Many companies have policies that people can’t come back as contractors for 6 months to a year. Why can’t you drop the rope, work your reduced hours and stop picking us the slack for 4 other jobs?

It's a bad idea if you are assuming without any basis that your current employer will bring you back as a contractor. That may or may not happen, no matter how "nicely" you resign. Your company may be just as likely to simply replace you with another employee, at the same or lower cost.

People who return to their former employers as contractors have typically made those arrangements in advance of a scheduled retirement.

Don't forget to plan financially for the impact of self-employment taxes; you're not going to net your hourly rate even without the deductions you are used to for various kinds of insurance. You'll also lose any employer match to a 401(k) or other self-funded retirement plan.

I’m a VP at a big company. I’m facing health issues where I have to slow down. My company will not accommodate my needs. Part of the issue is they have not allowed me to backfill 4 empty positions on my team. Even though HR agreed to “reduced hours” there is no one to pick up my share of the load — and I’ve been covering those junior jobs too. I can’t put anything more on my existing team - that’s not fair to them.

I’ve been interviewing elsewhere, even a step down and less money, but nothing has closed. The clock is ticking.

I had a crazy idea to nicely quit and then see if I could be a part time contractor. I was a SME earlier on and that skill set is much needed at my company and others. I don’t need benefits right now.

How bad is this idea?