Join Date: Aug 2011
Location: Aboard currently in Cape Breton
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I'm probably closer to your age than the average poster, so I'll share what I'm hoping will work for us. We're coming up on 30 years old but we spent nearly 7 years in university.
We were lucky enough to come out of school with technical grad degrees and without debt. Internships, scholarships, Canadian tuition and generous parents all played a part in that. Then he got a decent job with good raises and I switched jobs until I got somewhere that was also good. It took about 5 years to get there.
All the while we've known we wanted some freedom in life so we've never taken on debt and we've saved as much as we could while still enjoying good food, sailing and travel. No tv, keeping cars for 8+ years, lots of home cooking, etc. If we'd had student debt, we'd have an older beach cat, spend less on food, and take all our vacations camping.
We've also resisted having kids when peer & family pressure kicked in.
We've accumulated some decent savings and equity while watching friends pile on lifestyle debt and buy bigger houses & new cars. We didn't know exactly why were we being conservative but we were knew we couldn't be happy as "wage slaves".
We'd fallen in love with sailing at that point, bought a beach cat, and read lots of sailing books. In retrospect, it was inevitable that one of us would ask whether we could take off and go cruising.
From the time we decided we'd probably go, it'll take 3-4 years before we can actually go. Then we'll be gone about 3 years. Before we go we need get on a more conservative budget, buy a boat, get used to it, outfit it, ... Then we'll sell the house and set off. After 3 years we'll come back with enough cash to handle a 6 month job search. As long as one of us works we can get by.
My husband was offered one job with a company that had a provision for a 1 year leave of absence after 2 years. It was brought up by the hiring manager who has a Vindo for Great Lakes sailing. I'm in software so I should be able to step back into a crappier job than I have pretty easily.
So if I were you and I wanted to go on an extended cruise instead of vacations, I'd figure out how to pay down student debt or get it forgiven as soon as possible. Then start accumulating some cash and figure out what it'll cost you to cruise. I've seen figures from $800-5000/month, though most are in the 1000-2000 range.
Once we were comfortable with our financial position, we starting trying to negotiate extra vacation instead of extra pay. That worked really well when my employer was going through a slow time but my husband hasn't had any luck with it. He'll be changing jobs shortly and more than 2 weeks vacation is requirement. With my vacation, I could do a few 2 week charters to scratch the itch, so that could be an approach that could work for you. Took me 5 years to get here, though once I found a small business where I could take on responsibility that would start me at 3 weeks, it was much quicker to get even more vacation instead of raises. Lieu time instead of having overtime paid out might work too.