I was working together with a freelancer on a project here in my company for about 18 months. As he had some knowledge, that no one here had, this work was very educational for me (and in certain cases for him). Interpersonal we got along very well.

I mentioned in a Smalltalk, that I am interested in another technology, that we both do not master. I told him about my plans how I want to learn this. It came out, that he has a quite similar problem and offered me a side job, so that we both struggle through this new material in a team. We both know that, as being a newbie, a serious side income for me is not our focus. It will be more something like a “community study” with some participation fee.

I am bound to indicate any side incomes to my employer. I have not seen any problems or conflicts for an agreement, because this new task would be a program in a health service environment and I am working in the industry. But as I talked to my boss, he looked somewhat puzzled. He said that he will not (and cannot) forbid this, because I just have to indicate this side income, but do not need an agreement from him. But he does not recommend this. He fears that there might be situations in future where others may ask if I always can separate these tasks or if I can prioritize my tasks in times of heavy workload and/or trouble. He explicitly mentioned that he does not think that this will ever be reality, but if I/he/whoever needs to start explaining about some rumors, this can lead to a bad taste and in a loss of reputation for me here in my company.

Here is my dilemma:

  • Learning this technology would complement my skills and widen my view for future projects.
  • Working on a concrete project does significantly increase my knowledge.
  • It won’t be possible to make a project here with this technology as there is nothing in sight soon. May be this will be interesting for this company in 2 to 7 years from now. But I want to become prepared and recommend myself for new projects.
  • I want to keep on learning and not become rusty.
  • I do not want to annoy my boss by just ignoring his recommendation.

Our discussion is suspended and we want to talk about this on another day this week. How can I prepare myself for the next round in this discussion?

Note: I tried to keep this question generic. For those who think it will be helpful to know more about the “new technology”: I am currently programming Windows applications (WPF). The project with the freelancer was a Silverlight application and we both want to learn HTML5/JavaScript.

  • depending on your current level of knowledge of html/js, it's incredibly easy to pick up and learn. Try going to codeacademy.com. it's incredibly low-level material, but can point you in the right direction. I would also recommend learning PHP after you've got html/js down. being able to script on a webserver VASTLY improves html/js's functionality. Submitted as comment because is off topic for your question.
    – acolyte
    Commented Aug 6, 2012 at 14:14
  • 3
    What kind of agreement are you looking for, exactly?
    – yoozer8
    Commented Aug 6, 2012 at 14:23
  • 1
    Your boss already said he would not prevent you from doing it. His advice was that you not go through with it. It does not seem you need an agreement so what is it you are looking for? Commented Aug 6, 2012 at 14:47
  • Silverlight isn't a new technology.
    – Donald
    Commented Aug 6, 2012 at 19:12
  • 1
    @Ramhound I believe OP is saying that the original project that caused him to be in contact with the freelancer was a Silverlight project. He would like to learn HTML/JS alongside the freelancer.
    – Codeman
    Commented Aug 6, 2012 at 19:41

4 Answers 4


It sounds like both this side project and your current job are in the same industry, right?

If so, that may be the crux of the problem. Company's vary considerably in their approach to freelance work, but in general, the closer your project comes to day to day work, the more jumpy a company will be.

Most people who work side projects or freelance have a way of clearly separating the work. More and more, I see them avoiding the use of company resources in any way (use of personal computer, personal phone, personal software licenses, no work in the company's physical location, etc), and usually it's easy to make a distinction. It becomes harder when you've built an app for an external use that borrows heavily from your problem domain knowledge on the job - where it becomes hard to separate something that might be company proprietary from the work you've done off the job.

For ease of use, I'd say learn the tools without working in your existing industry - either with a goofy side project that has little marketable value, or something so far from your day to day work life that you have little doubt that crossover is minimal.

If not that, then figure out an agreement with your boss where it's very, very clear what is the company's and what is the side projects, in particular use of ideas and business logic.

  • No, this will not be the same industry. I am working in the automotive industry and the other project will be in health service. But your ideas are interesting. Perhaps I need to clarify my priorities and look for some totally independent project like a "goofy side" or whatever. May be it will be helpful to clarify that he will get a benefit due to my experience.
    – Markus
    Commented Aug 7, 2012 at 4:20

Just go for it. You already talked to your boss and he said you don't need an agreement. Don't press the issue and try to get one. This will make you look bad as your boss explicitly told you, you don't have to get an agreement as he probably can't give you one anyway.

And don't take the concerns of your boss too seriously, they are just a way trying you to give the company all your attention. They are also just a safeguard mechanism to say look i told you, please go back to your work.

If you look at it from the point of your boss why would he encourage you to get a side-income? You may find your new job/income much more interesting and leave or don't devote all your time to your existing job. There is no real reason to encourage you to do freelancing on the side.

Btw. don't work on company time on your side project, or use company resources like Fax, Phone, Time or e.g. Webservers or Noteobook. This is a no-no and may result in IP/Copyright problems.

  • 4
    I would just add that you should talk to your new partner, and ensure that s/he knows that your top priority has to be your full-time job. Then if the boss brings it up again (he likely won't), reassure him by saying that in the event of a conflict, your top priority is to your company, and that all parties are on-board for that.
    – jdb1a1
    Commented Aug 6, 2012 at 15:04

Please make sure any side-work or additional income is noted in writing. Even though you've spoken to your boss, it would be good to ensure this is noted in your employee file if it ever comes up again. E.g. you don't want the boss denying knowledge of your outside activities in the event something happens.

  • 1
    I don't like your and @pap negative outlook just because it shows up a risk, that I want to deny. But damn, this is something possible and I should be prepared. Thanks for the valueable hint. +1
    – Markus
    Commented Aug 7, 2012 at 12:28
  • I've been through it in my career. Since then, I've even had my employee contracts modified to allow or acknowledge "outside, non-competitive business interests" and to ensure that the company's interests come first.
    – ewwhite
    Commented Aug 7, 2012 at 12:57

Sounds like your boss has decided to take a negative outlook on this from the start, which is a bit sad. While it's a legitimate (and expected) concern that your side-project might interfere with your job duties, he doesn't seem to really give you any benefit of the doubt, flat out assuming that it will become an issue.

My advice, which might sound paranoid, is to carefully track and record time and effort spent on this side-project and your "real" job and a brief journal as well. Anytime in the future when something slips or gets delayed that you are in any way involved in, he'll blame you and your side project. If (when) that happens, you'll be well served if you have some way to show that you haven't been neglecting your duties.

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