Outside Opportunity (employment, work from home, company, pay)

[JrzDefector]

I've worked for a company that has been in some sort of start-up mode for the past decade or so. I've worked there for about 8 years and have good job security, in addition to being one of the executives' first hires. I'm fairly respected in my field, but my job is very demanding and can be pretty stressful, and the pay isn't spectacular. The upside I work from home and my co-workers are awesome, and the bosses do let me pretty much come and go as I please. However, I have never gotten a bonus.

A good friend recently took on a job at a company that has been in the international news constantly in the last few years. She had a bad experience with one of the team members who reported to her partially, and the team member was later fired for insubordination and incompetence. My friend is redefining the role of the position and outsourcing part of the responsibilities (anticipated at about 10 hours a week) - and she thought of me.

We work well together, and she is confident I have the skill set necessary to get the work done to her standards. She's in a totally different field with me, but the job isn't really all that dependent on subject matter as much as how one "packages" the subject matter. I'm intrigued.

I have no ambitions or interest in building out my resume, but for 10 hours of work, I will be grossing more than my monthly take-home pay. Essentially I would be doubling my income. The projects sound fun, and like they would be a great learning experience. The problem is that my contract (signed when I had far less experience) says I can't take outside work.

The heads of my company could easily grant permission and are people I am very friendly with. I want to approach them with the assurance that this is just a fun (but lucrative) side project, but in all honesty it WOULD also bring me knowledge and experience that I can use in my current field. Because while the other company is outside of my company's field, their product is something we use actively.

Any thoughts on how I should approach this? Doing this under the table isn't an option - I am not good at deception, and I don't want to risk the security of my current position. I just see this as a really cool opportunity I would love to try.

[jaypee]

Address their concerns as to how this project will not interfere with your current workload (esp since you're out of their sight most of the time) and assure them that your main job is a priority.

[HockeyAndRugby]

First start with looking over your employment contract. What does that say about side jobs?
Next consult an employment lawyer, so you know your rights and obligations. Then test the waters with casual conversations, without actually revealing what you want.