What would you do if you weren't afraid? with Jennifer Lien

Jennifer Lien has been a marketer in tech for the past fifteen years. She was born in the United States, raised in Taiwan, and has moved across the Pacific multiple times to pursue new and exciting opportunities. 

In this episode, Trinity and Jennifer discuss embracing  uncertainty both in cultures and careers. Listen as she shares her insights on how to approach decision making, empowering you with takeaways to reach your goals. 

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The hosts:
Trinity Nguyen
Christian Kletzl

In this episode, you’ll learn:

  • The importance of going outside your comfort zone
  • Things to consider when making a big decision
  • How to not be afraid in  pursuit of your goals 

What to listen for:

  • [01:30] Where does the inspiration from travel come from?
  • [03:08] Why move to another country? 
  • [05:43] Jennifer’s advice for taking any big  leap
  • [09:49] Is there an ideal timeline when making decisions?
  • [11:19] When does it make sense to leave the corporate world?
  • [13:31] Understanding the impact of life coaching 
  • [17:07] Jennifer’s words of encouragement
  • [18:08] The breakdown with Trinity and Christian 

Check out Jennifer's blog post: "Transitions—plan yours and make it happen."

Reference Links:
Guest headshot

Besides being a tech marketer, Jennifer Lien is also a trained life-coach, and especially inspired to support introverts, people going through transitional life stages and women as they balance between career and family. Outside of work, Jennifer enjoys discovering delicious exotic foods, watching musicals, swing dancing, and spending quality time with her husband and their two beautiful kids.

Read Transcript

Jennifer: I would say the hardest bit also about leaving or letting go is having the courage or the confidence, rather, to know that I can go back if I want to.

Trinity: Welcome to The First 100 Days, a show for revenue practitioners by revenue practitioners, giving you unscripted access and tips to help you navigate any new transition or initiative in life and at work. I'm your host, Trinity Nguyen from User Gems. Jennifer Lien has been a marketer in tech for the past 15 years.

Most recently, she was at Facebook as Head of Enterprise Marketing for Asia Pacific region. Jen was born in Taiwan, raised in San Francisco, Bay area, moved to Chicago for grad school, then moved to Singapore, back to Taiwan. So, as you can see, Jen has moved across multiple cities, across the Pacific ocean multiple times, when this new, exciting opportunity, whether it's for work, or simply because she's curious for new life experience. In our conversation, we talk about how she's been able to embrace the uncertainty and have a lot of practical insights to help you do the same. Have a listen.

Jennifer: I feel like I just have this itch to travel and to be in different places. And this really does value around exploration and just trying something new. For me, the Bay area was where my first real job was and its such a comfortable place. My family's around, my best friends are around. You get nice tech jobs, like hang out with cool and smart people.

That's where the innovation is happening. But for me, there was always something that felt like, what's missing? Like it's almost too comfortable. For me, it was important to go outside of my comfort zone and do something different. I didn't want to look back and regret not trying it out. And also it was really, what's there to lose?

So, for me, that was the driver, leaving the Bay area in the first place. And I think, as I think about all the different moves, it's never about leaving somewhere bad. It's always about going to somewhere exciting. So there's either a really exciting opportunity job-wise or a really exciting place that I've always wanted to live in – Singapore was one – or it was just the right time. Right now, in the midst of COVID, for me, really reprioritizing what's important to me, and that's being closer to family and home right now. So, I think there's always something that kind of anchors me, to drive me to move. Do you think 

Trinity: you have this edge to travel around because of how you were brought up, being born in Taiwan and then grew up in the Bay area and so on and so forth?

I don't 

Jennifer: know. I mean, I didn't move around a whole lot when I was young, but somehow this idea of just being in a place for the rest of my life, even now that scares me. If you ask me, are you going to be in city X for the rest of your life? I cannot answer that because that scares me. It's like I have a commitment phobia or something.

