Recently, I went to Madeira, which, if you don’t know, is a Portuguese island off the coast of Africa.
I only say this because I didn’t know where it was until after I booked the flights.
Madeira is called the ‘Island of Eternal Spring’ for a reason. The climate there is so strange. Being a small, but mountainous island in the middle of the sea, it catches clouds and rain frequently in the centre, which then trickles down into the rest of the island.
The weather is incredibly random; you could be in a pocket of rain, looking at a beam of sunshine in the distance.
And the reason I went there is linked very closely to this Substack.
Back when I was trying to make something as an entrepreneur, I had no real plan in place, except trying to get followers and find work on various platforms.
In 2023, I posted my first Substack posts about copywriting. Back then, I had no idea what I was doing, but I had one target in mind, which was to try and grow a following online. I had about 20 readers.
I joined a group from
who at the time, was the only person I could find who was really specialised in growing on Substack. From here, I remember joining and connecting with a few people on a spreadsheet she had created, one of them being .Kenny was a very nice guy (and I have since met him in person in London) and he connected me with another financial copywriter called
.Mike and I immediately got on very well and found we had a lot in common. We were running businesses of similar sizes, both writing, both attempting to gain some kind of following online.
We met in London once (when my leg was fully infected and I hadn’t eaten in over 30 hours – that’s another story), and Mike had told me that his mum lived in Madeira, about 10 minutes from Funchal, and that they often visited in March. He told me that I should come and visit whenever I was free.
I jumped on the opportunity, and earlier this year, after a few texts, I had booked a flight and arranged to stay for four days with his mum, step-dad and girlfriend.
I prepared almost nothing. This is one of the perks of being an entrepreneur. You have no need to ask permission for anything. You are also gifted the psychological freedom to think of it in the first place.
Essentially, before my trip, all I knew was that he was going to pick me up at the airport. I had a vague address but nothing else to go on. Amanda (his girlfriend) laughed in the car about the insane trust combined with the lack of planning we had.
But it turned out well, and I had one of the best short trips of my life.
Meeting the neighbour
On the third night, their neighbours came over for dinner.
Emmanuel and his wife and new baby.
There was a running joke about Emmanuel that he was the most perfect man in Madeira.
A Venezuelan-Madeiran, Emmanuel was fluent in Portuguese, Spanish and English, and was also a real estate lawyer. The last time they spoke to him, they told me that he had injured his hand while building his new farm, which meant he “couldn’t relax by playing the piano”.
The first thing I noticed about him was his eloquence. He spoke in sharp, concise sentences with crystal clear pronunciation.
Most people pepper their sentences with ‘ums’ and ‘sort ofs’, but everything he said was a clear, well-constructed phrase. There was no hesitation.
He was offered a drink.
“No, thank you. I don’t drink.”
I asked him why he didn’t drink.
“I stopped drinking roughly two years ago. I simply felt no need to drink any longer, and therefore I just stopped.”
As it became dark, we spoke about politics, world events, countries and the usual dinnertime chat. He told us that in the bathroom of the new house, they had installed a fake ventilation system, which involved just sticking a fan on the wall to trick him. But he had subsequently installed a new ventilation system himself.
When others were away from the table, I congratulated him on his new house and baby. He thanked me and asked about me and what I did.
I told him that I was in marketing, and some copywriting similar to Mike. He seemed very interested, and then he asked how old I was.
I told him that I was 27.
“What an age man, what an age! What a beautiful age is 27.”
He took a moment to think about it himself, likely reminiscing about being 27.
He asked me if I wanted to hear his theory about the age of 27.
His theory was that when you hit the specific age of 27, he believed your brain goes through an existential change, and this is why the 27 Club exists. His theory was that the brain reaches a stage of enlightenment, but often an existential crossroads. Artists reach this pivotal point, and being more extreme souls, it often tips them over the edge. 27 is a make-or-break age.
He said that this is the age when many people become a lot more serious in life.
He himself was 36 and said that when he was 27, he met his current partner, which combined with a shift in his life. But only when he hit 27 did he notice this change.
I was captivated by what he was saying.
It was one of those moments when things feel so well-timed, where you are told something that you didn’t know you needed to hear.
Thoughts in the mountains
When we were out walking in the mountains, I thought a lot about what he said.
I knew before the trip I needed a holiday badly from all the burnout, and I had also been feeling on a knife-edge.
Having been on a journey where you so blindly push forward into the mist, it is sometimes hard to remember why you started.
I had been wondering why I was this way for a while. But now, thinking about the age of 27 in this way, it provided a good explanation. And the fact that a stranger had felt the same way many years ago gave me the reassurance I needed to remember why I started.
I was trying to not place too much divine significance of this event, but I couldn’t help it. After that conversation, I knew that I was in exactly the right place.
It felt like I wasn’t crazy after all.
And I was meant to be here in Madeira, which meant I was meant to be on Substack two years ago. And everything between then and now had been justified.
It only felt right to write about it here too.
Substack is also where everything started.
I started trying to make it on this platform, start some kind of online business or income, and had no idea where I was going in life. Substack was where I met Mike, and we worked together on a client, one that helped me massively when I was starting.
Then, fast-forward 7-8 months, with my own online business, I was here in this place because of him, because of Substack, meeting their neighbour who told me, without knowing me, that he knew I was going through a significant change.
It seemed like everything was by design.
It also reminded me of the seriousness of life. Make hay while the sun shines and enjoy it because some people never get a chance to change before it is decided for them.
The journey from 25 to 27 ended right at that dinner table, and the rest of my life began the next day.
Madeira is incredibly lush. The soil is a rich brown, and much of the island is untouched, simply existing as it always has been.
Maybe all the fresh air gave me a moment of clarity I needed.
Lovely pics and story - thank you!
I happen to be very old but I always thought 27 was the age when we had finally grown up. A generalisation that seems to ring true. However, I held my breath when you mentioned 27 - it's the age when so many talented people passed over (Hendrix, Joplin and more), albeit they indulged in drink, drugs and rock 'n roll! Glad you stuck to fresh air and long walks.
Wishing you well on your new adventures!
I enjoyed the pictures. Beautiful mountains.
How is your leg? You didn't mention it, or did I miss it?