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The speaker shares their journey of struggling as a beginner on Upwork, where they initially sent over a hundred proposals without receiving any responses. Despite spending $50 on connects and feeling discouraged, they felt a responsibility to succeed for their family's sake. Realizing that their Upwork profile was poorly constructed—essentially a copy of their LinkedIn profile—they decided to enhance it by learning from successful freelancers. The speaker emphasizes the importance of crafting a strong profile and offers a ready-to-use cover letter for beginners looking to win their first Upwork job.