Reach helps.
So he's a southpaw? Be grateful for this experience. You might even want to learn how to switch leads.
What experience do you have?
That's definitely a big part of the problem. What are you doing to telegraph?
That's unfortunate. If you hug the belt and work the body against a taller opponent his reach can't help him. Are you keeping your elbows in tight, sinking in, and turning your body to maximize the power of your body shots?
You're letting him beat you mentally.
Why? Isn't that just letting him rest? Remember it's not just aerobic, it's also anaerobic. Cardiovascular fitness helps, but it's not everything. You have to train both energy systems.
He can't block his face and hit you at the same time, right? So work his body and when he let's off his guard give him an uppercut.
You're definitely better off to his outside if he's a southpaw and you're not, and you definitely need to watch his left hook. When you do go inside, you need to be compact, crouched, and tight. Be ready with the bob and weave and be ready to protect your head. Above all, "get there first".
Just like on the playground? Are you saying that he's a southpaw but he's holding you off with his rear hand? Good! Takes his left hook out of commission.
I'd have to see the two of you fight to offer any more suggestions, but it sure sounds like you'd be better off crowding him, staying tight, and transitioning from body blows to uppercuts.
Hahaha! Well, yes. That could be part of the problem. Work on your technique. Don't swing wildly. Stay tight and compact.
Then work on the slip and the bob and weave!
Good luck.


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