- Hey, I'm Issa Rae.
And today I'm going to be answering old questions
with new answers.
Let's see what I was talking about.
[tape rewind]
[upbeat music]
- What sticks out to you
as a major highlight filming your show?
- I remember back then, it was just about
being able to shoot with my friends and just make something.
Make something that people liked.
Is that my ex-boyfriend?
Hey, oh Dee.
- Yo, what's, what's up?
- Hey.
- It's so funny.
I thought you were my boy Reggie from behind but,
came a little closer and, it's not Reggie.
- I like to have people come up to me and say
"I am an awkward black girl too", is incredibly amazing.
And now even with "Insecure",
the highlights are just telling these stories
these real stories from people in the room.
From my life, from my friends' lives.
It's really rewarding to
have people relate to what you make.
- Okay, now this is 2011 Issa Rae.
- Oh, what did I say?
- Let's go back.
[tape rewind]
- Being able to meet Donald Glover,
that was the best thing ever.
Yeah, it sounds superficial indeed.
But yeah, that's-
that's all I could think of right now.
[laughs]
Okay, I was super hype about Donald Glover.
I'm still a massive fan and think that he's just, you know
genius and has done so much.
Since then, you know that was 2011 and I don't,
I think maybe he was
on "Community."
But before then, you know
I've followed his career with Derrick Comedy,
and seeing his movie "Mystery Team",
and all these things
that he had done online before that.
And his music, his early mix tapes, his freestyles.
So I just thought like this is, he's so cool.
In in terms of exploring everything,
and,
doing it really
well and getting better.
So I, I hold to that.
I'm constantly inspired by, you know, people
that I consider peers, people that I consider peeroes
Peer and heroes together.
I love that it's not competitive.
Like there's, I'm always going to be a competitive person
with myself. But for me, I'll look at other people
whose work I like,
and it just makes me want to step my game up.
And there's just something special about being a part
of this time where we can look to each other and not
tear each other down, but just be like,
damn you're doing that.
Shit, what else can I do then?
- Since you've done so much work
that's pretty autobiographical.
I'm wondering where you draw the line
between yourself and her, meaning Issa as a character?
- I started off saying that with insecure in particular
Issa D was a younger version
of me who just kind of didn't know what she wanted to do.
But now as the series has progressed
I find that we're merging more
in our career aspirations and our love for the city.
I'm being more influenced by her, which is weird.
- Okay. Let's take it back to 2016.
[tape rewind]
- She's basically me. If I didn't know what I wanted to do.
And if I made different decisions in life,
I say 75 to 80 percent.
I think I'm a bit more empathetic than she is,
and I'd like to say that I wouldn't put my friends
on blast in the way that she did in the pilot,
but I probably have.
I didn't tell any lies.
This is 2016.
So yeah, 2016 me, I was still closest to her age.
So 75 to 80 percent, felt, it feels right.
- It took some time for "Insecure" to get from development
to HBO. What do you think was the most important thing
throughout that process to protect or preserve?
- Throughout the development process for HBO
I just remember being really impatient
because I had come from the internet and I was like,
why is this taking so long?
Like I could create this
in two minutes and it'll be out there.
And I think people will like it.
But, thinking about where the show started
and where it ended up.
I'm so happy we took that time.
I'm so happy that things played out the way that they did.
It ended up making a better show,
a show that I'm super, super, super proud of.
It really just taught me the rewriting process
in a way that I just hadn't experienced before.
I probably did about either seven to nine drafts.
I have to go back in my email
for "Insecure", and the show started off as a nonprofit.
It was more of a workplace show,
with the personal life stuff on the side.
And the Molly character was kind of on the side too.
And whatever love interest I had at the time.
And the more we were developing it,
the side characters just really started to shine.
And HBO wanted to see more of that.
Like tell us more about your best friend.
- Posed to be, ah, yes Lawrence. How you doing boo?
- Actually, I'm thinking about ending things with Lawrence.
- I'm sorry, what was that?
- Casey Bloys was an executive then, was just like
what does it look like for your Laverne shirt,
Laverne and Shirley show with, with, with Molly?
And with that in mind
I kind of just re conceptualized what the show would be.
[tape rewind]
- Let's see what 2016 Issa was talking about.
- The two most important things were that it was set
in south Los Angeles, and that we highlighted Inglewood,
Baldwin Hills, all these places where I grew up and knew.
Girl, what was you talking about?
I don't know.
I don't know that I answered the question accurately,
the first time.
Maybe I was still, like,
there was still a inpatient residue left,
where I was like, well at least we got to highlight my hood,
but I don't know. I don't know what I was talking about.
It has been extremely important to
showcase south LA, to showcase Inglewood.
When I was writing the show,
and filming it
I lived in Inglewood at the time and it was just, you know
my grandparents lived there all my life.
And so it just was very special to me.
It was proposed a couple of times to save time
and money to like shoot in The Valley
or shoot in other places and fake it as South Los Angeles.
And I just felt like that defeated the purpose
of shooting there.
You can't fake these locations.
There's something about being there that, that feels real.
And the entire point was to showcase that particular,
those particular neighborhoods.
- How has the definition of awkward changed
for you over the course of your life?
- I still abide by the same definition of awkward,
I think what's changed is just
I've recognized that it's just a part
of who I am and I don't sweat it as much anymore.
I'm lying, I do sweat it.
But I just, I just don't let it outwardly affect me as much.
And I've understood that everybody,
is whether they think they are,
or not awkward to some degree.
