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Dare to be Deliberate

This is what I'm after. Can you help me?

The definition of deliberate is ‘to be done consciously and intentionally.’ It’s a word that’s simple to understand, but difficult to implement. Especially when it comes to your professional growth.

We deliberately go out of our way to hit up Starbucks before we go into work. And we deliberately post on social media to keep up our appearances.

Now it’s time to apply deliberate practice to your career. And it all boils down to two sentences:

This is what I’m after. Can you help me?

Here are two things I’ve learned about deliberately asking for help and how it’s helped me in comedy.

Ask for small favors that don’t require money, or very little risk

Like every new comedian, my goal was to get on as many stages as possible. And when you’re starting out in the cruel world of comedy, those ‘stages’ are often coffee shops or bars in shopping plazas. Showbiz. Right?

When you’re trying to get on stage, you ask for ‘guest sets’. Guest sets are 3-5 minutes on stage where you are paid in experience – not money. Most of the time it’s a minimal risk for the promoter or booker of the show because there are three other comics to cover for you if you suck.

I cut my teeth through probably a hundred guest sets. I’d simply message or e-mail the booker or promoter, introduce myself, and ask for a guest set. Comedy bookers are emphatic to the fragile psyche of comedians, so most of the time they said, “Yeah, sure” or tell me they could get me on a future show.

No money was coming out of their pocket and there was very little risk. You build up goodwill doing free work. The payoff will eventually come.

Ask for someone’s expertise for no more than five minutes

One of my comedic goals was to figure out the all-elusive monologue joke. It’s the short ‘set’ that you see all late-night hosts do before they bring their guests out.

Monologue jokes follow a very specific formula. Two sentences max with a setup and punchline. Simple enough, right? Not really.

The beauty of monologue jokes are they have to be subjects or news stories that everyone can relate to, and the punchline has to be clever and clear. To write these types of jokes well you have to write everyday. It’s a volume game. You have to write A LOT!

Eventually I asked any and everybody in my circle if they know of people who wrote for late-night shows and before you knew it, I got some e-mail addresses. I knew these people were extremely busy so I came up with a plan:

1.) I would write 30-50 topical jokes and then narrow it down to 10.Why 10? Correctly formatted, 10 monologue jokes fill up one page.

2.) I’d email the monologue writer and tell him or her that I was trying to learn their profession, ask kindly for their feedback, and thank them in advance for looking at my work.

3.) Most importantly, I would ask them if I could send them one page of jokes. They knew a page of jokes would likely be 10-12 jokes, so it would only take 2-3 minutes of their time.

I’d say about 80% of the time I got feedback. Not bad. Showing a willingness to learn and a vulnerability to express someone as a respected thought leader isn’t a bad way to build great relationships.

Being deliberate in your professional life may take a little getting used to, but we need all the help we can get. Just ask me. Because I’ve asked for a lot of help!

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