May-Li Khoe on Design, DJing, and Growth

In this episode of Rerouted, host Nicholas Karamanian interviews May-Li Khoe, VP of Design at Handshake. They discuss May-Li's journey into design, her experiences at Apple and Microsoft, and her transition to Khan Academy. The conversation covers the evolution of design, the importance of observation, and the impact of creative pursuits like DJing and writing on professional growth.

Episode Transcript

(00:00):
Welcome back to Rerouted, where we explore unique career paths
to give you the tools you need to create the life you want.
On today's episode, I talked with Meili, Co VP of Design at
Handshake, the career platform for Gen.
Z. We talked about Meili's journey
into design, her work on early iPhones at Apple, and pursuing
different art forms outside of the LinkedIn lens.
Later in the episode, Meili gives some incredible advice

(00:21):
about starting from the bottom in a new discipline and not
needing confidence as a prerequisite for action.
There is no video for this episode, so thank you for
bearing with audio only. Let's hop into it.
Many problems. The problem.
Meili, thank you so much for joining me today.
It's great to have you. Thank you so much for having me,
Nicholas. Do you prefer Nicholas or Nick?
I tend to go by Nick, but kind of different people call me

(00:41):
different things, so I don't really mind.
All right. Well, thanks for having me on,
Nick. All right, so let's hop right
into it. Currently work as a VP of Design
at Handshake. You've had numerous roles before
that that we're going to talk about, but I want to start by
asking what led you to go into design?
Well, I think the first time I realized I should probably work
in design was when hours went by.

(01:02):
I was in a Photoshop file just mucking around and I realized I
hadn't noticed the time pass at all.
So I thought, well, what if I could do this for a living?
That'd be pretty cool. I didn't always been attracted
to like visual, like arranging things visually.
That's something I always did asa kid.
But I started getting asked to like design stuff a little bit

(01:23):
when I was in college. And that's all that time in
Photoshop is maybe when it clicked.
I mean, some of the first thingsthat I got paid to do were
things like T-shirt designs and whatnot.
But while I was in college also,I was making the front end for a
graduate students program at theMIT Media Lab with the software
agents group under Patty Mice. And the grad student was named

(01:43):
Anthony Chavez. It was actually, this is funny
to talk about now in the year 2025, but it was actually a
software agent marketplace, which like would you say that in
2025? It's like, oh, look, an agent
marketplace about that. Anyway, it didn't really have a
great front end. And so I redesigned the front
end and I build it. And it was like CGI scripted in

(02:03):
C because that's like what we did or what some people did.
And then, you know, the sponsorswould come by and see the demo
and say, like, oh, wow, like this, this looks great.
And the grad student told me afterwards, like, it made me
realize how important the interface to this is.
So it was gratifying, I think asan undergrad researcher to be
like, oh, like I can have some impact here.

(02:25):
They wound up picking our demo and like organizing the entire
Media Lab demo day around like an Asian marketplace.
This is again, in the 90s. So it, you know, it was pretty
cool the time, like there was like Times Digital did an
article on it As an undergraduate researcher, I
never got credit for any of thatstuff, but it was cool to be a
part of it. And I think that's when I was

(02:48):
like, OK, I think I want to do work similar to this type of
thing. And then when I graduated, I
definitely wanted to go into design.
I didn't study design. My undergrad degree was in
computer science and electrical engineering, but I had taken as
many art classes as possible. Art and design are not the same.

(03:08):
I'd actually wanted to be an artist, but like, that was not
really allowed for various reasons.
We can get into we want later. And and so I basically took the
only job I could coming out of college that would let me do
some design work because I had alittle teeny tiny portfolio and
it was a small agency and they were like, OK, well, you know,

(03:29):
you're going to be doing front end development, but we'll let
you do a little bit of design work every so often maybe.
And so that's how I wound up taking that job that was like my
first of multiple hybrid jobs where I was coding but also
designing and some of our early client work.
I'm gonna give you a highlight in a low light.

(03:50):
Sure. Highlight was I worked on a
billboard that went on the side of the NASDAQ building in Times
Square. And we did that all in flash.
And I programmed a little particle system of falling snow.
It was like a holiday greeting card and things had to kind of
fall around the windows because NASDAQ building in Times Square
has like a bunch of windows in it.
So we had a map of the windows and yeah, it was cool.

(04:11):
Also, just like coding particle systems from scratch at that
time was like really fun. Now you don't have to do it.
You can just tell something to make you a particle system and
it does. But another highlight was we did
a little thing for the Olympic Games.
That was a snowball fight and itwas on old school cell phones,
but there was like a little mitten and a snowball and a
table. I didn't work much on the table,

(04:32):
but I worked a little bit on theon the phone interface.
And so people were hooking snowballs at each other with
these little tiny cell phones and a table that like lit up
stripes. So that was cool.
And then a like what I would call low light, except it wasn't
a low light. And I kind of love telling
people this is that I also worked on a website that
organized all the manuals for the New York Department of

(04:52):
Environmental Protection. So it was literally like a way
of organizing manuals for like HVAC systems and sewer systems,
like sewage systems. So I, I say I like literally
worked on like poop anyway, It'sjust like, you know, people
don't know sometimes that like when you start out you just work

(05:15):
on whatever. And in that case, like, it was
pretty cool cuz that's like how I learned about a lot of like
city maintenance systems. Yeah, not something that one I'd
expect, you know, to be core knowledge, but definitely pretty
cool honestly and. It is.
Presumably. I mean, I have to.
That's cool. It affects all of us.
Yeah, yeah, yeah, yeah. So after those first few jobs,

(05:37):
you're kind of doing some of that grunt work, getting some
stuff like that, figuring it out.
You ended up moving to Apple. Can you tell me a little bit
about your time at Apple? Yeah, I could tell you about my
time at Apple. There was some other stuff in
between cuz I went from there toI was at Microsoft for a little
while and then, yeah. And then I did eventually wind

