From Above




My first time on the Whale Trail was a great experience of the Yin and the Yang, making lemonade out of lemons, seeing the bright side, checking out that half-full glass, etc, etc…

You get the drift.

It was 2014, and I was once again single. My continuous quest for a meaningful relationship was oddly not to be found jumping on airplanes to exotic locations or late nights buying drinks for inappropriately young ladies at Cape Town bars.

I was therefore delighted to be invited to go walk the Whale Trail by a lovely girl that I had recently met neither drunk nor in a foreign country. She was neither too young for me nor geographically or culturally too far away. I considered her to be a meaningful prospect, and the invitation to walk with her and her friends suggested she agreed.

Between the invite and arriving at the start, however, something had changed her mind. To this day I cannot fathom her reasons, but she had consciously decided to put some emotional distance between us. C’est la vie, there I was, the stranger in a strange land, embarking on a frigid five days with her and her friends.


Luckily, her friends were both warm and interesting, and I made the best of it. After all, the trail is a magnificent collage of beautiful coastal huts and mountain getaways. It is a gentle romp through fynbos and mountains and pristine coastal coral, and the best thing is: your luggage is ported, so you can supply yourself with both great food and fine tipple for the road.

I found, for the walks, I was somewhat left to my own devices. Once we arrived at the huts though, and we started up the fire and the food and the chats, her ambivalence seemed less of an issue.

This was fortuitous. Said lady was in the wine industry, and the entire cohort of participants (barring me) were wine people. In their nature open and gregarious, they were at pains to include me. Two of the chaps were some of the leading winemakers of Chardonnay in the country, and this is where it got good.

You see, when you spend five days hanging out around the fireplace with guys that are at the top of their game, and you kind of like wine too, it’s like a free seminar in winemaking. Add in that they decided to treat themselves to some of the top stuff from around the world (think Burgundy Chardonnays, ice-cold from the cooler) and they were not averse to sharing…well, I could just consider myself lucky.

I’m an Enneagram 7. We are Enthusiastic Visionaries, top at reframing bad situations and moving on to the next big thing. It does mean that you don’t sit with pain too much, and you often deny yourself the growth from the experience. I never did dig deep into why she had gone so cold on me, and maybe there is a learning there. But not dwelling on it also served me, I suppose, and I got an incredible amount out of it, both in new friendships, knowledge gleaned and memories created.

There is a nice little tale to the trail. The Whale Trail is set in the De Hoop Nature Reserve, and I go back there annually now for a Shoshin Walk, where I try to duplicate and even top up my first experience there in terms of food and experience…but also try to mindfully create an environment in the group where no one person feels excluded.

It is also the nature reserve where I met Caroline. On a mountain biking weekend almost a full year later, I met the woman who would become the love of my life, my partner, and the mother of my children. The full story of that meeting merits a chapter in its entirety and is another beautiful example of taking a bad situation and turning it into something marvelous.

You don’t always get what you were expecting. But I have learned to have a beginner's mindset and be open to whatever other gifts the situation can present. It’s the gift of being Shoshin, and I attribute the full family life that I now enjoy to the practice.

Have a good one on the trails this week!

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