Accurately assessing our experience is one of the hardest parts about the job search and where many of us actually underestimate our skills. For example, I regularly talk to: 

• Principals who only apply to “early career” jobs despite their background managing large staffs and leading entire schools; 
• Educators with contract curriculum experience who only apply to roles looking for “educators” even though they have created commercial curriculum products at scale; 
• Former corporate professionals who dismiss their pre-teaching careers as “dated” even though they have specific functional skills companies need; 
• Part-time school-based program coordinators who don’t apply to full-time program management jobs even though their cumulative project management skills easily reflect 2-5 years of full-time work. 

One reason people underestimate their skills is they start off applying to jobs that might be a good fit but don’t receive (many) interviews. Instead of blaming the difficult job market, they assume that their skills aren’t good enough. 

In reality, imposter syndrome is driving this calculation rather than an accurate assessment of their skills. Imposter syndrome leads us to undervalue our unique skills and expertise. When you undervalue your experience, your resume isn’t going to highlight your high-level experience but will focus on the same skills everyone else is sharing.

In the examples I gave above (all real examples from subscribers like you!), these candidates could apply to jobs they weren’t applying to. In today’s newsletter, I’m going to help you evaluate how to position your skills when your background almost matches what they’re seeking. 

The real problem isn’t that you lack qualifications—it’s that you’re not accurately assessing or positioning the experience you have. Most people skip the crucial step of evaluating how their functional skills align with what companies actually need, then wonder why their applications aren’t getting traction.

In this issue, I’ll walk you through my 5-step assessment framework to help you determine when a role is a strategic stretch worth pursuing. Then I’ll show you exactly how to position yourself in four common scenarios where your background almost matches what they’re looking for.

What’s Next:
How to Evaluate if the Role is the Right Kind of Stretch

Positioning Strategies for Common Scenarios:

• When your part-time experience equals their full-time requirement
• When you have relevant skills that aren’t obvious from your job title
• When your experience feels “dated”
• When you meet core requirements but lack preferred qualifications

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