(05:58):
up at Apple. What do you wanna know about my
time at Apple, Nick? I wanna know.
The IT was like 7 years. I know.
And you know what? You're right.
That was unfair of me to say. Tell me about the seven-year
period of your life, please, in a short and concise manner that
is audibly appealing. So thank you for calling me out

(06:19):
on that. I'm curious a little bit about
some of the systems that you designed, what it was like you
mentioned as well and kindness into Microsoft kind of working
on like that big tech. Obviously, big tech looks a lot
different now than it did when you were there.
But what it was like working there at that time, I mean, in
my mind, that was a really exciting era in terms of iPhone

(06:40):
development. So I'm kind of curious about the
systems that you worked on, the types of teams that you
contributed to those types of things.
Got it. OK, Yeah, Yeah, you know, it's
it's interesting because per what you're saying of it being
an exciting time both at Microsoft and at Apple, what was

(07:01):
really cool is that there was anaspect of like operating system
design and development that was happening.
And I think it's pretty rare that you get to work on an
operating system or even anything sort of adjacent to an
operating system. And while I feel like I didn't
necessarily work like directly in all of the main, main things

(07:22):
all of the time, I definitely worked along the edges of it and
every once in a while dipped into the core of it.
So it was really, really cool and a totally different thing,
right? Because like when you think
about like the way that a lot ofdesign works for a product
that's like a third party product, you know, there's a lot
of testing and like number gathering and will this work?

(07:43):
And can we optimize the number of people who like hit the
thing? And when you have like an
operating system mentality, you're thinking about what are
the, what's the hardware, what are the sensors?
What do people need to do? What are the patterns?
Like you're an architect. More like you're thinking about
what's reusable and how things all fit together across a
broader system. I'm realizing this now as I'm

(08:06):
speaking to you. I'm like, Oh yeah, that makes
sense. Which is very different from
like, optimizing click through rates on like, you know, the
front door or something. Yeah.
But when I started, I was actually, we were proving out
that you could have really dynamic web apps.
You know, like back then it wasn't just a given that you

(08:28):
could drag and drop stuff, that you could basically have
applications inside a web browser that are super dynamic.
And so the first project they put me on was going to be a demo
for like the top 100 people at the company to show that like
this stuff was possible. And I wound up working like day
and night for like a couple weeks to like make this thing.
And then I found out they were just going to use a video of the

(08:52):
demo and it didn't have to be like live and working in
dynamic, which obviously changesthe development of it.
I had like event snapping happening in the browser and all
this stuff. It was like all hand rolled
because back then they didn't have like a gajillion frameworks
for you to build on top of. Yeah.

(09:13):
So that though, I just remember like a few weeks in, I was like,
no, what have I done? But then I mean, it was also
really exciting. Steve Jobs is still alive.
Then he looked at our work everytwo weeks.
Sometimes I had a VP sort of designing over my shoulder.

(09:36):
And then this is hilarious, Nick.
Like he would put the stuff on athumb drive and then like run
over to demo it to Steve. For AirDrop existed.
I'm like, I'm like questioning myself now.
I'm like, if I'm remembering this correctly, like was that
actually happening? I think that actually happened.
So wild to think about. Well, the other thing that

(09:57):
happened back then was that the pixels were bigger, right?
Like right now we have these displays with like really high
points per inch, right? So like all everything looks
smooth. But back then, like you could
see the pixels. And so our work was expected to
be pixel perfect. What that means, and it's still
valid today, like if you learn how to see the pixel level,
which all of us did back then, you could see when because like

(10:20):
the way that a raster display works, right?
Like pixels are either on or off.
So if the pixels on like completely on, then you'll get
crisp lines. But if you make an icon or an
asset and it's not exactly on the pixel, you'll get like kind
of a bit in one set of squares and a little bit in others bit
of squares and it'll look blurry.
So all of us wound up with this like way of being able to see

(10:42):
when things were aligned and Steve Jobs could see it too.
So there's a lot of like subpixel work to make sure
things were really crisp. The lines were all crisp.
Everything was like very high quality detail and, and we
always worked out of stories. So we were like, OK, so a person
arrives and they do this. It was, it was almost like a

(11:02):
narrative. And then we would paint the
picture of what that experience looked like in pictures and then
make decisions off of that, which is very different from
like, literally how most of Silicon Valley works, where they
have like a bunch of PMS make you a PRD.
And then, you know, they tell you what number you're
optimizing and whatever, whatever.
The field that I came into and grew up in was completely
different from what happens now for most designers.

(11:25):
Yeah. So, yeah.
And then the next thing was I wound up getting pulled into
work on what we're called the first, the first apps because
when the iPhone was released, which by the way, the iPhone
wasn't out yet when I joined Apple, I think it was like a
month in or something like that,We got sat down at an Apple town

(11:47):
hall and and Steve told us he's like, we are going to totally
like the world will not be the same after this.
And there will be people who imitate us, but we're doing this
first. There might be people who even
do it better than us, but we're doing this first.
And yeah, I mean, it's like, youknow, you're like you're like,

(12:07):
what? What?
But yeah, I was actually behind multiple locked doors working on
what the first third party developers would have access to,
which is like more web apps, buton the phone.
And so we were working closely with the mobile Safari team.
There were a couple groups in the company that were building

(12:28):
these like demo third party apps.
And I was working on one for photo sharing, you know, and
trying to think which others. Oh yeah.
And the RSS reader, I think those were the main 2.
Anyway, I went into a lot of detail there that.
Was. Good.
There's like other stuff I wouldthat was, that was like the
beginning of Apple stuff, but I was like 7 years cuz then I also

(12:51):
like. So then I worked on that and
then there was like mobile me, the mobile me disaster.
There's the Mobile me gallery, then there's iCloud and like
drawing 5 gajillion little clouds.
But there were a bunch of us that did it.
I want to take all the credit for that there.
There's a team of people that were all trying to figure that
out and I also was part of figuring that out and you know,

(13:13):
designing sign in pages and likeseeing them get blogged about.
Then I wound up switching teams and joining A-Team called HID
Prototyping. And we were embedded in the
hardware organization, but like very working closely with the
firmware people. So basically anytime we had new
sensors or new ways of interpreting sensors, our team

(13:33):
would work with applications across the entire company as
well as the operating stuff to make sure that that sort of
magic that happens between the hardware and the software.
Like the way that you like move your fingers and a pain moves
with you or you have like a multiple fingers like pinching
in or zooming out, like all of that type of stuff.
That was all stuff that we woundup working closely on.

