First time Occurrence. Go. 

There's a host of variables to that particular question.

Only the guys who live through it and then brag about it.

if it was not deliberate I would say no. We are all learning for others and our own mistakes.

If a pilot knows, or thinks they might be fired you might not hear about it. But if a pilot comes clean it becomes a training exercise. 
if the guy keeps doing it, fire them!

I know this pilot means well but I for one am sick about the attitude "about coming clean". Look, if you go IIMC do what your training has taught you and execute the procedure to get yourself home. File a report, like you are suppose to and tell your company. If your idiot management decides to fire you then the heck with them. If the FSDO that handles your company has a problem contact your US congressman and senator and ask them for help filing a complaint against that person at that FSDO office.

Our job as a PIC is to do the right thing and bring those on board safely home. If a company wants to get rid of you for doing the right thing then they're not a company and more importantly they're not the right people to work for. 

Too many managers in these companies talk the talk but don't walk the walk. They want everyone to abide by the rules but then are the first to get upset when things don't go right. 

Always come clean and you may live a happier life

Well, maybe it is. "I" could be for intentional. Anyhow, it really doesn't count if it's less than 30 seconds.

It's what happens when you don't like hearing "You coulda made it" from the Chief Pilot and then getting ceaselessly hazed. As long as there's no one else out there as dumb, you stay away from the ground, and the company can maintain plausible deniability, it's Okay.

IIMC stands for 'inadvertant' instrument meteorlogical condition. So if it was 'inadvertant' he should not.

If the pilot made a decision to climb into the cloud because it was the best option at the time and was able to recover and make a safe landing I would say, be happy you have him.

Now if a pilot goes IFR intionsionally without a flight plan, the company or FAA may go after him.

Depends on circumstamces and decisions made in those circumstances.

Next

The correct answer is "it depends."  As one poster said, the "I" could be for "Intentional," not "Inadvertant."  In that case, then "it depends."  Was it arrogance, stupidity or a calculated decision?  Arrogance or stupidity?  Absoulotely YES!  A calculated decision?  "It depends."  Why was that decision made?  Was it the best option?  You get the point.

Once many moons ago, I was in an AMRM class for one of the major HAA players.  There were pilots, medical folks and mechanics in the class.  The instructor was making the point to the medical folks that IIMC was, by definition, an "emergency" because we were a VFR program, but that it wasn't a "death sentence," because all the pilots were instrument rated and knew how to handle the problem.  One of the longer time pilots in  the program took offense to that position and told the instructor he was "minimizing" the situation.  The instructor asked the pilot if he had "ever been IIMC before," and the pilot said, and I quote him verbatum, "yeah, a dozen times!"  Folks, I submit to you that pilot was part of the problem!

BTW, a few months later, that same pilot went IMC in a dust cloud while trying to land on a scene call and dumped the collective.  He landed so hard it spread the rear crosstube and wrinkled the tailboom at the attachment point.  He actually had to be told the aircraft was damaged and to shut down! 

Unless you are flying at night. IIMC should never happen! Total lack of pilot judgement or attention.

trying to flex authority and burn a pilot.