There is nothing like the excitement of an impending trip to Las Vegas. 

While every part of the process is fun, there are distinct stages that I enjoy. Here’s my routine:



For a logistics nerd like me, booking the trip is half the fun. 

I always book my dates on Southwest immediately, periodically checking if the fare has went down in the weeks leading up to my departure. I’m often able to get a decent chunk of frequent flier miles back, which helps make the next trip possible.

Logging in to all of the players clubs, comparing room rates, comparing them against the baseline, and finding the best deal is satisfying. I’m often able to save hundreds of dollars here, which my degenerate brain rationalizes as free bankroll.



Once the flight and room are booked, I think about what my trip will include. I add whatever ideas I fancy to my ever-growing list of possibilities. I typically plan for one anchor event each day, and deliberately leave the rest of the day free. Also, all plans in Vegas are subject to change, which is why the list keeps growing.

Knowing that I will stay up late and sleep in (at least until the realization that I’m in Vegas dawns on me), I won’t plan anything until the afternoon. I usually eat a snack for “breakfast”, and one big meal at the socially accepted dinner time.

The anchor event gives me guaranteed enjoyment and +EV outside of the casino, while also providing ample time to ride the waves of degeneracy and debauchery; it also gives me a socially acceptable safe-for-work answer as to why I’m going back to Vegas.



In Vegas lent, I do my best to forget that I have a trip coming. I know that may sound counterintuitive, but I find that time slows to a halt when I’m excited for a Vegas trip. So keeping it out of mind as best I can helps get me there quicker.


Binging FHBM

Once I realize a trip is imminent, I catch up on my backlog of Five Hundy By Midnight podcasts. I inexplicably quit listening when I return from a pilgrimage, so the first episode of my binge always concludes with my karma donation. Hearing Tim (and sometimes Michele) discuss my note always brings a smile to my face and reminds me that a trip is imminent.


Check In

As an almost-exclusive Southwest flier, I always have a calendar reminder set for 24 hours before my departure. The day of, I set an alarm for 1 minute before check in opens. When I’m 2 seconds away, I open the app. If I time it correctly, the button is yellow and I’m able to check in immediately. If I’m a bit overzealous, I have to pull down to refresh, and the loading wheel spins agonizingly slow until the yellow button appears to my relief. If I get a Bingo number (B1-15) or better, I’m happy.



No matter the trip, I always pack the night before. I make a list in the lead up to the trip to make sure I don’t forget anything, but I don’t put it in my suitcase (a trusty brown REI roller that has served me well since high school) until the night before. 


Cleaning the House

Once I’m packed, I clean up the house. I do the dishes, sweep the floors, clean the bathroom, fill the cat’s food/water, change the litter, take out the trash, and declutter. I love coming home to a clean house; it feels good, and it helps take the edge off of the return to reality.


Grooming Ritual

Having completed all of my preparation, I cut my nails, trim my beard, buzz my head, do whatever manscaping is necessary, and take a long, relaxing shower. This helps calm my mind, which has been firing on all cylinders making sure I don’t forget to pack anything and take care of everything around the house.


The Last Sleep

It’s always hard to fall asleep the night before a trip, knowing that I will wake up in Las Vegas the next day. I try to savor my comfy bed, rest as best I can, and bank a bit of sleep knowing that I will be lucky to get 6 hours a night in Las Vegas (I am typically a sleep diva who averages 8 hours a night).



The last day at work, I am hyperfocused as I knock out all of my lingering to dos and respond to any emails that require it. With the finish line in sight, I am highly motivated to get everything done so that nobody has any reason to bother me while I’m in Vegas. It’s also not to come back to a shitshow (but working at a non-profit, that’s never a guarantee, even when I’m not traveling).


Out of Office

I save the best for last: setting my out of office reply. I always set a fun message, which is sometimes the talk of the office when I return. It makes me smile when I come back and get a reply to my auto reply saying how fun it sounds and wishing me well. Setting the OOO is a magical moment; it marks the transition between work and play.



I make a detour to my credit union en route to the airport to enjoy a fee-free withdrawal of my bankroll. It’s important that I set the limit here, sober-minded and before the degenerate juices are flowing, so that I can make a rational choice. I divide this into a daily bankroll, sometimes leaving a portion for discretionary supplementation.