(13:56):
And so if we were able to like, demo a lot of potential in a new
method of human input, then it would get more funded and then
it would wind up in other places.
So we worked on like the iPad, the Apple Pencil, force touch
tactic feedback. There's a lot of work that went
into the force touch and the haptic feedback.
I'm trying to remember what else.

(14:16):
Oh, face effects, which are everywhere now, which have
stories about, gosh, I don't know, Nick.
I I But yeah, it was fun and I was there for some time.
You mentioned that what a designer did, what you were
doing, is a lot different than what a designer does now.
Would you mind kind of diving into some of those differences?

(14:39):
Yeah. I mean, I think the main thing
is that a lot of commercial quote, UN quote software as a
service products or like even now with like if you're
designing for like an AI product, like there's a lot of
stuff where you're like really optimizing your product's
success, right? When you're working on an
operating system or like a like a computational system, Like

(15:02):
you're not trying to optimize like how many times people hit a
buy button or something, you know, you're thinking about
like, what's the potential of computation?
Where like I have this in the case of HID prototyping, you
know, we would get a piece of hardware with a whole bunch of

(15:23):
wires sticking out and there'd be a screen and maybe the
screen. Usually the screen had, you
know, we had touchscreen capability.
And then we would start playing with prototypes of what we could
do with the sensor data and how that made sense for pro
applications, how it made sense for like the main iOS or the

(15:44):
main OS applications, or how it made sense like, and how you
move between windows. What happens if you swipe up
with four fingers, for example, you know, like, and then we
would wire the sensor data in and like fake out all of the
different ways that things couldwork.
So if you take face effects, forexample, imagine like now you

(16:05):
stick your face in front of likea Snapchat filter or an IG
filter, whatever. And it's like it's tracking with
your face. In 2010, it didn't, it was new
tech that it like tracked your face.
It was new that that was going to be performant.
So we were like, OK, cool, we'vegot the sensor data.
It's found our face, it can findour features.
What are we going to do with it now?
And then, you know, you started coding a bunch of like stuff

(16:26):
like what are we going to do with this?
It wasn't immediately like, OK, the goal of this project is to
make sure that we hit our target, OK R of blah blah
percent in order to meet our Q3 will be like that.
No, it was like we have a computer.
What can we do with it? That is going to be something
that sort of stands to test the time useful that isn't too for

(16:50):
people. And then a lot of how we learned
was by trying it ourselves a lotover and over again, getting
other people to try it, you know, within this disclosure
secrecy circles, of course, and a lot of like exercising our own
good judgement. I think we had to learn a

(17:11):
certain level of intuition that is not as common now.
Like, I think a lot of it now isjust like we need to test and
optimize out of like 5 gajillioncolors, but also because back
then you couldn't do that, right?
Sure. Like when the stuff I'm talking
about was like really before ubiquitous smartphone adoption,
you couldn't be like in someone's pocket collecting A
gajillion numbers and all of thedata all of the time in order to

(17:33):
optimize all of the things, right?
Like you had to just kind of have a pretty good instinct.
I kind of wonder what it would mean to like, design an
operating system and be like, I'm trying to Max, like what are
you trying to Maxima? I don't know.
I guess if I thought about it long enough I could come up with
something, but it doesn't feel like an interesting intellectual
exercise to me, frankly. I'm curious as well.

(17:53):
Work at Apple for seven years and you've had career past that.
But I want at this point, I wantto ask, what have you done in
the past and what do you continue to do to become and
continue to grow into like a really excellent designer?
My number one advice, I think for everybody who starts out
doing this, is it really? There's two things.

(18:15):
One is that changes the way you look at the world.
So just constant observation of everything.
If you're going, if you're walking up to a place and you're
opening a door, you're noticing if that door is like easy to
open, not easy to open, you're noticing like the tracking, the
kerning on the letters on the side of the building.
Like there's this one building awalk past all the time where the

(18:36):
zeros are too close together andthe one looks like it had a
fight with the zeros. And I'm like, you could have
typeset that. You could have.
Or like, I know some of it's dumb, some of it's just like the
dumb, but it's real. Like, OK Apple.
The corner, the corner rounding on all of the assets is done in
a very deliberate way where it'sa continuous corner smoothing

(18:58):
algorithm so that there are no discontinuities in the tangent
as in the curving of a rounded corner.
So like you learn that and then you go out into the rest of the
world and you see every time that that's not done right.
Like, or if you have outer and inner corners, like have people
like done the math right so thatthe rounding is correct?
And like those two curves like remain equidistant as they're

(19:22):
rounding. Like a lot of the times you're
walking down the sidewalk and you're like, OK, yeah, PG&E
didn't do this one quite right. So it's that that's our, the
people do our electrical here, electrical gas, whatever, you
know, the little manholes. And so you're, you're looking at
how the world is put together all the time.
That's just like a designer way of life.

(19:45):
And that's constant. It's like the kind of thing
where you're like, OK, I'm moving into a place.
I'm, I know that I am right-handed and the other
people in this house are right-handed.
So we're going to put the kitchen utensils on the right
hand side that we need urgently while cooking.
Like you think about those things, like you can't not think
about those things because you're a designer.

