ISBJORN Trans-Atlantic p. 3 // Rut or Groove?

14 Feb

19.02.04_Andy Midnight Writing.jpg

NOTE from Andy, Feb 14, 2019: I’m hesitant to publish this, for risk of it being too personal, causing too much interference with the public persona I’ve created about myself and of the business. But you know what – f&%k it. If I don’t publish this, anything I do publish would just feel like propaganda. Yes, there are certain things I’ll never publish – to this day there doesn’t exist an online photo from our wedding, for example, and while I talk all the time about the decision to have kids or not, you can safely bet that if the day comes, you won’t read much about it here. That said, re-reading this now, which I wrote over 3 weeks ago while tired and just getting started on the trans-At…well, as I sit on the new Swan 59 publishing this, all the feelings I describe below are basically gone – I’m STOKED! But, this is how I felt then…here goes.

I listened to a great ‘Dirtbag Diaries’ podcast on day 1 of this trans-Atlantic passage, where the host of the show, Fitz Cahall, wondered, at age 40, if he’d gotten into a rut with his life and career, or if that ‘rut’ could simply be redefined as a ‘groove’, depending on your perspective. I can relate.

In the episode, Fits & his wife, who work together running their own business (very similar to how Mia & I work together), decided to give themselves each a one-month sabbatical, where they could leave work & family behind and go do something they were passionate about, no strings attached. The other would stay back and tend to their 3 and 7-year old kids, and run the business in their absence. To make a long story short, Fits went on a one-month bike-packing trip, solo across Oregon, riding his mountain bike through the wooded trails and camping, sans tent, along the way. He concluded the journey, and the episode, with what I thought was a kind of corny, but mostly true analogy about how bike pedals work – that they’d always in opposition, and that opposition is precisely what translates into forward motion. Just like life – one foot up, one down, the bike moves forward. Life in turn, is made up of a series of ups and downs, emotionally, of worries and confidence, of grooves AND ruts.

I understand this. While Mia & I have not gone so far as to call them ‘sabbaticals,’ just this past fall we each took a week away to travel with friends, independent of the other person. Mia went to Rome and I went to Norway, and we both returned refreshed.

Rough seas on part of the crossing, and moody weather.

Rough seas on part of the crossing, and moody weather.

I wrote in this morning’s blog that I felt weary, down to lack of sleep from last night. Which is true. But my weariness also stems from that groove/rut feeling. The business is going great guns – we get the new boat on arrival in Antigua, we’re selling bunks like crazy, we’ve got other people involved now on several levels (as crew, skippers & behind-the-scenes helpers), a farm to call home, no debt, personal or business, and plenty of money in the bank to continue refitting and updating both ISBJORN and soon ICE BEAR.

And yet…doubt remains. I don’t doubt that we CAN do all this. We’ve proven that, to ourselves if no one else. Confidence in our business plan is higher than ever, and if we stay committed to being the ‘best’ at whatever new ideas we introduce, I’m sure we’ll find success. No, the doubt creeps in from inside. As much as I LOVE being offshore, sharing this wilderness with the people who sail with us, part of me can’t imagine still doing this for another 10, 20, 30 years. Then what? I have no idea what else I’d do, and therein lies the doubt.



And then there’s the kid thing. I turn 35 in three days (by the time you read this, when we’re back ashore and I’ve had a chance to publish it, I will BE 35). That number means nothing at all to me, and I feel like I’m 18 (genuinely), but it does mean something biologically, and sooner or later if Mia & I keep putting it off, this kid decision is going to be made for us, cause the longer we wait, the higher the risks involved in even trying.

So I doubt being able to put the two things together. Family life and the sailing/traveling life we love so much. I doubt even wanting to put the two things together. I like working and traveling with Mia, and I don’t care what anybody says, having kids WILL change our lifestyle, at least for a few years, because one of us will not be able to be on the boat. That’s a fact.

