>>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] So after Boston, we drove to New York.

>> Today is day five of the trip.

The actual trip since starting the road trip has gone so fast.

I think the next few weeks are going to go really quickly.

[MUSIC] >> New York was super fun.

It was me and Gaby's first time going.

Look at that.

There's so many people in there.

>> It was really exciting.

I couldn't wait to go and see all the touristy stuff.

>> It was great being able to walk around with people that haven't seen New York at all.

[MUSIC] >> We've all kind of gotten out of our comfort zone.

Each interview, I just feel like my wheels start turning more and more and what am I going to do with my life?

I'm always thinking of what the next possible thing could happen or the worst outcome.

I like to be prepared, but there's things that I am not going to be prepared for and that's something I'm definitely going to have to get used to.

I'd want a mentor as someone to kind of guide me in so I can turn to them.

[MUSIC] >> So, we went to the Jersey shore to interview Laura Woop.

>> And she is the Director of the Risk Management for Tiffany and Co. >> I can't get out.

>> Is it unlocked?

>> Yeah.

>> Push it.

Push!

[MUSIC] >> I'm excited to learn a lot about her because I'm leaning towards risk management, but I don't know if that's 100% what I want to do.

>> Hello.

>> I'm Jenna.

>> Hi.

How are you?

>> I'm good, how are you?

>> I'm Alain.

>> Hi.

>> I'm Laura Woop, I am the director of risk managment Payments and Credit Services at Tiffany and Company.

Risk management means we're responsible for insuring the assets of the company, whether those are our employees, our jewelry, our property, our building.

So there are a lot of really interesting risks happening within Tiffany every day.

>> So you'd consider yourself as a more risk adverse person?

>> I would say I'm not a risk adverse person, I'm a risk aware person.

>> [LAUGH] I like that.

[MUSIC] >> Could you tell us a little bit about your childhood?

>> My Mom was a nurse, my stepfather was a police officer.

I would say middle class working family.

Not necessarily the typical college push so it was kind of a shot in the dark to figure out how I was going to navigate my way through college.

I was good in math.

I figured, I'll do accounting.

I didn't really know any better.

So I went to school for accounting, and at my college they did a lot of recruiting with Tiffany & Co. And quite honestly I didn't know what Tiffany company was, I didn't grow up in a house where I had Tiffany jewelry or any of that kind of stuff.

Got a call from career services asking if I wanted to interview with Tiffany and I did and they offered me a position in the internal audit department.

So I went into audit, started there.

And kind of had my fill after about five years and it just so happened there was a position opening and went into risk management.

And when I went into risk management I had no insurance experience.

I owned an auto policy and I owned a homeowners policy and that was my insurance experience.

As I went into it, I had very, very strong resources through our insurance brokers.

That I could leverage and lean on, and I would ask all the stupid questions.

They really were my resource to train me and teach me what I needed to know about insurance.

And it's just been a learning experience along the way.

And I think be open to understanding that that is actually an option when you're talking about insurance.

It's still a field that is very open to folks from different backgrounds.

>> I did not grow up I'm going to go into insurance.

This is only my first year majoring in it.

So when I read policies, when I read my book, I'm trying to catch up on you know lost time too because people in the program were in there for three or four years.

And so I'm trying to catch up.

>> Well, certainly reach out to me if you need.

>> Definitely, yeah.

[LAUGH] >> Okay.

>> Thank you.

One of the biggest things that I have realized in my career is if you have the the right person teaching you something, we can teach anybody to do anything.

>> So are there any risks that you've taken that perhaps haven't paid off or any risks that you took that maybe you regret.

>> Well, I would say the one risk was moving into risk management, because I feel like I was kind of totally moving away from this thing called accounting that I went to school for.

And I was kind of sticking that right on the backburner.

Do I regret it at all?

No, not at all.

I think moving into risk and the fact that I've demonstrated strength in that area enabled me to be asked to do these other things.

I now have responsibility for running our credit card program, so it's credit risk, it's different kind of risk.

I have a fraud team that reviews all of our online orders to make sure that it's actually Jenna that placed the order online, and not someone like Alain, who stole your credit card.

[LAUGH] >> So all things risk has kind of blossomed into a very nice career for me.

