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Dear Quota Team,
I've spent the last 8 years selling payroll services. I'm consistently at quota, and frankly, can do this job in my sleep at this point. I've been approached about a sales role in medical devices—a field I have zero experience in, but with significantly higher commission potential and more complex sales cycles. The compensation package could potentially double my income if I perform well, but I'd be starting from scratch learning both the product and industry. My current role is stable and comfortable, but I'm starting to feel stagnant and like I’m “coasting.” Is it crazy to walk away from a role where I'm established to pursue something with bigger upside but substantial risk?
Deciding in Washington
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Dear Deciding,
The decision ultimately boils down to what you value more—security, or the growth from new challenges. If you genuinely feel stagnant, that restlessness will rarely resolve itself without action. Of course, any transition will require humbling yourself to become a student again, working harder than you've had to in years, and accepting a temporary dip in performance—BUT, you could always go back to payroll if it doesn't work out. Sometimes the biggest career risk is taking no risk at all, particularly when you know you’re ready to grow again. Go for it!