The Early Retirement Plan


Maybe all of us dream of early retirement.  For me, the idea probably started when I had my first job in manufacturing.  The idea of working 30 years and retiring to really enjoy life was appealing.  Twenty years and 4 employers later, if I’m going to retire “early” it probably needs to be different than those of the previous generation that retired at 55.  I can’t easily access my 401k until I’m 59 1/2, there’s no pension provision, and I think Social Security is up to age 72 for me.

As my wife will tell you, I’ve had all kinds of crazy ideas over the years. Writing is probably one of them.  My first book made money, not much – but at least it didn’t cost us more than it made, and we donated all the proceeds to the church.  This blog originated out of the writing of my second book – which is currently undergoing a mental transformation to get it back where I wanted it to be length-wise.   Film photography – there’s another one, and this blog so far has been mostly about my plunge back into film.

Some of my ideas are fleeting while others grip me and consume my free time.  They invade my dreams, and much of what I see and do each day starts being measured against the current “crazy idea.”  Every once in a while, one of them develops and it sort of changes our life.  From Mrs. Outspoken’s perspective, she says “I know you’ll analyze the hell out of it before making a big decision, so I generally trust your decisions.”

That’s where I sit with my current crazy idea – in heavy analysis mode.  And so far in 3-4 days of borderline obsessive thinking and digging through info on the web the idea only gets more viable; more worthy of giving it a shot.  The last two nights my dreams have been about us living this crazy idea.  So it’s worth writing about – because writing and spreadsheets are how I clarify my ideas and gather my information for future review.  And this is about retirement – I have 13 years until 55 – but I’m finding this could happen much sooner.

So what’s the idea?  The picture above was taken July 19th, 2014 as I headed up the “531” trail between Riomaggiore and Manarola in Italy’s Cinque Terre region.  It was a moderate effort climb – not the easy “Via dell’amore” coastal path most tourists would normally take, because that path is still closed from landslides in 2011.  I was soaked through head to toe after completing the hour hike over the mountain.  The hike started from the little protected cove, and went a good bit higher than where I took this photo.  Somewhere around this time I was falling in love with the Ligurian coastline, and my love of the water was calling me hard.

As I was resting, trying to cool off and catch my breath, I kept thinking how nice it would be to sail this coastline.  And then I thought about sailing near Genova.  And Napoli.  And Ischia.  And Sardinia.

That’s when it hit me – our retirement home in Italy won’t be a specific town.  We can buy a sailboat and live on it – exploring Italy’s coastline!  Crazy, right?

Maybe we can blame the sailboat in this picture.  As I sat in the cove at Riomaggiore, my eyes kept being drawn to that boat.  As I was atop the previous hill above Riomaggiore, I kept looking at that boat.  I know I snapped a few pictures, but of the rolls I’ve processed so far, this is the only one I’ve found.  But somewhere around that moment, the seed was planted.  We could live on a sailboat.

We have talked about retiring in Italy, or at least having a place to go in Italy when we retire.  We have for many years.  Now that I’ve been there several times the last couple years, it seems more like a possible reality.  Then this sailboat idea hits.  I start thinking about renting a boat for Sunday – not much I can find, and the one’s I do find are pretty expensive.  Hmmmm…sounds like a need that could be filled.   English speaking crew that could cater to the thousands of tourists that come to Cinque Terre each summer.  We’d probably only need a few week-long rentals per year to supplement our bank account.

We’ve also always been interested in boats.  We considering buying a boat as our first home.  Even considering being able to move it if jobs took us elsewhere.  Then when we moved to Buffalo, the desire for a boat was reignited, and every summer since our return to Pittsburgh it is a topic of conversation.  So I don’t know why I was surprised when Mrs. Outspoken was receptive to the idea.

Over the last few days, I’ve been looking for holes in the idea.  No major problems thus far, so I’m already in preliminary planning stages.  If we ever get to Italy with our sailboat, it will be in phases.  For example, Phase 1 is “buy a weekend sailboat”.  Something we can spend weekends or even a week on, to get us on the water, and learning to sail.  Phase 2 might be “Do the Great American Loop”, hopefully on that same weekender boat, but maybe something a little larger.  The final full-on retirement phase would be “buy a bluewater sailing vessel”.  Something for full-time live-aboard status that could cross the Atlantic and offer a private area for guests.

