I’ve bought a greater variety of picks than I could ever hope to document. That’s nothing special. I think we’ve all grabbed some expensive tortoiseshell wonders or wacky polymers that promise to stick better or help us pick faster. Many people get jazz iii’s and think their life has changed, that they are the first to discover these little teardrops that make arpeggios somewhat easier for folks with bad picking technique.
Maybe you like little teardrop shapes. Maybe you think a cartoon bulldog helps your strumming. Or perhaps you think something over 2mm makes you more metal. Whatever it is, we keep falling for gimmicks involving minor variations on the same theme. The fact that remains is that picks have extremely little to do with picking, and technique is pretty much all that matters. It’s like anything else, the equipment just has to be passable until the skill is so great that one can take advantage of better gear.
But it doesn’t matter, does it? We’ll always keep buying gear for the player we want to be, rather than the one we are. And that way it’s always the fault of the gear. Either we can’t afford or find the perfect gizmo and that’s why we suck, or we over-bought and everything is too complex. Just gotta go simple man, guitar, cable amp. Unless that’s what you’re using, then you just need something better.
It’s the same old story all the time. And for me, that story largely focused on picks.
I went through the same routine that most pickophiles experience. Everything from the jazz iii’s to tortex, v-picks, real tortoiseshell, wood, bone, etc, etc. I’ve definitely spent $20 on a single pick. I think I’ve spent a decent amount more, but I’d rather not admit that with any certainty. Sure I have my preferences and some fit my hands a little better than others, but they are all largely the same.
That took my mind on a journey to a world where the traditional pick was the problem. I genuinely do have rather inflexible wrists. Nothing weird, they just aren’t super coordinated and have some real mild arthritis. So I convinced myself that it was impeding my strumming. I started playing kind of a hybrid style where I would strum traditionally a bit but also use my free fingers for occasional downstrokes or fingerstyle work.
That lead to the belief that a thumbpick was the answer. Leaving my more dominant index finger 
available for the hybrid finger picking stuff. But typical thumbpicks are really just meant for fingerstyle. They are thick and long protrusions of plastic that really spank the string. Trying to strum with one of those is futile and will leave you with rattles, missed strings or just an overly metallic sound. so I discovered these combo thumb/flatpicks. They are essentially a flat pick with a rivet or something similar attaching it to a thumb ring. The idea is you can grab it with your index finger and do traditional picking. But it’s still attached to your thumb for fingerstyle. Like five or so people make them that I know of, and I’ve tried them all.
This may be more personal taste or playing style, but I think this is a great concept that fails in reality. When sitting, your natural arm position lends itself to pretty seamless transition between finger and flat picking. But when standing, your arm, or at least mine, comes at the strings at like a 30 degree angle. This means you have to contort your wrist a bit in order to play fingerstyle, where you just tweak your thumb angle for flat picking. Which means that one or the other is a bit uncomfortable and there’s no real natural switching styles. Again, not for me at least.
The other problem is these picks have some sort of ring that goes around your thumb. If that ring is easily adjustable to comfortably fit all sorts of thumb sizes and angles of attack, it will not hold in place when using it as a thumbpick. If it’s rigid enough to stand up to straight fingerstyle, it will likely be uncomfortable for flatpicking.
A solution might be something sturdy that goes over the tip of your thumb and stops before your first knuckle. Kind of like a thimble, but contoured for your thumb/nail. Would likely have to be custom fit. Nobody would pay for something like that, aside from me I’m sure. And I’m not even sure if it would work, but it seems better than the options out there.
Still, even if the perfect combo thumb/flatpick existed, it would be just like every other pick gimmick. Just a gimmick. A way to trick you into thinking that gear is your problem. More lies!
So what is a frustrated picker to do?
For me the first step is finally realizing that there’s no one solution. That seems obvious to some but it’s generally a hard lesson to learn. So many of us are creatures of habit and many more of us believe there is a single right answer to every question. That’s a mindset that will leave you frustrated and poorly wailing out cover songs in crappy guitar stores.
