How To Build A Rewarding Career Of Your Own [Chills 41 with Jeraldine Phneah]

Jeraldine: My name is Jeraldine. I care about the challenges and aspirations of our generation so I create content around how we can all cope with the high cost of living, build rewarding careers as well as lead more meaningful lives. 

Andrew: So today we’re going to focus on the rewarding careers and meaningful lives part because it’s closely related topics.

Jeraldine: All these three topics are kind of linked. 

Andrew: I first knew about you from your blog, of course, and you’ve been blogging about quite a wide range of topics, but it doesn’t really differ much from these three things that you talked about. 

Jeraldine: Yes, correct. So a lot of people think that you just write about finance, you need to focus specifically on finance alone. But for me, I don’t categorize my topic by the categories itself. My key focus is really about who am I writing for? So for me, I really write for our generation and every topic that is related to them will be things that I will cover. 

Andrew: Okay. So do people write into you, email to you or comment on your blog and ask you questions or advice? What do they ask you? 

Jeraldine: I think that happens pretty often. Not just from email, of course, email is like one of the channels. I do get a lot of LinkedIn messages, Instagram messages, Facebook comments and stuff like that. I think IG (Instagram) DM is particularly popular. 

Andrew: They slide into your DM to ask you a professional question?

Jeraldine: Yes, they ask me professional question. Typically, it depends on the topics that I’m writing about recently, like last year I got tons of finance questions. But this year, there’s slightly a shift towards maybe a little bit more softer topics like: mental health, little bit more on career planning, meaning, finding yourself and stuff like that. I got questions related to that as well. 

Andrew: Off your mind, what are the top three questions, for example, that you receive more often?

Jeraldine: Looking at the past two years, the kind of questions I’ll receive the most often would be like “Should I just leave my job?” That’s something really difficult to answer, especially if you don’t have so much context. They would just give me things like the salary that they want to get and stuff like that, where they’re at now and the struggles they are facing at work.

Because I don’t get the full picture, my role is really more of asking them questions. Diving deeper into what motivates you, what kind of things are important to you in a job and stuff like that. From there, they can discover the answers by themselves. So I try not to be so prescriptive, but more of playing the role as a friend who is asking questions and helping them to use these questions that I’m asking to uncover the answers on their own. That’s the first kind of question that I get. 

Andrew: “Should I leave my job?” That’s the kind of question you get? 

Jeraldine: Yeah, most common question. 

Andrew: Interestingly, you think it’s COVID and people want more job security. But you see all the news articles, headlines saying that people are quitting their jobs and therefore they are asking… you are getting more questions of that nature.

Jeraldine: Correct. I guess I don’t have the concrete answer as to why everybody… no, not everybody, but maybe many people are thinking about leaving their roles. But my guess is probably because of… spending time alone at home gives you a little bit more time to reflect and then when you minus all the other colleagues, the social element of work in a nice office and stuff like that, people really think about the meaning of what they’re doing, the kind of life that they want. This really changes their perspective and helps them to figure out “hey, maybe staying where I am now is not so suitable for me. Perhaps I should try something else” and stuff like that. 

Andrew: Do you have a framework for that? How do you advise someone who ask you that question? 

Jeraldine: Yeah. So when I first received this question, it would be like “Should I leave my job?” and stuff like that. The first question I ask them is “what do you want in your career?”

Andrew: Oh wow. That’s tough. It could be hard. 

Jeraldine: Yeah, because that’s really something that people don’t even think about. How does a career fit into your life? Because people know the conventional route. “Oh, I leave school, I graduate. I get good results. I come and work” and stuff like that. They don’t dig deeper into the second layer: what am I working for? Because everyone works for different reasons. 

Andrew: So… think of the most recent example. You asked a person “what do you want from your career?” What is the answer you got? 

Jeraldine: Yeah, they said that “there’s so… 

Andrew: Money! 

Jeraldine: … many things I want.” 

Andrew: Work life balance.

Jeraldine: “More fun. I don’t like my boss” and stuff like that. So what I try to encourage them to do is that there’s no perfect job in this world. Every job, no matter how much you love it, there will be some gaps of sorts so it would be good to first write down everything that you want, then prioritise what are the key important things to you. Because that not only helps you find a job that you want, it also helps you to stay in the job because you know exactly why you’re here, what are your deal breakers and what keeps you going? 

