Have I been bitten by the entrepreneurial bug again?

I have a suspicion that I have been bitten by the entrepreneurial bug again. After 20 months of slaving away at The Evil Empire, I have finally decided that it really hasn't been working out that well for me and that I need to "get out of my little box" and once again consider entrepreneurial opportunities. I intend to continue at The Empire for at least another year or so to finish off my current assignments and consider some part-time moonlighting opportunities during that period, but a year or eighteen months from now I expect that I will be on my own again. There are lots of interesting projects inside The Empire, but the overall style and approach just isn't such a great fit for me. There are plenty of people who fit in fine (tens of thousands of them), but I have never been much of an organization man.

I do not have any clue what sort of entrepreneurial opportunities I will pursue or even consider yet, but I do intend to keep my eyes and ears open and to be willing to be patient to wait for something which will really "sync" for me.

My initial thoughts are that within a couple of months I will seek to take on ten to fifteen hours a week of part-time work of some form. I do have to be careful that such work does not conflict with my current assignments or otherwise conflict with my employment agreement and company rules, but moonlighting is permited. You used to have to ask permission, but they changed that policy so that you do not need permission but are nonetheless expected to assure that outside work does not conflict with company policies or otherwise interfere with your work for the company.

There are four main approaches I might take:

1. Hook up with a start-up company as an employee.
2. Continue my old mode of freelance work (possibly at a start-up) to pay my bills, while contemplating my own ventures.
3. Focus on my own ventures exclusively.
4. Take a part-time job as a skill-building exercise.

There are lots of advantages and benefits to working at The Empire, including the opportunity to work with a lot of really smart people, and I will really miss them, but I find myself way too constrained (and pressured) by the organizational structure. I need a bigger box to work in. There are plenty of different boxes for a very wide range of opportunities, but each is still a relatively confining box, at least the ones that I can aspire to.

One additional option is that after leaving the company in a year or so I could in fact turn around and continue to work at the company on a contract or "contingent" basis. It is amazing how many people do this. It offers additional flexibility, albeit without a lot of the direct and indirect benefits of being a Microsoft "FTE." I do not think I will go that route, but it is an option. Sometimes, people even go from FTE to contingent and then back to FTE again in a different group. There are so many different groups within the company and opportunities are popping into existence on almost a daily basis. These really are great opportunities for a lot of people, it is just that I am not one of them.

BTW, managers at Microsoft frequently post ads in Craigslist, which is how I found my job. Also, another path into the company is by getting a position at one of the firms that supplies contract staff to the company and then apply for a FTE position once you have established a track record inside the company. Craigslist is useful for those positions as well.

-- Jack Krupansky