>> A Pulitzer Prize winning writer, editor columnist PBS News Hour political analyst and MSNBC host lays it all bare in his new book.

Jonathan Capehart shares his life story in more yet here I am lessons from a black man's search for home.

The recounted stories of his upbringing and career illustrate the challenges with embracing his identity and finding his voice.

He's found them both and he shares them with us now.

Jonathan Capehart is in town for the Chicago Humanities Festival.

Welcome to Chicago.

And think you very much, Brianna.

So what inspired you to write this book want to do that now?

>> So there are 2 books that I read 20 years apart that had the same thing that drew me to them and why a loved one is personal history by Katharine Graham.

You know, the world sure of the Washington Post or the Washington Post, but one of most powerful women in the country and certainly the most powerful women in journalism at the time in her autobiography Talk about laying it all out.

And she was Raw, Open, honest, introspective about about her own insecurities, about her fraught relationship with her mother.

And I thought when I finished it.

Wow, this is this is the kind of book I want to read.

You know, none of this puppy dogs and dandelions.

keeping it real.

Fast forward 20 or so years.

And Charles blows memoir Fire Shut Up in my bones comes out and I read that and it's the same thing.

Raw, Open, honest, introspective.

And it maybe understand the passion that fueled his columns for The New York Times.

And so I thought if ever I had the opportunity to write a memoir that I would do the same thing.

I would be open and honest and raw as I could be about.

Certainly my success is that most definitely about my shortcomings in my failures because that's where the lessons come in.

That's where people connect and see maybe a part of themselves, even if they're not black or even if they're not LGBTQ, certainly in the way that I felt a connection to Kay Graham and I'm nothing like >> in answer that comes with both to book recommendations, which I appreciate.

But also read the book.

You are honest and you also share some lessons which which hopefully will get But you also talk about the time you spent growing up as a kid, of course, and spending some of that time with your grandparents and Severn in North Carolina.

And you talk about the significance of your generation in how does that make you sort of an unlikely story as your title suggests yet?

Here I am.

>> So you know in 7, North Carolina is a town so small.

That you have to when you hit Google Maps and you hit that plus sign you've got you've got all the way in so that you can see the tiny of the streets.

As I write in the book, My Cousin Rita and I are the first generation in our family to not have to pick cotton.

And for people of a certain age, they will understand what that means.

But for the young guns out there, I was born 3 years to the day after the 1964 Civil Civil Rights Act was enacted.

2 years before 2 years after the 1965 Voting Rights Act.

Why is that significant?

Because with those 2 with those 2 laws that Constitution what now available, all of the words of the Constitution applied to everyone to African-Americans and so freedom of opportunity and access to education in everything.

We're now unbounded for my generation.

And so Rita and I were running around in the in the yard, in the sprinkler, during those summers, it wasn't.

I writing this book that I understood when At when our parents were our age, they were working.

They working in the fields, picking cotton pickin picking tobacco.

We did not have backing the way they were right.

They weren't.

>> You also you talk a lot about blackness and black identity as well in some very relay double ways over the years.

Black classmates and colleagues calling you sell out an Oreo uncle Tom.

Some other words I won't say right How did you handle that and what do you think we do that?

The black community?

>> You know, I'm still trying to trying to figure that out.

look, is viewed myself again as someone who is from that first, that first generation to live, you know, with in day you're a freedom in America as an ambassador.

And ambassador to other people to the race.

And so in a time when, you know, a lot of people didn't know black people.

A lot of white people did not know black people.

And as you know, for those African-Americans who are either the only one or one of the few in predominantly white spaces.

We know what that means.

The pressure that comes with that whether we want it or not, and I just decided to embrace it.

I mean, I'm an only child.

So I ran out there trying to make friends, but in trying to make friends, particularly in college, you know, that rankled a lot of people, a lot of a lot of my black classmates understand why.

What?

Why don't you hang out with us its like because I like my roommate.

I like I like my friends and for a lot of classmates being in that predominantly white space with something that was new to them.

And I understand and now really understand why they gravitated towards each other.

But for me, I had the reverse experience to me, you know, going to Carleton College in Northfield, Minnesota.

That was reverting back to the mean.

I was used to going being only want to go into predominantly white institutions.

And so I think that that.

hesitate to call it a misunderstanding, but it's just sort of sort of miss a mine man of ideals.

I was a member or an older classmate took me to task basically for getting into think about it.

And so I just I just had to chuckle at it.

But, you know, it is.

It's tough and it's not it's not something that goes away as you get older.

It's not something that goes away as you climb the socioeconomic last I would imagine for a lot of black people, but as they climb that ladder.

>> They are the only black person in the Absolutely more and more more more and more and for a long periods of time.

But as I write in, as I write in the book, you know, Blackness and we talk about we talk about black this and then to understand.

And so the audience understands that.

You know, blackness is in the eye of the ball holder.

So at any given point in in my day, I could be.

>> 2 black.

I could be not black enough.

I could be not black at all.

And it has nothing to do with any us.

Some people, I mean, either right?

Nothing that I've done.

But it's all because of the other person's other person's perception.

>> And so our level of blackness is in the hands of other is in the hands of other people.

And again, no matter where you are on the socioeconomic level ladder, you are going to have to deal with it and maybe in reading this book people will see like, you know, what?

That's what that is or I've had that experience.

That's what's that about.

That is what that is about.

So I want to jump ahead to your time at The Washington Post because, of course, the stories that you have shared their have a.

>> Maybe cause a little bit of controversy for some folks who are close to the post host, of course, where you are still a You write about your experience on the editorial board in for about what, 15 years being the only black person on the for most of your time there.

You also write about.

When the time came for you to leave that Gordon sort of the straw that broke the camel's back for and editorial that the board wrote around the Georgia election with a statement that you 100% disagreed with how you told your federal your fellow editorial board members as much.

You did not talk about it at the time.

Why did you not want to talk about your the reason for leaving the board publicly at the time?

>> look, it was a a very searing moment.

I did everything that I did that you now read about privately because that was the way I wanted to handle it.

And I don't think it would have been wiser proper at the time to just go out there and and spout off.

That's just not me.

I mean, this is now what?

2 years, 3 years after the fact with that time I had perspective.

And could look back on on what happened.

In the end.

And I do urge people to really read the chapter fine, but do not read the chapter in isolation of everything else.

It is a live in pages in more than 270 pages.

And there are 10 or 11 chapters before that.

The reader will not truly understand the context of that chapter if they hadn't read the earlier chapters.

And so, you know, I understand people being upset that I put down on paper.

You know why I left the board.

And I knew that this would, you know, folks wouldn't be happening, folks.

We even start talking about it and saying things and that's fine.

You know, when you when you speak out and speak your truth, it comes with it.

Come sometimes with consequences.

That comes with accountability and I'm fine with that.

I'll stand by everything I wrote everything I wrote in the book gladly because the book is not about that chapter.

The book is about my life so much more than just that chapter.

Of course, we've got about 30 seconds see, wrote a book what's next?

What else?

else?

The next just does?

Well, you know what?

Instead of what's next?

Let's let's go with your professional advice to things that I picked up when someone asks you what you want tell them.

>> Yeah.

And everything you're doing today is an addition for later in life.

Those are the 2 big lessons because >> folks, I think folks self sabotage, they think I have dreams.

Therefore, I'm not.

I'm never going to say them because someone's going to squash them or they'll never happen.

But I encourage people whenever anybody asks you what you want, tell them because you never know with the answer's going to be yes.

And that's been might happen to be twice and then everything we do in life is an audition for something else.

We just don't know why yet.

And that proven