I run three side hustles and I am uncomfortable when my own people have one. I am not proud of holding both of those positions, and admitting it is the only honest starting point for anything useful on this subject.
Mine are a heritage railway preservation association I chair, a board seat with a South African non-government organisation, and an online shop importing American everyday carry products, which I took over from my father. The last one involves selling keyrings. Yes, exactly the kind of boring business YouTubers have become so interested in lately.
Set against that, here is what I think as someone who pays people’s salaries: a team member with a side hustle demonstrates ambition, curiosity and the organisation required to run two things at once. I also like knowing that when I pay somebody, they are entirely with me and my projects.
Both of those sentences are true and they contradict each other. Most writing on side hustles resolves that tension by picking a side, usually the employee’s, which is comfortable and useless. I want to keep the contradiction and work out where it actually comes from, because the answer changes what an employer should be asking.
| The usual framing | Why it goes nowhere | Where the tension comes from |
|---|---|---|
| Loyalty against freedomDiscussion of the side hustle divides into two camps. One treats outside work as evidence of divided commitment, and the other treats any restriction as an attack on personal freedom. Both positions are stated with confidence and neither settles anything. | Two true statements in conflictOutside work genuinely signals ambition and organisation, and it genuinely divides attention that somebody is paying for. Employers and employees each quote the half that suits them, which is why the argument repeats without progressing. | A bargain that changed on one sideBenjamin Chaminade’s position is that expected exclusivity was one half of an older exchange offering security in return. Where that security has been withdrawn and the expectation retained, outside work looks less like disloyalty and more like a contract being repriced. |
What counts as a side hustle
A side hustle is any secondary activity run alongside a main job, generating additional income or pursuing an interest. It differs from a second job in flexibility and in intention, since the person controls the time, the resources and the direction. Financial return is frequently the smallest part of what it produces.
It is not yet the norm in Australia, and it has become common enough that treating it as an exception is a management error.
What separates a side hustle from a second job
Part-time work for another employer trades hours for money on somebody else’s terms. A side hustle is built around the person’s own interests and objectives, which is what makes it a development activity rather than only an income one. That difference matters when you are deciding how to respond to it.
It also functions as a low-risk test bed. Someone can try a business idea without leaving the security of employment, learn what fails, and refine the offer before committing.
The skills travel in both directions. Pricing, negotiation, customer service and supply chain problems teach things a job description rarely covers.
My three, including the one I inherited
The shop was not my idea. It is my father’s business, launched in the nineteen eighties, and I would never have picked it up without his insistence. I took it seriously once I understood the brand, which comes out of American railway history and is owned by its own employees, an arrangement that is not especially common in California.
There is an odd symmetry there, since the association I chair preserves a narrow gauge railway. I did not plan that either.
The board seat is the one that looks most respectable and takes the least time, which tells you something about how these things are judged from outside.
Moonlighting, and the opportunistic version
Moonlighting describes the shorter, more opportunistic form: paid work taken on the side without any long-term intention behind it. It is not the same animal as a business someone is building, and conflating the two is where most workplace policies go wrong. One is an income patch and the other is a career decision.
The distinction matters practically. A policy written to stop moonlighting will also stop the activity that develops your people.
Where this connects to a wider career design question, I have written separately about building career option capital.
The employer’s honest position
Most business owners hold two views on this at once and only say one of them out loud. Outside work demonstrates qualities you would pay to develop, and it also removes attention and energy from something you are funding. Pretending only the first is true makes for better copy and worse decisions.
I would rather set both out and then look at why they conflict.
What it signals in somebody’s favour
Running something alongside a job requires initiative nobody asked for, the organisation to hold two commitments, and a tolerance for uncertainty that most roles never test. Those are the qualities employers say they want and cannot easily assess at interview. Somebody with a functioning side project has already demonstrated them.
They also arrive with a network you did not pay to build, and with customer-facing experience that is difficult to acquire inside a large organisation.
I have hired people partly because of what they were running on the side, which sits awkwardly beside the rest of this article.
What it costs the person paying
Attention is the cost, and it is real rather than theoretical. Anything that needs regular maintenance competes for the same finite hours and the same recovery time, and the effect shows up in judgement rather than in output. Tired people still deliver, and they decide worse.
There is a second cost that employers rarely name. Somebody with an alternative income has less to lose, which changes the negotiation.
Naming that honestly is uncomfortable, and refusing to name it produces policies dressed up as concern for wellbeing.
