10 Steps to Sailing Off into the Sunset

You’re not believing the trap of the “I could never…” crowd, are you? The ones whose INSTANT reaction to anything other than working-in-a-cubicle-until-you-retire-at-65 is a gasp, followed by a (barely masked) eye roll?  The ones who would never even think of actually sailing off into the sunset?

These days, it seems the communal reaction to anyone trying to do something different is:

  • But how will you afford it?
  • What will you do about your (kids, car, home, _____)
  • Won’t you miss your family/friends/neighbors?How to Sail Off Into the Sunset

But all too often, those of us who crave something different let the naysayers get to us.  We buy into the idea that no one could possibly retire early, or that everyone who’s anyone should own a home – not a sailboat!  Or that having a “real address” is truly necessary.

One way to counteract all those “I could never!” voices is creating a roadmap of how you’ll get where you’re going.  It may change over time, and goodness knows that it will need adjusting (a good battle plan never survives contact with the enemy, right?), but having a guide to get there is a must if you’re going to reach your goals, whatever they are.

I hope you find this useful as a general guideline.  There are a finite number of steps needed to get to the day that you actually sail off into the sunset…or RV away…or whatever your dream is.  Once you understand what they are, getting there is the easy part.  A lot of these steps can be re-arranged to fit your own personal journey; we’ve put them in the order that makes the most sense for us.

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1. Set a Goal

You’ve all heard the saying that goals must be specific and measurable?  Set a date – put it on your calendar, and work backward from it to figure out a timeline for the rest of the steps.

2. Offload Major Barriers

Unload the things keeping you tied to your current location.  This step is the hardest – because there are a MILLION things keeping you where you are right now.  Everything from a house, to storage units, to unnecessary vehicles…start with the BIG things that would be barriers to your eventual escape.

3. Build Your Support Network

Have people in your life telling you it won’t work or you can’t do it?  Forget that!  Build up a network of people who have either done something similar to what you want to do – or who are also on their own journey.  This step is critical to success – when you’re wondering why you ever wanted to sell everything you own and move onto a sailboat, they’ll keep you going.  Hanging out with the people who are doing the same-old-thing won’t keep you motivated.

4. Stop Buying Stuff

One major difference in lifestyle between the white picket fence and sailing off into the sunset is the sheer number of belongings you will have.  Every item you own bogs you down and limits your flexibility – so the sooner you get used to owning less, the better.  Changing your mindset to using what you already have or making do will also serve you well onboard!

5. Cut Out Unnecessary Expenses

In addition to limiting your purchases, take a hard look at where you’re spending your money, and whether those things get you closer to, or further from, your goal.  If you sold a home in step 2 to free you up to leave, consider renting something in a less-expensive area for a time to help you reach your goals.  Drive a less-expensive car so you can sock away a bit more.  Every dollar you can stop spending now is another dollar in the sailboat kitty.

6. Build Your Momentum

As you get closer to your goal, you’ll find that things naturally start to align to help you on your way.  It’s happened with every major change I’ve made, and it’s a sign that you’re going in the right direction.  During this journey, you won’t have as much time for other pursuits and goals; this one will be all-consuming.  As you build upon each step, it will get harder – build in rewards for yourself to keep your motivation high.

7. Brush Up Your Skills

Even if you’ve been sailing all your life, there are likely offshore or cruising skills that you could brush up on.  Longer charters and more advanced lessons are great opportunities to build your skills.  Consider taking courses online or at a local community college in other skills you might need, such as small engine repair, general boat maintenance, or even scuba diving.  Take a moment to visualize what your life looks like after you sail away; what skills will you need for that lifestyle?

8. Replace Your Salary or Other Income

There are a thousand ways to get together the funds you’ll need to sail away.  But whether you intend to keep working or have another means of supporting yourself, you’ll at least need enough saved up to buy a boat.  You’ll also need either another source of income to live on while you sail, or enough saved to live on.

9. Buy a Boat

At some point in the process, you’ll need to select a boat that fits your long-term cruising needs.  It’s completely possible to work your way up, starting small and trying a few different styles of boats before you land on a suitable boat for your journey.  Another approach is to bare-boat charter a few different boats you’re interested in to get a feel for them first.  It will take you longer to outfit and retrofit the boat than you think, so plan well ahead of your final departure date.

10. Sell Everything Else

While you’re busy outfitting the boat and getting comfortable with it, one of the last things you’ll do is get rid of your remaining belongings that won’t fit on the boat.  We recommend selling anything worth more than $50 and donating or giving away the rest.  Ask around to find college students just starting out who might appreciate some of your household goods.

Sailing off into the Sunset

Finally, you will reach the big day.  That accomplishment, and the changes you’ve created, are going to be amazing – your grandchildren will probably be telling the story one day!  Every step in the journey to get to that day will build skills you’ll need while you’re cruising.

What step are you on?  What’s your next big challenge?

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