You should consult your tax adviser for tax advice. We will work hand-in-hand with your CPA or tax adviser to make sure everything is coherent and everyone is on the same page.

Your taxes have the ability to change significantly. You will be responsible for calculating your own taxes and making quarterly estimated payments if you become self employed or become a "1099 contractor" for someone. You will also have to pay the corporate side of your payroll taxes, if you start working for yourself.

You will want to continue to save for retirement, but it will look a bit different. If you open your own business you can open a solo 401(k) if you or you & your spouse are the only employees, if you have additional employees, getting a group 401(k) has become much more simple and affordable that it used to be. We can help you with this setup process and on-going maintenance.

Depending on your situation, we might suggest an IRA rollover, especially if your 401(k) plan has a lot of fees attached to it or has a limited number of investment choices.

When you leave an employer, you have the option to go on COBRA, but it's expensive. Depending on what your next move is, you can either get a group policy (if you are going to a small business that has enough people to create a group) or you can get an individual policy. Even ssme college alumni associations have group health, disability, and life insurance.

Most, not all, group life plans have coverage ending when you leave. However, some corporate group life plans have a portability option. Look through your group benefits plan document to see if your coverage is portable.

For disability, we have never seen a portable group disability policy. Therefore, it will be important to obtain individual coverage.

This is where the phrase "your health is your true wealth" rings true. As you step away from the group policies, you will want to replace them with individual policies if you are not going to another employer that has them and thus, will need to be in good enough health to obtain them on your own. If you are going to start your own business, you might be joining a trade association that has a group policy available as part of your membership (this is actually how Will, the owner of HFP, has his disability policy). Some alumni associations offer access to group life and disability, but the coverage amounts and terms vary widely.

Most of the time, any unvested amounts are forfeited. There might be special circumstances where you are awarded the full value of your equity compensation at departure. Bottom line: don't count on keeping any unvested equity compensation such as RSUs or ISOs.