Honestly? I had a colleague who thought a master's in advertising would fast-track their career. They came back with a fancy degree and a heap of debt, but zero real-world insight. The only thing it impressed was the HR system when they applied - and even then, the creative directors just rolled their eyes. A degree doesn't teach you how to sell an idea to a client who hates everything, or how to get a brief right after the third rewrite.
I've spent years on the customer side before jumping into marketing, and the best education I got was on the job. Picking up the phone, listening to real people complain, then figuring out how to fix it. That's where the skill set for account or strategy starts. For creative? It's all portfolio, portfolio, portfolio. I've seen juniors who went to a six-month portfolio school outperform a master's grad on day one, because they had work that proved they understood visual literacy or copywriting.
Sure, a master's might help if you want to teach. But if you want to be a creative director? Nobody cares about your thesis. They care if you can art direct a campaign that actually moves units. The path is exactly what that other person said: junior, regular, senior, associate, then director. Jump agencies, build a book, and learn by failing. That's the real degree.