I wait until I have several calls that I know are going to have long holds like insurance companies or the IRS. Then I call them both at the same time, one on

I wait until I have several calls that I know are going to have long holds like insurance companies or the IRS. Then I call them both at the same time, one on my phone and one on google voice and push the buttons on both to get to the hold sequence. Typically one will answer first and you can finish with that call before the other answers. If they both answer at the same time just hang up on one. I plan on getting a sideline phone number and a second line phone number and trying this with 3 or even 4 phone numbers. The ideal outcome would be for one hold to end right after you finish with the other and you can smoothly transition between all 4 calls. However, in all reality, you'll probably end up hanging up on one or two.