Career advice for a gaper (more flexible hours)

So figured I'd ask for some advice in this part of the forum. Here's my current situation:

- graduated school 2 years ago in software engineering
- working for a software company since graduation
- pay is pretty good
- job itself is okay, not the best, but I don't hate it either
- job schedule at the moment isn't flexible, basically have to work 8-5 weekdays, have to take vacation in advance

I'm mainly looking for advice as to how I should go about trying to get more time for skiing next season, but the thing is, I don't simply want to be able to just ski more. I'd like to be able to go out at least a couple days during the season if there was a snow dump that day. Right now, that's not possible for me during the week, only during the weekend. And I can take vacation once in a while, but I tend to always miss the snow storms for some reason.

I know my situation isn't bad by any means, after all I can afford to go skiing often and I live in western Canada. That being said, I'm still pretty young and I do love skiing a lot, and I would like to try to find a way to do more of it, while still earning a living. Possible things I've considered, but have not done yet:

1 look at part time jobs in software/engineering in the area
2 look at finding a job with more flexible schedule
3 look at working for self
4 ask current employer to give me more flexible schedule?
5 other ideas?

Are you sending it at work? IE, are you a top performer? If not, get yourself there, then ask to meet with your boss September-ish after crushing it for a bit and ask for a more flexible schedule.

The correct answer is always 3.

Before you jump into freelance, think about if you have the kind of contacts that can sustain you for the long haul. If you don't, work on those first and then leave. Do you do any freelance stuff now?

Try to see if there is anyway to work remotely? Getting out for 4 hours or so on a blower day would be easy if you could work from home. Can you do 1-9PM from home? I worked for a software company in the past and the engineers were pretty much there only when meetings were coming up. I pretty much expected my emails to go unanswered for hours as they would do different stuff during the days. But I was sure to get an answer at 10PM if I sent an email out then.

I would NEVER go with #1. When you get your next job and they ask why you worked part time for a few years and you say "so I could ski more" you aren't really going to be high on their list of candidates. And besides, like you said, you're still young. I'm still young at 33. Age doesn't mean shit. Put your nose to the grindstone for a couple years and work to that money position I was referring to up there. If you can be 27/8 doing what you want everyday and for the rest of your career making more bank and having more free time, you'll be happier than bumming it and fucking your career over for you early-mid twenties.

I "retired" for my twenties and skied and played full-time after grad school,
earning just enough for to have the life I wanted, and I've never regretted it.

I work now (will for a long time to come...so be it), and live in a place where access to all sorts of fun is <10 minutes from my door.

Fuck it man, you only live once. Every choice you make is a trade-off in one way or another.
If you are good at what you do there will always be work.
-plus you have health insurance, so you've got that going for you (I lived for 10 years without)

This is just my $.02, most people don't follow their dreams, be different

get a job with a company in the outdoor/action sports industry. Lots of companies are cool with flexible hours if you are killin it

Thanks for the advice guys. If I was to work for myself, it would be for my buddies' company (buddy from university) and it would be working from home. Right now though, his website isn't big enough to pay me though.