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Pursuing a Path With Purpose With Gina Wong


Get ready to meet Gina Wong, an incredible Living Benefits Specialist who found her true purpose in helping families protect their financial well-being. Raised in the San Francisco Bay Area and having ventured to New York City, Gina's journey led her to a career that deeply resonates with her values.

In this enlightening episode, Gina shares her inspiring story of leaving behind a 13-year career in advertising and marketing to pursue a path that aligns with her purpose. Discover how she became a passionate advocate for living benefits, ensuring families are shielded from financial hardship during critical illness, disability, or loss.

Join us in listening to Gina as she reveals the challenges she faced growing up in an Asian American family and the expectations that came with it. Gina's story will ignite your own desire to find purpose and contribute to the well-being of others. To connect with Gina, check her out on Instagram @livinglifewithgina


Watch Gina's Story



Jennifer: Welcome to the I Don’t Give a Should Show – a podcast exploring ALL the ways that women SHOULD all over themselves. How many times do you find yourself acting out of obligation or doing what everyone ELSE expects from you without stopping to consider why? Where do all those beliefs that are driving you come from? If you’re tired of feeling resentful, overwhelmed, stuck, exhausted or pissed off you’re in the right place. Shoulding all over yourself is a real thing, but it doesn’t have to be in the driver’s seat.

I’m your host Jen Sherwood, and I spent waaaaay too many years trying to prove that I was good enough and worrying what other people thought while avoiding conflict at all costs. Today, I don’t give a should – well not as many anyway and neither should you. I’m talking to women like you who figured out how to stop shoulding and start LIVING.

I am so happy to introduce you to my guest, Gina Wong. Gina was born and raised in the San Francisco Bay Area. Both of us are the same in that she left though and went to New York City for a few years before coming back to California. She went to school for advertising and marketing and had a 13-year career in that space, but she didn't really find her purpose.

Instead, she ended up finding her purpose as a Living Benefit Specialists helping to ensure families have living benefits in their plans so that if a critical injury and illness or disability, or death were to occur, their family doesn't wipe out their savings or have to go open a GoFundMe page and struggle financially.

Gina, welcome - I'm so happy to share your story.


I mean, Jennifer, I just love your energy.


Oh, that's so sweet, and I'm thrilled to have you here.

You all watching should know that Gina and I do know each other. I've heard some of her story before, and actually, before we hit record today, I was like, hold on, stop talking - we have to get this on tape.

How old am I? You know what I mean? But, like, we have to get this in the interview for other people to hear. So I literally like the thing in the films where we were like, cut.

Okay, let's jump in! Gina, can you tell us what it was like when you were living under the shoulds?


Oh, my goodness.

Well, first of all, I love the title Stop Shoulding All Over Yourself because I was like, that is genius, because number one, I feel like a lot of us shit on ourselves, you know, we're so hard on ourselves. And oh, how cannot, not this, but then I love the shoulder because how many people in life? Have you heard those expectations from our family or, you know, our grandparents or parents and whatnot? Or when we compare ourselves to others? I should like this person, so I'm going to tell you, so being raised in an Asian American family. Well, I mean, my parents are from Asia, so I'm the first generation there. They were really hard, they had a lot of expectations, and I don't blame them. They came from Hong Kong, so my mom, you know, just to kind of give you a background of my mom's please do? Yeah, he was raised in China - she had a really hard life.

You know, she had about seven or eight siblings. Um, and you know, as you know, back then in China, you could only have one son. My grandma was popping all these babies out, and she went against the government's, and I'm not killing any of my babies. You know, because they would literally throw the baby off the bridge, you know, and drown the baby because he only had one.

Jennifer: As a mother, but even not as a mother as a human being, to hear that and think about it and let yourself sit in the humanity of that.

How horrible, and your grandma's kind of a rebellious rockstar.


I love her.

Yeah, she was amazing, and so my mom had one brother, and the rest were girls. What's funny is my grandma had the boy second to the last kid. She was hoping for a boy, you know, because being a boy in Chinese culture like that carries the name, so I think my grandpa was like, well, let's keep it going.

