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Paul Ollinger

๐Ÿ‘ค Speaker
See mentions of this person in podcasts
423 total appearances

Appearances Over Time

Podcast Appearances

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

So I thought when I left my job, I was like, I'll figure it out. But it's really interesting how easy it is to fill your day with lots of fun stuff that aren't work. You work out, you get healthy, you travel, you read books, you spend time with your kids, you play a lot of golf. Life's pretty good until a certain point where you wake up one day and you're like,

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

So I thought when I left my job, I was like, I'll figure it out. But it's really interesting how easy it is to fill your day with lots of fun stuff that aren't work. You work out, you get healthy, you travel, you read books, you spend time with your kids, you play a lot of golf. Life's pretty good until a certain point where you wake up one day and you're like,

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

So I thought when I left my job, I was like, I'll figure it out. But it's really interesting how easy it is to fill your day with lots of fun stuff that aren't work. You work out, you get healthy, you travel, you read books, you spend time with your kids, you play a lot of golf. Life's pretty good until a certain point where you wake up one day and you're like,

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

wait a minute, what, what am I doing? Who am I? I don't know how to answer the question. What do you do? Like, I feel like a loser. Like I'm very, very lucky, but I feel like a lucky loser right now. And eventually I had no purpose, no purpose. And eventually I even took another job I shouldn't have taken. I just sort of took a job that I thought would look good.

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

wait a minute, what, what am I doing? Who am I? I don't know how to answer the question. What do you do? Like, I feel like a loser. Like I'm very, very lucky, but I feel like a lucky loser right now. And eventually I had no purpose, no purpose. And eventually I even took another job I shouldn't have taken. I just sort of took a job that I thought would look good.

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

wait a minute, what, what am I doing? Who am I? I don't know how to answer the question. What do you do? Like, I feel like a loser. Like I'm very, very lucky, but I feel like a lucky loser right now. And eventually I had no purpose, no purpose. And eventually I even took another job I shouldn't have taken. I just sort of took a job that I thought would look good.

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

And it wasn't, it wasn't a good fit. And it, Just wasn't, my heart wasn't in it. And so after a year of that, I said, I'm going to just, I'm going to, I, I've, I was, I was afraid. That is the word. I was afraid to try to do standup comedy again because I had failed. I had, I had quit. I didn't fail. I quit before. Just stopped. And I was ashamed that I like, what are people going to say?

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

And it wasn't, it wasn't a good fit. And it, Just wasn't, my heart wasn't in it. And so after a year of that, I said, I'm going to just, I'm going to, I, I've, I was, I was afraid. That is the word. I was afraid to try to do standup comedy again because I had failed. I had, I had quit. I didn't fail. I quit before. Just stopped. And I was ashamed that I like, what are people going to say?

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

And it wasn't, it wasn't a good fit. And it, Just wasn't, my heart wasn't in it. And so after a year of that, I said, I'm going to just, I'm going to, I, I've, I was, I was afraid. That is the word. I was afraid to try to do standup comedy again because I had failed. I had, I had quit. I didn't fail. I quit before. Just stopped. And I was ashamed that I like, what are people going to say?

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

What would people that I worked with in the technology business think that I was going to go back? That did I look wishy-washy, whatever. And of course, worrying about what other people think is the worst thing you can do. And so I just said, screw it. I'm going to write every day. I'm going to start going to open mics again. And this is in 2014 and we'll see what happens.

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

What would people that I worked with in the technology business think that I was going to go back? That did I look wishy-washy, whatever. And of course, worrying about what other people think is the worst thing you can do. And so I just said, screw it. I'm going to write every day. I'm going to start going to open mics again. And this is in 2014 and we'll see what happens.

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

What would people that I worked with in the technology business think that I was going to go back? That did I look wishy-washy, whatever. And of course, worrying about what other people think is the worst thing you can do. And so I just said, screw it. I'm going to write every day. I'm going to start going to open mics again. And this is in 2014 and we'll see what happens.

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

And so that's what happened. And I, and you know what, when you start, when you declare what you stand for, what you want to do, you eventually meet fellow travelers and you eventually find people who are going to you know, be your partners on the journey and you know, some way or be people that can, you can, you can help and they can help you back.

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

And so that's what happened. And I, and you know what, when you start, when you declare what you stand for, what you want to do, you eventually meet fellow travelers and you eventually find people who are going to you know, be your partners on the journey and you know, some way or be people that can, you can, you can help and they can help you back.

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

And so that's what happened. And I, and you know what, when you start, when you declare what you stand for, what you want to do, you eventually meet fellow travelers and you eventually find people who are going to you know, be your partners on the journey and you know, some way or be people that can, you can, you can help and they can help you back.

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

And that's, and that's eventually what happened in Atlanta. And I started doing comedy again. I started doing a lot of comedy, um, got better. I've done, you know, every festival except for like the top two or three in North America. I've, you know, headlined around the country. I'm doing the thing that I want to do. I write every day. Um, you know, I've got a, I've got a,

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

And that's, and that's eventually what happened in Atlanta. And I started doing comedy again. I started doing a lot of comedy, um, got better. I've done, you know, every festival except for like the top two or three in North America. I've, you know, headlined around the country. I'm doing the thing that I want to do. I write every day. Um, you know, I've got a, I've got a,

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

And that's, and that's eventually what happened in Atlanta. And I started doing comedy again. I started doing a lot of comedy, um, got better. I've done, you know, every festival except for like the top two or three in North America. I've, you know, headlined around the country. I'm doing the thing that I want to do. I write every day. Um, you know, I've got a, I've got a,

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

I'm here's the thing, man. I'm very good at several different things. I'm a very good podcaster. I'm a very good comic. I'm a very good writer. Uh, I'm a very good speaker too. I just did a great speaking event last week. Um, I might even be great at speaking, but you know, as somebody, the guy that ran the guy that ran the New York comedy festival, he's like, you know, you're good.

Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success

I'm here's the thing, man. I'm very good at several different things. I'm a very good podcaster. I'm a very good comic. I'm a very good writer. Uh, I'm a very good speaker too. I just did a great speaking event last week. Um, I might even be great at speaking, but you know, as somebody, the guy that ran the guy that ran the New York comedy festival, he's like, you know, you're good.