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Then there’s the business thing. I spoke to David Hows the other day before leaving Las Palmas for his Ocean Sailing Podcast, and I told him that part of my motivation for getting the second, bigger boat is this idea that I want to live up to my potential. All through high school and college I just drifted. School and sports (golf) came naturally to me, and I didn’t have to study or practice much to be successful. I recall some of my better teachers recognizing this and telling me about it – that gosh, I had so much potential – if I could succeed without even trying, just think what I could do if I applied myself?!

I started this sailing business by following the parable of the fisherman, to an extent – work only as much as necessary doing what I love to pay the bills and “get paid to sail.” By expanding, I’m breaking that original rule I set for myself, and justifying it because I feel like I have more to give. That I’ve not yet reached my potential with the business, that there’s more on the table, that I can create some kind of legacy, create a handful of dream jobs that my 21-year-old self would have been so excited for. I’m justifying it too because I know if I don’t try, it’ll always be there in the back of my head, and will always have wondered if it’d have worked or not, if I’d have LIKED it or not.

Surf’s up.

Surf’s up.

So when I’m in the groove, all of this is extremely exciting and the future is bright. When doubt creeps in, usually when I’m physically & mentally tired, that groove feels like a rut and I wonder why I’m putting the added pressure, risk and anxiety on myself when what we have now is pretty darn nice. Ups and downs, all moving forward.

Now, the question is – by publishing all of these thoughts, does that help or hurt the business? Do I need to present myself as the un-feeling, hard-nosed sailorman to inspire confidence in those who choose to sail with us? Am I, by doubting my own motivations, inviting others to doubt my performance when it counts? I don’t know, but writing this just feels like the right thing to do. So f*%k it.

It’s going up.

How I feel today!

How I feel today!

This article was syndicated from 59º North Sailing // 59º North Blog


  1. Justin Wolf

    “Do I need to present myself as the un-feeling, hard-nosed sailorman to inspire confidence in those who choose to sail with us?” Respect doesn’t come from having a hard shell. Respect comes from knowing your shit. Be you, be excellent, and be stoked.

  2. Henrik Christophersen

    Andy, talent is both an asset and a liability. Motivation becomes the driving factor. Some people thrive on starting a business – the challenge of building up something from nothing – while others enjoy running something that is already established. Two different personalities! My advice to you:
    1. Recognize that you may be a “starter” and plan to hire a reliable staff to manage the boats.
    2. Once #1 is complete, take a break from the business, have a couple of kids, and then always do a bit LESS than you want to. This will ensure that you will always enjoy the work.
    Btw, I hope to sail on one of your boats this summer!

  3. Dave Sanford

    Andy, you are not alone in the doubt line… many of us working together with our better halves have endured the same feelings. For me and my wife, after starting our business from scratch and building it up to about 12 employees over 8 years or so, and with a 9 year old at home, had a doubt-filled few days. We had disagreed about something to do with the business, and she declared she was “… not going to work anymore, just sell the business”! Of course, i figgered well, then I’m not going to work either! SOOOoooo, we both lazed around the house for a few days, not talking, just reading and thinking about what ELSE would we rather be doing for a living?!?! At first, I had plenty of ideas, but the more I thought about each the less I liked any of them. After 4 days, we both sat down and discussed our alternatives. Turns out, neither of us could imagine doing anything other than what we were doing for the same amount of time we had already invested, so we went back to work together. THAT episode was 25 years ago, and we are planning to turn the business over to our youngest son – the 9 year old – this coming January! At 66, looking back, I have no regrets, and find it easy to admit that, whether it’s a morning rut or an afternoon groove, mine suits me well. If I am controlling my own time, enjoying what I am doing, and keeping the bill collectors off my butt, I’m a lucky guy! Godspeed your future endeavors and family!

  4. Shorty

    So, to you thoughts about building the business or being a sailor. I started my woodworking business at age 23 wanting to do the woodwork. 20 years later I had 50+ employees. Things changed and grew and I had my hand in lots of different things. In 2008 I was looking to exit the business and the financial world collapsed taking lots of folks with it. In 2013 I finally admitted it was time to close up and move on, and I am so very glad I did. Life changes, sometimes for the good, sometimes not. Go with your gut & keep your eyes open and know when a change is due or, in my case, overdue.