Don't just think of it as insurance because yes, it is the insurance industry, but I'm not living my day in an insurance policy day in and day out.

There really are other opportunities, it's not going to remain static.

The entire insurance industry will change.

It's changed because of social media, it's changed for lots of reasons, and it will continue to do that, so I would say just be open to exploring it and find the resources.

And don't be afraid to ask the questions because when I went into this it was ask all the dumb questions.

Ask smart question too, but ask the dumb ones too or what seems like it.

Don't be afraid to ask questions.

Take chances, but be hashtag risk or winner.

[LAUGH] >> Ready?

>> Why did I go with high tops.

>> That was foolish of you really wasn't it.

[LAUGH] >> Wasn't it.

[MUSIC] >> I really like Laura Woop because she just seems really awesome.

And I've just felt a connection with her.

She's just the super laidback humble person and works really hard and really love what she does.

[MUSIC] >> She picked one company and stayed back which is kind of what I was afraid of doing.

But it sounds even though she's stayed in one company, she's had like a variety of different jobs.

So, yeah, that was really interesting.

[MUSIC] >> Laura Woop said, to be risk aware.

It's like, you can take risks however you want, but you need to understand that.

[MUSIC] >> There are a lot of worries in the beginning about how I could live with other people in a small, rectangular room.

Sometime it's very challenging.

But now, [MUSIC] I feel rather comfortable.

[MUSIC] >> After New Jersey and New York, we went to Danville, Pennsylvania.

[MUSIC] >> There's so much to learn from Jenna and Gabby.

I feel that they have a lot of passion in what they do.

And I have still a lot to learn.

[MUSIC] We are about to interview the Chief Actuary at Geisinger Health named Kurt Wrobel.

I'm very excited to see him because he's the guy I aim to be.

One of the top things I wanted to do on this road trip is meet someone who can be going potential role model for me.

So Actuarial Science is a field of study where you use probability to calculate how much loss you're going to have.

Actuary as a whole, it's meant to kind of predict the probability of accidents and different disasters.

Actuarial Science is also a lot about the Actuarial exams.

I will take my third exam, it's next November.

In the process of studying for these exams, it could be very difficult to go through.

>> Alain was super excited.

He was like picking out the right outfit before and everything Like he just really want to make a good impression.

>> Well yes, I dressed up.

Roadtrippers assemble.

>> I don't really know too much about actuaries, what they do?

So I'm excited to learn more about.

I mean, I know it's like Math and stuff but.

>> I was nervous, yes, as you were able to tell.

>> Welcome to Geisenger, how fine you guys?

It's great to have you here.

>> Well, yeah, okay.

[LAUGH] >> I have a question if he's still not ready.

>> Okay, go ahead.

[MUSIC] >> My name is Allen and I'm a student at the University of Connecticut, Majoring in Actuarial Science.

And I'm currently working up the ladder with a couple Actuarial exams.

And I'm here to kind of explore the different fields, and learn more about the career of an Actuary.

So could you tell us a little more about what you're focused on as a Chief Actuary here at Geisinger?

>> So what we primarily do here is we sell health insurance products.

Our single mission is to provide the best quality healthcare to the people of Central Pennsylvania.

We have to make projections on what healthcare costs are going to be at for the th e upcoming year.

Part of my job is to take historical information, look at that historical information and trend it forward to that projection period.

>> So.

>> Okay.

[LAUGH] >> So >> Just shoot away Alain I'm with you my friend >> You're just starting the exam process too >> Exactly, okay, and so, what are certain character traits that you think are important to become who you are?

>> You have to have a certain degree of, I would almost say tenacity to get through the process.

Going through the exam process is can be fairly lengthy, and if you do have a few times when you don't pass exams you need to continue on with the process.

I can tell you in my own exam process, I probably failed about 25% of the time.

So it was certainly not an easy road, by any stretch.

But one that I think in the end was worthwhile.

I knew I really wanted to be different and have that rare and valuable skill.

>> So you made, a couple mistakes and failed a couple of exams over the whole course of taking all of them.

How did you kind of like bring yourself back up when you happened to fail?

>> I think opening yourselves up to failure is one of the most important things you can do in life.