(20:07):
It's just like touches everything.
And then from like a tactical perspective, like the advice I
give people when they're like, OK, I'm trying to like mock.
What I want things to look like is observing what are the
choices in things that feel really great?
And why do you think people madethose choices?
The best way to do it, like for any creative field, is to

(20:28):
literally recreate it from scratch.
This is often the case from likeif you're an artist, you're a
musician, or any medium you're doing, you're trying to figure
out how did somebody get that effect in that thing that's
really good. When I first started out, I had
to draw over top of a lot of mocks that were coming to me
flat, so they weren't coming to me layered.

(20:49):
And so I had to come in and likeliterally redraw them, get the
type right, get the tracking right, the type, the, you know,
type, weight, spacing. So then I learned from doing
that, like what are all the spacing and type and shape
choices that are being made in any single mock?
You know, asking myself why? But then I was able to learn how

(21:13):
to recreate it anyway. That's the advice I give to
anybody in any creative field, is like, recreate a thing that
you think is good. You also need to, like, learn
how to notice what is good and then ask why.
The same thing happens in writing.
Yeah. Music, literally anything.
Why do you think he paused there?
Why do you think they accelerated there?
Did you notice that they singinga wrong around the beat?

(21:33):
They're not on the beat. Sustaining a note.
Like all those things have an effect, and the same thing goes
for design. So after your time at Apple, you
joined Khan Academy. What led you to move into
nonprofit and work at Khan Academy?
Khan Academy is well, so there was an engineer that I had
worked with a little bit who wasbeing recruited to Khan Academy

(21:55):
and both of us were really interested in what the potential
is for like digital interaction and learning.
I think what we were particularly interested in at
the moment might have been currently, I think it might be
called like digital manipulablesor something.
Anyway, I forget what the name of.
It's a whole category of stuff now, but back then there wasn't

(22:15):
much of it. And they basically Khan Academy
was like, OK, we really want to get him.
He doesn't want to come without like having a designer that he
respects and wants to work with.So why don't you the 2 of you
come over and then you can mess around and kind of do whatever
you want and as long as it has something to do with education

(22:35):
and we were like cool. So I was ready.
I think after like 7 plus years at Apple, there were other
reasons why I left. Honestly, I, there were a lot of
really nice people at Apple, butthere were also like some
environments that were just pretty hostile, to be honest.
And I hate saying that sometimesbecause then people assume that

(22:58):
like it's me, but but it's not because I, they, I, I, I, I
thought it was me and then like I left and then like found out
that there were other people that did the same thing.
And also the stats of one of theplaces that I was in, they
literally just were not able to retain people and they

(23:19):
especially weren't able to retain women.
And it's not because we're worseat it in case somebody's having
that thought, like cuz people sometimes have those thoughts
anyway. But, you know, it was time,
seven years and like, going to Khan Academy and kind of being
able to muck around and do stuffin education and do something

(23:40):
that I felt like was gonna be like, new and fun and
interesting and a little bit more concrete of a problem was
exciting. And the other thing is that,
like, I know it sounds weird, but sometimes new technology
just becomes new technology because if you work on new
technology over and over and over and over and over and over
again, it starts to become its own thing.
And you're like, OK, I've done enough of that.
Now I want to do something else.I want to apply it.

(24:02):
Let's apply it. Let's apply the new technology
to some problems I understand orthat I think I understand.
So yeah. So then I came over to Khan
Academy with my research partner, Andy Mutushak, who's
brilliant and and we had a yeah,and we're both pretty silly.
So that was helpful. But then they kept on asking me

(24:25):
for help or I would see things that I could fix.
And so then I just kind of woundup having more and more scope
over time. And then I wound up VP ING the
design team, which by the way, Iwasn't setting out to do.
I wasn't actually trying to havea job in management.
I, but at some point in time they had a new CEO join and she
said, do you think you need to have design at the executive
level? And I was like, well, if you

(24:45):
want to hire serious designers, then they're only going to join
if you have designers in the executive level.
And she said, OK, well I think you should do it.
And I was like, does that mean Ihave to manage people?
And she was like, yes. And I was like, I don't want to
manage people. And she's like, look, if you're
at all curious about managing people, then you should do it.

(25:08):
And so I was like, fine, I'll try it.
But most of the reason I did it was just because I was trying to
fix stuff. I was like, I wanted to prove
that we can design things well for teachers and students.
Because most of the times when people design stuff like really
nicely, it's like for, I don't know, for somebody that already

(25:30):
has like a lot of money to be OKin some other way.
You know, that's why those things are like premium.
And so I think part of it is that I wanted to democratize
access to like well designed things.
Yeah, yeah, it's funny because as you're talking about the
different things that you're working on, it very much tracks
along with like my like tween age years.

(25:52):
I would say like, it's very muchlike I've like my first phone
was like an iPhone 6S and I had the haptic feedback and I was
like, this is the coolest thing ever.
And then I like learned like HTMLCSS through Khan Academy,
like my 4th grade classes, like when there was like downtime.
So it's very personally for me and I know this is not very,
this is very much not a unique experience for people my age.

(26:14):
So it's very cool to kind of, you know, see what's behind it.
I remember the getting the little guys in Khan Academy that
was like you're kind of like your collectibles.
I had like the Winston one because I did the coding classes
and I thought that was the coolest thing ever back in the
day. I remember Winston.
So yeah, I appreciate that. You know, I'm kind of able to

(26:37):
track along with like my own life milestone, so to speak.
Yeah. And I don't study computer
science now, but it very much was AI mean.
I did the courses. There was clearly some interest
and they're still, you know, it's a very much an early
grabber and interest. So it's very neat.
Yeah, that was like such a cool part of the Khan Academy
offerings. That was, I'm trying to remember

(26:57):
the name of the person who put abunch of that computer science
stuff together. It was like Pamela, I think was
her name. Maybe you remember because you
were taking a bunch of those. Yeah, but that stuff is really
cool. Yeah.
Anyway. OK.
Anyways, I am curious, So you mentioned that you didn't want
to be a manager at all. I'm curious what it was like
kind of stepping into that management position when you
didn't necessarily want it. Were there benefits to kind of

(27:18):
how having that like larger scale, what was that like?
What was that like for you? I think, I mean, initially it
was hard. There's like a big change from
being what's called an IC in theindustry, which is like an
individual contributor to being a manager.
There was a brief moment when people were like, oh, but we're
all leaders. And I'm like, yes, the
difference is as a manager, you make decisions around hiring,

(27:45):
firing, performance and pay. And those are real.
That's like the real life. So like, I, I just think that
sometimes people like put all kinds of like fluffy, you know,
leadership and blah, blah, blah.But like you're making decisions
about people's livelihood. That's a huge responsibility.

