>>What does it look like to confront risk face-to-face every day?

To build a career-and a life- around unpredictable odds?

For professionals in the world of insurance, risk isn't just a possibility: it's the job itself.

That's why this summer, Roadtrip Nation sent three people across the country to uncover what it's like to make improbability your profession.

They hit the road to explore the risks behind betting against unknown odds —and the rewards of being able to help people when they need it most.

This is Roadtrip Nation Risk & Reward.

[MUSIC] Hello.

>> Surprise.

>> Surprise >> Hey >> What's up guy's?

>> Did she notice us?

>> Hello.

>> Hey.

To the RV!

>> How's it going?

>> This is day one, and we're in Boston.

>> I think the best way of developing yourself is to meet different kinds of people, and all three of us are from completely different backgrounds.

>> It was weird, because I was really happy to see them as if they were like my old friends I haven't seen for ages.

So yeah, I was just excited for us all to be together.

>> Are you more of a Bachelor person or Bachelorette person?

>> Probably more of a bachelorette.

>> When I was talking about this show to someone, they're like, so it's basically like The Bachelor?

There's so many jobs out there, you're choosing out of- >> It's similar in the fact that they're on cameras and that's about it.

>> [LAUGH] >> Cameras.

>> There she is.

>> Really exciting.

>> Stands out.

>> We are really doing this.

>> So as you can see here the risk of dying in a crash over the course of the entire trip is a total of 0.00346%.

But this is for an average car, but we're driving a big RV.

I've had a couple records of accidents.

Considering all those factors, our new risk of dying here is about 25%, and that was just an estimation.

But that's what insurance is for right?

[MUSIC] >> So exciting, this is home.

I'm in.

This is really nice.

>> Yeah, I like it.

>> Beautiful.

>> Nice, big fridge.

>> Yes.

>> Is that a freezer?

>> That's a freezer.

>> Amazing, we can have like ice cream.

>> [LAUGH] >> Yes, it's a tiny house, it's got everything, it's got a kitchen, it's got beds, CD player, it's my dream house.

>> Sorry there's no CD player.

>> There's no- [MUSIC] [LAUGH] God.

>> I'm really excited.

I'm glad to be in the RV and to unpack my bag and know that it's unpacked for the next four weeks.

This is where we're gonna live.

And Alan brought a rice cooker.

>> Behold.

>> [LAUGH] You brought a rice cooker!

>> My baby.

Is there like an outlet here?

>> Jenna the microphone which is the best thing I have ever seen.

>> Hello Roadtrip Nation!

>> [LAUGH] >> It's rose gold.

>> There's so much power in this.

I think that I packed way more than I needed, the other two packed lighter than I did and I just kinda came in like [NOISE].

>> [LAUGH] [MUSIC].

>> My name is Jenna I'm going to be a senior at Olivet college and I'm from Fraser, Michigan.

[MUSIC] It's small enough where you know people but it's big enough where you don't know everybody.

[MUSIC] As a kid I was super outgoing, loved to play sports and be active.

I was always singing and dancing even though I'm awful.

Always just doing something to entertain somebody.

In high school I took a lot of honors classes, a lot of AP classes.

So, my transition to college was really good, academically.

Emotionally, it was hard being away from my family.

My mom's my best friend so I was literally calling her 20 times a day.

Very, very homesick.

[MUSIC] I originally went into Olivet doing general business, I was like play it safe.

[MUSIC] The guy that recruited me to Olivet, he later became an advisor in the insurance department.

So he kept asking me to change my major to insurance.

And he kind of like explained to me that insurance is really about helping people and making sure that people have peace of mind.

Because everything you do you need insurance.

And so, I was like you know what?

I'm just gonna do it.

I haven't looked back, I love insurance and I'm like a little nerd now.

[LAUGH] I'm leaning towards risk management.

[MUSIC] But I don't know if that's 100% what I want to do.

I definitely think fear of failure has stopped me from maybe like, taking different chances on things.

I kinda played it safe so I wouldn't have failure.

I mean, I'm scared of it.

So I think doing this road trip will be really good for me cuz I think this road trip is a big risk.

Being away from my family and driving this huge vehicle.

