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Job Hunting Over 50? Tips to Land Your Dream Role!


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As a seasoned job seeker in the tech world, I feel like I’m constantly battling stereotypes. Recruiters often seem to think my cover letter should start with “Greetings from Jurassic Park.” But the truth is, I’m eager to keep contributing to the field. As a respected angel investor, I collaborate closely with tech leaders who value my insights and experience.

Recently, I faced a frustrating situation with a prominent tech company. I was thrilled to see they were hiring for a head of events position, and in my cover letter, I proposed adding a public relations component and establishing a speaker’s bureau. After being turned down for the event role, I was shocked to see them post a job for a “product communications lead” just ten days later—essentially a rehash of my suggestions. I did reach out to express my interest, but I’m not holding my breath for a response.

— Anonymous

I totally get your frustration, and trust me, you’re not alone in this.

This kind of situation happens all too often. In my experience, it’s wise to hold back on offering unsolicited advice or insights to potential employers until they ask for it. When crafting your cover letter, focus on your achievements and how you can be a valuable asset to the company. Save the strategic advice for later—preferably in a follow-up memo. You can tease at the specifics without giving everything away upfront.

I’m not suggesting you play coy; rather, keep some strategies to yourself. You’ve put in the hard work, and you deserve to maintain your competitive edge. Especially in an industry that often favors youth, sometimes less is more.


After leaving my marketing communications job, a colleague attempted to erase my contributions by taking my name off the publications I created and claiming them as her own. I know the copyright belongs to the company since I produced them on their time. Should I take action to preserve my professional reputation?

— Anonymous

Let’s unpack what you mean by “preserving your reputation.” Are you worried that your colleague’s actions are tarnishing your standing in your field? Do you feel overlooked or undervalued because you haven’t been credited properly?

I get it—what your colleague did is not just unethical; it’s downright infuriating. But based on your brief account, I don’t see any reason for you to panic about your reputation. I’d love to know more about how she’s “promoted” your work. Did she do it internally, to higher-ups, or externally to clients? Or maybe a mix of both? And do you feel your contributions have been adequately recognized from the start?

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