Andrew: What are the answers you’ve gotten when you ask people what is it that they want from their jobs? 

Jeraldine: People always say very fluffy things like meaning. But what is meaning? Meaning also can mean different things, right? Is it about giving back to society type of meaning or is it that personal fulfillment type of meaning or is it more like learning? Meaning can be defined in different ways so I would try to ask them “what do you mean by meaning?” 

My role is really not to prescribe like “here, you should leave” because at the end of the day, I’m not a career counsellor or I’m not fully aware about all their life circumstances and we’re just talking on DM.

Andrew: You’re like going so deep into this particular person, he’s telling you… he or she is telling you about meaning, this is what I’m looking for in life. Because work is part of life, right? It’s almost like a life coach but you’re not charging… I assume. 

Jeraldine: No, because I’m not certified. I don’t think I’m a professional. What I’ve always been communicating with my audience is that I’m just learning like all of you. I’m passionate about these topics because I think that would make an impact to our lives so I’m here to figure out answers together with you. I’m not the expert in this topic, I’m just a peer who is just sharing what I’ve learned, what has worked for me.

Let’s say I asked you and then you told me “what am I looking for?” and I say “meaning”. Then you probe me further and let’s say I want to have work-life balance and I want my job to feel meaningful and feel that I’m contributing something, how would you carry on this conversation? 

How do you define contribution? Contribution has many layers. Contribute what? Your colleagues’ lives, your company goals or to the society? So probing into different elements to find out what do they really mean and that’s how I actually helped them to figure out the answers on their own. 

Andrew: I’d like to leave an impact on society.

Jeraldine: So what about your current job? (It) doesn’t give you that? 

Andrew: I have to make up a role on the spot. Let’s say I’m doing a marketing role. Okay… “not really, it’s a B2B product. I don’t really see how it helps me play an active role in being a contributor to society. Not just a society, but my community.” Let’s just talk about that.

Jeraldine: You know community is such a broad word, right? Which aspect of community are you looking at? 

Andrew: Let’s just say my neighborhood, but couldn’t I get into, what do you call it… get into community initiatives or charity organizations, for example ? Or religion, for example? Does it have to be part of my job?

Jeraldine: This is the thing I’m trying to get them to figure out. I’ll ask them “what makes you stay?” If they say “oh, I need the money” then of course I will not say leave, quit, and then do a pro bono. I will say “do you think it would be impossible to maybe perhaps stay in your current role since you like so many things? You like your colleagues, you like the pay and everything, but at the same time, carve out your weekends or after working hours to use your skills that you picked up in a corporate job to contribute to maybe the NGO who represents the cause you care about.” 

Yeah. So my role is not to prescribe. It’s really to ask questions because everybody knows what’s best for himself. Here I am just to share knowledge and to facilitate that whole process of self discovery.

Andrew: What we have just done in this mock up scenario is that you’re really getting me to think and explore and really dig deeper into what I really want. If I were to reflect that back onto you, how and why did you get into your current career? 

Jeraldine: Yeah, so for me, I also went through this whole reflective process on my own. When I was in university, I had this idea that I have to do a job that I am passionate about, I feel excited about and stuff like that. This is really something that many people believe in, especially when they are young. They have big lofty dreams and stuff like that. Not saying that it’s wrong, because personally, I think that if you are someone who is doing your job for a passion, you are absolutely lucky. But how many people can do that? 

So that got me thinking: what is the meaning of a job to me? What do I want in a career? I thought about a few things. For me, of course you know, financial independence is a key objective for me. Definitely, compensation plays a part.

The second thing that I care about is of course having future-proof, because I do lots of house visits and stuff like that. A very common scenario that I sometimes come across would be an elderly… not elderly. A middle aged person, maybe two kids, elderly parents to support, but he’s retrenched because they either move overseas, the company moves some of his work overseas and outsources it, or maybe perhaps he has not been able to keep up with the way technology is going and stuff like that. That’s really a situation that I don’t want to be in. So being future-proof is definitely something very critical for me both in terms of… it could be myself with the right skills, as well as aligning myself to the industries which are booming. I’m in cloud computing and all that. I’m working in cloud basically. 