(28:07):
And I think that it's may sound trite, like with great power
comes great responsibility. But like, but actually, yeah,
you know, sometimes people do itbecause they're like, I'm
climbing a ladder and like, I want a fancy title.
And it's like, dude, like people's future relies on your
judgement. And like you, if you are not

(28:27):
thoughtful about the way and youcan't be perfect, of course,
also like it's very different when you're responsible for
hiring and like performance management, meaning like who
gets a bonus or who gets a raiseor like, who do I have to let go
for whatever the reason might be?
Like, it's it the, the way that I put it to a lot of people's.
It's kind of like, you know, when you're a little kid and

(28:48):
you're like, why are the adults like sitting around the table
still talking? Like you'll be, you'll gone
outside, you'll have like playedout an entire world.
You like built a Fort and like an empire like got built and it
fell and you had a battle And like, then there was like magic
and like, I don't, you know, like a whole multiple lifetimes
are lived outside in the playground.
And then you come back and the adults are like sitting exactly

(29:09):
where they were sitting, like still having the conversation.
And then one day you like emergeinto adulthood and you're like,
oh, like taxes and that boring stuff that that radio guy is
talking about all day every morning.
Like that thing is effects things that affect my parents,
that affect the food that like lands on our table.

(29:30):
And whether or not like, you know, mom, dad, uncle,
grandparents are able to like get treatment for their
condition. Like you start realizing all of
this stuff. And I feel like coming into
management is, is like that samething, like you come into the
other side of things, like when you're not a manager, like why
are they in meetings all day? And then you become a manager
and you're like, oh, you had allthis that you're trying to talk

(29:52):
about. Like, oh God, yeah.
So that's that's one of the waysI would describe the transition.
The stuff that I like, do love about it is I call it designing
the design team. So you are designing the culture
and the processes and like who you want to bring in, what they
stand for, all of that stuff. So you can actually like create

(30:15):
a group of people who work together in a certain way who
wind up developing certain kindsof relationships.
And when you do it really, really well, like you can create
something that outlaw the organization.
So for me, that's actually like,you know, you build software,
the software gets shut down. You like work at a company, the
company maybe it'll last 100 years.

(30:35):
But but like some of the people that I've like brought together,
those friendships have long outlasted them working together,
see them support each other. I see them help each other like
move on in their careers. And to me that's like the most
gratifying thing. Like I help bring those people
together and I help set up an organization in which they, like
managed to like feel, you know, there's some people love

(30:57):
creating like places where there's constant like suspicion
and competition and all that stuff.
But there is that's not the onlyway to do things.
So yeah. So I've done things in other
ways and been really proud of the way that the people should
have gone on to move in the world.
Designing the design team is cool, not part I really love.

(31:21):
And I think that leaks out into like all kinds of other aspects
of my life where it becomes veryeasy for me to like organize a
gathering or whatever because I'm like, Oh yeah, this is I can
just this is fine. It doesn't take much effort cuz
you do it over and over again. Yeah.
OK. I wanna jump to something a
little bit different as well. I'm curious, can you tell me

(31:44):
everywhere about you? When you look online, it always
mentions DJ ING and creative writing.
And when we spoke earlier, you mentioned DJ ING and creative
writing. Can you tell me about that?
I mentioned DJ ING, that's funny.
OK, the DJ ING part actually don't do that much anymore, but
I did for like 11 years, so it makes sense.
I'm mostly playing live music now.

(32:05):
I am thinking about getting backto DJ ING though Nick, so I
don't know. You tell me, what do you think?
Do you do either of them? Personally, I do not, no.
This is kind of my DJing to be honest with you.
This has become this growing, starting and looking starting to
grow. This podcast has become my DJing
in a sort of way, has been my creative outlook.

(32:26):
I love that. I think it's great that you're
doing this. I love it when people want to
see a thing in the world and make a thing.
Yeah, so let's see the DJing thing.
So similar to like what you're doing with this podcast is like,
there was a thing we wanted to see in the world.
It didn't exist. So we're like, let's make it
happen. So in 2008, me and my partner

(32:50):
Federico and my friend Danielle,Danielle Aracon, we were
travelling to a festival in the Pacific Coast of Colombia and
it's called Festival Petronio Alvarez.
And it is kind of this incredible sort of, I guess I

(33:16):
don't want to call it a secret, but it's like it was very little
known at that time. But the, the, the vibe was
incredible. And when we were coming back
from it, we were on a bus and there was a landslide.
And we were sort of stuck on thetiny highway that sort of wound
its way through the Andean Mountains.
And like, what? Well, what are we gonna do?

(33:37):
We're just hanging out, fogging up the bus, and eventually we
all pile out. You know, it's incredible.
Like, you're in the Middle East mountains and there's like a
little Hut in the corner. And the concession guy is like,
you know, so sweet. And he didn't hike up his
prices. He was just trying to make sure
everybody got some food and drink.
Like, you know, anyway, that's like where we were.

(33:57):
And we were having a conversation about how, like, we
there just wasn't the kind of party that we wished existed in
the Bay Area. So we figured we need to make
one and we wanted a party where like people just come in and get
down. You're there to dance and you're
there open to all the different kinds of music as opposed to
being like, I think there's a lot of places where people go
out, but they're not really going out because they're going,

(34:18):
they're really actually trying to have a good time.
They like go out because they think that looking like you're
having a good time while like, Idon't know it there was a lot of
stuff that was just like, this is this is not our thing.
Yeah. So then we came back.
We're like, OK, we're gonna haveto figure out how to DJ.
So we started DJ ING started like just like playing a bunch
of music in like Danielle's spotin the Fruitvale to like 5:00 in

(34:41):
the morning. And we just go.
We were all playing music. He had turntables.
And then our friend Jacob also taught us.
Jacob was had been DJ ING for longer.
He taught us like how to actually mix and key match and
do all those things, made us do with 40 fives because he's like,
you're gonna learn it old fashioned way first.

