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I'm hoping to learn bigger double jumps and maybe some tricks, but there's not much around the bay area. I'd really like to progress faster as I'm in my mid-30s and I'm not getting any younger. I can clear the jump lines in Lake Cunningham on the DJ bike (never tried on the enduro bike). I cannot clear the bigger double jumps at UC or Pacifica on the enduro bike, mostly out of fear of trying even once.

I'm not looking to die on a remote trail with no cell phone reception and limited EMT access. But I'm also not exactly interested in taking a skills camp with a bunch of pre-teens. Anyone have a suggestion on where to go from here? Maybe hire a coach at Woodward? People always seem to progress rapidly after some time there. I'm open to suggestions, though.
 

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Haven't been to Woodward... yet. Though I saw they're offering day passes.

I'm more than a bit older than you, but in the past, I've done a group lesson/demo package and a private lesson at a bike park.

So much is about getting the right bike to build confidence, and have being able to follow someone at the right speed to get the feel for the jumps and landings. I remember doing the group lesson with friends, and how we progressed from small air in the morning to just all-out launching by afternoon.

The other big thing is repetition. I just spent a week+ at the Snowmass Bike Park. Rolling the same berms and launching the same jumps over and over is so valuable. You get to know the setups and the landings. You learn to use those berms (especially when there's 6-8 berms linked together) to build and carry the appropriate speed for the upcoming jumps. It's so fun to feel yourself progress day after day.
 

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Not sure where you're from but you mentioned Lake Cunningham so I'm guessing the bay. Have you been to Pleasanton bike park? or if you're willing Elk Grove bike park? There are some others in the Norcal area, Folsom, Auburn and Truckee is my absolute favorite in that area.

I think more ride time on your DJ with a variety of spots will help you gain confidence. The confidence will also help you gauge your abilities when you want to progress to a bigger line of doubles. Chat it up with the 'pre teens' while you're out there, they've helped me in the past. Mostly reminding me to tuck my rear tire in the air so I'm more dipped on the landing (my biggest reason for casing landings). Also there are those other older guys out at these parks so you'll find more riding buddies for dirt jumping.
 

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If mid 30s are old, I am ancient. You are talking about hitting some huge jumps. It sounds like you have the skills, just not the experience. Your best bet may be to try and find some better riders than you at the jump park and see if they will lead you into the new bigger jumps to learn the speeds, as over and undershooting is your big risk.
 

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This is a tough year for coaching, uncertainties about travel have likely cut back the options.
Northstar cancelled their lesson for the summer.
Not sure about Mammoth, but it's worth a look.

If I could swing the $$, I'd go to Whistler for a week. The border is open soon, they have more and better terrain, more schools offering instruction, so more instructors and likely better instructors.
 

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I highly recommend Dirt Gypsy Adventures in Truckee: Mountain & Gravel Bike Tours, Shuttles & Rentals-Truckee-Dirt Gypsy Adventures
I've used their guiding and shuttle service over the last few years, and this June I worked with their coach Mark for a few days. Mark raced downhill, and is an excellent rider and teacher. My skills and confidence grew exponentially after riding with him. I did private lessons and combined them with rides in Truckee and Tahoe so I could immediately practice what I was learning.
 
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