Everything I play has different nuances to me, and a different approach to picking. Whether it’s a practice exercise, song of my own or someone else’s. One piece of equipment will feel more comfortable based on what is being played. Sometimes it will be just my fingers, other times a little pointy pick, other times a big floppy one. Picks don’t take up much space, there’s no harm in having several varieties on hand.
The other part is to really think about how you play. What little habits and tendencies you have in your playing will definitely impact pick selection. For me, it’s a few things. I like to do kind of sudden upstrokes ahead of the beat. Maybe I listened to too much funk when I was younger, maybe I can’t keep a beat. Either way, it’s a thing. I found that really thin picks don’t emphasize this enough. They move slower and take a lot more effort to strike the strings cleanly. I try to stick with 0.7mm or thicker for this reason.
I know, no need to say anything…
I also tend to hold the pick with the tip of my thumb more than the pad. It’s kind of in-between, but definitely leans toward the tip. If I hold a pick the way you’re generally “supposed to” there is a small tip protruding that allows for easy strumming and arpeggios. But the way I hold leaves less thumb in contact with the pick. This means more pick sticking out. Which means when I’m doing alternate picking and stuff like that, there’s more plastic to get caught on the strings since I’m not a super precise player (out of lazy practice habits, not some stylistic intent). So picks with a sharper tip are a lot easier to control. I used to take a lighter and knife to my tortex picks for years to give them a little curve to form to my thumb and sharpen the tip. Then I came to my senses and just started exploring what else was out there.
It can go deeper than that. I tend to squeeze my picks too tightly (I do the same thing when I write with a pen/pencil and get nasty cramps). I’ve seriously tried padded picks, but that’s just silly. More than anything, a larger surface area to grab means you can adjust your hand position a lot during playing without losing control. Which means I can do the little jazz picks, but not for extended periods of time. That extra surface area means it’s a lot easier to roll your thumb away from the strings and expose more pick for nice folky strumming. If you have small hands you can do that with the tiny picks, but at some point you’ve got kind of a hinge created as you’re only holding onto the far edge of the pick. This means lots of sloppy control, dropped plectrums, embarrassment.
These days, I’ll carry a couple of 0.72mm Claytons (the translucent yellow ones) and an Eric Johnson Jazz iii in my pocket at all times. I’m somewhat at peace with it. Although the Claytons are a fairly classic shape, they have a tight enough angle at the tip to prevent the whole “too much tip” problem I mentioned above. They are what I think most people would agree is a reasonable compromise of thickness that allows for decent strumming and single string stuff. My major gripe is they are a somewhat hard material. I mentioned heating my tortex picks to add some curve to them. Whatever those picks are made of is malleable enough that you can shape the grabbing end of it while the business end remains nice and straight. The Claytons tend to be all or nothing when it comes to trying to shape them. It’s a minor annoyance, but I can live with it for now. I’m hardly playing 5 hours a day anymore to where such details bother me. The jazz iii’s are utilitarian enough. If I’m playing something that has some detailed string work, they seem to compensate for my mediocre technique. They’re mostly useful if I’m playing something that has a lot of heavy accents as they can make the strings bark with ease.
I’m still unhappy with that solution, but I try really really hard to remind myself that it’s my fault and not the equipment. If it really burdens me, I’ll throw the picks away and do my best Jeff Beck impression (which is NOT a good impression). That right there is a nice exercise though. Throwing away all your tools can make you appreciate them a lot more. Sure, there’s that nonsense about how a dramatic change may make you more creative, and maybe it can at times. But more than anything it puts you on the proverbial other side of the fence. If you do it long enough, grabbing your old nylon friend will really feel great. You’ll feel like you can do anything. That’s certainly how it is for me.
I think the point of all this is that for all the hyper-analysis of playing style, obsession over how other people play/sound on youtube and whatever the gearpage is crushing on this week… it would seem you can get way more joy out of your gear by throwing it aside than you can out of acquiring more of it.