ooh i actually love this combo for this question

page of pentacles reversed in present can mean you're in that stuck/overthinking phase before you actually commit to learning something new. and 5 of cups is about fixating on what went wrong instead of seeing what's still there

so together? might be saying you're letting past disappointments or fears hold you back from even starting

omg I got almost this exact combo a few months ago when I was dragging my feet on starting a side project

for me the page of pentacles reversed was like... I hadn't even let myself be a beginner yet? like I was scared of not being good at it right away so I just... didn't start

and the 5 of cups was the grief of all the time I'd already wasted worrying about it lol

but here's the thing - once I actually noticed that pattern, I was able to break it. the cards weren't saying "you're doomed" they were saying "hey, see what you're doing?"

started the project the next week and yeah it was messy at first but I learned so much