If everyone you ask for advice tells you what you want to hear, ask someone new.

Advice that always agrees with you is company rather than information. People who like you, or who want an easy conversation, tend to reflect your plan back at you, and that feels supportive while telling you nothing new. If every answer has matched your hopes, the sample is the problem. You have been collecting agreement, not opinions.

Take your plan to someone with no stake in it and ask directly what the weakest part is. Ask an adult who has done the thing rather than a friend in the same position as you. When somebody says what you did not want to hear, stay in the conversation a little longer.