Sometimes, it's "good trouble" to be anti-authoritarian unless you live in a dictatorship.

I say, if the record doesn't already exist, make them do their due diligence to discover the "lie." Then, if they do, apologize and provide all documentation. I've lied on forms with serious jail time as a deterrent, went to the admin hearing and lost, and called their bluff - no jail time or fine. I challenged the validity of enforcement to force the government to show how well/poorly they are able to uphold ridiculous rules. It was inconvienent and cost the taxpayer money, but it felt really good fighting ridiculous regulations.

So, don't crash, collect SSA disability benefits, or commit identity theft and they won't catch the lie, got it.

Also, "If you make an inadvertent oversight, and the FAA picks up on it, a letter of explanation and supportive medical documentation will usually resolve the issue before it gets out of hand." - Worth a try to get away with it first and ask for forgiveness afterwards.

For example, unless they scan your brain for indications of lying, why admit to using cannabis in a legal state? If you're not under the influence at the time of flying, it shouldn't matter if you have a trace amount attributable to rubbing cannabis lotion on your sore muscles from a ski trip a few weeks prior. Sometimes, regulations (like the prohibition of cannabinoids) is not based on sound science, rather anecdotal evidence, shotty tests on rats, and the holy word of Harry Anslinger and Richard Nixon. - this argument applies to the Olympics, too.

*** Exceptionally Bad Advice

Pilots have recently gone to jail for lying on their medical application.

If you concurrently contradict yourself in other gov records that makes the prosecution very low hanging fruit and while I agree that's more dangerous than simple non-disclosure there's no guarantee that they won't prosecute if they can document the case with medical records, etc.

Also, the FAA can emergency revoke all of your certs and that's much easier than making a federal case.

Don't go there.

Two posts and you're already in deep...advocating both fraud and falsification on a federal form. Substantial penalties are attached.

Don't you dare quote John Lewis and muddy his advocacy for "good trouble" with what you're professing; drug use, lying, cheating, falsification, fraud, and a federal crime. That's not "good trouble." It's a crime. A very clear crime. It's also an outstanding way to torpedo a career. Permanently.

If you can't be trusted to fill out a god damn form correctly, how in the hell can you be trusted to pilot an aircraft? Good god. Do you think before you write? Obviously not well. Try again.