Freelancing on the side: Do you tell your boss?

Maybe I was fortunate in that my last boss was understanding of doing freelance work provided it didn't interfere with what he was paying me to do. He even gave the odd job to one of the team to do outside of work if it was something smaller that the business couldn't deliver within the client's budget. I even had a couple of print jobs delivered to me at work (obviously I checked whether this was ok first). To be honest though I didn't do a huge amount of freelance work at the time and it tended to be for the same couple of clients who were understanding of the fact that they couldn't normally contact me during work hours. I was open with my boss about doing this work right from when I started working there so I never kept anything secret and certainly never did any freelance work anywhere other than at home. That's not to say I told him every detail of what I was working on but I gave him enough information for him to know it wasn't a threat to his business in any way. I think it's probably that honesty that helped, plus the fact that I never allowed it to cause my standard of work to slip. In my previous job I'd kept it all secret which caused more problems than being honest about it (on the occasions I did need to speak to the client or printer during office hours I'd have to go and find somewhere to make a call in private. This looked more suspicious than it needed to – it looks like you're setting up interviews or going behind your employer's back somehow).

In short, I think a certain amount will depend on your employers attitude but perhaps more important is an honesty about what you are doing and having the integrity to not allow it to interfere with your main job. The freelance work should fit around your job, not the other way around.

I think you probably were fortunate, to an extent, my last boss particularly was slightly scathing of all the staff (great for motivation!) so I am heartened to hear that honesty paid off in your case. As you say perhaps also that 'cards on the table talk', plus just as importantly, that there was no threat in finding clients were about to be snaffled by staff moonlighting, was what paved the way to it working for you. Can't have been easy broaching the subject so good for you, it's nice to hear.