So when they had the boy, they had one more girl, which is my youngest, and she's, she's like a mom to me too. Going back to my mom's story, when my grandparents decided to move to Hong Kong, the only person that didn't want to move with them was my great-grandmother. And she's like, if you think my grandma was a relevant, rebellious, rebellious person, my great grandma was even more so.

My grandma assigned my mom to stay with my great-grandmother, so it was just them too, while everyone else moved to Hong Kong. I didn't tell you the story, so you're just like, oh my gosh, and like, my mom, she ended up staying with my great-grandmother. She was always talking back to the police. There was a time when she actually went to jail. My mom had to make food for my grandma and would walk miles from where they lived to the jail to deliver food to my great-grandmother.

Jennifer: Oh, it was your great-grandmother that was talking back? Oh, I thought it was her mom; oh, my gosh, and then your mom went to deliver food.


I think, like 10 - around 10 years old, and so then finally, my great-grandmother said, okay, fine, we'll move to Hong Kong, so she joined the rest of the family.

Growing up, my mom just had a really hard life, you know, and as she got older, she was like, you know, I really want to give my future offspring the best opportunity. I think she was in her mid-20s, and she had already started dating my dad, which is a whole other story, but they started dating.

My mom was a nurse at the time, so she was like, you know what, I want to move to America. My dad said no, and she said, okay, I'll just go there temporarily, so she moved here. She didn't get to do nursing in America because it's a different education.

She worked at a restaurant; she worked as a tailor, and she also worked at cleaners. She didn't speak a lick of English, so for her to come all the way here with nothing to start from scratch, and then as the years went by, she ended up bringing my habit, convincing my dad to come here, you know.

With that said, she does have the right to have these expectations because she worked so hard to build this life and his empire for her and her kids and even generations to come. The thing is, having those expectations on like little kids, you know like you should do this, you should do that.

Plus, being Asian, you know, there's obviously that whole tiger mom thing, right? My mom wasn't a tiger mom; in the fact you have to get straight A's like I got; I got C's. I've gotten a few days in my truth-telling time here, right, Gina? I think the most consistent ad I've ever got was in dance, and she would say to me, why do you keep getting A's in dance? Are you going to be a Broadway dancer?

I was like, I don't know, I might be, but, you know, she would always say, you know, make sure you know when I was older. Make sure you go to school, you know, and then you go to the career of that education that you got, and so I was in advertising and marketing work for that field. You should work there until you retire.

Jennifer: Stay there until you die, Gina.

Get the job and never leave.


At first, I would do that, right, but working in advertising, there's a very big door that keeps swinging. You know, the turnover is very high, so at work, I mean, I've worked for a company for five years.

That was even a long time because I leave every two years because they want that promotion to the next level. I just didn't feel filled, so I do want to

Jennifer: Okay, so wait, let me back you up a step, though.

You've got this mom who has these big expectations, and Gina and I were joking before we got on here when she started talking about her mom. I said, Oh yeah, so your mom moves over because she really wants this other life for you guys.

Then it's basically, and here's how you're going to do it. So as your mom is kind of giving you this prescriptive life, and you're deciding you're not going to do it. Was there a time where you did what she said to do? Or were you always rebellious?


My rebelliousness did not come out until later, so being the youngest, my sister is seven years older than me. Like right when she had a chance to move to LA, she moved like she just upped and moved to LA for the film.

Being the youngest, and the fact that my parents were older, you know, my mom had me when she was, like, 43. They owned a business, and they own a dry cleaners and a laundromat. Being the youngest, they felt obligated to stay. I didn't go away for college. My mom wanted me to stay locally. Oh, why don't you stay locally so that you can help Mom and Dad with the business? And even and I was always like, okay, yes. I was always told to be a good child, right? You know, and I was like, the favorite, my sister knows this - I'm the favorite.

It was always, you know, putting my family and the business first. I didn't choose a school far away because of that. But also, even after high school, you know, I had a regular job. I worked 30 hours a week and had a full-time schedule for school. Then on my extra time, or on my Saturdays, I would go to my mum and dad's laundromat and dry cleaners and help them out.


