You can only win what you’re willing to lose

“Based on the rate menu we sent, we’d be looking at about $75,000 for this work. Is that impossible for you on this one?” That’s a line from an email I sent to a client recently. I shared a rate menu with them a few days prior. They came back and asked for a scope of work in the $50,000 range. After chatting with a couple of my team members, we decided that we were in a strong position to negotiate based on the work we delivered to them in past projects.

The client came back quickly to lock in our new budget. 

This reminded me: you can only win what you’re willing to lose. This is a lesson I’ve been learning at the poker table recently. Playing safe and small might net you small wins and small losses. But playing bigger gives you the chance to win more. Of course, playing bigger only makes sense when you’re in a strong position. When you look at your cards, look at the table, and look at the person across from you, that’s when you can decide how much you’re willing to lose. 

Our client could have walked away. They could have had another vendor on deck to work for $50k. But we were willing to bet $50k that they didn’t. It earned us an additional 50% on top of their first offer. 

At a different time of year, with different cards, I may not have made that bet. I may not have been willing to lose at that time. I might have played it safe. 

This time, we won. 

Reese Hopper

Reese Hopper is the author of What Gives You the Right to Freelance? He’s also a prolific creator on Instagram, and the editor of this website.

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