A friend is a person with whom I may be honest. Before him, I may think aloud. –Ralph Waldo Emerson
To initiate a deeper conversation with a friend, find a quiet place and sit down. You cannot connect well while in constant motion, looking at devices, or in a noisy environment. Set the tone by saying, “I need to talk about something, would you mind just listening for a moment?” Then express yourself simply, straight from your heart. An example might be “I’m really worried that I won’t be able to make this new project work. I’ve paid a lot of money; I might have just made a big mistake.” If they are a good listener, they will sit quietly, giving you an opportunity to say more, or echo your concern with an “oh my, that is worrisome” or even encourage you to dig deeper by asking “what is your worst fear”? If however, they seem uncomfortable or barrage you with unsolicited advice they have not yet learned how to deeply connect.