But I'm super excited to make connections and hear people's stories.

Getting different ideas and opening myself up to even more parts of insurance that I don't even know probably exist yet.

I think that I will learn a lot about myself.

I'm not sure what I'm going to learn about myself.

So that's something I'm looking forward to.

[MUSIC] I like to think of myself as a duck, because like on the surface I'm, like, chill.

And underneath I'm paddling like mad.

>> [LAUGH] >> If you could shape-shift into any small animal what would it be?

>> Gerbil.

>> I'd be a Squirrel.

>> A Sugar Glider.

>> That!

>> A what?

>> My name is Alan Hishida.

I am 21 years old.

And I was born in Tokyo, Japan.

[MUSIC] I moved here when I was five.

For college, I moved to University of Connecticut where I currently study Actuarial Science.

It's a field of study where you calculate how much loss you're gonna have.

When I got into high school, my parents gave me an option to go to a prep school for a prestigious college in Japan.

And the other option was to just keep going through high school.

They really, on one side wanted me to spend my life in Japan.

But at the same time, they respected my decision to stay here.

But I was given the freedom to choose which country I want to live in.

I have to really show them that they made the right decision of trusting in my decision.

That they made the right choice of keeping me here.

[MUSIC] In high school, I really didn't have an ambition or a drive.

I just did what I thought was right at the moment.

And my guidance counselor, she was the kind of person that knew my strengths and weaknesses.

So when she said that I would be a fit for actuarial science, I was very hopeful that I could really thrive in this major.

So right now, insurance is my focus.

[MUSIC] My biggest fear Is not being able to present my value or be able to apply myself in a workplace and okay, no, no, no, no.

Who am I kidding?

That's not my biggest fear.

My biggest fear is really just coming back home to this house And then saying to my parents, I don't have a job.

Just not having any direction after college.

As I go into senior year, what's important for me right now is to be able to become independent.

And show my family that they don't have to worry about me.

[MUSIC] For me, I think it's really important to find that path for yourself.

Go full speed for something that you really want to do.

That's why I think it's really essential to find people that went through the same kind of road as me, and this road trip is perfect for that.

[LAUGH] I'm excited to see what valuable lessons I learn.

[MUSIC] >> Why is it making that of noise when I put my foot on the break?

>> It's the parking break.

[SOUND] Start it.

>> Well, first release the parking break.

>> Is that this?

>> Yeah.

>> What do I do?

Pull?

[MUSIC] Okay.

This is all very strange.

So part of this roadtrip is we're going to be interviewing people who have found like awesome work that they love within the insurance industry.

>> Left here?

Kinda get their story of how they got to where they are, and know what lead them into insurance.

>> So today we are going to FM Global to interview Grace Ries >> How are we doing?

>> We're there already.

>> Yeah, well, I was looking through all of our notes on like what to ask and everything I don't think it'll be awkward just because all three of us are super talkative.

That will be our first interview and I'm really excited for it.

[MUSIC] >> I can't get out.

[LAUGH] >> Hi!

>> Hello, hi.

>> Welcome, I'm Grace Ries.

>> It's nice to meet you.

>> Nice to meet you.

>> So FM Global is a property insurance carrier.

We're a specialty company because what we do know is how to prevent a property loss.

And what I am doing now is heading up a team to help our clients to mitigate cyber risks as well.

It's so much more than just issuing a policy, it's so much more than just talking about premium.

When you can burn things up, when you can shoot things, and shake things.

If that's what insurance is, sign me up.

>> Right now we're gonna be doing the wet lab.

Sprinklers are good, but not enough.

So what we featuring in years is how to evaluate that water supply, and that's what you're gonna be doing today.

Have you ever done anything like this before?

It's fun.

[MUSIC].

Whoa, that is hard, that is hard.

[SOUND] [INAUDIBLE].

[MUSIC].

>> Growing up, I came from a culture where my parents were advising me, you have three choices with your career.

You can either be a doctor, a lawyer, or an engineer.

And I went to college, wanting to be an engineer.

I didn't think about going to an insurance industry, but sometimes you just take a leap of faith.

And before I took this job manager of cyber risk insurance products.

Brand new, nobody has done it.