How do you think that was? How not? What do you think that was like for you? Were you looking at your sister in Southern California and sort of wishing you could go do something else? Or will you just head down following the rules?


I would just stamp on the rules, and I think I didn't feel like I had to help them, but I felt, gosh, my parents are older, like, yeah, I can go out and party and stuff like that on a Saturday afternoon, but it just didn't feel right to me.

I think because of the way my mom raised me, you know, I'm always at the store working like I've been working, like, don't have a mom arrested. We have been working since we were six years old, and we went from, like, untangling the hangers all the way to ironing sheets and shirts and stuff like that.

Knowing how hard my mom worked, I wanted to go there on my off date to help her because I know she's older. She's already working so hard, so as my dad, why can't I just, you know, sacrifice my Saturdays just to help them?


Yeah, that's a lot of responsibility.

For somebody who was as we're talking, I mean, I realize you're sort of college or out of college at this point, but it's still a lot of responsibility to carry.



Even when my dad was sick, so when my dad was sick with stage four lung cancer, and this was 2006. Quickly, I just took the reins, and I was like, okay, so here's, here's the game plan, dad, and my dad never cried, never complained. Other than, like, I don't want to eat that, you know, like he cried when the doctor told him finally, like a year later, that there is no other treatment that we can do to save your life.

Even at that time, when my dad was sick, you know, I put a lot of stuff on my shoulders. I was like, okay, I'm the youngest one. I'm the only daughter here to take care of my parents, okay, I'm going to care, give my dad, and I was like, nobody's going to care for my dad better than I can. I can do it myself. My work allowed me to work from home, and then my sister was like, hey, I'll come up to the Bay Area, and I'll help you.

We were kind of going back and forth, and my sister would come up for weeks at a time and then go back and then kind of relieved because caregiving is a lot of work. It's a lot of work. It's mentally, emotionally, and physically draining all of that.

It's like, and I even talked to people that are currently doing that for their daughter and their mom, or their daughter and their wife. And he's like, you know, I'm officially their caregiver. You know, I get paid as their caregiver, but it's a lot, you know. So, with that, I even help with that. And of course, I would never, you know, complain about right? My parents, you know, and, but it was a lot on my shoulders. I feel like growing up, you have to be with your parents, you have to take care of your parents you have to and which I have no, you know, nothing against, but I think that it's also good to just branch out and ask for that help.

Jennifer: Yeah, yeah. I'm curious. Can I ask you a question? That's going to seem a little bit unrelated, but I just want to orient myself to a time in your life when you were caring for your dad. Was that before or after you went to New York?


Oh, actually, that was before because I was never okay, but that's funny that you say that because a year after my dad passed away, I was thinking to myself, gosh, if I were to die today, what am I happy of where my life has gone?


Oh, what a profound question.


I was like; I have not done anything that I don't even dream of. It wasn't just because you were following that path. Like, here's the expectations, and here's the next thing.

I was never told to dream. It was never, you know, inspired to drink either. Whereas, like, now we have all these motivational speakers. We got Gary Vee, Tony Robbins, you know, Mel Robbins - we were just never inspired to dream maybe, you know, but I was like, gosh, like, if I were to die today, like would I be what I like, fulfilled. It's almost like, Okay, well, my sister is about to move away; maybe it's my time. So I visited New York once. I said, Mom, I'm gonna move to New York.


I can't even imagine that conversation.


My mom was like your dad just died.

What do you mean, you moved to New York? I'm like, Mom, I know - you don't understand it now, but if I don't do this for me, I'm gonna regret it, and I don't want you. I told her that, and she's like, oh, I don't understand this. Why can't you just move to LA near your sister that way? You can drive five, you know, five hours at Mike. I know you want me to move to LA again. She wants to help me plan. I was like, no, I'm gonna move to LA.

Jennifer: Can I just call that what that is? She's trying to control helping you plan. It seems like the end result is I want to control what you're doing.