I’m always on edge until I get through security. I am a strict 2 hours guy, even though I fly out of COS — a 12 gate regional airport that never takes more than 15 minutes to clear TSA. I check my bags (using my memorized Southwest frequent flier number to generate my boarding pass and bag tags) and go to Precheck.

I’m often through Precheck and at on the concourse 10 minutes after parking, which barely gives me a chance to revel in the smugness that I don’t have to take off my shoes or remove my large electronic device as I breeze through the metal detector.

My first stop is always the gate. Even though I almost always fly out of Gate 12, I insist on going there to physically confirm that it still exists and hasn’t fallen off the face of the earth. My anxiety placated, I then proceed to pee, fill up my water, and incessantly do laps for an hour and a half until boarding begins.



I like to buy candy (usually Reeses, fun size chocolate bars from Dollar Tree, or anything else individually wrapped) to give to the flight attendants, along with a note of appreciation. They have to put up with so many inconsiderate people and/or be taken for granted that I like to recognize their hard work. I give this to a flight attendant as I board, and it’s always so heartwarming to see their surprise and appreciation. They often hook me up with a full can of pop or some extra snacks, sometimes even offering me alcohol (which is no longer enticing being sober, but it’s the thought that counts), but their genuine smiles are the best reward.

A few of my followers tag me when they do this, and it makes me smile again. this is one of many illustrations of how acts of kindness can radiate far beyond an isolated incident.



Once I land, I tweet something cheesy like “TOUCHDOWN LAS VEGAS” (something Raiders fans could seldom say this year, especially in that grotesque game against the Vikings) or “The bird has landed.” The wait to deplane feels like an eternity.


Slot Machines

The flashing lights, simulated coin sounds, classical music scores, bonus-bonus-motherfucker dings, and reel clicks assault my senses as soon as I walk off the plane; I’m home. I do my best to resist the pull of the one-armed bandits and make my way to baggage claim.



As you descend the escalator to baggage claim and the LED banner says “Welcome to LAS” I know that I’m home — let the games begin.


Baggage Claim

I always swing by the Library (the Liquor Library, that is) before finding my luggage carousel. I get a six pack of Heineken 0, crack one with my keychain bottle opener, and wait for my bags in style. Where else can you do that? (I put the remaining 5 in my backpack and use them as morning shower beers subsequent days).


Cab Ride

I always price check between Lyft, Uber, and cabs to see which one is cheapest; the flat rate cab zones make it easy to compare. It varies by trip, but I sometimes do value the speed of getting to a cab as opposed to the clusterfuck of rideshare pickup if the difference is negligible, since time is money and time in Vegas is even more precious.


Check In

Once I’m checked into my room and drop my bags off, I usually plug my quick charger in to top off my phone as I rinse the travel yuck off of me with a warm shower. I turn the AC down low (since I love to sleep in an icebox) and unwind a second until the degen juices start flowing and the casino beckons. As my buddy Eric knows, any elevator that has a CASINO button is a superior elevator, and pressing the button for the first time brings me great joy.


First Blood

The first win of the trip is always a rush. Ideally it comes on the first bet (always a good omen), but the masochistic MN sports fan in me is used to defeat, so there’s equal joy in a delayed win (at least I eventually win on a machine, unlike my 29 years and 363 days of Vikings fandom).


Waking Up in Vegas

After a late night (and sometimes early morning) of debauchery, I get to my frigid room and pass out naked in the crisp cotton sheets and fluffy comforter; as the travel weariness sets in alongside the adrenaline comedown, I crash out hard. I set an alarm for noon, but never make it that far because my internal clock (or is it my internal degen?) always wakes me up earlier, and I am wide awake when I realize that I am waking up in Vegas.

As I start my day, I listen to my Vegas playlist, consisting of:

  • Viva Las Vegas by Elvis Presley
  • Waking Up in Vegas by Katy Perry
  • Shot at the Night by The Killers
  • Poker Face by Lady Gaga

As I shower and get dressed, whatever wins I’ve booked (or more frequently, losses I took) yesterday don’t matter — it’s the dawn of a new day. A fresh start in Sin City. I’ve got a new daily bankroll to tap into. As I open my window to the bright desert sunlight, the dry air is full of promise, potential, and possibility.

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