I guess the third thing that really matters to me is of course having the work-life balance. Because for me, work is just a revenue-generating portion in my life and I will give my best when I’m in my job, but I think that my life is really so much more than just my work. It also has people I love like my family, my friends and being able to you know contribute to my generation and helping other people through my content creation process and volunteer work as well. 

Andrew: You just mentioned three criteria. Number one is your financial independence, number two is that it’s future-proof and number three is your work life balance. How does your current role help in all of these three criteria? 

Jeraldine: Actually it really aligns to all of that so I’m super, super happy. But I think… 

Andrew: It’s a sales role at a cloud company?

Jeraldine: It’s a software as a service company. Basically, I think it really aligns with what I’m looking for, my career path as a whole. But of course, if it comes to career, these are the criterias. When it comes to the job, there’s also one more element that I look at it. Because career and a job is different. A job is like a role in a company and a career is like a role, I guess. 

When it comes to a job, I do look at one more thing which is of course the boss. The boss is absolutely critical and it can make or break someone’s working experience.

Andrew: You mentioned a job is a function but career is more like a path and whether it leads you to the future, that’s the future proof part. 

Jeraldine: I’ll explain that. Maybe career is like doctor and then job is like GP (General Practitioner) at X Clinic. 

Andrew: But your whole entire career path is a doctor… what are you going to do and all. 

Jeraldine: That’s how I define it. 

Andrew: That’s how you define it. We all have different definitions, but this is how you carve out your path for yourself, your definitions for yourself. Correct me if I’m wrong, so the financial independence part, it’s really dependent on how much sales you are getting in. That settles the financial independence part. Later we can talk about how do you excel in a sales job.

Number two is your future proof and is that why you’re in a software as a service company? Like you see in the future, we all need this? 

Jeraldine: Yeah, I mean the whole world’s moving towards cloud, right? So that makes sense to position myself in this field.

Andrew: How about work-life balance then? 

Jeraldine: I think that the good thing about… if I wanted to do sales, there’s a lot of options that I can choose from. Every job basically needs sales. But I picked B2B because I was thinking that my customers may not be awake, not awake… at work after 6pm, so nobody will be disturbing me. 

Andrew: Oh, okay it’s B2C, right? Let’s say insurance agents. At 8pm, I’m concerned about my own insurance policies. I might text you. But if B2B, 6pm, pang gang (knock off). I’m not going to text Jeraldine. 

Jeraldine: That was my logic back then when I was choosing (job). 

Andrew: Okay, okay.

Jeraldine: It kind of worked out for me. 

Andrew: It kind of worked out for you and I’m going to guess that the flexibility plays a part in the work-life balance. 

Jeraldine: Yeah, of course. This is why I picked tech because tech companies tend to be more flexible with the way you do things. I would say that in tech, I’d be so lucky to meet leaders who are very progressive. Not so much more of the traditional mindset like come at 9 and leave at 6 kind of thing. Really more… of course, there are people like that but in the past few years, I’ve been very lucky to work with very open-minded bosses who really trust the employees to spend their time in a way that is meaningful and to get the job done basically.

Andrew: Yeah, because someone else in a similar role, meaning tech and sales, might not have work-life balance. But you managed to find a company that gives you that and which is why you mentioned on top of these three criterias, you need to have the boss and actually your colleagues as well. So let’s talk about bosses and colleagues. How do you manage them?

Jeraldine: I think that it’s really important that in any role that you’re doing, you have to work well with your superiors and also your peers. One of the other questions I get from younger people is that “I joined this company and I joined remotely. How do I get to know my colleagues?” 

I think it’s really about being proactive, right? Scheduling dinner, arranging one-to-one zoom chats and just trying to figure out in this organization, who will be the people who are… you’re going to work the closest with, who are able to support your goals and you can support theirs as well, who do you find interesting and who do I learn from, and then map all things out and just be proactive about reaching out to them for lunch, for dinner and stuff like that. 

Andrew: So how do you do that in a remote role? Let’s say I’m in Singapore but I’m working from home. And then I should proactively reach out to all my colleagues or my boss to meet up at least for a meal or something, so I get face time right? Face-to-face with people I’m working with. 

Jeraldine: As much as I love technology, I think nothing really replaces the whole face-to-face element of things.