(35:03):
And then we started a part partyseries.
We also had a name for our groupwas called La Pelanga.
And like back then, there weren't as many people playing
music from like between the tropics and around the world and
through the decades. So yeah, so we started the Bay
Area party series. I think one of the first big
ones was like a fundraiser for Haiti at the time been hit and

(35:24):
and then we did it for another 11 years.
OK. We we wound up opening for a lot
of like pretty incredible musicians.
Like a lot of them weren't like huge, but then they became huge.
We had a whole bunch of friends like in East LA that would like
come up and then we would like spin.
We would host them and we would promote and then like, next
thing you know, they're like blowing up.

(35:47):
So, yeah, I mean, we, we played before Celso Pina, but there's
like other Latin Grammy Award meaning like, anyway, so like I
could name a bunch of bands, butit was it was just, it was fun.
And it's also like a job, yeah, especially if you work New
Year's Eve, then it's just a job.

(36:08):
But but it's also, yeah, it's also a blast.
So from the creative writing side, I, I wrote a lot when I
was tiny, like especially in elementary school and all my
teachers were like, you need to write more stories.
And then like over time people are like, wow, you're good at
math, go into STEM, there aren'tenough women in STEM, blah,
blah, blah. And I was like, OK, cool, I'll

(36:28):
be an engineer because it's fun.It was fun.
Like I like building robots and like making games and whatever.
So I was like, cool, I'll do that.
And I always thought that I would come back to writing
somehow. Was it when I was like, when I'm
old and I got nothing else to do?
I'm going to be a writer. But then my godmother, 65 years

(36:54):
of life, and this is a longer story, but she managed to
reunite with the person she had wanted to marry 65 years earlier
and Sparks flu. And I was like, I have to write
about this. And then I lost her during the
pandemic. And so then I was like, like, I

(37:16):
really got it right. I mean, the intention had been
to go and stay with her and collect stories.
You know, you get to a certain age, you start losing your
elders. My elders are from Indonesia.
And there's all these stories ofwhat the world was like back
then. And so I had started to try and
dedicate more time to collectingtheir stories and writing them

(37:38):
up. But then, yeah, I lost my
godmother, who's kind of like the closest thing I had to a
mother for most of my life. So then I was like, well, yeah,
I'm gonna apply for an MFA program in creative writing.
And I got in. And then I started studying
writing. I was like, well, may as well
get good now. I'm gonna be doing it another.
If I'm lucky, I'll do it anothercouple decades and then I'll be

(38:00):
able to be good at some point, hopefully.
Writing takes a while. You know, it's not a fast
process, not an instant gratification process.
And in order to like really treat it creative writing as the
art form that it is, you can't just be like, OK, cool LOM spit
out a thing. You know, cuz you are, you're an
artist. And that's different from

(38:23):
output. Yeah, it's like a.
Hard thing to explain to people sometimes, So yeah, so I went
into the Santa Fe program and then that's when I got scouted
by Handshake, which I think you were gonna ask me about, but
yeah. Well, we'll get there.
I do have a question that just arose.
Have you? Did you?
Were those skills you were talking about earlier, about
incorporating design to every aspect of your life, recognizing

(38:46):
where there's good design, wherethere's bad design, where it was
that built up ability that you had, Did that really help you as
you're trying to dive into creative writing?
You know, that's a great question, Nick.
That's such a good question. It turns out that when you work
in multiple creative fields, youstart to see patterns across
them. And I think that's where the
like, quote UN quote, interdisciplinary artists like

(39:06):
term comes from. But like, OK, so my first
semester, this creative writing program, I was so like, it's so
humbling when you were in a field and you're like, make some
headway in that field and then you move to another field and
you're like, I'm nobody and likeI've done nothing, you know,
because it's a new field and I have multiple friends and like,

(39:27):
even just watching like, I don'tknow, Andre 3000, like switch,
switch up what he does. I have other friends who are
like super accomplished in one field and they switch fields and
we all go through this thing of just like, Oh my God, like I've
done nothing. I have no way.
And then you get into this workshop and there's these, you
know, there's people who would like just come out of undergrad,
but they studied writing an undergrad and I didn't study

(39:47):
writing an undergrad. So I'm like, Oh no, I don't know
what I'm doing. And so they have this thing
called the workshop, right? It's like people read each
other's work and they give each other feedback.
And so I'm like, Oh no, everybody's going to be able to
tell that. Like I don't know it.
Anything. But I was talking to a friend
later and they're like, no, I had no idea that that was your
first writing workshop. Turns out, turns out design

(40:10):
crits and writing workshops are very similar.
So when you are designing something, you can say like, OK,
like what was the goal of this design?
Like what were you trying to accomplish here?
And then the same thing goes forwriting.
You're like, OK, what are you? What are you hoping to invoke
emotionally in your reader? And then you could be like

(40:34):
alike, you know, I have this onehad this one or two classmates.
Well, one of them specifically was really into body horror.
And like, I am not into body horror, OK, but like their
writing was like deeply in body horror territory.
So if it if I was writing for me, I wouldn't have given him
this advice about how to make iteven more disturbing.

