I had the luxury of working for the great Bill Connor at NBC Guest Relations for five years. There were many great things about working for Bill (the trust he had in his employees, the care he had for the page program, his even-keel temper when problems would arise), but one of the most impressive things about him was his flexibility when it came to vacation time. Anybody who knows me knows I’m not the type to abuse vacation (or even take too much of it), but Bill was always very gracious about granting vacation requests for his employees.

And my superb co-worker, Catherine Caudle, and I had it down to a science. When she was gone, I’d cover for her. And when I’d go on vacation, I knew she’d cover my job without a problem.

So imagine my surprise when back in October of 2011, Bill and Catherine gave me a look of death when they realized I would be on vacation when the President would be coming to visit. I had put in a request months earlier (almost the beginning of the year to be exact), telling them that Kelly and I would be making our annual trek to visit her family back in Illinois.

And it was just fine. No problem. Go have a great time, Raf.

That was, until it was revealed sometime during the second week of October that Barack Obama would be making a surprise visit to The Tonight Show. Mind you, it's all pretty standard to see Presidents appear on talk shows now (#ThanksObama), but this was the same President who made headlines only two years prior by becoming the first sitting President to make a guest appearance on a late night talk show. I'm almost positive it'll likely be a standard of some sort going forward, but any time a President makes an appearance on any show (especially one with a giant audience), it takes a giant team to help make it happen.

Nonetheless, my absence was not met with a ton of enthusiasm.

“That’s the week I’m on vacation,” I said.

“No,” Bill said with a stunned look on his face.

Catherine’s eyes bugged out. This was not okay, she thought. Me gone meant that all of my usual day-to-day tasks would unfairly fall on her.

“I’m really sorry,” I said, “I planned this vacation months ago and they’re just announcing this now?”

Bill, ever the optimist, only took a few minutes to find his trademark lawyer cool, “I’m sure we’ll be okay,” he said reassuringly, as Catherine’s eyes almost stretched out of their sockets.

Naturally, I was bummed that I’d miss my opportunity to see the President who I had campaigned and canvassed for. And sure, it’d be nice to see him and Jay interact on stage, but I had met him a couple times during his time as a senator in Illinois. It was a minor bummer, but like any guest booking on the show, I just shrugged and said, “it wasn’t meant to be.”

The next few days, not wanting to let anyone down, I walked the President’s secret service through every detail of the audience procedure -- getting many in his staff to compliment our show’s efficiency and “military-like precision” (their words, not mine). When it came time for me to head out for vacation, I went up to Bill and Catherine and told them I did all that I could to help get them ready. They told me to “not worry about anything and go enjoy my vacation.”

Which I can’t do. I’m a bit of a workaholic and leaving my team made me feel uncomfortable.

I happened to be flying out the morning of the taping (one of the rare times we would ever tape in the mornings). It took everything in me not to message them until I knew they were completely done with the show.

By the time it was all said and done, I used my free wi-fi from the plane to send them an email and ask them how the show went. I had a bad feeling and I had a whole four hour flight to think of the worst.

Hopefully, I thought, they’ll just send me a quick note back that said, “all good, have fun.”

When Catherine, normally lightening fast with her email response time, didn’t immediately respond. I knew my instincts were correct. Something was up.

It wasn’t until we were about to touch down in Illinois, nearly three hours after I sent my message, I got a response back from her saying, “Terrible. Everything went wrong.”

“All right then,” I thought. “This is my nightmare.”

You see, at the Tonight Show there are very few days anything really goes wrong. Sure, it’s a daily show with a rapid turnaround time for the 180 people on staff. And the production staff and crew certainly have their work cut out for them, but many of the folks have been working there for so long (almost 20 years by that point), that just about everybody could get out of work at a reasonable time. Jay kinda insisted upon it.

However, when it came to audiences, there were very few days something would go wrong.

An occasional small fire here and there: a headache audience member, a staff member who had a few demands or a guest who was requesting a few last minute seats for no good reason. But very few days something, let alone EVERYTHING would go bat-shit wrong.

Sadly, for whatever reason, the audience gods were not on the side of NBC Guest Relations. From rain delays to missing audience members to people getting lost to staff members being called to fill seats. You name it, it happened. It was such a mess that even Bill -- perhaps the leading expert in all things audiences -- couldn’t be even-handed when he responded, “yeah, it was basically a disaster.”

Granted, not like my being there would have changed much. I just would have been another hand on deck to help mitigate some of the problems (at least, that’s what my brain likes to tell itself).

So by the time I came back from vacation to check back in with Catherine and Bill for a report on the damage, they walked me through the progression of unfortunate events with each additional detail making me wince just a little bit more. By the time they finished their full account of the events, both of them also recounting exactly how much alcohol needed to be consumed to ease the pain, they ended by saying, “you are NEVER allowed to go on vacation when the President is coming to the show.”

They were not joking.

Literally any time I put in for a request for vacation from thereon out, Bill would respond, “... that’s fine, as long as the President isn’t coming to the show.”

During my tenure at the show, the President would come back to visit us a couple more times (both without incident). And both times, we got high marks from his staff (one secret service member even deputized me, see photo attached). Hell, I even remember taking photos of the President’s secret service with Jay after the show (the two people who were designed to “blend in” with the audience were the best old guys passing as young surfer dudes I have ever seen).

So I know there are many who put up memes that say #ThanksObama in jest, but I have two co-workers who can literally say that without batting an eye. They lived it (and lived to tell the tale).

On this night, however, I thought it might be nice to share this little piece of my late night history as a number of my friends recount their favorite President Obama memories. Historians and critics will have plenty to say about his legacy, but this story aside, I’m glad to have voted for him twice. I’m happy I printed out a photo in the Illinois State University speech lab, predicting his presidency in 2004, the day after John Kerry’s lost the election to President Bush, proclaiming that Barack Obama would make a legitimate run at the presidency with Oprah (which, totally called it). I’m glad I was able to get my dad the best seat in the house at The Tonight Show when he came back to the show the next time (the old man actually got dressed up in a suit and tie “Because President…”). I was happy he fought for many of the things I also believed in and that he always strived to inspire Americans -- even the ones who didn’t vote for him. And I’m happy that we got to call him President for eight years.

But we’re cool now, Mr. President. Even though you put my boss, my ace co-worker, and many of my pages through hell the one time I ever dared to ask for a vacation.

Here’s hoping you continue the fight.

Thanks Obama