It turns out that a whole lot of life is about managing expectations. I get that. I know it, yet I fail time and again. I can’t help it. I get excited about things and truly believe they are going to be the greatest thing ever or, when I am riding the opposite side of my bipolar coin, I get down about things and truly believe they are going to be terrible, no matter what. This is not only wrong, but wrongheaded, which is worse. I have studied all the science, I understand the how’s and why’s and, intellectually, I know better. Still, when it comes to managing life, it feels like I’m riding a rollercoaster, even when the actual journey is way more merry go round. So, in the spirit of exceeding or failing to live up to expectations with little middle ground, won’t you join me now as we stand and make the Paper Plane.

This is a modern classic created in 2007 by Sam Ross. Yep, the same Sam Ross who gave us the Sunflower, Midnight Stinger and, most importantly, the Penicillin and its many variants, so I have high hopes for this one. There I go setting up false expectations again, looks like I just can’t help myself. To be fair, I stacked the deck against this drink, since I bought yet another expensive Amaro that can be challenging to find, so I guess I am pot-committed to this one. It’s an equal parts drink, which I love and though the ingredients are wildly different, it is actually riff on one of my favorite cocktails ever, The Last Word. Ross is known for his work in the New York bar scene, but this drink was actually created for the opening menu at Chicago’s classic The Violet Hour. Later, he tweaked it a bit, swapping the Campari for Aperol before it found a home on his menu at Milk & Honey in New York.

Grab your tins and pop in 3/4 of an ounce each of freshly squeezed lemon juice, bourbon, I opted for Weller 12 year; Aperol Italian aperitivo and Amaro Nonino Quintessentia before adding ice and giving it a good hard shake to M.I.A.’s “Paper Planes“, which was actually the inspiration for this drink name, since Ross had it playing on repeat when he first worked this one up. When well chilled, strain into a coupe and garnish with a tiny, expertly crafted paper airplane.

It’s excellent, there is no denying that. The ingredients come together for a wonderfully well balanced cocktail. It is more astringent than I anticipated, which makes sense, considering it is 1/4 lemon juice. This is one of those weird times when I love the drink, but it is not what I expected it to be. I thought that the bourbon and Amaro Nonino would push through stronger, but they take a back seat here to the Aperol and lemon. It’s wonderful, just not what I thought I was getting into. Even though Weller 12 is an excellent bourbon I don’t think the fancy wheated stuff was the right call for this drink, so I made it again with Four Roses and that seemed to hit a more interesting spot in the flavor profile.

It’s a great drink, nearly ruined by my expectations. I figured that it would be similar to The Last Word, with its equal parts formulation of gin, green chartreuse, maraschino liqueur and lime juice. Both cocktails strike a beautiful balance between bitter, sour and herbal notes, but I always feel like the gin rises to the top in The Last Word with the other flavors supporting it, while this one is more balanced across the board. It was just kind of surprising to find a bourbon cocktail where the whiskey did not dominate the flavor. It is actually one of the features of this drink, but I walked in expecting a whiskey forward thing with an herbal, autumnal finish from the Amaro Nonino. That amaro is an interesting super flavorful, grappa based liqueur, with a wonderful orange, caramel, vanilla, thyme and wormwood herbal thing going on. It can be challenging to track down and some folks suggest subbing in Amaro Montenegro, but there are enough differences that I’d say that the trouble and expense of finding this bottle are worth it. That said, I really expected it to assert itself more strongly in this mix. So, instead of this whiskey orange vanilla thing, I was surprised by a fresh, almost spring like cocktail with a wonderful bitter finish.

That’s when it hit me, that everything that I was using to judge this drink, lived in my head. The drink was great, but it did not match my expectations. How often does that happen in life? Some of my best days ever have started out terribly and there is no question that a sudden change of fortunes and having things turn out better than expected temper those memories. On the other hand, I know that my biggest disappointments have all come from times when I built something up bigger than it could have ever lived up to. I always advise folks to underpromise and overdeliver, that is how I try to approach my dealings with everyone else. However, when it comes to dealing with myself, I fail at this, nearly every time. I am always getting myself worked up for the next “best thing ever” or my “latest and greatest yet failure”. One of my biggest fears is letting someone down and not living up to their expectations of me. It’s definitely a blade with two edges, but when it comes to internal monologues, I am like Ado Annie, with me it’s “All Er Nothing“. I am working on it, though. Like most of the lessons I preach, I forget to apply them to myself. So, while I am reminding everyone how important it is to be kind to each other, I am going to try to be kinder to myself. It may not work, but I am going to try to just take things as they come and see if a more reasonable approach with fewer expectations, for good or ill, leads to more general contentment. I am pretty sure it will. Stay safe, stay hydrated and stay sane, my friends.