(40:57):
But I know that like this, you know, if he's submitting a piece
and I'm like, what's your goal? And he's like, I want to really
creep people out. I'm like, Oh my God, you know
what? Make it even more creepy, right?
That's like, OK, I know what he's trying to do.
Here's some ideas of how to playthat up.
As opposed to, I don't know if you're not used to like giving
creative feedback and being like, OK, it's this word that

(41:19):
you used or the ways that you paused here or the way that you
used white space on the page. What if you, like, broke up the
rhythm of these sentences a little bit so that you kind of
built up the moment a bit more? What if you, like, took this
moment and you blew it out so that, like, people have to wait
longer while that thing is dripping down the wall?
Like not knowing what it is Or, you know, those are all creative

(41:40):
choices. And the same thing happens in
design. It's like, OK, like, how do you,
like, hype someone up to get to that moment, like, as they're
going through this flow or whatever it is?
So those are the ways those two things have helped each other.
Did I answer your question? You did.
You did. You did.
I'm very much wondering have howhave DJ ING and creative

(42:01):
writering, have they impacted your professional career in any
sort of way? But I mean like your design as
somebody who's like a design professional and whatever ways
you see yourself in the quote onthe LinkedIn lens, I'll say.
The LinkedIn lens. Yeah, it's, I'm, I've just
coined this new term. That's what we're going to say
in the LinkedIn lens. How has it affected you, if at
all? Oh my God that is amazing

(42:22):
question. I have no idea.
All right, well, here's an attempt at an answer.
I think that like having a life that you care about deeply
outside of your quote UN quote LinkedIn life slash LinkedIn
lens, it can serve a number of different things.

(42:45):
OK, So one of them is it changesyour network a little bit and
you sometimes wind up with strange overlaps so that when
you need to get something done in an unexpected way, you have a
bunch of contacts. So here's an example when I am

(43:09):
thinking about where to bring a team for food.
I used to work with the DJ ING. We would often times work pretty
closely with a bunch of people who work in Bay Area food
related stuff. And so now I'm like, OK, like
here's the here's the food spots.
Like I know the places where I'mgoing to want to go get food.
And then, you know, you reach out and to contacts and it's
your homies and you're like, hey, what's going on?

(43:30):
And like, oh, look, I brought the team and whatever, right?
So that's like a different thing.
It's a different way of being the things things do wind up
kind of connecting and not obvious ways.
Another thing is it does make you, and actually this is like
kind of advice to students. It does give you that little
moment, especially, you know, ifyou're a designer, I don't know
for other fields, but in design,oftentimes you have to do a

(43:52):
portfolio presentation at the beginning.
You do say a little bit about who you are.
It is like you're a little moment to stand out.
And I think I do wind up like being memorable to people
because they're like, oh, it's that person who does these other
things. And so I think if you're like
early in your career and you're like, I'm trying to figure out a
way that I can like stand out a little bit.

(44:13):
If there's other things that you're doing, oftentimes they
wind up demonstrating something about you.
And where I say like the event organizing or like that stuff,
I'm not like, like I know how toput together an event.
Like it also comes from working in entertainment, right?
Yeah. Like, yes, part of it's from
management, but part of it is also the fact that like we were
literally literally running events for like 11 years, right?

(44:34):
And doing the promotion and doing the all of the stuff,
right? So, yeah, those things affect
each other. The creative writing, I mean, in
design, it affects it very directly because I actually like
have content strategists on my team who are writers, and I've
hired writers before and also like the way that words are on a

(44:55):
page, like make a big differencein interfaces.
So it's like literally part of the field.
But at the same time, it's not because creative writing is
pretty different from like writing for interfaces, but
they're related. And then what else?
I'm sure there's other ways thatall those words worlds will

(45:16):
collide, but like, yeah, LinkedIn lands, I don't know.
OK, what do you? Think about LinkedIn.
I want to know what you think ofwhat do you and like your
friends think of LinkedIn? Nick, I want to know.
The answer that me and my friends would give are pretty
different. I am chronically online,
LinkedIn online on LinkedIn. I use LinkedIn more than I use
Instagram most days, which is pretty bad.
I think personally for my it depends.

(45:38):
It's it's tough being on Instagram all the time is tough
for people in a different way than being on it.
LinkedIn is tough for people. You know, neither of them are
good. They're not great habits.
You know, a lot of times, like especially, you know, people go
on Instagram and go, man, I'm fat, you know, I'm not doing
cool stuff. You go on LinkedIn, you're not
doing cool stuff in a totally different way.
So you kind of getting smacked from both ways.
You know what I mean? In terms of whether that be

(45:58):
imposter syndrome, whether that be certain things that you're
perceiving, you're seeing highlight reels on both things
from other people that you know or you don't know or who look
like you or who don't like you like you, But now you're seeing
it in personal life and also professional life.
So I would say that there's goodand bad also though as well.
LinkedIn is my right now. I'm growing up, growing on
Instagram, but right now it's mymain form of promoting this

(46:20):
podcast. LinkedIn algorithm gives you a
lot of views to a lot of people and that's kind of similar.
I don't think it's as refined aslike the TikTok or the Instagram
algorithm. But in terms of being able to
reach people for something that's like this, that's very
hyper relevant to career stuff, it's very good.
And I like games. I like the LinkedIn games, so

(46:41):
you know, you can't stuff to beat that.
They're like the New York Times games.
So, you know, I enjoy that as well as a small thing.
They're games, like they're literal games.
Got it. Have you tried Handshake I?
Have actually I recently. So one thing is I don't use
LinkedIn for career search. Actually I do a little bit I do
for a little bit of job search, but LinkedIn I will it's not

(47:04):
great. So actually the other day, cuz
internship season, it's on us. So I'm going through my
recruitment and I was like, you know what?
I don't like using LinkedIn anymore.
I'm seeing the same sponsored adjob posts every day.
I go on a handshake. I'm like, oh, here are three
jobs I'd actually be interested in.
So yes, I do use Handshake. Oh wow, we should get you

(47:24):
posting on the feed. I did post, I promoted the
podcast because I got a message.There was a promotion for like
you post and they were giving like $250 for Pearson with like
the most comments or the most likes on their post.
It was pretty good. Yeah, send it.
To me is that is the promo already got done.
I was like I can I can comment on your thing.

