Advice: "I really want to quit my job, but I've got a big deal in the pipeline. I feel like I'm wearing golden handcuffs, but it may end up being Fool's Gold"

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Dear Quota Team,

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I’m an enterprise AE at a public SaaS company selling security software to Fortune 1000 accounts. I’ve been interviewing quietly because I’m burned out and honestly don’t see a long-term future here.

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The problem is I’m mid-deal on the largest opportunity of my career. It’s an eight-figure, multi-year contract that I’ve been working on for almost a year. Procurement is engaged, legal redlines are flying, and if it closes, it would blow out my number and my commission.

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Part of me feels irresponsible even thinking about leaving before this is done. Another part feels trapped — like I’m staying for a deal, not the job. Is it stupid to walk away now, or am I already wearing golden handcuffs?

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Impatient in Location Withheld 

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Dear Impatient,

Opportunities like this don’t come around often, and walking away mid-flight is one of the few career moves you can’t undo. Even if you land somewhere better, it could take a year or two to build the relationships, trust, and pipeline needed to see a deal of this magnitude again.

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Close it. Collect the commission. Then reassess with leverage, clarity, and options.

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