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Dear Quota Team,

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I'm 26 and sell enterprise HR software with deal sizes ranging from $150K to $500K. I've noticed a disturbing pattern where I consistently lose deals in the final stages, often through my own actions. Last month, I had a $300K contract ready to sign when I suddenly started overthinking every detail, called the client with "one more clarification question" that reopened negotiations, and watched them get cold feet and postpone indefinitely. Two weeks ago, I was hours away from closing a $400K deal when I impulsively offered an unnecessary 15% discount "to sweeten the pot," which made the buyer suspicious about our original pricing and caused them to demand we re-justify our entire value prop. I think I'm subconsciously sabotaging these opportunities because I grew up poor and part of me doesn't believe I deserve this level of success—these single deals represent more money than my parents made in a whole year combined. How do I stop getting in my own way when I'm this close to life-changing commissions?

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Self Sabotaging in Location withheld  

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Dear Self,

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Your self-awareness is already half the battle. You need to reframe the way you think about these deals. These aren't undeserved windfalls, but validation of the value you're providing to clients. When that voice of doubt creeps in, remind yourself that your prospects chose you because you earned it through competence, not luck. And of course, remember some old sales wisdom: once you get to “yes,” stop talking.