You woke me up this morning at 5 past 6 to go to work. You weren’t tired but had this weariness in your body. Because the worst has happened again: Monday. The weekend is over. You spent most of it studying (or trying to). You hate your job. And you’ve got 60 hours under fluorescent lights coming your way.

As I make my own hours, I used to commute with you to work. It was my way of balancing the scales, giving you the benefit of the flexibility I have in excess. And in return, I got something rare: routine. I could turn my brain off and know that rain or shine, I’d be sitting by my computer eating a full English breakfast, brightly caffeinated before the sun comes out.

But today, I was tired. While your work is demanding, mine requires building something that doesn’t even exist, creating rules as I go along. Sometimes inspiration strikes at 3 in the morning, or after a morning of lying in bed doing nothing. I could tell without even lifting my head off the pillow that today was one of those days.

Lazy, I murmur, I’m lazy.

And you assure me I’m not but I know we both know being in the office by 7AM was not just a win but the bare minimum, regardless of how you’re feeling.

You also tell me that your colleagues don’t like you, and you don’t like them. I don’t say that it seems like a chicken and egg situation. I don’t bring up the urban planning professor I met in design school whose career highlight was writing a 500 page book on map design. For 12 weeks, we were expected to explore different symbols to annotate hospitals and parks and reimagine the world we live in. Intriguing, meaningful work, except he wanted us to hand draw them on stacks and stacks of washi paper longer than my full frame. In a world of AI, I deemed this a luxury as greedy as sin. And in return for insulting his life’s work, I was told I was unserious and I’ll never make it in a creative industry.

You text me later that you hate your job, and I see your face in every person I’ve met at a networking event. You say what you do and shiny object syndrome infects the recipient as they momentarily wish they could abandon their life’s work to try something else.

When you are your own brand, you are forced into desperate acts, weaknesses you can never expose. At some point as a freelance designer, I started tutoring, making less than I did at university. I fluctuate between wondering how I ended up with nothing left in the tank and no choice but to keep running, and deep down knowing, this is the first time I’ve ever worked on something that truly matters to me.

While I was still half asleep, a halfbaked thought filtered through: you should quit. Become a chef, an artist, a journalist. Fail a couple times, pick yourself up, understand there’s no floor, but there’s no ceiling. You taught me that no amount of money you make ever fills the hole of giving up your dreams to do a job you hate. But my experiences taught me that life is too short to work longer hours for less.

So where do we draw the line?

One of the reasons I think we were meant to meet when we live such vastly different lives, on such different career paths and operating on such different worldviews, was to show that when you could technically do anything, struggle stays the same.

Thinking about it, planning it, analyzing it, isn’t work. Only doing the work is the work. And the discomfort is unavoidable no matter what you do, to not be good at something, and not make it about yourself by internalizing it as some assessment of your own abilities, or procrastinating by thinking the grass is greener.

You weaponize your intelligence by reading too much into it. Maybe it’s posturing. Maybe it’s the way an artist doesn’t appreciate their own paintings because they know the layers of paint behind it. Or perhaps, our feelings were never meant to be a compass. It won’t get you further if your journey is about reaffirming your wonky self belief instead of making actual progress. Being good enough is the least important question to ask, all that matters is if you’re doing the work and making progress.

Working on something that could fail feels like gambling, but if you acknowledge everything in life is a gamble, you’ll see that life, however cold and calculating and unfair, is the one game where the house not only doesn’t win, it doesn’t exist.

Whatever you choose you will regret it. The choice was never some flawless life with regret or without it. You simply choose what regrets you can live with. And if you’re not willing to pay the price of freedom of choice, life will choose for you.

Getting up every day and showing up with conviction to a chosen path is the only choice worth making.