Today, I faced the awkward task of reaching out to an old boss for a reference. It's been years since we worked together, and I always feel uncomfortable asking someone from my past to vouch for me, especially when I haven't been in touch. My recent supervisors have already agreed to be references, but they are from a different field than the one I'm applying for now. I feel it's important to include someone who can speak to my experience in this specific area. This will be the third time I'm asking this particular person for a reference, and while I believe they'll be fine with it, I still cringe at the thought of sending that email. I also wonder if they even still work at the same company. It's a nerve-wracking part of the job application process that I wish I could skip.
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