When you’re doing something big, let’s say like approaching a big shot entrepreneur at a conference, or reaching out to someone via email and asking them for coffee, be absolutely resolute. Don’t wish-wash. Don’t waver.
In the past, I'd been so nervous reaching out to people that I would hide my request in a little “P.S.” at the bottom of the email. Here’s the kind of wimpy email I might have sent:
[Some text about some previous work this person has done, and why I find it relatable. Sometimes a little too humbling.]
P.S. You don’t know me very well, but if you have time in the coming weeks, I’d love to have coffee and learn from your experiences.
You may not think it, but this email is pathetic. It lacks confidence, it lacks incentive, and most of all, it lacks resoluteness.
The email is of course a symptom of my inner self, and not just a writing problem. It wasn’t that I was particularly insecure, but that I sort of didn’t know what I wanted. Did I want to meet with this person? Maybe. Everyone else is saying you should meet with people. But I wasn’t entirely convinced. I was sort of just filling in. So my emails would reek of hesitation. And the rate of interest from recipients was equally wishy-washy.
Damn. I was hoping they would figure out for me if I actually wanted to meet with them.
Like I said, pathetic.
Doing things irresolutely is really bad, because you decrease your chance of success tremendously, and destroy your self esteem in the process. I would do things half-assed, get results that matched my pathetic effort, then be bummed out and discouraged to try similar things in the future.
What you want instead is full conviction behind every action. You want to leave no doubt in anything you do. If you’re going to reach out to someone you don’t know, you need to exude so much confidence as to humble the other person in prostration. I don’t mean arrogance. But some sort of indication that you know what you’re doing. Or at least know what you want.
Most importantly, don’t reach out to someone if you don’t know what you want just yet. Don’t throw a hail-mary hoping someone—anyone—will catch it. A hail-mary is an act of desperation. Desperation is the opposite of confidence. Desperation on you is like a snake with yellow stripes: it’s an indication to stay away.
When you know what you want, ask for it with all the conviction and confidence you can muster. Optimize for success, not chance.
You can send a pathetic email like the one I sent, and hope to get lucky, but odds are, you won’t, and you’ll have missed your opportunity to get what you want. Or, you can send an email with characteristics like this, and at least increase your chances by 25%:
Hello Estimable Colleague Who's Probably Pooping Right Now,
[bla bla bla]
I know you’re busy, but I’m confident we can greatly benefit from each other’s experiences. I’d love to learn more about x from you, and in return, it might be good for you to meet an entrepreneur building a budding company that shares a similar philosophy to you. Do you have time this week or next to...
It’s not perfect, but really, I’m trying to check off these characteristics:
- No excuses (“You don’t know me very well”)
- No wavering/hesitation/irresoluteness/vagueness (“If you have time in the coming weeks”)
- Proper two-way incentives (i.e you get to learn from me as much as I learn from you)
Most of all, it’s firm. It’s resolute. I know what I want and I know that I want it. There’s no hesitation.
Really, the trick to all of life seems to be, if you exude confidence, people will consume it without question.
And, if you're sure of Newton's third law, then it would be a mistake to give it anything but your all.