Which all sounds crazy to me in some way.  It seems like a dream life.  But if Phase 2 is “Doing the Loop” (no jokes about me being Loopie, thanks), my initial investigation says we could do that for $1500 per month.  We could do that now!  Sure, we’d have to sell the house, the cars, and quit our jobs, but if the boat was paid for we could do The Loop now.  And with the change in the workings of the economy, I could probably make $1500 a month from almost anywhere.  In reality, it might be our current life that’s preventing us from retiring now.  On the flip side, we wouldn’t be able to contemplate this without our past and present putting us where we are today. We have options, and options are good.

So over the coming weeks, I’ll be trying to understand availability at marinas, how much bridge clearance I need for a sailboat in Pittsburgh, what boats offer the right features, what would be our operating budget and tax implications, etc.  with the objective of possibly being on the water next year, taking the first big step towards a potential early retirement into what seems like a dream lifestyle.

For now, I’ll let the images of sailing to various Caribbean, Italian, and North American destinations be the wind in the sails of this dream, and with a little luck, maybe we’ll reach the point of the trip where dreams come true.  One thing I’ve learned: dreams do come true – it just requires hard work and a little luck.  Thankfully, luck favors hard work too, so working hard on your dreams is the key.

And really, what’s the point of life if we don’t chase our dreams?



5 thoughts on “The Early Retirement Plan

  1. Aaron, come and join us! I live on a boat on the Chesapeake Bay, and I’m certainly not the only one. In my marina we have a Pentagon worker, a crane operator, an accountant, a teacher, a social worker, a software engineer, a couple of retired folk, and more. Living on a boat is not nearly as bizarre an idea as it first sounds (especially in Pittsburgh!) (However, it’s not as easy as it used to be because a lot of marinas are being bought up by waterfront condo developers, don’t have facilities for liveaboards, etc.)
    By the way, I’m from Pittsburgh, too. If you go up the Allegheny River, just below the New Kensington bridge, you’ll see a big sailboat (??!! in Pittsburgh?) belonging to a liveaboard (he was in the local papers this past winter.)
    Check out the little book “You Gotta Go to Know” – it’s about a couple from Tennessee who sold their house so they could move aboard. It doesn’t have a lot of specific how-to advice, but it overflows with enthusiasm.
    Check out, too – lots of info there.
    I’m not so sure about your idea to rent out your boat, though. Two problems: insurance, and some idiot sinking your home. Taking people out for a sail might work fine, though. You’ll need a “six-pack” license (six passengers) and insurance.
    For your Phases I-III, I suggest for Phase I getting a small, trailerable daysailer and sailing it until you can figuratively horse it around without thinking much about it, the same as riding a bicycle in the backyard. Lake Arthur might do you okay for most weekends. For Phase II, don’t bother with a mid-term boat. Instead, spend your money on some sailing courses and then charters in the Caribbean. The Great Loop is a fine trip, but understand that it is nearly all motoring, even up the coast in the ICW. Also, moving up in boat size (the handling of them, that is) is surprisingly easy because bigger boats weigh more and react less quickly to the wind and helm. You’ll find that the hardest part of handling a sailboat is bringing her in and out of a marina slip! That’s where your experience in a small boat comes in, understanding, for example, that moving one end of the boat to either side affects the other end! (You’d be surprised at how some people can own expensive boats but not own any boat sense.)
    For Phase III, the trick to buying a good boat is to own a small boat and hang out at marinas: you will meet people who are selling theirs or know someone else who is, trust me. (I have some stories about this posted on my boat blog,
    This fall, come on down to Annapolis for the boat show. Don’t even think about buying a boat there, but come to see all the different kinds of boats and layouts (just take off your shoes and walk on about 100 nice boats!), wander through the extensive gear display tents, and attend some of the seminars (I met Tania Aebi there!) When you see the thousands of people flooding the downtown area (go find pics on the net), and all the cruising boats anchored in the creek and their dinks crowding the dinghy dock, you’ll be assured that your idea – though it needs fleshed out and refined – is at its core perfectly sound. You just might have found your tribe . . .


    1. Thanks for all the info and tips! Just to clarify – I was referring to taking people out for a sail, not renting out my boat. I’ll see what I can do about making it to Annapolis for the boat show. I have some experience with power boats, but the romance and economy of a sailboat seems to be calling me. Plus, it’s hard to beat the peaceful feeling of sailing – the few times we’ve gone have been amazing.


    2. Re: You Gotta Go to Know – their boat, Vacilando, is for sale. It’s one of the one’s that was high on my list; just not sure it’s wise to take that big of a plunge. 🙂


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