"Should I?"​ Yes you should.

There have been several moments in my career (and I assume in yours as well) where I have wondered whether or not I should do something.

I've been in discovery calls where I wondered if I should ask a certain question. I've raised my voice in operating rooms and stopped surgeons from proceeding because I saw something I didn't like. I've driven across town to see someone without an appointment because I just had a feeling they might be willing to see me.

I've never been let down by that intuition.

Okay, my prospects weren't able to meet with me on the spot every time, but there was never a time I regretted one of those trips across town.

I was reaffirmed multiple times this week, as I called people to follow up on meetings and even showed up in person to an event where I knew another prospect would be.

Each time, I hesitated for a second. "Should I do this? is it too bold?"

Then I remembered the objective, and I move ahead. 

Do you know what happened? They thanked me.

Every.single.time.

"Wow, thanks for calling. I don't normally pick up, and I didn't recognize the number, but I'm really glad I did."

"Thanks for coming out this evening. Let's reconnect at the end of this month or after the new year."

I was talking to my wife about some of these interactions and how it felt a little edgy to pick up the phone and call someone who didn't explicitly give you their phone number but puts it in their email signature.

She said, "Wow, you've really got to believe you've got something worth talking about if you're going to do that." 

That's exactly my point. 

There's so much attention paid to "the rules" as if they actually exist. There's no strict playbook to follow. Every situation has its own nuance.

The key in these situations is knowing what needs to be done and being willing to do it. Your gut instinct will never lead you wrong. Do you believe enough to follow through? 

Do you believe enough in what you need to talk about to start the conversation? Or are you going to hesitate and let Resistance get the best of you?

Fortune favors those who act, those who make the extra call, and those who are willing to disregard "the rules" and reach out because they really want to continue the conversation and they believe the other party will benefit.

Don't talk yourself out of doing these things. While you're waiting for your prospect to pick you, they're waiting for you to lead them.

There will always be a little voice inside your head that second-guesses whether or not you're doing it right. Don't forget where the initial urge came from. That intuition won't do you wrong.