I'm ~2 years into my own very similar transition. Be wary of too much value being placed on benefits packages, and be aware when you are signing yourself up fo

I'm ~2 years into my own very similar transition. Be wary of too much value being placed on benefits packages, and be aware when you are signing yourself up for golden handcuffs. Also, signing bonuses can tie your hands, so review the terms and be conscious of what you are signing yourself up for. If you are evaluating whether or not this is a good idea, think about your existing customers and which ones you would like to work for and which ones would hire you. Those are the people who know you best - your work ethic, your potential, etc. You might want to go outside that bubble, but the process of evaluating will make you more aware of the details about your desired environment. As a business owner, you are used to making decisions. Many individual contributor roles don't have a decision making component. It's something to seriously consider when evaluating positions. As far as the finances go, it's a whole different ball game. My health insurance costs were night and day - although the whole once-a-year chance to make changes is frustrating. Employee and group discounts can be significant. But if you aren't going to take advantage of them, you have to leave that off of your evaluation. I found online paycheck calculators pretty good at estimating income for budgeting. There is a certain level of stress associated with being self-employed and that's gone for me now. Some of it has been replaced, but overall I'm a much more relaxed person. Good luck!