Just because you fail doesn't mean you're a bad person, or unable to pass exams, or unable to kind of go beyond a particular failure.

The best measure of an individual is not how they are when their doing really well.

And when they're at the high point of their lives.

It's when they've been put down and are kind of on the ground for a bit.

And, I really have a lot of respect for people that are able to shake themselves off, get up, and then succeed.

Failure should be looked for rather than avoided, I think.

And you're not necessarily going to jump into your first job and say this is absolutely the job of my dreams.

And I've absolutely found my purpose.

A lot of times it's not that easy.

Give your career some time to kind of mature.

There's going to be more opportunities to find a job, a purpose.

>> Are there any mistakes or anything, that maybe you didn't learn right away?

And you kept making them?

And how do you feel about that?

>> I think I've made plenty of mistakes.

[LAUGH] >> I feel like I've, probably learn from most.

>> Okay.

>> But, I think sometimes you got to look at, specially personal decisions in a broader context.

A poor decision where you learn a lot about yourself, isn't necessarily a bad thing.

And I think opening yourself up to risk, personal and professional, allows you to grow.

And so I wouldn't just shut yourself off to those opportunities.

There's growth opportunities that are so important in life.

There's a lot of things that will happen in your careers that are completely out of your control.

And really defining way you control is so important it's part of the Stoic Philosophy.

It's thinking about things that you can control.

Focusing on those and letting everything else happen.

[MUSIC] >> It felt really assuring to hear from someone that's already gone through difficult experiences, and being in the middle of it right now, is kind of discouraging.

But I believe that data is something that I can really thrive in you know?

At the same time, it's more of the environment that I'm scared of being in.

[MUSIC] >> We're going to go straight up north and a little to the west and hit Niagara falls [MUSIC] >> I feel like all the interview have been awesome, I've taken in a lot.

I have a new favorite every time.

[LAUGH] I'm like that's so great, thats my new favorite I'm like wow, this is amazing.

[MUSIC] >> Before the trip, I hadn't had much experience of putting myself in situations that maybe I didn't really want to be in.

I think coming on this trip is pretty big risk for me.

Driving from the East to the West Coast of a country that I've never been to before.

I was definitely putting myself outside my comfort zone.

Hopefully, this will be the start of me becoming a less risk-averse person.

[MUSIC] >> I wanted to definitely see some nature.

>> [SOUND] Niagara is the ultimate nature attraction in the US.

>> We got to go out on an actual boat and drive towards the falls.

That was just so much fun.

The water was beautiful.

[MUSIC] >> I was expecting just to turn up, take some pictures, go on a boat ride, and then come back.

We went to the corner of it which is where you get drenched.

it was a lot of fun.

>> So I was very sensible.

I liked to put my hood up and tighten it really tight under my chin so that no water could like get down.

>> I kept yelling at Gaby was like no hood, no hood, put your hood down.

[MUSIC] >> The water was so powerful.

I couldn't open my eyes, couldn't open my mouth.

>> She was not very happy because she got literally drenched.

>> Yeah, I'm holding her responsible.

[MUSIC] I like our team a lot we're very different and we have different roles.

Now Gabby is from Whales and she's here to experience everything so just be the explorer of the crew.

Jenna, she is very bright.

She is always driven to go forward with all three of us, and kind of, she's the glue that holds us together.

>> My gosh, Alainn he's the most entertaining person.

One of the most entertaining people I think I've ever met.

I just like being around him, he's really funny.

>> I admit I'm a pretty goofy guy.

What I'm really fearful of is, say in a corporate company where everyone is expected to conform.

I feel like it will be like the loose guy.

It feels a little suffocating.

[MUSIC] We are in Chicago, and we're about to interview David Shotts.

>> He specialized in events insurance.

>> Concerts.

>> Entertainment.

>> Yeah.

[MUSIC] We went to a music festival that David Shotts did the insurance for.

And it was a lot of fun!

We all wore tie dye shirts and we looked like a little family.

[MUSIC] >> My name is David Shotts, and I am the vice president at Ascend Insurance Brokerage.

>> We worked directly with the entertainment industry.

We worked with music venues, music festivals, touring artists, events safety, events security companies, television and film.

