This is an abridged list of the things I've climbed. I included climbs either because I'm proud of having lead them, or because they were memorable or enjoyable.
These are leads that I didn't redpoint or onsight, but are worth mentioning.
5.8 Bolt Line
This was my first attempt to onsight 5.8. I had only ever led one 5.8 before (City Lights, which is a 5.8- at that) and the style of this route is one I'm not extremely accustomed to (lots of slopers), so in many ways this attempt was a display of overconfidence. As a result, I hung on the early crux. Nevertheless, I then re-attempted from the ground and got it on the second try.
This route was longer than it looked from the ground, due to a false top. Overall, the experience was a bit demoralizing, but I did make it through, and it was a good lesson in setting reasonable goals.
5.8(5.5PG13) City Lights
This was my first 5.8 lead, and ironically I led it before my first 5.7, Reach Around, which I led the next day. I had led Laurel before, which many people call 5.7 but felt 5.6 to me. City Lights has a move that most people would consider 5.8, but it's near the ground and very well protected, which made this mentally easy to lead.
I followed this once, and instantly knew I would be able to lead it, because I could easily get up to the crux and it would just be one hard 5.8 move. I slightly underestimated the 5.5 runouts later in the climb, but ultimately this was a fairly accessible first 5.8 lead. While the crux itself was 5.8, other aspects of the climb made it overall easier than many 5.7s I've climbed since.
Did this in a group of three with LB and Brett. I led the fourth pitch. Red Rocks 5.6 is easier than Gunks 5.6, but my lead head was very bad at this point. I was too afraid to extend my gear properly and ended up backing off my pitch due to rope drag. After letting a party of more experienced climbers pass us, I attempted the pitch again successfully.
Despite the route being wonderful, I didn't really have a fun time because I was down on myself for my less-than-stellar performance. I spent a lot of the climb comparing myself to my partners. Brett led the final (crux) pitch, which has a delicate slab protected only by a well-run-out bolt. Despairing that I'd ever be able to lead such things, I found myself unable to solo the 4th-class scrambles above the route, requiring my partners to belay me through much of the low-risk/high-consequence terrain at the top. The extra time this took caused us to run out of time before the topout chimney, and we ended up retreating only a single pitch from the summit. To make matters worse, I didn't give myself time to recover mentally, and ended up backing off a lead of Physical Graffiti (5.6) the next day having barely left the ground.
Because of my failure here, this route was a very important learning experience in my progression towards becoming a better climber. Initially, I had to cut myself some slack and stop comparing myself to other climbers. In the long run, this route helped me realize that fear, not physical strength, was holding me back. This caused me to seek out routes that would challenge my lead head, culminating in my lead of Moonlight (5.6PG13) four months later. My hardest lead at the time of this writing (Psycho Crack Right 5.8) is also a fairly heady lead, with insecure moves over some pretty big falls (albeit safe ones into air). Neither Moonlight nor Psycho Crack Right could have happened without failing on Cat in the Hat and learning from my failure.
5.9 Big Bad Wolf
This is just a beautiful climb. It's not listed under my onsights becuase I only led the middle (5.8) pitch.
5.4(R) Beginner's Delight
Beginner's Delight was the setting for my first serious trad lead fall. The fall occurred while I was liebacking up the dihedral, when I attempted to pull out of the lieback into a stem and my left foot slipped. Overconfident, I had run it out a bit since the last piece, and anticipating the traverse, I had doubly-extended the piece to reduce rope drag. The result was a 30-foot fall onto a blue #3 C4.
Falling on this route is extremely ill-advised. Had I fallen at the long, unprotected traverse, I would have pendulum-ed into the corner, and I was lucky to have fallen in one of the few places where the wall was vertical enough that the fall was fairly clean. This is neither a beginner climb, nor was I delighted.
After the fall, I lowered to the bottom of the pitch and gathered my nerves. Feeling that if I didn't face my fears then, it would be even more intimidating to climb the pitch, I began a second foolhardy attempt. Luckily, I succeeded. However, terrified on the traverse, I fixed a black tricam in a flared crack in the traverse. Thinking that would be the only way this marginal protection would hold.
Upon emerging unscathed from this lead still shaking with adrenaline, I nervously babbled about my experience to a neighboring belayer while belaying up my follower. He told me that some people just quit after their first lead fall, relating to me this tale:
"A new leader the other day took a big whipper onto a purple C4, and immediately asked to be lowered off the climb, saying that he was never trad climbing again. I offered to retrieve his gear, but he insisted that he would not be needing it. I retrieved the gear anyway, but when I reached the ground, he was gone, and nobody online claimed the gear when I posted about it."
Hearing the climber's tale, I realized that despite my terror, I wanted nothing more than to climb the next pitch. So that was the moment I knew that I was going to be trad climbing for a very long time.
Thanks LB for the catch!