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Embracing Freedom: The Irony of Deadlines in Creativity

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Chapter 1: The Paradox of Deadlines

It’s a rainy day in Long Beach as Hurricane Hillary makes landfall. I’m cozied up with a cup of Philz Coffee, my cat, and the latest interview between Colin and Samir featuring Ali Abdaal.

Many of us have our go-to productivity experts, and for me, that’s Ali. He made the leap from being a doctor to a full-time YouTuber, and now, five years later, he’s raking in over $4 million annually through his videos. His influence inspired me to kickstart my own YouTube channel back in September 2020, diving into the exhilarating world of building an audience and getting paid for what I love.

While Ali is undoubtedly a master at creating and monetizing YouTube content, he often overlooks a key element in the monetization process: sponsorships. Even he, the productivity guru, finds himself postponing videos that include sponsorship deals. His rationale?

“I entered this space to forge a career and life on my terms. I wanted the freedom to pursue what I love and the ability to sidestep what I don’t enjoy.” Deadlines for video uploads feel akin to another job.

During my school years, I adored English class. Writing was a joy, as I relished the challenge of translating ideas from my mind into something concrete. However, the moment I recalled the ominous "due date," that joy evaporated. Initially, I thought this was merely a byproduct of traditional education — homework is tedious, after all. But I soon recognized a deeper issue: deadlines were hindering my passion for activities I truly enjoyed.

In my eagerness to expand my business and connect with my audience, I set self-imposed guidelines: "Post one YouTube video each week," "Distribute five newsletters this month," "Compose three tweets daily." At first glance, these seemed like straightforward frameworks for consistency, yet the reality was far more complex.

I often found myself hurrying, truncating my creative process to meet these timelines. More than once, I hit 'upload' with a nagging feeling that the content wasn’t quite ready. But the commitment I made to myself and my audience loomed large.

The complexity escalated with sponsorships. While I appreciated these collaborations, they frequently required me to alter my content schedule to accommodate sponsored segments. I often worked late hours, refining my work, only to release videos that felt rushed.

Isn’t it ironic? We embark on this digital journey seeking freedom and independence, yet we inadvertently bind ourselves with self-imposed constraints.

Ali understood this dilemma and set a new vision for his team: “I aim to work towards never having to confront another deadline.” This sentiment resonates profoundly. Why leave a stable career in medicine, invest countless hours, and spend significant money to create a YouTube empire only to feel like you're racing to meet a school assignment's due date?

The ultimate objective has always been autonomy. Reflecting on my path, I feel inspired to adopt a similar mindset. Yes, I will continue creating and maintaining consistency (look out for my new post next Tuesday!), but with a refreshed perspective. One that allows creativity to flourish unencumbered by time constraints.

There will be occasions, like today, when I might surprise you with an unexpected article or video, not dictated by a calendar but inspired by a sudden burst of creativity.

It’s time for a new chapter — one where the joy of creation takes precedence, free from the pressures of impending deadlines.

Watch the full interview with Ali Abdaal here:

Chapter 2: The Essence of Autonomy

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Until next time, Nomads. ✌️

P.S. An earthquake shook things up while I was penning this post! How wild!

— Jack Ross

If you want more insights, subscribe to The Jailbreak (my weekly newsletter), follow me on Twitter for updates, and check out my YouTube channel for travel vlogs, tips, and insights on achieving freedom in the digital era.

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