3 Part 61 Checkride Busts - Career Limiting?

In the NW we recently got a break in the weather and I attempted to finish my multi, but yesterday yielded another bust. It was my second attempt at taking the CMEL add on ride. Between my two CMEL busts and my instrument oral eight years ago, I am now up to 3. Interestingly, all of my busts are with the same DPE, all of my other rides including CFI were passed on the first go with other examiners. I had to use this guy because he was the only one the FBO would use with time in the Twin Comanche.

At this point, I am trying to figure out if I have a career ceiling. I get the feeling based on what I've read and growing up in the industry that flying for a legacy or 121 cargo is almost out of the question. That was my end goal, I have zero desire to fly corporate, or career 135.

Basically, I am trying to figure out if I am going to continue. Should I start investing my time and money in another profession, or fall back to being a dispatcher?
I know several guys who are now flying for the Regionals who busted multiple rides. One guy failed the CFI ride 7 times!! Yes, that was seven, and that odyssey included shopping examiners and FSDOs. And, yes, he is now flying for a Regional. Still wanna buy that cheap ass ticket??
 
I will not be going back nor sending students for reasons beyond the busts.

I did learn from the previous two busts. I busted the first one on the instrument oral based on not knowing the minimum IFR climb gradient in the FAR-AIM at airports with out a published ODP. I studied the heck out of my ground material for every subsequent ride. The second, I learned to slow down after, almost feathering the wrong engine, went back after practicing in the sim and airplane and had the emergency procedures down cold. Practiced engine out scenarios in high density altitude enviornments, and experimented with various configuration changes to find the sequence that would minimize the descent rate.

The one yesterday, I busted after not getting the gear up fast enough when he failed an engine immediately upon coming out of an emergency descent. I identified and verified the correct engine but based on my sim experience I secured the engine first to eliminate the largest source of drag and then intending to raise the gear after the engine was feathered.

This was after two previous engine failure scenarios in clean configuration where I ran through the troubleshooting procedure, secure, shutdown and restart procedure keeping the aircraft above blue line, with in 50 feet of altitude and on heading.

Going forward I'm going to follow the standard procedure of blue line, directional control, forward levers, clean up, identify, verify, troubleshoot (if possible), and secure. Or what the manufacturer or operator specifies.
Mixtures-Props-Throttles-Flaps up-Gear-Up-Fix or Feather is what I always knew. Never heard of anyone advocating for fixing/feathering before raising the gear.

The DPE was probably testing that procedure.
 
Thank you all for the feedback and encouragement, I spoke with HR and a pilot recruiter at my target regional, and I should be okay so long as I don't bust another ride. Going forward, I'll review the emergency procedures in detail specified by FAA or Manufacturer for the aircraft I am flying and drill the flows to the point where I do them in my sleep, so this doesn't happen again. Similar learning the nitty gritty of regs. after my first bust eight years ago.

In applying to a target legacy, based on feedback from the examiner who I flew with on my Comm SEL and CFI rides, my best bet is doubling down on networking, company recon, interview prep, and outwork my completion on resume building to get my foot in the door. My survival strategy in a 135/121 training environment is learning the intricate details around regs., equipment, company policies, procedures and culture above and beyond what is expected for a new hire.

Fortunately, I have a head start on resume being a career changer from inside the aviation field combined with strong education credentials
 
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