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Dave Chappelle Live: Sometimes a Splurge is Worth It

Sometimes a Splurge is Worth It

If you’re new to personal finance, it may seem like all the movement preaches is abnegation and the stifling of your desires.  “Don’t buy that latte!” or “avocado toast is your ruin!” could almost be the tagline of some hardcore personal finance enthusiasts. You don’t have to wait until you’re retired to live life.There are some situations when a splurge NOW is worth it. For me, seeing Dave Chappelle live was one of these situations. Read below to find out more about the show and how to decide if a splurge is worth it!


Dave Chappelle is my favorite comedian by far. I first became a fan of his when I saw him in movies like “The Nutty Professor,” “Con Air,” and “Half Baked.” His sense of timing, unique observations, and quirky delivery hooked me at a young age. He became my favorite comedian after “Chappelle’s Show” aired. His show helped me get through some tough times at West Point.

L.A., Land of Conspicuous Stuntin’

Several years ago, my work brought me to Los Angeles. The food, perpetual sun, and beaches are lovely. Along with those, however, come lousy traffic and conspicuous stuntin’, or the temptation to outshine everyone around you with material possessions.

Living in a high cost of living area doesn’t mean you have to spend like a loon. You can, in fact, make a high cost of living area work for you. If you play your cards well, you can combine those strategies with geoarbitrage and retire much earlier and with a higher relative standard of living!

Luckily for me, I got my head out of my fifth point of contact shortly after arriving in Los Angeles, and I’m living a lifestyle that enables my family to retire early. This can be difficult to do with the many temptations in Los Angeles: fantastic food, trendy bars, and a robust nightlife.

Get the Most Out of Your Situation

As much as I’ve gone out of my way to avoid lighting my money on fire, I’m aware of the rare opportunities that living in Los Angeles can provide. There’ll come a day when the family and I decide to leave L.A., and I don’t want to have any regrets about things I should have done.

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A serious regert.

Seeing Dave Chappelle live is an example of such an opportunity. He did a couple of instantly-sold-out shows in Los Angeles before his Netflix stand-up specials. I had a chance to get tickets both times, but the 100 tickets sold out within minutes. I HAD TO see him perform stand-up once in my life.

Seeing Dave Chappelle Live

I received notice about a pop-up secret show that Dave Chappelle was having on the day before it happened. Since I’m on a mini-retirement, my schedule is flexible, and the timing worked out.

The venue was not a comedy club or a bar, but a swanky restaurant called Delilah in West Hollywood. Since I like having money in my pocket, I don’t venture out to West Hollywood much, but this show drew me out.

I arrived 30 minutes before the show and luckily managed to find seating within feet of the main stage. The show was scheduled to start at 9:00 PM, but this being L.A., the crowd didn’t arrive in full force until around 9:30 PM. Dave (we’re tight like that) started at about 9:45 PM.

How Was It?

I don’t have any snazzy photos of the restaurant or the show because of Chappelle’s “no cell phone” policy. No complaints. It’s a good policy.

Because of the no cell phone policy, Chappelle was raunchy, candid, and hilarious. I laughed so hard my sides and my face hurt. He covered topics like the #MeToo movement, Harvey Weinstein, and Chuck Berry. You don’t want to know about Chuck Berry.

Aside from seeing Dave Chappelle work his magic, the venue was packed with celebrities. Puff Daddy aka Puffy aka Diddy aka Sean Combs was seated at a booth approximately 10 feet away from Dave. They had a few moments back and forth through the night. Also in attendance were DJ Khaled, French Montana, Marlon Wayans, and various models whose names I don’t know. John Mayer, who is apparently a good friend of Chappelle’s, went on stage with him and they jammed out for part of the night. He is a ridiculously good guitar player.

As the evening drew to a close, I got the distinct sense that I was in a special place at a special time. I’m not into celebrities, but the attitude was relaxed, and it felt like we were all hanging out in someone’s living room. Also, I was glad not to be in the embarrassing position of having my credit card declined, like the guy next to me who was trying to impress his date. I’ve been there before, and it sucks!

How Much Did It Cost?

Ticket, with fees and taxes: $116

Uber, to and from: ~$35

Total: ~$150

Parking in West Hollywood is a nightmare, so I decided to Uber it instead. One of my credit cards offsets a decent chunk of Uber charges every month, so that brought my cost down from the $150, and parking would likely come out to the same or more.

Is $150 a colossal splurge? Not really, I’ve spent way more than that in a prior life. But it is unusual for me now. How did I decide that spending this money was worth it?

Should I Splurge?

I’ve got a few items I have to check before I drop an unusual (for me) amount of money on something. They are:

  • Is it repeatable?
  • Is it on my Bucket List?
  • Is the expense one-off? 
  • How long have I wanted it?
  • Will the decision set me back?

Is It Repeatable?

Sure, I could see Dave Chappelle again. Maybe. He doesn’t do a lot of stand-up live and tickets are almost impossible to get. I also am likely to leave Los Angeles in the near future. If I do move, my odds of seeing Chappelle do stand-up live, in a tiny venue with less than 100 people, go down dramatically. Who knows if Dave Chappelle will decide to retreat from the spotlight, again, in the future? Additionally, I doubt I’ll be able to get a ticket again. I failed to get them twice already. Check.

Is It On My Bucket List?

This one’s easy. Yes. Check.

Is the Expense One-Off?

What does this mean? It means that I’m not going to start dropping $150 on shows every week. It’s not a subscription box or a lifestyle inflation-creating habit, so I’m ok indulging myself with this bit of fun. Check.

How Long Have I Wanted It?

More than a decade. As I mentioned earlier, Dave Chappelle didn’t do any shows for many years after he conspicuously left the “Chappelle’s Show” in Season Three. He started doing standup again in Manhattan, but it was always a surprise so I couldn’t see him then. Check.

Will the Decision Set Me Back?

While I know the power of the Money Multiple, in the grand scheme of things, this one-time expense will not set back my early retirement by a lot of time. If your Bucket List item is buying a new Ferrari, ponder this question a bit more.

It All Checks Out

As you can see, the decision to see Chappelle perform live was a no-brainer. I had a lot of fun, and I’ll never forget the night I got to see one of my favorite performers do his thing. If you ever have the opportunity to see him, DO IT.


This post isn’t so much about a comedy show as it is about knowing how to wisely and selectively give yourself a break. As long as that splurge, whatever it is, meets the criteria above and you’re not about to start making a habit of splurging, do it without guilt.

What are some of your Bucket List items? When was the last time you splurged? Was it a good splurge or a lousy splurge?


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