Andrew: I think that’s truly a concern nowadays, especially with COVID and work from home, remote work. Out of sight, out of mind, right? We’re all worried that the bosses might be thinking “actually, you’re not in office. I don’t really need you for the role.” How would you advise someone who’s worried about something like that?

Jeraldine: What I’m hearing from you is basically their concern is that if they are not seen, they may be forgotten.

Andrew: Your solution was to actually get the face time. But how do you actually execute it? How do you bring it up to your colleagues? Hey, you know, let’s meet up for lunch. 

Jeraldine: Usually, I’ll start off with a Zoom call of sorts and say “hey, I saw that… I just joined! This is what I’ll be doing. I know that I might be working with you quite a bit and supporting you in this few areas as well so let’s just have a catch-up” and then during that video, then you try to build some rapport and… “hey, oh, where you live? Oh, I live near there too”. Or you know… “somewhere there. Oh I used to study in that district. Oh, I’ll be there in the next two weeks” or something like “how about we catch up? Love to see you in person” and all that. 

Andrew: Someone’s got to do it because this just reminds me. There’s this person he’s called Chungsoon. He is part of The Financial Coconut team. He’s in Malaysia, he’s based in Malaysia. We work together over livestream, we host the livestream together. And then over Slack, we’re just saying that “we should really just get online to get to know each other better?” And I said, “sure!” I didn’t follow up after that as well. That is usually what might happen if I talked to a colleague. Let’s say I just joined a company I’m relatively new and I say “hey, I think it would be good to… maybe not a meal, maybe just catch up over Zoom first.” But it’s just… it’s still a bit weird, right? The other person might say sure but didn’t realize you were serious about fixing a call. 

Jeraldine: Just add one more line: “let me send you an invite. What time works for you?” 

Andrew: Okay. 

Jeraldine: One second to solve this problem. 

Andrew: How do you approach it? Because you also don’t want to be too objective-oriented about it, right? Oh, I want to get to know you better and there are certain objectives I want to fulfil, right? Because it’s truly being casual and getting to know someone as a friend. 

Jeraldine: Yeah, I think, I would guess it’s like a date, right? You don’t like… “oh, my objective is to find…

Andrew: Get married, have three kids, lay out the whole plan.

Jeraldine: Because that person may not end up to be the correct person for that. Who knows, you make a good friend in that case? Just keep it open. “Oh, I want to get to know you and stuff like that. I want to know a lil more about your experience working here” and all that and just arrange something.

Andrew: Okay, okay. I’m guessing that if the other party or if a few colleagues are not too willing to have that phone call with you, then probably that might not be a very friendly environment as well. It’s a way of knowing.

Jeraldine: I have a trick to get people to say yes. 

Andrew: Tell us. 

Jeraldine: Basically offer to treat. 

Andrew: This is for face to face.

Jeraldine: Yeah. “Let me buy you”… Because Singaporeans love free food. Me too! I love free food. 

Andrew: You mentioned “where do you stay? Oh, we stay nearby. There’s a good restaurant over there. My treat since I’m new.” For example, let’s say I just joined this company. I want to make this effort. But that’s for Singapore. What if my company is overseas, my colleagues are overseas? 

Jeraldine: Then no choice. You have to do it via Zoom.

Andrew: We can only do it via online meetings. How else do you build relationships with your colleagues? 

Jeraldine: I guess it’s things like giving praises, especially when you have people supporting you and stuff like that. I think sometimes that kind of recognition is very important because we’re all working from home. You don’t really receive that when you get a job done so I think giving regular praises is pretty good. Being able to say that “oh, I really like this”, highlight something that makes their day and stuff like this, another way to build rapport with someone that you’re actually working with as well.

Andrew: You mentioned earlier that you also want to get to know what their objectives are or what’s important to them. How do you ask that question?

Jeraldine: “Hey, you know, you’re in this role, right?” Maybe you are doing a junior sales role right now. “Where do you see yourself in the next two to three years? Why do you join?” It’s through asking questions that you can find out like where they’re heading… or maybe they don’t know where they’re heading so you can guide them on that process also. You can also ask them what they like to do in their free time. “Oh, you play basketball? Hey I want to learn. Let’s organize something.”

Andrew: That’s a more casual question. But the question before that was where do you see yourself in three years as a junior programmer for example.

Jeraldine: If you are talking to someone more junior, you can ask that.

