Most People Face Their Toughest Challenge Later In Their Careers. Mine Got Me Right At The Beginning.

When the hardest boss in the game is in the tutorial level.

Oje Ojeaga
2 min readMay 6, 2024

I met my most difficult client just as my career was taking off.

Fresh-faced, barely 2 years into copywriting, and I already faced a new fear – the toxic client.

Imagine presentations interrupted with mocking laughter, documents thrown across the room, the works. The verbal abuse was a constant punch to the gut, leaving my colleagues dazed even minutes later. People were regularly reduced to tears.

This client was a little less brutal with newbies like me (probably had a soft spot for a fellow copywriter starting out). But the damage came in the feedback – or lack of it. I often reworked work until it lost all meaning. Approval? Tied to their mood that day. Oof.

For 3 years, this was my reality. I’ll admit it broke me – this was the closest I ever came to quitting advertising. My morale was in the gutter, my creative spark gone.

How did I survive? I had a great boss. He ran interference, backed me up at meetings, and went over my client’s head when things got crazy.

But here’s the thing: you need bosses who fight for you, but not too much. Some battles you have to face alone. Fixing mistakes, taking a few on the chin – that’s what builds resilience. My boss understood that.

Over time, I learned to push back, lost my newbie ‘immunity’ (lol), but it felt empowering. The client left, life went back to normal.

Experiencing bad clients early on is a twisted blessing. It teaches you to lower your expectations, develop tons of patience, and secretly, you get to smile a bit when your modern day colleagues stress over a tough email.

Rookies. 😈

Bad experiences suck, but some make you better. All of them, however, teach you something.

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Oje Ojeaga

Founder and CEO of Up In The Sky NG/UK. Reluctant writer. Enthusiastic creative.