  5. Bob

    Good for you. If honest musings are bad for business, it’s a bad business. Don’t have children until you want to, and if you “age out” of the children business, then it was not to be. But, if you want children, they are a bigger joy even than sailing; different risks, different worries, deeper musings, but having children is even braver than setting out on a long voyage, and even more rewarding. Imagine someone like you AND your wife; someone you can teach to live, and perchance to sail. If you want children, have some, even if it means living ashore for a decade or two. It would seem hard to “take turns” alternating raising children and sailing. You are young enough to do them together, sequentially.

  6. Mic

    Even if you “get paid to sail”, running a business and providing for your family is stressful hard work. So like Fitz & his wife, it’s critical to find time to recharge and rejuvenate. Make time to take of yourself, and feed your relationships with Mia, your family and friends. They are the true source of bliss. But then you knew that.

    By sharing your inner thoughts, both highs and lows, makes you more human and relatable. And is the definition of integrity. If anyone doesn’t want to sail with you because of that, then they’re probably not someone you’d want as crew anyway. Keep up the GREAT work, both on the water and with your writing.

    Fair winds!

  7. Bill

    Andy, I made it through my rut raising my family and working crazy hours building a business. I just bought a new boat and reading articles on cruising, feeding my dreams and getting ready for my next chapter in life when I retire soon. Kids are a beautiful thing, and when they mature you have some great friends that you helped get a foothold on life. Don’t miss the opportunity. Raising a family has a relatively short time table to it whereby sailing is much longer. I envy your lifestyle!

  8. Brian Deeks

    How do I learn more about opportunities to sail with you and learn to sail?
    Currently trainee sailor on square rigger Picton Castle about to depart Cape Town for Lunenburg, Nova Scotia, Canada.

  9. Bill Fraser-Harris

    35…you are done, toasted, over the hill, hang it up. 😉 Andy , I always look forward to reading what you and Mia are up to, mainly as I was there when you both met and got started but also because you are doing what I thought I might be doing with my life until LIFE got involved. Thanks for sharing the more human side of sailing for a living, expressing it so well AND actually doing it.
    All the best to you both and the life/business path/rut you are in/on.

  10. Pete McLiverty

    Andy, I grew up working on boats from the age of 10. It was a great way to grow up and learn to sail. I had many wonderful adventures and memories. One memory that sticks with me to this day was that as much fun as it was, I was still working while those around me were playing. It was still work, like any other. I’m not sure everyone realizes that. I left the business for years to pursue a family life on shore. Never regretted it. My only regret was my kids never knew the joy of sailing. I’m back sailing again in my 60s and it’s purely for fun. Life changes, sh*t happens but if we have the right attitude it all works out…whatever you decide, I’m sure you’ll find happiness….

  11. W.D. McCants

    The sea is unrelievedly honest. Anyone who assumes otherwise would be well-advised to avoid it. So your post should help your business continue to attract the right kind of customers.

  12. robert angle

    I get it!! I went feral at 59, quit my CEO job and spent the next 11 years hitchhiking on boats needing crew all over the world. The best years of my life. 55 bluewater miles on 17 different yachts. My friends thought I was nuts until I realized they were jealous and in a rut and didn’t have the guts to follow a dream. I had second thoughts once in a difficult storm at the bottom of Africa but got over it the next day when the sun came out. Go with the flow and your feelings.

  13. David Walsh

    I agree with Ron, that sums it up for me, life at 74, after 40 years at a career, that I dreamed, planned and worked for, starting as a child. I wish I had followed my sailing dream instead!! The journey might have been more enjoyable and satisfying – but who knows?

  14. brad peek

    …Andy self-doubt is a healthy thing but there’s one thing I’d remember if this is rut, there are a heck of alot less pleasant ruts to be in this world!! Fair winds.

  15. Ron

    That about sums it up. LIFE At 79 I still have days like that. Just keep on keeping on.
    Thanks for your reflections

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