Dream Sailing

When you quietly lament dissipating adolescent aspirations but the spark indeed ignites one day.

6/4/20252 min read

We've all had those conversations with our close friends in the night time.

When one of you is down on their luck. The other is simply tired with it all. So you dream.

And you shoot the breeze. But you are semi-serious. You get excited for a few minutes. "What if we set up our own Philly cheese steak stand? Come on! You know we can do it”.

"Yes! We can definitely make like a sandwich bar or jacket potato stand or something work.”

"Or what about mojitos? High margins and easy to make!"

"We can sell cookie dough and make it a full desert shop alongside the drinks. People like choice.”

“There’s those slam burgers too. But yeah, let’s think about it and we’ll definitely talk about it more.”

Then reality hits. You have college the next day. So you agree to meet up on the weekend to discuss again.But now you’re busy on the weekend.Okay, well it’s now going to have to be in three weekends time - there’s a couple weddings to attend.

You give it more of a think - you don't have the money though. You’re only a student and what do you know about business? You’ve struggled with math before and you’re not sure if you can do it. One of you has exams coming up. The other is simply distracted. Life.

Years go by.

We meet again, we dream again. Then some time passes.You’re cities apart but if feels like your world’s apart. Months can go without talking but it’s like nothing has changed when you talk about the good ‘ol times. But you’re both only early 20s. Scarred by adolescence and harbouring a bleak view of a tortured future.

The times have changed. You develop in new and diverging ways. So you drift apart.

We still do talk to each other. It's not really how it used to be though. We now joke about our teenage dreams. How naive we were! We reminisce. We don’t meet anymore - we ‘catch-up’. So much to talk about through the university years and the many jobs but nothing really to be said. Somehow, 10 years have passed.

We now less seriously imagine a future of becoming free. Certainly no honest vision of doing cool business with your friends. We live separate lives. We’ve learned to be more present day-focussed. We don’t really dream anymore. A slow decade-long sad dissipation. We’re sailing away…from each other and we no longer dream.

This once innocent idea has become not just a betrayal of each other but of ourselves. Our dreams represented hope and desire but now they’re sailing to Byzantium along with the thousand other childhood friends ‘what if we did…!’ pipedreams. Our entrepreneurial spirit now dead like the driftwood floating in solemn fragments some ways away in the horizon. Back-view.

Then some more years go by.

We meet and one of us brings it up again.

A gleaming in the eyes. We say “Fxck it!”.

Of course we can do it.

It’s our time

We're going to figure it out.

Let's just get started.

And it all clicks.

And here we are.