Keeping the Wind in my Sails

Off the coast of Riomaggiore
Off the coast of Riomaggiore, Italy – shot on Svema 64

Over the past couple weeks my Early Retirement Plan hasn’t met too many obstacles.  Well, other than I don’t know how to sail, we don’t have a sailboat, and there’s no way we could do it with our current family situation and mortgage.  But the point is we see it as a real possibility, even if my wife is tentative.  And she has good reason – I have a lot of interests and pursue knowledge in all of them until they either become uninteresting or they get rolled into the fabric of who I am.  They sometimes run their course and I move on, but usually because something else is more important.  Everyone changes; my interests are just the visible result of my personal growth.  So the real question becomes:  What are we going to do about it?

Well, first I’m working on turning one of my other hobbies into a business that we think would provide the income to support “retirement”.  It’s not location dependent, so it wouldn’t really matter where we are to keep it running and to do the work.  The litmus test on it will be whether I can generate the revenue from the business to buy a boat.  Initial results are promising, since I started right after I made my post last week.  I also have a second hobby that could provide supplemental income, so eventually I’ll test that theory as well.

I’ve looked into sailing classes and membership at a local sailing club.  I’ll join and start those probably in the spring.  I thought about trying it out this fall, and I still may if I can get into their last class or two and schedules permit.  Once I attend their classes and pass their US Sailing Certification, I can use their fleet of small sailboats to get time on the water.  So that might be most of my sailing time next year.

We’re considering attending the US Sailboat Show in Annapolis, thanks to some info provided by Mik Hetu, who lives on a sailboat on the Chesapeake Bay.  He read my post, and offered some encouragement. It’s the week before our anniversary, so it might be our anniversary weekend getaway.  We won’t know if our schedules will permit us going for a few weeks, but if we go, we’d like to attend a couples cruising seminar while we’re there.

My wife also wants to start looking at sailboats and wants to buy one for next summer.  She wants us to get a taste of spending significant time on a boat.  It looks like we’ll need to clear 40′ to keep the mast up in Pittsburgh, so we could go as large as some of the 27′ boats if we want.  IF the business generates the income and IF we find a boat we like, we’ll see if we can find marina space and maybe we’ll do it.  Of course we’ll be motoring most of the time, but it would be nice to get a few opportunities to try sailing on the three rivers.  🙂


As a result of the other decisions, we’ve also decided to shut down a side business that is not location independent and takes a lot of my time.  All the proceeds went to charity, but the margins were low, so the reward for effort wasn’t great.  We will be able to give more with the new business while still saving for the boat.  So while it was a tough decision, we spent last weekend in Lexington, KY (there’s a roll of photos coming to a blog post soon) with a lot of relaxation time and it made it clear it was time to wrap up that venture.

This dream is alive. It’s probably more like a 5-year plan now, but that would have me “retired” by 47, which is 8 years earlier than I had ever dreamed.  And speaking of dreams – almost every night there’s some aspect of this vision in my dreams.  For me, that’s usually a good sign, and I take it as this is something I need to do.  God willing, I’ll see you on the water soon!


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