Good advice, Canadianbombar. Good stuff.
Micio - I'll just reiterate from above. Hours at the sticks to become the best you can. That's what you need. In terms of supervisory or management, you need to think about people. In a supervisory or management role, you are a leader. Your groomers/snowmakers/etc. look to you for direction. It is best to work your way through the ranks, starting in the trenches, learning along the way, ultimately landing a higher position. That way, you can relate to your employees, and vice-versa. You're not asking them to do anything that you haven't done/wouldn't do yourself.
For Bear's assignment, just setup a bullet list of goals with a subpoint or two about each. In fact, for reference, here is my "plan" from Intro to SAO two years ago:
>2 years
-----Night shift groomer
-----Training for mogul competition during day
-----I'd like to have a job grooming at night in order to train hard every day for mogul competition. 'd also like to keep up with my musical interests, ideally putting a jazz trio or quartet together to play local gigs.
>5 years
-----Competing in mogul events
-----Consulting for [hopeful] Mt. Ellen expansion/redevelopment at Sugarbush
-----Grooming night shift @ Sugarbush when not competing
-----Playing jazz gigs
>15 years
-----Mt. Ops Manager/VP Mt. Ops @ major resort
-----Still rockin' the mountain-sponsored bump competitions... beating all of the young'uns who think they're something special
-----Playing jazz piano and folk guitar at the resort
-----Happily married with a family (assuming she can put up with a ski area manger's hours/weekend/holiday work

-----In 15 years, I'd like to be settled in as a General Manger, Mt. Ops Manager, or VP of Mt. Ops at a major resort. If the [hopeful] Mt. Ellen expansion plays out as I envision it, I would be honored to take the helm there. I also plan to continue competing in the bumps, but just for fun at this point. I'll clean up the Sugarbush events and the Bear Mountain Mogul Challenge, and various other New England bump comps. I'll also be playing jazz piano in the resort restaurants and playing folk guitar in the lodge. If I'm lucky enough to find a woman wonderful enough to accept the schedule and hours of a competitive mogul skier, mountain manager, and professional musician (which may be impossible, by the way), I'll hopefully settled in and have family by this point, and be able to share my passion for skiing with my kids (assuming they're interested).
Paul will tell you, I was always an overachiever. You might not have to be that detailed.

But there's something for reference. Come up with some life/career goals, expound a bit, and all will be well!