In August of 2017, we were given a speaking spot by Politicon, a conference at which we'd previously brought Ed Snowden back to US soil, to enormous acclaim.
This time, obsessed with how to win back our country from the newly autocratic Republican party, we asked Politicon to promote our appearance as an official Democratic Party event, and they agreed. What we wanted to do was use humor to promote the fact that if the Democrats really wanted to win elections in the future, they should abandon their corporate partners and adopt a populist platform.
We did our research, built our dream planks for the Democrats' new platform, and wrote up a talk to announce it as well as an announcement with research links, to spread it far and wide. We were ready.
Then, by sheer coincidence, a few days before our scheduled slot, Sen. Chuck Schumer, the Dems' leader in the Senate, announced a new "populist" platform that would supposedly respond to the new populist political moment. It didn't, not even slightly—but we emended our talk to include a reference to that platform, and said that a few "minor" details had been left out of Schumer's announcement: Medicare for All, Universal Basic Income, etc.
We expected planted two questions to come after this momentous 10-minute announcement, and expected to be laughed at and have to explain our reasons for doing this... but instead we received question after question after question, and Andy had to improvise for another 40 minutes. Afterwards, even libertarians approached us with glee—saying their version of UBI was quite different from ours (phew!) but at least we both saw it as necessary.
We realized from this experience that it might be time for a different approach to politics, and that satire might not be the answer... but then we kept on making the same mistake again and again and again. (See the main "insight" we gained.)