I sometimes do that, but the results are heavily dependent on the situation. A tough climb on a chilly day may only attract committed cyclists, so my +/- is gonna be bad. A modest climb on a nice day brings out a crowd I have a better chance of passing. I also ponder whether a peloton that passes me really just counts as one.
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When I get passed, itâs always ok because this isnât a race.
When I get to reel them in later up the road, itâs race on!
At least (and probably only) in my mind. 
In my mind, the people passing me are on e-bikes.
Iâm reasonably competitive in the moment but understand that at the end of the day sports are a hobby for me and my goal is just to improve relative how I did yesterday.
That being said, Iâm highly motivated by competition. I absolutely loved masters swimming because every set, youâre trying to catch the person to the right of you, and someone to the left of you is trying to catch you. When I started weight training I found it incredibly boring because there wasnât anyone to measure up to. After a few years I got bored and got in to crossfit, and just like in my swimming days you have that built in friendly competition of people doing the same thing you are doing at the same time. I push myself way harder in that sport than I did at the gym by myself.
In triathlon, I never tracked or followed other athletes. That seems a bit obsessive to me. I would always try to catch the person ahead of me but thatâs it. I think I was more competitive training in group settings than racing.
But if I beat someone who beat me am I not superior to my former self?
Not necessarily
If someone beat you when you were, letâs say 20, and you beat them years later, like 40; unless you did better than your 20 y/o self, itâs a wash
My opinion YMMV
However, I have IRL example: dude I worked with beat me by a few minutes at Broad Street, his first time running it
The next time we raced, I beat him by a couple of minutes PLUS beat my own time from our first encounter
He praised me to a dude HE worked with, who fancied himself a trash-talker, in this conference call
"Aaron. Aaron, câmere. I have a man on the phone; a REAL man. A man, who sets a goal, formulates a plan, performs to that plan and achieves his goal. Then this MAN, after his success ⌠does it AGAIN. Thatâs a man, Aaron!â
I only do the bike part of racing and am âlocally fast.â As in the truly fast guys recognize me but donât know me, and I always compare where I stack up against them. My definition of the truly fast guys, have or are currently participating in UCI level events. Most of the fast guys have built a life around bike racing, where I am fitting in bike racing (without kids, so a little less life expectations).
My wife is quickly realizing she missed her calling on racing bikes. As she is gaining fitness and more bike handling skills her strava times are putting her behind some properly strong riders. On a recent easyish ride the name directly above her is Paige Onweller
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I once removed a decent amount of skin off my tail bone to win a sit up contest at work with a bunch of navy seals 20 years younger than me. I won. But it hurt to sit for like a month. And they stopped doing the contests at future trainings. I donât think middle aged moms were supposed to beat them.
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Ha, wait until you guys get to the 70+ age groups. You do look at performance in your competitors, but more so you just look to see if they are still around. The drop off rate to injury, death, and burn out is quite bigly at that age, so many obstacles one has to overcome to keep competing at a highish level. I canât tell you how many ex olympians this ex division 3 wash out has taken down, and provided I get through my gauntlet, there will be many more to come⌠(-;
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Happened yesterday. I latched on, then dropped off (or got dropped).
Feels like the +/- is neutral, depending on the duration of time âriding togetherâ. 
About ten years ago I was training on Mt. Lemmon in February. I was riding a 27 lb. steel mountain bike, working steadily but still chatting next to a nice guy on a tri bike. We started getting caught by a 20-strong peloton. Tri guy says âI met those guys yesterday, theyâre a junior team and coaches from Ohio.â
I started lifting the pace and caught onto the back. Stayed there for about a mile, letting guys back into the paceline, not interfering. And working pretty hard by this point.
Eventually one of the adults dropped to the back of the group after a long pull. He silently looked me over, then rode back up to the front. Some words were exchanged up there and suddenly the pace lifted to a whole 'nother level. And I got spit out the back in short order.
Perhaps they thought it was bad for junior morale to have a gray-haired dude on a mountain bike keeping up with them. 
ETA: once youâve been beaten in a race by a dude wearing a giant foam Dunkin coffee cup, youâre pretty much done, self-respect-wise
I neglected to add that in 2015, I ran the Rock & Roll Philadelphia Half-Marathon on Halloween and got beaten by a maybe a dozen Darth Vaders, a few Princess Leias, Han & Chewie, Boba Fett, all The Avengers, Batman, Catwoman, The Dude, Walter White, Sponge Bob, a slice of pizza, and the Stay-Puft Marshmallow Man
Imagine getting beaten by these chumps
My wife ran a 5K with me many years ago. She is not a runner, not saying that I am, but she was passed by a woman pushing a stroller and randomly stopping to pick up soda cans.
This was at least 20 years ago and she has not run another 5K or any race, since.
If they pass you as a group, you can rationalize itâs just one, plus a bunch of drafters. If you try to latch on and canât hang, then they all count.
Competitive siblings came up at the dinner table, a bit ago
âI sleep with an eye mask (which is really just a Buff which I pull over my face), and play podcasts in my headphonesâ I commented
âMy brother sleeps with a CPAP mask like an Alien Xenomorph Face-Hugger ⌠one could argue that Iâm winning!!!â