And, you know, and he comes from, wherever she got it from?

Jennifer: Yes, no criticism; just let's look at it.


I was just like, no, I'm gonna move to New York, and she's like, oh, my goodness, I can't, you know, and I was the one that was helping a lot in the business. Yeah, like, stuck in a hard place and was like, do I stay and help my mom because she's the only one that's here? She had a laundromat and dry cleaners. Or do I go and live? You know, in New York City, where I just want to just try, I've never lived alone. I've never been so independent before. I just need to do it. Because if I don't do that, I'm always going to just be here.

Jennifer: I think your story can resonate with people, maybe not under the same circumstances, but that struggle between do I do what I want to do for myself? Or do I do it for others? That is a really hard place to be.

What do you think it was that helped you decide to go and live a dream? Was it the fact that you had lost your dad and you were thinking, I don't know what you were thinking actually, like? Did you think there's more to life?


I felt like there was more to life than just going off of what someone else is trying to, you know, plan for you. Yeah. Because I kept doing, you know, my family was everything to me. And, yeah, it was like, I need to do something for myself. You know, I can't just do everything my mom tells me to do because, I mean, knock on wood when my mom's not here, then who am I supposed to turn to? Yeah, what to do?


That's a really good point.

If you've got someone paving the way for you or planning the way for you, then yeah, you would be completely lost.


That's why I decided to move, and my mom was really upset.

She was like, oh, my goodness, but, you know, when I moved to New York, so before I moved to New York, my mom would always call me. Like, it's not even. Hello, how are you doing? It's, hey, go to the bank. Do this. Hey, did you do this? When I moved to New York, Jennifer. Hi. Did you eat? Changed our relationship entirely.

When my dad was sick, my mom had to because she's always had a driver's license, but she was always dependent on my mom or my dad. My dad was sick, and she had to be okay; I needed to be independent. I need to drive on my own. I can't always have Gina take me because she has a job.

I used to take her to work, then go to San Francisco to work. oh, my gosh, pick her up, and so she was like, okay, it's a lot for you. Let me be independent, so when I moved to New York, she had no choice but to depend on herself.

She grew up on her own and I grew up on my own in New York City, and we went whenever we talked, it was very quality conversation versus, hey, do this, hey, do that, and so I think she realized, you know what, this is a really great move for Gina to move to New York, you know, and so, and I told her, I was like, hey, I'm only gonna move for two to three years. She's like, okay, two years, I was like, no, two to three years. I was like, no, Mom, two to three, and she's like, what do you say to a three-year-old one? If I don't come back in two years, you're gonna get mad at me, and I'm gonna give you a range.

I ended up coming back after like two and a half years because I just could not stand for all four seasons of the year, okay, the snow.When it's hot, like humid weather in New York City is no joke, and there's only so much clothing that you can take off before you can get arrested.


For those of you watching who don't know, Gina and I live in the San Francisco Bay area, where we are fortunate to live in, the best climate; we have very, very mild winters, lovely summers, and pretty much nothing in between.

So you come back from New York, you're back home, but before I go there, I really want to point out, particularly for women who are watching this, so many women don't want to make a choice for themselves because they feel like it's selfish somehow. By Gina going and allowing herself to grow, it benefited her and her mother; this is the thing. I can't say it enough that oftentimes when we choose ourselves, it ripples out to the people around us, and I really want to emphasize this. Okay, so you're back home, but you're not in advertising anymore.


Oh, no, I still am.

I moved, and I think that was the second to the last job because this was back in 2011. I moved back here.


Okay, so how did you switch because there was a career switch?


I moved back here, I worked for XO group,and it's like wedding planning and then I moved on to a different company, which was local and Palo Alto, which housed Hulu, ZZ dock. I worked there for, I think, almost five years. I don't know, for some reason, every current company that I worked for, there was always this five-year expiration date, like, oh, interesting, really weird. I don't know if it's like, in my past relationships - seven was seven years as always. Anyways, I think it was when I went to Tony Robbin's seminar. In 2007, it was called "Unleash the Power Within. I was like, Oh, I'll go to this because it'll help me with my business.