We're kind of premier agency in that space.

>> What is your favorite thing about what you do?

>> Working with the entertainment industry.

I mean it's kind of cool that I get to go to music festivals.

It's cool that I can make calls and say, hey hey, I need tickets to this and like yeah, no problem.

Really, that's so rad.

[MUSIC] >> So, could you tell us what you were doing around our age, we're all 21.

>> I was actually 21, I was a musician, I was playing in a band and we were touring the country and having a lot of fun.

Not really thinking about insurance to be quite honest.

I got into this industry by accident.

I was in a completely unrelated field.

I was in the private security industry.

I was running a company.

My broker said no one knows this industry like you.

Come to work for me and I just kind of found out I was really good at it and that sales role was I was good at at 16 when I was selling skateboards to kids.

And it was something that I just continued through my life.

I genuinely enjoy it.

But my first couple of years were pretty tough on me.

It took me a while to grasp everything, to really learn risk management.

I mean, I was in my late 20s, sitting there going, is this what I want to do for the rest of my life and I kinda had a big question mark like I don't know.

That's when I started to go, I don't really want to do the corporate thing anymore I want to go back to enjoying this industry and enjoying this business.

I need to focus on the stuff that I enjoy personally if I'm going to continue to enjoy this industry.

So I think that was more I as a person identified all right, I know this and I can rock this all day.

>> What would you say is a memorable risk that you took, like a big dive.

>> Getting into the insurance industry [LAUGH].

>> Yeah?

>> You're not going to accomplish anything if you don't have a little bit of risk, all right, I'm going to throw caution to the wind and just go for it.

Anyone who ever did anything, started by rolling the dice, taking a risk, right?

I mean, I left really a pretty ready made situation where I was going to be given the keys to the castle if you will.

And I said no, I don't think I want to do this.

And I went into the insurance business.

>> Probably a lot of people who are going to watch this are going to have a negative impression of insurance, they're going to think it's really boring.

Would you have agreed with that before you worked in the industry and how has your impression changed?

>> Yes, I would have totally agreed with that.

I would have thought of kind of the commercials that you see on television.

It's cool because I'll talk to people and I'll tell them what I do.

And most commonly people are I didn't even know you could get insurance for that.

I think that's kind of the beauty of the industry is that insurance is everywhere.

I mean it doesn't just stop with home, auto, life.

If you're into extreme sports.

I know a brokerage in California that focuses on extreme sports.

If you're into hunting and fishing I know underwriters that specialize in that industry The insurance world is your oyster.

What you want to do?

He just wanted to do more and be really happy with what he did then he ended up finding the music and entertainment with the brokerage side.

So it's cool that he didn't just give up on being a broker in the insurance world all together.

It's really nice to know that I can always find something else within insurance.

>> The opportunity is really getting better and better.

Because your looking at an industry where the average age is 58.

I've been doing this 10 years, and I'm in my mid 30's.

I'm a kid in this industry.

>> Yeah.

I mean most of the industry there looking to retire and there's all these positions that are going to come open.

I mean, I admire the fact that you're doing this at your age.

Your leaps and bounds from where I was, I mean I commend you all and then like, good luck.

It's a great industry.

I enjoy it, I enjoy what I do.

I like going to work every day.

>> There is so many different opportunities and cool things out there, like insuring for concerts.

That really just opened my eyes.

Part of his work is actually play.

And part of his play is work.

That kind of way of life is something that I really admire about him.

[MUSIC] >> Everything's going by so fast.

I can't believe it's almost halfway through.

It's crazy to think we're going to be done soon.

[MUSIC] What I wanted to get away from this road trip was get an idea of what I want to do, but now I'm just trying to soak in a lot of their advice.

Little things that are sticking with me and it's good to have going into my last year of school and then starting my career after that.

>> I think the people we've interviewed and some of the stuff we've seen has made me rethink insurance.

I'm not feeling so hemmed in I must do this job forever kind of thing.

There's so much out there.

[MUSIC] I really like these interviews, the more I get to hear their stories, the more it really gets me exited about what I'm doing.

I just want to keep going, I just want to stay there, kind of absorb as much as we can.

By the end, I really hope to be sure of what my next step is.

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