(47:46):
I don't, I just posted to be honest, because there was a
prompt that was, you know, what's something that you've
really been enjoying doing recently?
So I was like, hey, I'll post about this.
And then I did and I got, I got some, got some likes from some
University of Illinois peers. I got some random people
following me now, which is strange to have, you know, my
handshake profile is not very fleshed out.
I have one piece of content. It's strange to have people
following me on it, I think personally, but I have, I have a

(48:09):
couple followers now. So you know, maybe, maybe my my
handshake content creation erroris the era is just beginning, I
don't know. OK, well, I mean, they're
working really hard on making itgreat for you, so yeah.
I it's actually I do quite like handshake.
It's good as well for career fairs.
Everything's through handshake for us actually, even on the

(48:31):
school level, it's interesting. Yeah, OK, cool.
And I go you members of Illinois, it's a huge school,
especially for computer science and tech.
So it's cool to see that it's very actually pretty widely
adopted. I would say on our campus we're
all forced to make Handshake accounts at some point, so.
Yeah, wow. All right, I wanna ask.
We got about 5 minutes left. Gonna do a quick thing.
Can you in 20 seconds tell me about handshake God?

(48:54):
Yeah, actually. And what you do there, not just
the company as a whole, sorry. In 20 seconds you're.
Halfway through, I'm joking. Nick, Handshake, I think until
this point has been the career network for Gen.
Z that's been helping democratize opportunities for
people regardless of what they have access to coming into the
game. So that is my 22nd spiel for

(49:17):
like what it's been. However, Handshake, like many
places, is evolving into the network for the AI economy and
figuring out what we're doing with the changing nature of the
labour market and how we can help people navigate that as if
everything changes. So what that means is that we're
also helping and at the center of some of the forefront of AI

(49:38):
model creation. So that's it, OK.
And I'm the VP of design there, so I take care of designing the
design team. Yeah, very nice.
That's what I'm doing right now.Yeah.
And then so my final question for you to wrap things up is I'm
very curious, how was your view of yourself changed as you've
gone through your career? My God, Nick, what a question to

(49:58):
end on. I lined it up perfectly.
I know amazing. How has my view of myself
changed over the course of my career?
So when you know how you work out and you're like, OK, I'm
going to do push up and then or I'm going to hold a plank and
then like you do it and it's like terrible.
Or you do burpees and they're terrible.

(50:19):
And then like you do more of them.
And then I don't know, say you do ball game split squats or
whatever. And then all of a sudden these
things that were like really freaking hard become a little
less hard over time. So I think that there are over
the course of my career, I don'tnecessarily think that I know
everything. Like part of the problem of like

(50:39):
knowing more is that you learn always that there's more for you
to do. And part of the problem of
getting better at anything is that you realize that there's so
much better that you could be ifyou have that kind of
personality, which I do. Some people aren't.
Some people are like, I'm the ship, let's go.
And like, if you're that person,like that's amazing, That's
great. I'm so happy for you.
And I wonder what that's like all the time.

(51:00):
But that's not who I am. I'm the kind of person that
always sees like what I could bedoing better.
But what I do know is that I nowhave a track record of all the
times that I went into somethingand I was terrible at it.
And then I learned and I got better.
So I know I have learned that I know how to learn and I have
learned how to learn. I've learned how to collect
feedback on what I'm doing, to look at it with a critical eye

(51:23):
to like not despair for too longif I'm not hitting my own
standards yet. Because I know that I've already
been through the journey of likenot hitting my own standards
yet. And then eventually like getting
better at the thing and being able to look back and be like,
oh, I did get better at that. And that's growth.
So that's cool. I don't.

(51:43):
I have never and this is my likemy fun spicy take to end on.
I have never had confidence or attained confidence as a
prerequisite for doing anything.That is a hill I will die on.
I don't think having the confidence to do something is a
prerequisite. I think if you're fascinated by
something and you really go for it and you get into it and you

(52:04):
get out of your own way, it doesn't matter whether or not
you're confident or not. Just like let yourself be a nerd
about it and then and forget about yourself.
Like this whole idea that you have to have confidence in order
to do a thing. Like it centers you in a way
that I'm like, you know what? No, it's not about you.
It's about the thing. Just like get the thing done and
then do it and over again and then look at what you could be
doing better and then do it again and then keep getting

(52:27):
better. And like don't just get yourself
out of the way because like we are, we just get in our own way
a lot. And I certainly have the kind of
brain that gets in its own way alot.
So like advise against. If you have a, if you have a
sort of self esteem that works similarly to mine, which is like
a little bit brutal or like verybrutal, then like you need to

(52:48):
learn how to just get it to doesn't mean that it's like
fixed itself. You just need to be like, hey,
I'm not gonna take a blankie andsome hot chocolate and I'm gonna
go focus on the thing I'm tryingto do right now.
And then you come back and you might still have low self
esteem, but she's sitting in thecorner and she's busy right now,
so you can focus on your thing. Does it make sense?

(53:11):
Yeah, yeah, it does okay. I don't know how you are.
You like how are you? How would you categorize
yourself with that? I whether or not I am, I have
the confidence of a mediocre white man.
So I am, I am a pretty I'm I'm pretty blessed in that sense.
I try not to be mediocre. I try to be excellent, but I do
feel pretty good about myself asin my pursuit.

(53:31):
So I. That's amazing.
I love that for you. I heard that term the other day.
Somebody was like it was. But anyways, yeah, So yes, but
I, I appreciate you sharing because it's very difficult for
me to communicate those ideas because that's not my
experience. So thank you for that.
Well, for so shout out to those of you who feel similarly to me.

(53:52):
Hi, we're out here. You might wind up doing like a
whole bunch of great things in your life and then and not
really realizing it. Is there something I sent that?
Well, all right, I know you haveto run.
Thank you so much. This has been a really enjoyable
conversation. Thank you for joining me today.
I appreciate your time. Thank you so much for having me,
Nick. I hope you enjoyed the episode.

(54:12):
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I'm looking forward to seeing you next week.