Why I hold both views at once
The contradiction is not hypocrisy so much as a leftover expectation. I inherited a model of employment in which the employer’s claim on somebody’s productive capacity was total, and I have never examined the terms that claim originally came with. Most owners have not either.
Once the terms are on the table, my discomfort becomes much harder to defend, which is the useful part.
That examination is the rest of this article, and it is aimed at owners more than at the people who work for them.
Exclusivity was one half of a bargain
The expectation that somebody’s working capacity belongs to one employer came bundled with something in return. Progression inside one organisation, a long horizon, and reasonable protection from the consequences of a bad year. Exclusivity was the price of that security rather than a moral property of employment.
Read it that way and the current argument looks different. One side of the exchange has moved substantially and the other has not.
What employers used to offer in exchange
The older arrangement offered a career inside one organisation, training paid for by the employer, promotion by tenure, and an implicit understanding that loyalty was reciprocal. None of that was universal and it was real enough to justify the expectation attached to it.
What made exclusivity reasonable was the length of the horizon. Committing everything to one organisation made sense when that organisation was committing to you for twenty years.
Remove the horizon and the same request becomes a demand for an unsecured investment.
What was withdrawn, and what was kept
Australian working arrangements make the withdrawal measurable. The ABS counts 2.4 million casual employees, 19 per cent of all employees, alongside 1.1 million independent contractors, and 17 per cent of employees hold no minimum guaranteed hours at all.
Add restructures as a routine management tool and career progression that now runs across employers rather than within one. The security half of the exchange has been substantially reduced.
The exclusivity expectation survived all of it intact, which is the part worth explaining rather than defending.
The question that replaces asking whether to allow it
An owner’s useful question stops being whether to permit outside work and becomes what they are currently offering that would make exclusivity a fair trade. Guaranteed hours, a visible progression path, funded development, and protection from the first restructure are all answers. Vague talk about culture is not.
Answer it honestly and you will know whether your discomfort is a legitimate commercial concern or an inherited reflex.
Mine, on examination, is mostly the second, which is why I have stopped raising it with people who work with me.
The Australian version of the question
Australian employment adds specifics that change the practical answer. Contracts commonly address secondary employment, intellectual property and conflict of interest, and the tax treatment of a side activity depends on whether it amounts to a business. None of it makes outside work impossible, and all of it rewards checking before starting.
I am not a lawyer and this is not advice. It is a list of the things worth reading before you find out the hard way.
Contracts, conflicts and intellectual property
Three clauses matter most. Secondary employment provisions may require disclosure or consent, intellectual property clauses may assign anything you create during your employment to your employer, and conflict of interest provisions apply whenever your side activity touches your employer’s market or customers.
The intellectual property clause is the one that surprises people. Some are drafted broadly enough to reach work done on your own equipment in your own time.
Read your own contract rather than a summary of somebody else’s, and take proper advice where the side activity is close to what you do at work.
Where the line sits between a hobby and a business
Australian tax treatment turns on whether the activity is a business rather than a hobby, which affects income declaration, deductions and registration obligations. The distinction depends on intention, scale, repetition and how commercially the activity is run rather than on how much it earns.
Selling occasionally at a market sits differently from running a store with suppliers, pricing and a marketing plan.
Check the current position with the Australian Taxation Office or an accountant before the first year closes, since retrofitting the paperwork is unpleasant.
The right to disconnect changes the arithmetic
Australian law now recognises an employee right to refuse unreasonable contact outside working hours, and that has a direct bearing on this argument. An employer whose model depends on informal availability in the evening has been relying on time it does not pay for, which is exactly the time a side activity occupies.
The two questions turn out to be the same question. Whose hours are those, and what were they exchanged for?
Organisations that treated the change as a compliance exercise missed the useful part. It draws a line, and a line makes the remaining exchange visible to both sides for the first time in years.
The legal effect varies by circumstance, so take advice on your own position rather than mine.
Field note
The hours nobody warns you about
The hardest part of my own side hustle has nothing to do with strategy. It is packing and shipping orders, which takes several hours every week and cannot be moved, batched away or delegated cheaply. Customers order when they order, and a parcel that leaves three days late generates a message I then have to answer.
Everything else about the shop taught me something I use professionally. Importing meant learning customs regulation and building relationships with logistics specialists. Building trust with customers in a market that had never heard of the brand meant transparent communication and answering every complaint personally. Pricing, competitive analysis, supplier negotiation and web usability all became things I had done rather than things I had read about, and I now use the shop as an example in sessions on business models. The shipping, though, is just work. It sits in the same part of my week as everything else that has to happen whether or not I feel like it.