I really don't. I really don't. But it's just wanting to, wanting, wanting to be somewhere new, wanting to not be locked down for no good reason. If there is something, if there is an opportunity to go somewhere, to try something new, to learn a new set of skills or experiences, I think the learning bit is huge for me. That was the huge driver behind leaving the Bay area. It's like, well, I've only worked in the states, but as an Asian American, to me, I always feel there's a sense of calling, if you will. I want to go to Asia and try it out. And I want to learn about the different culture and just learn a different set of skills and experiences and that was important to me. 

Trinity: I can totally relate, being an international person, myself, leaving Vietnam, coming to the US, and then moved all over the place so far. So, I can totally relate to what you just said, but was there any concerns or hesitation that crossed your mind when you decided to move? 

Jennifer: I think sometimes when people feel like, well, you know, I bought a place or I have kids or I'm married and therefore I cannot move.

I think, I personally don't buy that, but I think it's what everyone is comfortable with as well. For me, I'm like, well, what's the worst thing that can happen? And usually, it's not that bad. And then the upside is so much more. It's, well, if it doesn't work out, we'll just come back. And I also...just exposure to different cultures and diversity is something that I want my kids to be able to experience as well. 

Trinity: Right. You have kids now so that usually would stop a lot of people from thinking about moving to another city, let alone moving to another country, but you guys made it happen anyway.

So, a lot more companies are offering this hybrid or remote working option which gets a lot of folks to start thinking about working abroad or moving to a different city. Since you've done this multiple times now with family, with houses and everything, what are some tips you would give to anyone as they evaluate if they should do it, and what are the things they should keep in mind to make sure that the transition goes as smoothly as possible?

Jennifer: I mean, I think before you even make that decision to move is to really think about – and take a step back – and think about what it is that you want in life and how will this move play a role in that? Or where does, like, job and career, what role does that play in your overall ambition or aspiration for you in life before we even talk about considering moving abroad or working abroad. I think it's really important to first take a step back and validate that and understand there will be trade offs, right? Not every company, not every industry is as forward-thinking or, like, it may be logistically impossible to allow you to work from a different place, a different city, different country, whatever it is – so there will be trade-offs. And there will be trade-offs of perhaps being far away from home and more practically, there may be trade offs, as you think about like tax implication or even salary implications. I think those are all the things that I would really think about before making the move.

And then once you've decided, like, Hey, you know, it is, it is what I want to do, then I would say really talk to people that have done it. So talk to people that have moved to this country that's even either from there or not from there, talk to people, understand what they like, what they don't like.

Don't just have a rosy image of what to expect, but get the good, bad, and the ugly. Really have a good perspective before going in so you can make a really informed choice about whether or not you want to do it. It's also a good way to just like network as well, so when you do at go out there, you already have a support network.

The other thing I would say is give a timeline. My husband and I decided, okay, we were going to put a timeline of two years, and we actually marked our calendar for us to have a talk in two years to say do we still want to do this? I think the older you get, the more life builds on, I don't know what the word is, momentum or inertia.

Sometimes you forget and you just carry on with it or other things take precedence. But I think it's important to take that pause and really think about like, Okay, well, it's been a year, it's been two years. Do we still want to do this? If not, then where do we want to go next? Or if yes, this is what we really like, well, you know, then what's next here? So I think it's important to have those check-in milestones. Then the other tip I would give is really making sure that your family, people you're moving with, are all on board with this. Like I said, I'm very lucky to have a very supportive husband and partner.

I cannot stress enough how important it is to make sure that you have the buy-in from your partner, from your support network, because the move is not just you, it's it's you guys doing this move together. And the final, final tip I would give is really around being open-minded. Being open-minded and being humble, once you make it out there, to connect with people, not just... I think a lot of us, it's easy to connect with expats when you move to a new culture because that's comfort. But I think it's also important to make sure you connect with, really, the locals, because that's how you're going to learn and that's how you're going to make the most out of your experience.

Trinity: So that's a lot of things to keep in mind. And it's true, moving to another country, especially with a family, is a huge transition and people usually spend a lot of time planning for it and thinking about it. But on the flip end of things, you could go into like analysis paralysis where you over-planning or you're overthinking and ended up not taking that leap of faith in this case.

Is there a right amount of time that you would recommend for folks to prepare for this kind of decision? Is it a sweet spot? Is it three months, a year, two years? I mean, it's kind of a big question or also a very subjective question, but I'm curious from your point of view. Yeah. 

