You might not even want to leave the security of your job.

People who leave their development in the hands of their employers will fall behind the ones who take it on themselves. People who think that learning is just reading & listening will never really gain the experience of the people who put it into action.

Pick a project that’s where you want to be in your career, and it’ll give you the chance to either take your job a huge step forward, or maybe even turn it into your next career move.

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Stephen Pratley

Marketing for experts with something to share. Get weekly campaign breakdowns at stephenpratley.com