As the saying goes “do what you love, and you’ll never work a day in your life”. But is really it that simple? For those who have taken this adage to heart and decided to turn a loved hobby into their livelihood, it can potentially end up being a decision you regret.
According to psychologist Eloise Tomkins, monetising one of your hobbies isn’t just a financial decision; it’s a psychological one. Tomkins has dedicated over a decade to working in mental health, including with high-performing professionals navigating anxiety, burnout and major life transitions.
“One of the biggest advantages of monetising a hobby is that you already care about the work, and that authenticity is often what initially attracts people,” Tomkins says.
“The flipside is that once money enters the picture, the relationship changes, and it’s no longer just about enjoyment. There’s pressure to make money, meet other people’s expectations, and keep things moving even when motivation is low or life gets in the way.”
“If someone hasn’t built the capacity to tolerate uncertainty, rejection, or slow progress, stress and burnout tend to appear quickly.”
Another key element to examine is how closely you tie your self-worth to your work.
Without contingencies, the stress of thinking “this has to work” can quickly overwhelm the passion that motivated you in the first place.
“When a hobby is deeply personal, things like pricing decisions, client feedback, or rejection can feel like a judgment of the person rather than the product. As a result, people often undercharge, avoid raising prices, overdeliver, or take rejection personally instead of treating it as normal feedback that can be used to strengthen your business”.
Prospective or new business owners should try to ensure that a love for what they do doesn’t dominate decision-making, so business decisions can be made strategically, rather than emotionally.
When it comes to pursuing a hobby as a side hustle, it’s not just the extra hours that might make you tired – but the mental load. “People often plan for work time but forget about the administration, marketing, decision-making and the cognitive effort to switch roles after a full workday,” Tomkins says.
Another side hustle trap is dedicating every spare moment you have to it. This can drain the joy and passion out of the very thing that once felt exciting and fun.
“A useful question is, ‘what am I willing to deprioritise to make space for this?’ If the answer is ‘nothing’, then stress and burnout are almost guaranteed,” she says.
For people looking to find a new hobby with the intention of to eventually monetising it, the question isn’t just “can this make money?” but “would I still enjoy this if it took longer than expected?”
Tomkins shares she’s seen many people start businesses they weren’t genuinely interested in because they assumed it would be easy money.
“Monetisation almost always takes longer and feels messier than people expect. If the interest isn’t genuine, it becomes very difficult to stay motivated once the novelty wears off and the income isn’t flowing as easily as anticipated.”
How to side hustle effectively
Tomkins encourages having clear boundaries and protecting some rest and recovery time. “Ironically, it’s this very downtime and relational space that supports creativity, problem-solving, and long-term motivation.”
Then, there’s taking the leap of quitting a job to make a hobby a sole source of income. The two major ingredients needed? Grit and belief.
Tomkins works closely with women who are capable, driven, and competent, but find that money decisions trigger stress, avoidance, or self-doubt.
“I’ve seen many women in business face pressure from partners or family to return to a ‘real job’ even though building a sustainable and profitable business takes time. That external pressure can create self-doubt and guilt if someone isn’t prepared for it,” she says.
“Without contingencies and support in place, the stress of thinking ‘this has to work’ can quickly overwhelm the very passion that motivated the leap in the first place.”
Even if you don’t know how things will go, there’s one inevitability: you’re going to need to learn how to speak a base level of tax and business – even if you’re not interested.
”It means planning for things that traditional employment automatically covers, like sick leave, annual leave, inconsistent income, and periods where your effort doesn’t immediately translate to results.”
If you’ve made it through this, you’re not deterred, and you’re eager to charge forward, think about consulting an accountant upfront. They’ll be able to help advise whether to set yourself up as a sole trader or a company. The ATO website also offers information on both routes.
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