“Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” – Mark Twain

Doubts, Second Guessing: Is this normal?


A couple of weeks back I had what will very likely be my last review as a professional environmental consultant.  It was a good year for me.  I completed a lot of work at a good profit margin for my major oil client.  I won a major contract with a public school entity that I had previously had at my former employer and that I have worked to get back for two years.  Our office is one of the most profitable in our company and I was a good part of the reason for that.  Not to blow my own horn but I am good at my job.  Despite the fact that I dread going to work every morning when I wake up.

I also have a pretty good setup.  I can talk Summer to work with me every day.   I work with good people who are fun to be around for the most part.  I have a bar in my office.  I have a corner of the warehouse to keep my stuff like our sails, dinghy, kayak, outboard, etc. where I can work on projects over the winter in warmth.  I will now be working from the boat 1-2 days a week so I don’t have to commute in Boston traffic.  And with the generous raise I got in my review and typical bonuses we now have a combined income that puts us in the top 5% of the US.

So why would I want to give this up to live hand-to-mouth on a small boat?

I had lunch with my friend Tim the other day and for the first time voiced this doubt. By most conventional standards we would be considered to be successful.  We are essentially debt free, make a good income and have professional jobs.  Why can’t I just be happy with a few weeks vacation and weekends off like most people?  Why give this all up?  Why does everything in my life seem to be an all or nothing choice?

Don’t get me wrong, its not all roses.  I have had issues with the manager.  Just a couple of weeks ago he and I got into pretty good.  No matter how hard I try to change my perception, I am working in a box. Eight to ten hours a day or more.  My clients can be irrational, demanding and difficult.  I feel like I work in an industry of whores.  Everyone is willing to undercut the other guy. Steal clients. Trash talk on other firms. Etc.

I just can’t seem to get past this desire to get more from life than weekends, vacations and retirement.  I want to explore now.  I want to experience new things now! I want to forget what it’s like to run my life by a clock, an email inbox and an Outlook calendar NOW!  I don’t want to wait another 20+ years.  This may be selfish.  This could be childish and immature.  Its definately cliche.

We don’t have a lot of time on this earth! We weren’t meant to spend it this way! Human beings were not meant to sit in little cubicles staring at computer screens all day, filling out useless forms and listening to eight different bosses drone on about mission statements! – Peter Gibbons Office Space 1999

I am not looking at our impending cruise as a vacation.  This is a lifestyle change.  A change that is driven by far too much to go into in this post.  But a change away from the way of life that lead us to have a house, 3 cars, lots of stuff and a boat to a life on a small boat scarce with belongings but rich in experiences.

I wonder if those who have cut the lines had these doubts?  It’s not a topic that is often covered in cruising blogs or books. Is it normal to have these small moments of doubt?

15 thoughts on “Doubts, Second Guessing: Is this normal?

  1. Great perspective! I wish I was starting this journey from a place of security at a well paying job but for me this will be merely a transition from one hand-to-mouth to another much more interesting one! Looking forward to reading more when I have the time! 🙂

  2. Oh! and where did you get that great countdown widget on your side bar? I would love to have one for the Emuna Endeavor blog! 🙂

  3. That doubt is normal. It doesn’t last long. Just take a deep breath and remember all the bad parts of your job.
    There is always a way to survive. You have a great advantage over most. Use it. Don’t dream. Live like a dream.
    Required reading: 4 Hour Work Week, The $100 Start Up, The Lean Start Up.
    Required listening Podcast: Side Hustle Nation, the Fizzle Show.

  4. I think it must be normal to have doubts. I sometimes think the same thing. What if we get rid of all our stuff and sail off in to the sunset and don’t like it!?! I love weekends and holidays on my boat, but how will life be once we have little/no income? I guess it doesn’t have to be a one way journey. If the life of tropical islands, new adventures and living differently doesn’t work out, you can always come back to the 9-5 cubicle. I think that transition might be harder though…!?

  5. Yes! Everyday! I think this doubt and sense of uncertainty is a driving factor in why so many people would like to give it all up and sail away but actually don’t. I’m sure I’ll be a scared, stress-out mess for a little bit, but I’ll get over it! 😉 Honestly, the scariest part for me will be the transition back to work…whenever that comes and whatever that looks like. ~Jackie

  6. Having just gotten past a week of failed repairs and having to dish out more cash than I would have liked, I can safely say I think we all have those thoughts from time to time. But we do it for the reasons you outline above…heck, that picture alone speaks volumes. At the end of ones life, looking back at it all, I doubt anyone thinks “gee, I wish I had spent more time sitting in my soft-walled container (cubicle) in corporate America.” You aren’t crazy for giving up “stability” for the chance at more…or if you are, we are all right there with you.


  7. I’d be much more worried about you if you DIDN’T have doubts, because that would mean you weren’t being realistic about the cruising life. More than anything, when I was working I resented being employed in a job that was all about the natural environment, yet I spent my days locked up in a little room, unable to see said natural environment at all, or even how the colors of the sky shifted over the hours in the day. Sigh. Mike (above) said it well.

  8. Doubts = normal. They’re a piece of my own barrier, admittedly. BTW, normal sucks. Normal is trading time now for freedom later. School + job = savings -> retirement. I hate that equation. Sounds like you’re being rational and have your financial ducks in a row (no debt, etc.), so full speed ahead with the cruising plans!

  9. Yes. Yes. Yes.
    Years ago when we first were putting our little plan in place, I kept hearing how untying the lines would be the hardest part. I laughed -not for me!! Yeah, says the girl who has now watched several departure dates slip by.

    So, yes, others have doubts too. Funny thing is I have NO doubt that I DO NOT want to spend the next twenty years locked up in a windowless room every single day helping to make someone else’s dreams come true. But it is still hard to walk away when you are already in possession of what our culture has defined as success. Even if you have your own definition of success. Especially when the chance to come back to what you are walking away from is most likely not an option, which we believe to be true for us.

    Then there is, at least for us, the flip side-just toughing it out for a little bit longer now, affords us more time “out there”. But each day of delay is not without risk. Tomorrow is not guaranteed. And this is the one item on my bucket list I NEED checked off.

    Doubts, second-guessing………..yes. But I have faith that they will fade once we get past the hurdle of untying the lines and start living a lifestyle that is more in line with OUR ideal definition of success. At least I hope 🙂

    Thanks for writing this post, you wrote it well. See you in the islands soon!

    Deborah (s/v Wrightaway)

  10. Doubts are so normal! Love the picture of the corporate office – great reminder about what’s really important!

  11. Great office picture, can I use if for my campaign?

    • Good day,
      Yes, please feel free to use the picture but please be sure to include:
      Photo from “The 8 Reasons You Hate Your Job in Corporate America” by Ashley Fern
      Thanks. 🙂

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