Jennifer: It's hard to put a timeline around it.

I would say it's whatever that's right for you. Some people are very spontaneous, you know, they can decide and pack up their bags and move within three months. Some people are more comfortable if things are a bit more planned out, only if they have lined up a job, then will they move. So, I am, kind of, a long-term planner.

So, I have in my head, like I said, three years before moving to Singapore, I already knew that was my plan down the road and I was going to carry through with it, with or without a job lined up. So I think really, it depends on the comfort level and also just like the life stage that you're in – you're single, married, have kids, no kids.

I think all of those will play a role. And of course, the other thing is, whether or not you already have the opportunity, but the advice I will always give is if it's something that you're interested in, and the opportunity presents itself, like, jump on it. And the question that I have been starting to ask myself more is what would you do if you weren't afraid?


Trinity: a great question. It's going to be the motto for this episode. What would you do if you weren't afraid? I love it. So, speaking about taking a big leap of faith, you recently took a big leap of faith, in a different sense. You left a very comfortable job, basically leaving the corporate world. Can you share what's the motivation behind that major transition?

Jennifer: I had been with my previous company now for close to seven years. So it's really quite a while. And I've learned so much. It's probably the job where I grew the most in. It was also the job that brought me to Singapore. Very grateful for the job. Really grew up with the job as well, and I think it just is the time to try something different.

Like I said, for me, it really is, being in Taiwan for now, spending more time with family here, it's also taking a break to then think about what's next. And going back to that line, what would you do if you weren't afraid? That's, actually, one of the poster slogans that we always have around work and that always inspires me.

So it's so hard to leave a job that's so comfortable and that you're so used to, and that you've been in for so long. Once you take the leap, then you realize, oh my gosh, there's so much more out there and that's actually quite liberating. And for me, I would say the hardest bit, also, about leaving or letting go, is having the courage or the confidence, rather, to know that I can go back if I want to – I can go back to the corporate job or, you know, I have a choice. I think you, kind of, lose confidence, too. You're like, well, if I walk away from this job, am I going to find something as good? Or am I leaving something great behind on the table? Am I going to regret it and forget to really think about looking ahead rather than backwards.

 I'm just like excited to see what's to come.

Jennifer: And something that I also feel very passionate about right now is coaching, in the realm of life coaching. And it's something that I've been doing on the side for the last year or 


Trinity: Can you tell me a little bit more about the life coaching? Like what is the purpose behind the life coaching?

I'm not very familiar with, I know about career coaching, but we'd love to learn more. So, coaching 

Jennifer: really is to help people live the more, fulfill the best version of themselves, if you will. And let's say that you come to me and say, Hey, I really want to declutter my house that's the topic and that's your goal.

If you went to an advisor or a mentor or someone who's an expert, you might be going to the Mari Kondos, and she'll be like, here's the best way to clean up your house, and these are the principles, like this is the things you can do. And you're like, great. If you go to, let's say, a therapist, a therapist might come and tell you let's go back to your childhood and talk about all the reasons why it's been a blocker for you to declutter your house.

You know, what might've been the challenges. And then when you go to a coach, the coach will ask you questions and help you like reconnect decluttering to things you value. What's possible when you think about what does the living space mean to you? What values are you honoring if you are living in a beautiful place, for example, or we may talk about putting on different perspectives.

Maybe you are like, I can't get myself moving because I just don't have what it takes. I'm like, well, let's take a look at it from a different perspective or it might be that I sense there is some emotions that's tied to this topic and that we need to talk about it and process it until you can move forward.

I love that 

Trinity: you, as the life coach, it sounds like you don't really give an answer or are like prescribing a solution or like being a guru, but more like asking questions. You help the other person come to the answer themselves. And I think that sounds like a much better way for the person to internalize it because they essentially come to the answer instead of hearing you and on the receiving end.

So how do you push your clients to move forward? I 

Jennifer: think it's really by asking questions and getting the client more in touch with themselves, with their values. It's by no means giving advice, actually, because advice that's right for me might not be right for my clients. So it's by asking questions is by staying curious and asking questions and looking out for the things and helping the clients realize for themselves what it is that they want and how they will achieve what it is that they want.

