THIS is why most entrepreneurial journeys lose steam



Hey Reader,


A few days ago, I had an epiphany.

It was as clear as a bright orange neon sign flashing the answer 2 mm from your face, a connection I was oblivious to all along. It struck me while watching a YouTube video on language learning that emphasized the importance of cultural immersion.

The idea is to soak in the culture— audiobooks, music, movies and communities— like a dry sponge. Allowing the language to seep into every crevice and fold of your brain, even when you don't understand a thing.

Then, the bright orange neon sign lit up: If cultural immersion is crucial in language learning, couldn't the same principle apply to the entrepreneurial or any journey?

I’m sure this was the missing link in my failed attempt to start back in 2017.

My first encounter with the enchantment of community was through "Ship 30 for 30," a 30-day writing course + community I joined in August 2022. I published 30 short essays in 30 days.

For my first few posts, pressing ‘submit’ felt like an anxiety bomb detonated in my chest that sent my pulse soaring. Post-publish, I'd find myself in a battle, my finger hesitating over the 'delete' button in a high-stakes standoff. I'd have to talk myself down each time, shocked by the audacity.

However, the positive peer pressure from the flood of published essays pulled me forward like a rip current; even the "I'll do it tomorrow" voice in my head couldn't fight it. Gradually, with each post, the dial on my internal radio adjusted, clearing the fear-induced static and paving the way for building my online presence.

Then I discovered the 'Indie Mastermind' and 'Indie Worldwide' communities — absolute treasures. Like reaching into your pocket and finding a crisp $20 bill in your jeans every time you put them on.

These groups offer a variety of helpful sessions and resources — daily virtual stand-ups, mastermind sessions, book clubs, and more — providing the scaffolding and a wealth of insights that have initiated steady progress.

I vividly remember the contrast before joining.

I spent months passively observing business forums like Indie Hackers. Like a fly, pitched comfortably on the wall, binoculars in hand. Non-stop scrolling, often with the cursor blinking mockingly while I sat paralyzed by the confusion of where and how to start.

As a result, I never did.

My mistake was equating consumption and observation with progress.

One of the first small breakthroughs was their help in identifying the right prospects to interview for a concept I had. Initially, the thought of cold outreach would tighten my chest as I was unsure how to find and approach them.

I received advice on the ideal social platforms and tools, help to refine my messages, and even stories with insights about their struggles – tales of sending hundreds of messages and sometimes needing up to five tries for a single response.

Their guidance has been like a GPS, steering me from confusion to clarity.

It's not enough to quietly observe alone from the sidelines (like I did for 6+ years).

This is the enemy of progress.

The sorcery emerges when you lean all the way in, ask and answer questions, join calls, attend meet-ups, and rub shoulders with those who carry momentum and are actively working towards goals similar to your own.

Active participation and the silent nudge you get from being surrounded by motivated individuals recalibrate your mindset and fuel progress.

It's brainwashing in the best possible way.


Engineering Freedom

Sharing lessons from my entrepreneurship journey to help you overcome fear, avoid setbacks & get off the bench. Go from idea → prototype and iterate quickly.

Read more from Engineering Freedom

Hey Reader, Exactly a year ago, I was perched at the edge of a Grand Canyon of decisions. As I peeked over the edge, the cold air rising from the darkness below was crisp with anticipation and work-induced despair. All the unknowns of life after 9-to-5. Behind me, the three-headed work serpent hissing and slithering closer. Its three big ass heads stretching high above, glaring down. Deadlines, career improvement goals, demanding projects, and all the other junk I never gave a rat's ass...

“Justineee! Thanks for joining Indie Mastermind. Tell me about what you are working on and how I can help you.”Ayush, the founder of Indie Masterminds – an entrepreneurial community I joined a few days prior – asked with an encouraging tone, unaware of my simmering frustration.I had just wrapped the experiment for my first business idea that hadn’t worked out. I was at the all too familiar crossroads of not knowing what business problem to pursue next. Ayush presented a challenge that...

Hey Reader, In Feb 2015, I was fired. I avoided as many eyes as possible as I scrambled to gather my things and exit like the floor was hot coal. Then I passed the intern’s desk and felt his eyes like daggers in my ribs. For a nanosecond, the knots in my stomach released. It was the last time I'd endure his backhanded jabs and the intricate knots weaved into my intestines by the culture when I sat at my desk each morning. This was my first job as a Canadian immigrant and a software engineer....