On the Difficulty of Casting Off the Lines

Several years ago, a couple friends and I were hiking Mt Rainier’s Wonderland Trail when we came upon an elderly gentleman stopped to admire the view. He was in his 70s or 80s, and spoke to us with a deep gravelly voice. As we stood on a lookout over a ravine cut into the glacier, deep reds and browns showing in the dirt, he said: It’s always over too soon, isn’t it?

At the time I didn’t really recognize the wisdom in that one sentence. I thought, it’s not going to be over that soon – I have a heavy pack on, three more days of 18 mile days, and my feet hurt.

Later I realized his comment had life wisdom beyond what I was capable of seeing at the time. He may have been talking about the hike, or maybe he was talking about life. The good stuff is always over before you wish. That’s why it’s so important to savor it and live in the moment.

That’s what we find when we go sailing. Yet, getting to the part we know we’ll love is sometimes more difficult than it seems.

Untying the Lines

In sailing lingo “untying the lines” means casting off dock and setting off to fulfill whatever your dream cruise is. There’s even a YouTube video blogger with a series called “Untie the Lines”.

Over time I’ve noticed many people have difficulty getting off the dock. Life gets in the way. Even though we live aboard our boat we sometimes still have difficulty getting off dock. And getting away for that “big” cruise – whether it be a month, a year, or even an multi-year sail around the world – is super difficult. There are a lot of competing interests keeping you tied in one place.

Live Your Dreams

That’s also why I’ve felt an urgency for 3 or 4 years now to live our dreams. Go adventuring and cast off the chains of a cubicle work life. It probably sounds cliche – everyone’s doing this right? (if you go by the hundreds of YouTube channels). The truth is everyone’s not doing it, and that’s because it’s really hard. Stepping outside the normal path of work, consume, acquire debt for a big house, nest in place – is not that easy. Society has greased the skids into that path and it’s the route of least resistance.

Jobs provide structure to your life, and an automatic social network. Corporations are the college campus of adult life. Most people without a job wouldn’t know what to do with their time, and would have to find new social networks to make friends through.

Change Aversion

Embracing change is hard. So many people are averse to change and don’t even realize it. It’s easier to just continue what you’re doing, basically forever. “I have a great life,” you say, “why should I change it?”

We all want a good life, but at the end, do you really want to say “I had a consistently good life with little change”?

In reality, change happens in life whether you like it or not – family members die, you may get sick, recessions happen, jobs are lost. Would you rather have change happen to you, or be the one in control of change?

Do You Seek a Comfortable Life?

As you get older you start thinking more about what you want out of life, and eventually you realize you have to decide do you want a comfortable life or a life of adventure?

Sailing is often not comfortable. So if all you seek is a comfortable life, definitely do not go cruising!  There are things you can do to make it more comfortable, and many people go to great lengths outfitting their boat with comfort-generating devices, but ultimately you will always face discomfort – when the weather turns against you, when the heater breaks, when you’re dead tired, etc.

If comfort is the main thing you seek, you would never leave the dock. Sitting at the dock drinking beers is quite comfortable. It took me a while in life to realize most people are fundamentally comfort seeking – their foremost concern in their choices is increasing their comfort, at all times. After that they may seek entertainment, or social status, or whatever, but if they’re not comfortable they’ll be greatly stressed.

This is simple Maslow’s hierarchy of needs stuff. It also ties in to the Pleasure principle of psychology. The fact that people are fundamentally comfort-seeking may be obvious “duh” stuff to you, but I didn’t realize how it really permeates everything.

Yet some activities like sailing, backpacking in the wilderness, mountaineering, long distance biking, etc, all require putting up with discomfort and temporarily suspending your comfort-seeking instincts.

I don’t want a comfortable life. Sure I want comfort much of the time, but that’s not the primary attribute I seek in life. I want adventure, I want challenges. When I die hopefully a long time from now, I want to know I didn’t just sit at home and count away the jelly beans (YouTube: “The Time You Have (in jellybeans)“) in the daily grind of work, go home, watch TV.

I’m reminded of the scene in “It’s a Wonderful Life where George Bailey burst out: “Now, you listen to me! I don’t want any plastics, and I don’t want any ground floors, and I don’t want to get married – ever – to anyone! You understand that? I want to do what I want to do. And you’re… and you’re…”

George Bailey wanted adventure, but he passed that up in order to look after the family banking business while his younger brother went off to adventure abroad and came back from the war a hero.

In some sense I’ve always thought George Bailey’s brother got the better deal.

6 Tips for Casting Off The Lines

To keep this post a bit more upbeat and practical, here are my tips for casting off the lines (which we’ve done 3 times for medium duration trips, and plan to do a 4th time soon!):

  1. Set a date.
    Having a fixed date for when you’ll leave gives you something to hold yourself accountable to, and a way to plan.

  2. Get money issues out of the way.
    Start saving years in advance, get good at cutting down to a bare minimum budget, and recognize when you have saved enough.
    Many people fall into “just one more year” syndrome and are using money as an excuse to keep working and avoid change. We’ve met couples in high paying jobs who thought there was no way they could ever take a month off work. They had everything except for control over their own time.

  3. Get the boat ready. 
    The boat should be ready to go as soon as you are able, but bigger cruises require bigger preparation. Start this way before you think you need to.

  4. Figure out a realistic plan of what you want to do.
    It’s easy to make the mistake of jumping in head first with a dream in your head that you’ve never actually tested out. We did this when we bought a boat thinking we’d want to sail to Mexico, yet had never experienced sailing offshore.
    The best way to figure out what you want to do is to always be doing mini test runs and experimenting. Think you want to sail for 3 months? Ok, try one week first, then one month.

  5. Address Your Fears.
    Everyone has fears about cruising or making a big change. There are safety fears (what if you get into boat or weather trouble?) and FOMO fears (what will you miss out on in terms of time with friends/family or work opportunities).
    To be able to cast off the lines you need to figure out which fears are real and which are not worth worrying about, and what you can do to alleviate some of the fears (ex, more training or safety measures).

  6. Be honest with yourself.
    Don’t make excuses for why you aren’t casting off the lines. If your dreams changed and you no longer want to do that big cruise, that’s fine. But if you do want to cast off, and you’re ready, then do it!  
    Part of being honest with yourself is not succumbing to other’s machismo – some armchair sailors on the Internet think it’s their job to criticize cruisers who didn’t sail long enough, far enough or tough enough. But there are no rules – casting off means whatever it means to you. Transparently examining what your goals are might be the hardest part of all this.

3 thoughts on “On the Difficulty of Casting Off the Lines

    1. Patrick

      Hi David,
      Exactly – sometimes there are good reasons for not casting off lines, but also a lot of times people want to but haven’t figured out how to or have been delayed. We haven’t changed our minds about making the Big Left Turn. Casting off the lines for us is more about how long we can head out for than where we head out to.


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