I talk to several others to make sure I'm sane, it's not crazy.

And they said, if not now, when Grace?

I just wanna give it a try to see if I will like it.

And then, I'm still here I must really enjoy it.

>> What advise would you give to us- >> I was gonna say that- >> for the start of this trip, for the next couple of weeks?

>> Think about what excites you the most, right?

What do you wanna be part of?

>> Yeah, our RV is named Thelma.

>> Sign yourself up for something that it's even uncomfortable to you.

Don't need to fit in, just try to be part of it.

And see what type of difference you can bring to the table.

[MUSIC] >> The more I learn about the industry, the more I think there's cool stuff that I could work in.

So I feel, I just need to carry on building on that so that when I go back to the UK, I don't have another mid life crisis [MUSIC] [SOUND] My name is Gaby, I'm 21, and I'm from Wales in the UK.

While I was at college most people either go down the humanities or the sciences route.

I was so afraid to make a decision, that I picked both.

Because I was just so scared to rule out an option.

[MUSIC] And I had some friends whose parents had always said to them, you'll be a great doctor, or you'll be a great lawyer, or that kind of thing.

And that's always what they wanted to do.

They kind of have the decision made for them, and I was kind of envious of that.

And I was kind of I wish someone would tell me what to do.

But my parents were like, we can't make this decision for you.

And I was always good at math, so I ended up doing math and science.

My parents, they've had some really hard times in their lives we struggled financially when I was younger.

My dad changed jobs quite a lot, he would start a job he would think it was great, and then got into it and realized actually wasn't for him.

He never found something that he really loved.

[MUSIC] That was really sad to see because he was never happy in what he was doing.

When I was making the decision about what I wanted to do with the rest of my life, that was all I really cared about.

All I wanted was to find something I was happy doing.

and not feel a couple of years down the line that the job wasn't for me, and I had to change again.

[MUSIC] I finished university this year.

Now I'm kind of free, and I don't really know what to do with that freedom.

I ended up with an interview for a car insurance company.

They offered me a full time job for when I graduated.

It's never what I thought I would do, but the job would be really interesting because it's looking at statistics, and numbers, and seeing whether something is statistically relevant.

Which really appeals to the mathematics side of me.

The more I learned about those, the more interested I became in insurance as a whole.

I never really thought that insurance would be that exciting.

I never thought, I gonna get up one day and really not wait to get to work and talk about insurance.

But here we are [LAUGH] [MUSIC] I think that a lot of things I can be excited about I have a great job to look forward to.

But at the same time I always think about what if I am worried that I'll pick a job and be in it for the next 40 years, and end up being very miserable.

So, I'm really looking to talk to somebody who at my age felt, they didn't really know what they were doing with their life.

Because I feel like a lot of people know what they want and they chase it.

And I haven't done a lot of chasing.

So I'm really looking for somebody to say, it's okay to love something that you didn't intentionally go out and find.

And also how to know when you found that right thing for you.

So I'm just looking for reassurance more than anything.

[MUSIC] Hi, I'm Gaby, it's so nice to meet you.

>> Hi, nice to meet you.

>> I'm Janna.

>> Hi, Jenna.

>> Nice to meet you, Karen.

>> Could you give us an introduction of like who you are, what your company does, that kind of thing?

>> Well sure, Basically what we do is we help determine what potential losses are from different types of natural catastrophes.

So what was very unique about the models, and I guess the industry, that I guess I'm credited with inventing so many years ago, I hate to tell you how many years ago.

>> [LAUGH] >> But was to create the lost data, essentially by creating a model that could simulate potential future earthquakes.

[MUSIC] >> I read a statistic a couple of weeks ago that basically said in the FTSE 100, there are more CEOs with the name John than there are women.

And I was just like, that statistic is crazy.

>> it's terrible.

>> Yeah.

>> [LAUGH] >> So I want to find a female CEO who is kind of self made An d then, I did more research and I was like, my God, you've done so much.

So I was like, yeah, I really wanna come and interview you.

Just to start, what were you doing at our age, and how did you go from there to what you're doing now?

