Where do you see this? If you are retired, then you would select retired or enter your income as retirement income in the retirement income section. This will include the 1099-R and the SSA-1099.
Not sure where you are seeing "boxes" to check for employment. For "occupation" in MY INFO you can use whatever you want to, including "Retired"---the IRS only uses occupation for statistical purposes. If you will not have a W-2 then skip W-2's or tell the software you do not have any W-2's.
If you have Social Security benefits:
Go to Federal> Wages & Income>>Retirement Plans and Social Security (SSA1099 and 1099RRB) to enter your SSA1099.
If you have a pension or income from a retirement account like an IRA or 401k:
To enter your retirement income, Go to Federal> Wages and Income>Retirement Plans and Social Security>IRA 401 k) Pension Plan Withdrawals to enter your 1099R.