Trinity: The ability to ask questions instead of prescribing answers is such a great skill to have in the workplace. Not just like in the context you're talking about, right, but also in the workplace as the manager, trying to help your team or trying to develop your team. So instead of giving them an answer that you think is right, you ask the right questions to help them and coach them to come to the right answers.

So what do you like most about coaching so far? 

Jennifer: It really connects me and grounds me in my values. I think if you had asked me a year or two ago, I would have not been able to articulate what's important to me in life – what are the values that are really truly important to me. I think once you are more aware of these values, it makes the hard decisions so easy because you just make those decisions.


Trinity: Well, Jen, it's been great. Thank you so much for sharing all your tips. As we wrap up the interview today, can you share some words of encouragement or advice for sales and marketers who are listening to the show? 

Jennifer: It really is a very different time. I feel like this has been said so many times, like in the last year, like with COVID, but it really is a very different time.

And that means so many more opportunities to get in front of your users and your audience. And with all of that, I think it can be a very exciting time, but the thing to keep in mind is not to lose sight of who your audience really is. That's true for a B2B or B2C marketer. I think sometimes right now with things being a little bit more chaotic, things being up in the air, like products, pivoting, and marketing channels changing around, I think sometimes we can get lost in the flashier things or in the things that everyone else is doing or in the chaos in general. But I think, yeah, I always goes back to really just being really focused on who your users are.

Trinity: Christian, what do you think?

Jennifer: It reminded me a little bit of Sinje's episode, and we always talk about the first 100 days. This makes sense, it's the name of the show, but we actually forget about the last 100 days. So it's very interesting to hear what goes through someone's mind when they start to make the decision after a huge life change.

Trinity: And Sinje's Gottwald is one of the episodes in, I believe, season two, where she talked about leaving the corporate world and traveled around the world on a motorbike for three years until COVID hit. So, yeah, there's definitely a lot of similarities between this episode and that one, but I think, also, what's interesting is Jen not only talking about like leaving the corporate world, but also about this moving to different countries. I mean, during these days, people working remotely, everyone wants to work remotely these days. So I think her tips are so practical. Like the list of, here are the things you should consider, all the advice.

I think it just so timely right now. It's all relevant. And I think what's 

Jennifer: interesting was that when she talked about the coaching, how every situation of her clients is different, so she can't just give advice. The best thing she can do is ask the right questions and through that to come to a conclusion.

And I think that's the same for us. Like when we want to make a decision, we just need to ask ourselves the right questions. 

Trinity: Talk about question, my favorite quotes. And I think you've probably heard that from the interview is when she said the question that I have been starting to ask myself more is what would I do if I weren't afraid? Maybe it's a common, popular one, but it still hit home when I listened to it.

Jennifer: I think it's on a 

Trinity: Facebook wall. It's on the Facebook wall. 

Jennifer: Yeah. Oh, absolutely. No, no. The first time I heard it, I think that is such a good question to ask ourselves. 

Trinity: Another one is the revisit your decision every two years. Where she said, when you move to a new country or new place, put a reminder for yourself and your family to revisit. Is it still worth it? Yeah. Like every two years. Once you heard it, it's like, yeah, no brainer, but I think most people don't do that. They just make a decision and then just go forward and never actually evaluate, they should keep doing it or go another route or go back. I think that's so amazing.


Jennifer: No, we live our life and suddenly five years go by. Exactly. I'm thinking about that. Reevaluate what were the reasons you made the change and that's the situation still applies to something else 

Trinity: I'm looking at. And I think that applies to everything. It's not just a move to another country.

It's for every job that you're in, sometimes relationships. I think it's a great episode. Usually, you always end with the last words.

Jennifer: No, I feel like I had the mic drops already sprayed into this conversation. So the mic is already dropped.

Trinity: Are you undergoing a major transition within your organization? Do you have a first 100 days journey to share? If yes, we want to hear from you. Email me@podcastatusergems.com. Thanks for listening. .