Then going to Tony Robbins, Unleash the Power Within. I was like, knocking down all these barriers that I had from just growing up, you know, I'm not enough. I'm not good at, like, I'm not smart enough. I'm not this and that, like, all these limited beliefs because of X, Y, and Z, or I, you know, I don't have the background or whatnot.

Tony Robbin's seminar really helped me through those limiting beliefs. I signed up for his bigger self-motivation or self-development program, which is called Date with Destiny. They have one in Florida, but I decided I'm gonna go to the one in Australia.

I went up there for, like, a whole week, and from there, I met so many amazing people. It's hard not to be in with people there because everyone's hugging and, you know, yes, you can do it with those limited beliefs. My flatmates in Cannes, Australia, you know, we were, you know, had discussions in between, like the days of this program. And so I said, you know what, I think I'm gonna quit my job because she told me, you know, Gina, you have your hands in so many different things like you do your regular job and advertising.

You have this group called women supporting women in San Francisco; you do your wedding business, but every time you talk about your advertising business, it's like, or your advertising career is like, right? Right. You know, whereas when you're talking about your other things, your face lights up. She's like, you know, you can live at 10, but you decide to live at 2.

Jennifer: Oh, that is powerful.

You can live in a 10, but you're deciding to live in a two, and this is where when women think they don't have choices; think of Gina, and this moment; we always have choices.

You were choosing to live in a 2.


I was choosing a limit because I wanted that security check, you know, and everyone. I mean, of course, it's not that you want to be rigid because it's what money does for you; it helps you that security.

The next thing I was like, I'm going to quit my job, and she's like, oh, perfect, what's the date? Are you gonna quit? I was like, huh, and I had to think about that.

So we're in the car driving to this progress seminar, and I'm thinking, okay, it's June, and she's like, don't think about just giving me a date right now because I'm putting my calendar, and I'm gonna be accountable to you to this date. Oh, like? Sure. October 31. That's Halloween. Like, that's great!

Jennifer: Why not just pick that date it really didn't matter - it was just about having the goal and working toward it.


I literally end up putting a week before Labor Day - back to, you know, regular reality, like my regular job, and I'm sitting there at my desk, and I'm like, you know, doing my daily duties and I'm like, I can't do this anymore.

Jennifer: Once you see it, right, it's really hard to stay there.


I realized, like, okay, I'm just going to put my head down and just keep doing my work and I quit. I didn't have a plan, Jennifer; like, in every job that I've left, I've never told my mom because I knew that she would stress out and not sleep. I quit and I was like, okay, well, at least I have enough savings to kind of get me through, right? Then I remember I was talking to a friend that was also in the program before. He had told me about, you know, what he does, and it was just like, oh, well, like, how come? It's called living benefits, and it's what I do now, and he's like, yeah, you can access your death benefit while living, and I was like, wait, my dad and mom never had that.

Financially, we suffered as a family because we lost my dad's income, and then when mom, it's not like, she can go get another job. I was helping as much as I could, and my sister was as well, but having living benefits, I was like, how come nobody knows about this?

My mom's not even heard about it, and so that's how I got into this shift of, I don't want to be advertising, I couldn't quit. I was like; there has to be something else out there. I feel like I was given the gift, you know, and it's not that I'm super religious, you know; I believe that there's a higher power. I feel like my gift, or the gift that was given to me was the gift of connection. You know, I love, like, within five minutes of meeting someone, even at a bar, or like a networking event, or just at a park, you know, naturally, I have this gift of drawing people in having a really genuine conversation, and then them trusting oh my god, can I have her number? Can we?

I felt like because I have that gift, I have this gift of connection. And I can educate people on living benefits where I'm not like a pushy salesperson, like right? So I want someone to help me solve a problem, ao that's how I basically run my business. I'm here to give you a solution in case life happens.

That's how I shifted. I was like, and I have not turned back. I actually had someone reach out to me on LinkedIn; hey, I saw your, you know, your career and account managing, you know, we're looking for someone to fill a physician, I'm looking at the job description. I was like, I'd like to be an entrepreneur.