[tape rewind]
- Let's take it back to 2014.
- I think in my younger days, middle school, high school
it was more of a stigma.
I wanted to be like everyone else,
and I didn't really want to stand
out in a way that was weird or uncool.
It wasn't until I got older,
where I was able to embrace my awkwardness.
That's real shit.
In middle school, high school, for whatever reason,
Nia Long and
Laura Winslow,
[laughs]
was like the type of black girl I wanted to be.
If I could just be a mixture, I would,
I would be killing it.
So, shout out to the two of them for being role models.
- What was your big "ah ha" moment in the business?
- I guess, I'm just more hip to,
how and why things are made
and who is kind of in charge of saying yes.
But the politics of this business
have just become, more clear to me
in a way that I could at least intentionally
like go around
and avoid making things that the studio system
thinks is like, great or poppin'.
Mind you. I like I'm, I'm, I'm a business person and I don't
want to make things that suck, and that won't sell
but I do want to make things that are, are very true to me.
And I have found
that while Hollywood is like, we love original voices.
We love originality, all those things.
Uh, they really don't.
So it's like just about finding those people who
do appreciate that and who are willing to take risks.
[tape rewind]
- Now this is 2012 Issa Rae.
- The "ah ha" moment for me was when I got representation.
I was taking all these meetings
during the day and they interfered with my job.
And I couldn't just, like I was getting all these interviews
and I was like, it's time to leave this job.
It's not helping me in any way.
My dumb ass. When was this?
- 2012. [laughs]
- 2012, because I got- [laughs]
I thought representation, meant like oh,
I get an agent and manager.
Money's just about to start coming in.
Whoo, finally it's happened for me
and I quit my job and was broke as fuck.
So this was not an "ah ha" moment.
This was a very dead moment for me.
It worked out, but I should have held
onto it a little longer to save because whew,
there was a struggle.
Before you quit your job, you should have savings,
you should have a plan, and also make sure
that you have a support system.
Whether that's your friends,
or a team in place to help you make stuff.
You have to have accountability partners
to, to keep you on track.
- What's an average day been like for you lately?
How do you organize your time between your various projects?
- An average day for me is usually, it depends
on whether I'm filming or not.
When I'm filming, you know
15 to 16 hours of my day are dedicated to that.
And I have no schedule.
When I'm not, I usually, you know,
wake up early in the morning, go for a walk.
And then whether it's a Monday, Wednesday, or Friday
I write. I'm creative in some capacity.
And if it's a Tuesday and Thursday,
then I'm doing all the work meetings,
business stuff that I have to do.
And then weekends are usually
for either shoots or free time.
[rewind]
- Let's take it back to 2014.
- I set aside two days in the week for meetings,
and four days in the week for creative work.
Writing, producing, shooting, et cetera.
I leave my evenings
and at least one weekend day for family and friendship time.
But no day is the same,
and I honestly have no idea how I really get stuff done.
Ain't shit changed.
Barring the pandemic.
I have been able to like try to,
spend time with family and friends.
I think I probably gave this answer
after I had struggled with time management.
Like there was a year that passed where
I realized I was only taking business meetings
and trying to, you know, make money and advance my career.
And I hadn't done anything new or creative.
And so I think after that moment, I was like, you know what
let me have a regimented schedule.
Then I got too busy and was like
let me make time for family and friends.
Now, I feel like I've, I have a good balance.
- How do you know who and what to let go of?
And how do you know who to bring into your circle?
- I've always been, especially now.
I just don't like negative people.
I just, I can't stand pessimism.
Like I will do that on my own.
So I don't need you to add to it.
I don't like yes people by any means, but I like realist
but I don't like people who just go
to the worst case scenario
cause then I'm going to be in my head.
So I think it's just been about weeding people
out who just have a lot of negativity in their own lives.
If you can't help yourself, then I can't help you either.
[tape rewind]
- Let's check out you in 2015.
- My experience has taught me
that these things kind of work themselves out in a sense,
you know?
Like when you reach a certain level, you realize
that some people aren't ready to go there with you
or you realize that some people are ready to take
on more responsibilities. But as you're going
through the trenches together, people kind of fall
off and I've experienced that in many parts of the journey.
Yeah, that's true too.
I will say that this version
of me was kind of less confrontational
about actively removing people from my life.
It was more like, oh, they'll just fall off.
But now I'm more intentional about distancing myself
from certain people just cause it's better
for my mental health and not feeling bad about it.
- Okay. Last question.
What's your advice to this version of yourself?
- If I could go back
in time and give advice to my younger self
it would definitely be,
stop trying so hard to be someone you're not.
Stop trying so hard, period.
You don't have to.
If people don't like you for who you are then,
those people aren't meant to be in your life.
You don't want them there anyway.
So stop trying to impress people
by being someone you're not.
- What advice would you give to this Issa?
- I would tell 2015 Issa, first of all
clean your room and your apartment.
Like don't be making no videos and shit is cluttered.
Two, just stop comparing yourself to others.
Stop comparing your own journey to others.
I know during that time, I was really thinking like
you know, why isn't this happening for me?
Why is stuff taking so long?
Is it ever going to happen?
Is this all that I have?
And that came from comparing my journey
to other people's journeys.
Yeah. I still stand by that as well,
but this was very painful to watch.
[laughs]
Thank you for taking this trip down memory lane with me.
If I could give you one piece of advice
I would say, everything takes time.
Everything's on your time.
Your journey is your own.
So just ride with it.
[chime]