I am a first-time employer, and recently hired a freelancer for a full-time job with the job title "Need assistant for a monthly contract requiring stock trading/finance-related work".

In the job post, I said the job is assisting me in stock trading all day like tasks like research, tracking my portfolio all day long, sending me constant alerts related to my portfolio and market change, and grunt work related to trading.

I also added a small point in the work description "Any other personal assistance work."

Now I wonder where do I draw the line in personal assistance. I have many personal assistance tasks that I need frequently like "Research for a good doctor in my area for X health issue and book an appointment", "Call everyone and find who has this product available", "Look for best and cheap flight connection between these 2 countries".

Although part-time work, these tasks are completely unrelated to finance. I know a lot of white-collar workers don't like to do such thing and believe they are being treated like a servant.

So my questions are:

How do I know if my freelancer employee is okay with such work? I can try asking but I am not sure if he will say yes anyway since after all, I am his boss.

  • There are lots of 'virtual assistant' services out there to try, think it is worth investigating rather than employing people directly.
    – Webdevuk
    Apr 30, 2021 at 10:41
  • Ethically it's perfectly fine (If agreed on by both parties). Depending on your locality there may be tax/accounting implications. Business activities are a business expense. Personal stuff isn't, so you probably need the infrastructure to track, expense & pay these seperately
    – Hilmar
    Apr 30, 2021 at 11:30
  • It would seem totally normal, @CodePanda . The last time I had a p/a, the person did specifically exactly the last two items you mention. (And many other whacky tasks!) Regarding the issue "was it clear when you hired them" , it would really be impossible to know that unless we were privvy to every single communication between the two of you. Suggest you JUST ASK them.
    – Fattie
    Apr 30, 2021 at 12:45

3 Answers 3


IMO, just ask them.

Hey X, I’m looking at hiring someone to do some personal assistant work for me such as [the examples you listed above].

Would you be interested in adding that to your paid work? Just wanted to give you first refusal before I go looking externally.

The key points are:

You’re going to hire someone either way (so they don’t feel pressured to accept).

If they do accept, they’ll get paid for the increased workload.

If they do say yes, then you should draw up an actual contract and make it clear that they can terminate the personal assistant part if they decide it’s not working out.


Generally you don't write a job description that isn't clear in the hopes that you don't scare away candidates. Because it's better not to have a candidate than hire someone who quits or has morale issues shortly after joining.

So, your first recourse is to decide exactly what you do want, discount the maybe/optional/wishy washy stuff and advertise the role for what it is.

  • No one is interested in doing extra tasks outside their field of expertise like checking your dating stats etc,. they're interested in getting paid to do what is in their job description with minimum fuss. You should make up your mind if you want those things done by the staff member or not, not make it optional... hence wishy washy
    – Kilisi
    Apr 30, 2021 at 18:21

Assuming that you are paying for it, it is perfectly fine. Now if you were the CEO but not the owner of the company, and I did work for you privately paid for by the company, that's like stealing from the company and should be a reason to fire you.

Now the job I'm doing pays quite well. More than cutting the grass at your home pays. I would most definitely not cut your grass if you pay less than my normal salary. If you pay the same, I actually don't care. I quite enjoy cutting grass. I would be very expensive compared to a gardener, but if that's what you want...

As others said, just make sure this is all on board tax wise etc. For example the time where I cut the grass isn't a business expense. It has to be paid from your own, private, already taxed money. But that's your problem, not mine. And of course some people would refuse to do these jobs.

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