Let's be real.... Could I pull this off?

I think you could do it with 6 months.  Your biggest obstacle in my opinion is not getting hurt.  The beginner HIM plan on BT is 20 weeks.  If I was you and really wanted to do it I would plan on getting through swim/bike and then I'd would probably be planning on a run/walk.

Possible? Sure.  But it's going to take a lot of commitment and consistent training between now and June to get there.

As a starting point, I'd suggest you take a look at the beginner's HIM plan here on BT to get an idea of what you're up against.

I wouldn't suggest that you try to take the weight off too quickly with a gimmicky diet.  You'll be better off cleaning up your diet, exercising good portion control and letting the weight come off at a healthy and sustainable rate.  If you're worried about your weight affecting your running then you may want to focus more on cycling and swimming until you lose a few pounds. 

Sounds like you've got a great boss to support and encourage you!

Good luck,

Mark

Of course you can but is it the best way to do it? 

There are a few things that jump out at me that give me caution:

1. The weight gain - although muscle memory is an amazing thing it's going to be hard to start and hard on your body. So building volume too rapidly will be a bit of a crapshoot in terms of keeping injury at bay - especially if you jump in to HIM training now (which is about the time - many plans are around 20 weeks)

2. The length of absence - if you haven't been on a bike in 2 years you really should just spend some time building volume and focus on shorter distance races - although you sound really committed, building sensibly from where you are today will pay off in the longer term if you want to keep at it. 

All that said, there are several things going your way:

1. You sound like you want to do it

2. You have done the volume before - coming back is easier that starting out. 

I think if you do choose to do it - don't set any time goals. Make it all about finishing - which as your first it will be a PB no matter what!  My recommendation would be to set your goal to do an Olympic distance in that same time frame. 

Best of luck getting back at it! 

Honestly, I don't think it's a good idea to target a HIM 6 months from now given that you're basically starting over.  You would have to bury yourself training-wise to get there and how much fun would that be...not.  I think targeting several sprint/oly races this spring/summer would make everything more enjoyable.

It's great you're getting back in the game.  You'll drop weight and feel better with consistent training.  I would suggest getting on a consistent workout schedule (preferably 3x a week for swim/bike and 4-5x a week for run).  Running is going to be the toughest on your body given your current height/weight. Keep the sessions short at first (I'm thinking no more than 10-15 minutes for the run).  Think long term...you want this to be an enjoyable experience.

It can be done with the willpower, but probably not the best thing to do IMHO.  I would talk with your boss and tell him that mentally you could probably do it but right now that physically you need more time to get there to achieve a lifestyle modification that could truly last.  Realistically there will likely be a week or two of illness, periods where it feels like you are taking two steps forward then one or two steps back, etc. 

No shame at all in going shorter to build up and see progress.  I personally prefer the short higher intensity races these days.

Let us know what you end up doing.  BTW there are some Mentor groups that will be forming which could be of some good assistance for you if you go after it.

I also meant to add that a factor in your favour is being young - i think you said you're only a few years out of college. You probably won't need quite as much recovery time as older folks - it doesn't mean you shouldn't have it in your schedule, though.