That should work. There's usually a volume knob for headphones and sometimes you have to press a button to send the output to the headphones.

This DI box can be used in conjuction with 1/8"to 1/4" adapters.

https://www.amazon.com/Behringer-DI400P-Professional-High-Performance-Passive/dp/B000KUA8G6/ref=sxin_7_ac_d_pm?ac_md=2-0-VW5kZXIgJDUw-ac_d_pm&cv_ct_cx=DI+box&dchild=1&keywords=DI+box&pd_rd_i=B000KUA8G6&pd_rd_r=ba3785c2-773a-4833-aac4-c3eb157062ae&pd_rd_w=nyrwW&pd_rd_wg=nFXJi&pf_rd_p=56b8ab64-8f22-43d4-8319-4b30f162b5e2&pf_rd_r=BC0XSAZW3GQ1ADYP9WN8&psc=1&qid=1591112693&sr=1-1-22d05c05-1231-4126-b7c4-3e7a9c0027d0

This computer audio interface does the same thing without the need for the adapter (and the volume knob is handy).

https://www.amazon.com/Rapco-Horizon-LTIBLOX-Laptop-Interface/dp/B003MLFCMA/ref=sr_1_15?crid=359AYC3W6M59A&dchild=1&keywords=computer+audio+interface&qid=1591112604&sprefix=computer+audio+%2Caps%2C255&sr=8-15