1099 is a great transition if you can swing it, both from the perspective of finding work and being able to weather potential increase in volatility of earnings. The benefit of the employment relationship is generally income smoothing, but if you can tolerate additional risk (after perhaps building savings cushion), then the tax benefits and greater take in total compensation are worthwhile. I was at that stage in my previous career, but stepped away for academia...once done with this i'd prefer either being an entrepreneur and/or 1099 contractor.