Jennifer: What I love about this is how you chose yourself at each step of the way and without a safety net at this point. Then you found this work that you're passionate about - it's clear because what that woman said about the way you kind of laugh about your old job, you are lighting up as you talk about this.

You can see it's like my family went through this. I don't want another family to go through this, and so where you said you didn't find your purpose in advertising, but you found your purpose here. I can totally see it.

So, Gina, I want to give you a few minutes to just share with us. By the way, you guys Gina's socials are so fun to follow, so I can imagine people are interested in following you in general and probably learning more about what you do. Why don't you share how people can get in touch with you?


My Instagram is @livinglifewithgina, and my Facebook is Gina LivingLife Wong.


I can double-check well we'll put all the information up when this is posted so people can grab it.

I'll double-check your Facebook handle.


I live life, you just have to live life to the fullest, and I feel like a lot of people are so scared of doing that number one because of a change, right? They want to stick with their routine, and any type of change scares them.

Well, what I've learned is, if you continue to say I can't, I can't, I can't, you're just basically limiting yourself. You're basically pushing yourself down and saying, Oh, I can't write. changing your mindset. Even if you don't think you can, just say it out loud. Sing it out loud. Sing it to your mirror, look at yourself in the eyes, and just say it because when you continue to say it, and I do it as a daily affirmation.

When you start seeing it, you start believing it, and then you start feeling it.

Jennifer: Yeah, I love this.

I love that little tip, and so we were talking before we got on here that if somebody wanted to come and talk to you, they could do that, right?


Yeah, so reach out to me because I know a lot of people they're like; I don't know what living benefits even are. The company I work with, broker for ,You can access up to $1.5 million in case of a heart attack and stroke, cancer, or a disability; how many times do people have life insurance when they have to die? Which is super important, right, Jennifer? Yes, the thing is, from now, until that, something always happens in between yes.

For my dad, it was stage four lung cancer, and I'm part of the Relay for Life in Greater San Jose chapter, which I love because, you know, we're helping, you know, donate or raise money for Relay for Life, because they do have programs that help people that are going through cancer and the families too. But you know, having that, that peace of mind, you know, when I work with weddings, I give peace of mind to the couple, hey, by the time your wedding day, you don't have to worry about a dang thing, because I'm going to take the reigns of your wedding day. Usually, after the wedding, couples are like, oh my gosh, I'm so glad I hired you because I didn't have to worry about anything. When I saw this opportunity to become a Living Benefits Specialist - I saw it as I'm giving people peace of mind.

I can literally say, don't worry about it, we're gonna give you a check, and being able to give, you know, what, you got a $100,000 check because of a cancer diagnosis. Do whatever you want with the money. We're also going to have our bills, even if we can't work due to an illness or disability. Pay your bills, use it for treatment that's not covered under medical insurance.

Like you guys, if you think that medical insurance is covering everything, again, make sure you contact me. I can just assess what you have, and consultations are free, but at least you know your options, you know, know what your opportunity is because before, you don't have the opportunity to get living benefits.



I just want to say I love the way you've described this - this 800,000 is the peace of mind. Alright, my friend, we're going to wrap up here - what is your website? Is that your website? How could people schedule the consultation?


Yeah, so you can go to Living Life with Gina on Facebook or Living Benefits with Gina.

Jennifer: Gina, this has been so delightful!

Number one and number two, I learned more about you today than I knew before. And I just love it. So thank you so much for being a guest today. Thank you for sharing your story - I have no doubt people are inspired by this, and we'll come and find you.

Seriously you guys, follow her even if right now you're like, I don't need to talk about this. She has a lot of really, really great information. She's very educational, so go follow Gina, and thank you so much for being here.


Thank you, Jennifer, for having me.

Jennifer: My pleasure.

Alright, friends - join us next time for another episode of I Don't Give A Should with Jennifer Sherwood.

3 simple steps laid out in 3 bite-sized videos to go from overwhelm to ease (even if you think it's not possible!)



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