The operational lesson is to identify the unglamorous recurring task before you start, because that is the one that decides whether the side hustle survives. Anyone assessing their own capacity should count the maintenance hours rather than the interesting ones, and any employer worried about divided attention should ask about those hours specifically rather than about ambition.
Telling your employer, or not
Disclosure depends on your contract, your organisation’s policy and the relationship you have with the person you would be telling. Transparency builds trust and clarifies conflicts early. It also invites a judgement you may not want, from somebody who may read ambition as divided commitment.
What follows is decision support rather than a recommendation, since the right answer genuinely varies.
Four situations compared
Read the third column first. In two of these four situations the decision is made for you by the contract rather than by preference.
| Situation | Considerations | Practical position |
|---|---|---|
| Side activity in an unrelated field, no contractual requirement | No conflict, no disclosure obligation, some risk of misreading | Your choice, and disclosure usually costs little |
| Side activity in the same market as your employer | Genuine conflict of interest and possible IP exposure | Disclose, and take advice before starting |
| Contract requires disclosure or consent | The decision is contractual rather than relational | Disclose, in writing, before you begin |
| Relationship with your manager is poor | Disclosure invites scrutiny you cannot control | Check the contract, then keep the activity clearly separate |
What to settle before the conversation
Prepare three answers before you raise it. How many hours it takes and when, how you will prevent any overlap with your employer’s market or customers, and what you will do if the activity grows. Arriving with those settled turns the conversation from a confession into a briefing.
Employers respond badly to vagueness on this subject and reasonably well to specifics, in my experience on both sides of the desk.
Where the relationship needs work before any of this is possible, the underlying question is about internal standing, which I cover in building influence inside your organisation.
Work out how much attention you actually have
Wondering whether you can carry another commitment? Read my method for designing a sustainable career and count the maintenance hours before you add anything.
How I work with organisations on this
I work with owners and executive teams on the exchange rather than on the policy, because a secondary employment clause is a symptom of what the organisation can or cannot currently offer. That runs as a keynote, a facilitated session with a leadership group, or a short review of what your people would lose by leaving.
The opening question tends to unsettle a room. What are you offering that would make exclusivity a fair trade?
Keynotes and leadership sessions
A keynote suits a leadership event where the group needs the bargain argument before writing or defending a policy. A facilitated session suits a smaller group willing to answer the question above with specifics rather than with statements about culture.
Sessions run in Australian English with Australian data, including the working arrangements figures used earlier in this article.
I use my own shop as a worked example, which makes the trade-offs concrete and costs me some dignity.
Reviews and policy work
A review suits organisations drafting or revisiting a secondary employment policy, where the useful output is a position they can defend rather than a prohibition they will not enforce. Policies that ban outside work without addressing what the organisation offers instead simply get ignored.
The connected question is what the management layer is actually for, which sits in my work on the management of tomorrow.
I will also tell you when your real problem is pay rather than attention, which is a shorter conversation and less comfortable.
Conclusion
I still feel the pull of wanting people entirely on my projects, and I now recognise it as an expectation I inherited rather than one I earned. Exclusivity was the price of security, and most organisations stopped paying that price some time ago while keeping the invoice.
So if a side hustle in your team bothers you, work out what you are offering that would make going without one rational. The answer is either specific or it does not exist.
And if you are the one running the side hustle, count the shipping hours before you count the upside. That part does not appear in any of the articles encouraging you to start one, including, until now, mine.
Frequently asked questions about having a side hustle
Do I have to tell my employer about my side hustle?
It depends on your contract. Many Australian agreements include secondary employment clauses requiring disclosure or consent, and conflict of interest provisions apply whenever the activity touches your employer’s market. Read your own contract rather than a general answer.
Can my employer own what I create in my own time?
Some intellectual property clauses are drafted broadly enough to reach work done outside hours on your own equipment, particularly where it relates to your employer’s business. This is the clause people most often overlook, and it warrants proper advice.
Should employers allow side hustles?
The more useful question is what the organisation offers that would make exclusivity a fair exchange. Where guaranteed hours, progression and funded development are absent, a prohibition is difficult to justify and harder still to enforce.
When does a side hustle become a business for tax purposes?
Australian tax treatment turns on intention, scale, repetition and how commercially the activity is run rather than on earnings alone. Check the current position with the Australian Taxation Office or an accountant before your first year closes.
What is the most common reason a side hustle fails?
The recurring unglamorous task, usually fulfilment, admin or customer service, which cannot be delegated cheaply and does not respond to enthusiasm. Count those hours before starting rather than counting the interesting ones.
