Death to Deadlines

Productivity-Booster or Creativity-Killer?

It’s a rainy day in Long Beach.

Hurricane Hillary has made landfall and I’m curled up with a cup of Philz Coffee, my cat... and the new Colin and Samir interview with Ali Abdaal.

We all have an internet business or productivity guru.

Ali is my guru.

He quit his job as a doctor to become a full-time YouTuber.

5 years later he’s pulling in 4+ million dollars a year making videos.

He is the reason why I started my YouTube channel back in September of 2020 and began playing the great online game of building an audience and getting paid for doing what I love.

Ali, while an absolute master of creating and monetizing YouTube videos, neglects one of the core components of how YouTubers make money...

Sponsorship deals.

Even Ali, the productivity godfather, procrastinates making videos that have sponsorship deals in them.

His reason is simple:

I got into this game because I wanted to build a career and a life on my own terms.

I wanted to have the freedom to do what I want and the autonomy to avoid things I don’t want to do.

Having deadlines on videos is like having another job.

Back in school, I loved English class. I loved writing and figuring out how to get an idea out of my head and into something real. Something tangible. Still do!

Each time I got a new assignment, my mind raced with all the different paths I could take from the intro to the conclusion.

But the moment my brain remembered the dreaded “due date”, the enjoyment disappeared.

I always thought this was simply a symptom of schooling.

Like, no shit, homework sucks. I’m not going to want to write an essay about The Count of Monte Cristo, regardless of a deadline… right?


I realized there was a real (and insidious) issue when deadlines were stopping me from doing things I loved to do.

In my enthusiasm to grow my business and engage with my audience, I laid down self-imposed rules:

  • "Upload one YouTube video per week”

  • “Publish 5 newsletters this month”

  • “Write 3 tweets per day”

On the surface, this seemed like a simple structure for consistency. But the truth was more complicated.

Many times, I found myself rushing, curtailing my creative process to adhere to this schedule. More than once, I hit the 'upload' button with a sense of trepidation, knowing deep down that the video wasn't entirely ready.

But there was always that looming commitment - the one I made to myself and, indirectly, to my audience.

It became even more complex with sponsorship deals.

As grateful as I was for these partnerships, they often meant adjusting my content calendar to fit in sponsored videos. I worked late into the night, refining and tweaking, only to publish a video that, in my heart, felt prematurely released.

Isn’t it ironic?

We start this journey in the digital world for freedom, for autonomy. But then, unwittingly, we create our own shackles.

Ali realized this and gave his team a new goal:

I want to work towards never having to see another deadline ever again.

It makes perfect sense. Why leave medicine, and spend thousands of hours, and hundreds of thousands of dollars to build a YouTube empire, just to feel like you’re rushing to finish your middle school English assignment?

The goal here is, and always was: Autonomy.

And now, reflecting on my own journey, I'm inclined to follow in those footsteps. Yes, I'll still be creating, and yes, I’ll still be publishing consistently (new post next Tuesday!). But with a renewed vision. One where creativity isn't stifled by the clock, but rather flows freely, at its own pace.

Sometimes, like today, I might surprise you with a random article or a video, not because a calendar dictates it but because inspiration struck.

It's time for a new chapter—one where the joy of creation stands front and center, unburdened by looming deadlines.

Watch the full interview with Ali Abdaal here:

Jailbreak your health & fitness with:

20% off Create Creatine Gummies using code “JACK”.

  • Build muscle 💪

  • Increase strength 🏋️

  • Improve recovery ❤️‍🩹

  • Boost cognition 🧠

Ditch the flavorless (at best) powder and eat a delicious creatine gummy. 🍊

Til next time, Nomads. ✌️

P.S. There was an earthquake while I was writing this post! Wild!!

- Jack Ross

Jack Ross (Data Engineer, Writer, Nomad)

If you're interested in seeing more, follow me on Twitter for regular updates, and subscribe to my YouTube channel for travel vlogs, tips, and insights on unlocking freedom in the digital age.