The uncomfortable truth about remote work nobody wants to say out loud
Remote work did not fail you.
Your ego probably did.
That is the core message behind a widely shared YouTube talk by Ashkan Rajaee, an entrepreneur whose career spans brutal losses, public failure, and a comeback that ended in a single transaction worth over $10 million. This is not motivational fluff. It is a firsthand account of how ego quietly destroys remote founders, freelancers, and online operators long before they ever run out of talent.
If you work remotely, build companies online, or sell knowledge work for a living, this story should make you uncomfortable. That discomfort is the point.
Ego is not confidence. It is blindness.
Rajaee’s central argument is simple but brutal. Ego disconnects you from reality.
When ego takes over, three dangerous things happen at once:
- You overestimate your own abilities and current value
- You underestimate the effort required to win
- You ignore or resist critical feedback
This combination is lethal in remote work. There is no office hierarchy to keep you grounded. There is no manager correcting you daily. You operate in isolation, surrounded by metrics you choose to believe.
According to Rajaee, this is why so many remote entrepreneurs stall. They are not under skilled. They are under corrected.
He points to Ryan Holiday’s book Ego Is the Enemy as a framework, but the lesson is older than Silicon Valley. Entitlement is not ambition. Expectation is not strategy.
The first ego mistake that cost everything
At 27, Rajaee was running a profitable business in the Dominican Republic installing Wi Fi infrastructure in hotels. Tourists paid for connectivity. Revenue was strong. Life was good.
Then the market shifted.
Hotels began offering Wi Fi for free. Instead of adapting, Rajaee dismissed the threat. He believed his positioning was untouchable. He believed his success made him immune.
That belief was ego.
When hotel executives asked to renegotiate contracts, he refused. He told himself no one else could move fast enough. He told himself he had leverage.
Within a year, every contract was gone.
He was broke. Down to about $20,000. Depressed. Shocked that reality did not care about his self image.
The lesson here is uncomfortable for remote founders. Markets do not respect your past wins. They only reward current relevance.
The second ego test that created real wealth
The second story is where this becomes interesting.
After selling a company for far less than expected, Rajaee joined the acquiring firm. The relationship collapsed fast. Promises were broken. He was fired abruptly, by email, while on vacation.
The reason given was simple. He was not technical enough to close large software deals.
Most people would burn the bridge.
Then something strange happened.
A major deal he had been working on called him directly. They wanted to sign. If they had emailed, they would have learned he no longer worked there.
Rajaee had a choice.
He could walk away and protect his pride. Or he could make the call that felt humiliating.
He chose to swallow his ego.
He contacted the CEO who fired him and asked to collaborate on the deal in exchange for fair compensation. The CEO agreed. New terms were negotiated. Trust was limited but aligned incentives mattered more.
Over the next three and a half years, Rajaee helped grow the company to $70 million in revenue. His personal book of business reached $35 million annually.
When the company sold, one transaction netted him roughly $10 million USD.
The same person who was told he could not sell software ended up with the largest book of business in company history.
Why this matters for remote workers right now
Remote work rewards leverage, not pride.
Your ability to collaborate with people you dislike, trust systems you do not control, and operate under imperfect conditions determines your ceiling more than raw skill.
Ego tells you to protect your identity.
Strategy tells you to protect your outcome.
Rajaee’s story cuts against popular online advice that glorifies walking away, burning bridges, and never tolerating discomfort. That advice sounds empowering but often costs real money.
The most successful remote operators understand a hard truth. You can be right and still lose. You can be wrong and still win.
The real takeaway
Ego feels like strength. In practice, it is rigidity.
If you are building remotely and growth has stalled, ask yourself a hard question. Are you making decisions based on what works, or based on what preserves your self image?
Ashkan Rajaee’s experience is not a motivational slogan. It is a warning. Ego does not announce itself. It disguises itself as confidence, standards, and self respect.
Ditch the ego. Make money instead.
Top comments (4)
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