Thursday Apr 30, 2026

Should I support my employee's side hustle?

It's careers Q&A day where we give you some personal attention by answering your questions.

Today's question comes from Siân, a senior manager in a growing organisation: "Should I support my employee's side hustle?"

What we cover:

Side hustles are no longer unusual - from Etsy shops and Substacks to AI tools and freelance work, portfolio careers are increasingly common. The real question isn't whether people should have them; it's what kind of culture you want to create around ambition and growth.
Start from curiosity, not control. Before jumping to risk assessment, get into a genuine conversation: what does this give them that their day job doesn't? Creative expression, new skills, autonomy, extra income? Understanding the why opens a far richer dialogue than leading with policy.
Look for the overlap. Side hustles often build exactly the skills you'd value inside your organisation - commercial awareness, marketing, leadership, negotiation, risk-taking. If they were volunteering in the same capacity, you'd likely be enthusiastic. Notice if the anxiety shifts when money is involved.
Agree healthy boundaries together. Support doesn't mean open-ended freedom - it means an adult, collaborative conversation about time, energy, potential conflicts of interest, and use of resources. Co-creating those agreements builds trust and means you worry less about what's really going on.
Leaders who welcome this conversation tend to build stronger loyalty, not weaker. If ambition outside the business feels threatening, people will hide it. If it feels discussable, they'll stay open - and often bring that energy back in.

Send your questions: Email or voicenote to pod@thecareerequation.com

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