>> Well, I have to tell you that at your age, I had no clue and I'm very impressed at all of you are pretty confident about what you want to do >> I remember in graduate school, I only went to one job interview and I took it right away.

And it happened to be with an insurance company, which unlike you I never thought I went, and in fact, I would have said no, I don't wanna be in insurance because it's so boring.

But I took a risk, I decided, okay, I'm just gonna go for it, and lo and behold, one of my projects was to do something about hurricane risk.

That was the first catastrophe modeling I started in 1987.

Long story short, I just ended up devoting my whole life to it.

>> I think for for me the biggest thing is I've kind of fallen into the job I have.

And so, I went on placement while I was at university, and it just so happened that this company offered me a job.

I kind of think to myself, am I just taking this job because it's the first one that was offered to me, or do I actually really love it?

And I was wondering, how do you know?

>> Well, you won't know, so just don't try to predict.

I mean, chances are, it's not gonna be the right decision.

I mean, chances are, you will not stay there forever.

But you'll learn something, and hopefully, you'll learn more about what you like and what you don't like.

I didn't know this was gonna be my whole career, but it definitely became a passion.

And it became something that I felt that I had to do.

And what you're thinking, you can influence.

I mean, if you really believe something, you're gonna make people believe that too.

One of my first presentations was to Lloyd's of London back in 1987, and people kept telling us that what we're doing now is impossible.

All the underwriters at Lloyd's are about 150 of them in the room, not a woman in the room.

So first of all, an American come in, and then an American woman come in, seven months pregnant.

I think, they must have thought it was some kind of a joke.

I don't even know if they were paying attention the first ten minutes.

So they're like, where's the punch line?

>> How did you deal with that like, how did you pick yourself back up?

>> Well, I was so bullheaded, determined, and focused on what I was doing.

I never remember feeling disheartened.

It was just, okay, well, how can I still do this?

What's my next step?

It's really important to just be focused on what you're doing.

>> Clearly, what you went through and how you started up your own company and tackling something that no other company has ever done, it's very scary step to take, right?

I just want to know if you had any doubts over the years on the process.

>> Sure.

I mean, there are a lot of fears and there are a lot of doubts.

But if you think you might wanna do something, you wanna try it, just go and do it.

If you really feel that you're not happy in your, what you thought was your chosen pr ofession, you're not happy when you get up every morning, you're not excited to go work on whatever you're working on.

And you really get excited on this, and you think you're good at this other thing.

I don't think people regret having done things, what they regret most is not having done things.

You have to make sure that you are going to be happy.

It must be fun, you must enjoy.

You must wake up everyday looking forward to the next 8 hours or 10 hours, or 12 hours, whatever it may be.

I mean, people look at me, if you talk to anyone who knows me, they think, I work so hard, and I tell them, you know what, I never worked a day in my life because I have totally enjoyed everyday of my career.

So be fearless out there.

[MUSIC] [SOUND] [MUSIC] >> We went to see the Boston fireworks for the 4th of July, which was really exciting for me because it's my first 4th of July.

I was amazed by how patriotic Americans get over it.

>> [APPLAUSE] >> Where we were standing, there were some like, performing arts students next to us and they were singing, and Jenna was like, I should sing too, to compete with them.

>> And then, we were just laughing and she's like, what are the odds you'd do that?

And I was like, okay.

>> [MUSIC] >> And then, half the crowd joined in with us.

It was like very patriotic, I was kind of just stood like, I don't know the words.

[LAUGH] >> [MUSIC] >> Thank you.

>> [APPLAUSE] >> Thank you, Boston.

Good job, guys.

>> [APPLAUSE] >> [LAUGH] >> That's made my night.

>> I can't believe that.

I can't believe that.

>> I'm gonna be in different person by the time I know it.

[MUSIC] >> The whole idea of my major is to avoid risk.

There's so much to learn from Jenna and Gabby >> I feel like we've all kind of gotten out of our comfort zone.

Kind of challenging each other's differences but I like, love that.

>> Today, it's been a lot of fun.

I think, the next few weeks are gonna go really quickly and I'm really excited.

>> Wow.

It just stay one, guys.

>> [LAUGH] [SOUND] To learn more about how to get involved, or to watch interviews from the road visit roadtripnation.com