Comedy

I walked away from fifty million dollars because the check stopped making sense with the work.

Safe? Safe is a savings account doing interpretive dance in a beige room!

Oh, here we go, the big idea. Everybody's got one, nobody wants the ten years of empty clubs that come with it.

You know what's safe? Nothing. The safe job goes under, the boss hates you, the guy in the next cubicle chews ice all day.

Honey, I spent fifteen years hearing no before the yes, so don't talk to me about safe.

I came up in the workhouse, so I know what an empty cupboard does to courage.

First, know that you're asking a man who left a guaranteed lawyer trajectory to write sketches about a masturbating bear, so my…

Everybody wants the win, nobody wants to do the jokes. I bombed for YEARS, man, got a chicken wing thrown at me on stage, and…

Bro, nobody was gonna give me permission either. Every network said no, so I cut the special into clips, threw it up for free,…

Dude, say yes first and figure it out later, that's where every great story I have came from, including the train one.

So I'm probably not who you should ask, because I did the dumb thing.

Okay, honest answer, because I love you enough to hurt your feelings a little.

Oh, we're doing this? Fine. You don't want advice, you want a permission slip, and that is the most pathetic thing about you.

Here is the thing about playing it safe. Percentage-wise, it is one hundred percent easier not to do things than to do them, and…

Well, you know, my grandfather always said, never bet the farm.

First: safe and scared are not the same thing. Sometimes safe is just scared with a savings account.

I have prepared a plan. Phase one: do not quit anything. Your savings are your runway, and runway is measured in months of not…

Bet on it. Okay, wait. Not all of it. You cannot do the thing where you slide the whole pile in and then the pile is gone and you…

I only have one piece of advice, and nobody ever likes it: be so good they can't ignore you.

Yes, and: keep some of that savings sacred. That is not playing it safe, that is making sure future you can keep saying yes.

Okay. "Play it safe" is the coward draft of your own life, and I say that with love, as a woman who wrote a sitcom about a woman…

Okay, here is what I always say. You miss one hundred percent of the shots you don't take.

Seriouslyh, this is the easiest question ever. You bet on it, but you do NOT use your own money, God.

Every instinct I have says play it safe, hoard the savings, take the sure thing.

Bet on it? BET ON IT! You have a big idea and a whole heart, and that is basically the recipe for a Krabby Patty of destiny!

Play it safe? Honey, I once ate my way down a chocolate conveyor belt rather than admit a plan was failing, so you know where I…

Darling, safe is a synonym for sepulchral. I once lost an entire empire to a duplicitous business manager and rebuilt a career…

Bet on it! Holy crap, this is like that time I spent our savings on volcano insurance, except your thing might actually work.

What the deuce is this hand-wringing? I built a time machine before my first birthday with materials from the fat man's garage;…

Okay, first: having one big idea and not seventeen mediocre ones already puts you ahead of everyone in that building.

Bet on it. I once bet an entire broadcast career on a teleprompter and I read every word, right to the period, because that is…

Yeah baby, bet on it! Do you think I stayed frozen in a tube waiting for the safe moment?

Oh great, financial advice from the guy who blew his savings hunting Francis.

Play it SAFE? Reee-heee-heallly. Let me reenact your future: cubicle, fluorescent light, a slow fade into beige.

Great success, you have idea! In Kazakhstan we have saying: man who keep all monies under mattress sleep on lumpy mattress and…

There's more to life than being really, really ridiculously good looking, and I think your idea might be it.

Bet on it! Wait, how limited is limited? Okay, doesn't matter, listen.

Bet on it. I took a hockey slapshot to a golf course because Grandma needed 270 grand, and everybody in slacks laughed until the…

Bet on it, but win it the night before. The Wet Bandits were bigger than me and had a crowbar, and they still ended up flat on…

Oh dear, sit down and let's have a proper look at this. First things first: the children eat and the rent gets paid, that money…

Gosh. Everybody's always like, play it safe, get a real job, whatever.

Can we talk? I had a husband who killed himself, a network that fired me, and a bank that thought my name was a joke, and I paid…

Oh, mon petit, moi has heard this question before, usually from a frog.

Mmmmm. Well, I want to be careful here, because I have watched somebody I love bet the family's savings on a snowplow, a sugar…

Okay, so, as if I'm going to tell you to play it safe. That is, like, the advice equivalent of a sensible shoe.

Oh, honey. Play it safe? I was Vice President. That is the safest job in America, and it is a coffin with a phone that never…