Andrew: “Are you my boss? Don’t so serious lah!” What if my reaction is like that? 

Jeraldine: All these things that I’m sharing with you work for me based on the context that I’m at, but of course cater it to the organization that you are at. I guess usually during the first two weeks, you can get a sense of the culture. I don’t know how to explain how to sense it, but it’s like intuition versus observation. Understand what kind of company it is, what kind of people they hire and then from there, you can tailor your approach to engage them accordingly.

Andrew: Because I understand your intention for asking the question is really to find out what they are looking for and what’s really important to them which is why the question “where do you see yourself in three years?” Let’s say my role is a junior programmer. 

Jeraldine: I guess it’s the way you ask it also. Where do you see yourself in three years…

Andrew: That’s an interview question, that’s why.

Jeraldine: “Hey, just curious. You’d been working here for some time…” so it’s like, how you ease into that question instead of like a checklist. 

Andrew: Which is… we go back to we don’t want to be too objective oriented about it because it’s like a date. You’re trying to get to know someone better. 

Jeraldine: It’s like you meet a girl for the first date. “Excuse me, you got a car? You got a house?

Andrew: Or vice versa. And then you ask all the questions they are looking out for. Could you think of one example though… like someone whose character is a bit more logical? How do you approach this question then? Let’s say you just joined this company. You’re new and you really want to get to know me. I’m role-playing a junior programmer and I am a more logical person. I’m not anti-social, it’s just that I like to do my own things and then you just joined this company. We might need to work together because you’re going to sell something that I program. How do you approach it? 

Jeraldine: I think for logical people or people who are more introverted and stuff like that, the approach is a bit more different, right? It’s not like “yeah, go for drinks!”

Andrew: “It’s okay! Don’t treat me, don’t treat me. I don’t want to leave my house. I’m working from home also and I don’t want to leave home.”

Jeraldine: I think that the approach is a bit different. It’s more like a softer kind of approach. “Can you help me with this? Oh, I am very curious to learn about how this works, can you explain it?” Because when people help you, they get invested.

Andrew: That’s a good point, you brought it up! Which is if someone helps you, we think that we have to help people. But when someone helps you, it makes them feel or think that you’re someone worthy of helping. That’s one.

Jeraldine: Ownership and invested.

Andrew: Yes, and the favour is like on your side. That means in a way, I don’t feel indebted to you. I’ve felt like I’ve helped you this one time and that builds the relationship. 

Jeraldine: I guess what I’m trying to emphasize here is also everybody’s different so it’s not just like taking what has worked for me today and then paste it to your own context. A few things to look out for again… look at your company’s culture. Observe for the first two to three weeks. Just observe people, try to understand them. It helps if you’re a bit familiar with stuff like certain frameworks like DISC… and some people like to use MBTI and stuff like that to… 

Andrew: Profile their personalities. 

Jeraldine: Profile at least a slight understanding of this person and stuff like that and then also catering your approach accordingly because the way you engage like an introvert or extrovert, it would be completely different.

Andrew: An introvert might not be so willing to go out on a meal with you but he or she might be okay doing a Zoom call. Then you do the Zoom call. Don’t force a meetup with a meal with that person.

Jeraldine: Especially if they’re not comfortable. 

Andrew: How do you identify what are the aspects of a company culture that you need to know about? When you say company culture, what do I look out for?

Jeraldine: I guess there’s a few things that you can look at when you’re trying to find out about a company’s culture, right? Glassdoor is one of the things that you can look at. A lot of people say that Glassdoor is not accurate and stuff like that but for me, I feel that there’s no smoke without fire. It’s always good to… it’s been accurate based on my own experience in working and interviewing different companies and stuff like that. 

Second is of course the background of the people, right? If they all study a certain kind of topic or stuff like that, typically people would be of a certain personality. It’s not about judging, but it’s trying to come up with some ideas of what they are… for example, this company hire a lot of SMU students like you, definitely outspoken, polished. I mean, this is my image of a SMU student. 

Andrew: I understand, so you might have this preparation work, but you go in with an open mind because not everybody’s the same. 

Jeraldine: Yes, corrrect. 

Andrew: We talk about culture. It’s just so hard to talk about it in specific terms. What about the culture? 

Jeraldine: Maybe just observing norms, maybe it’s a norm for people to do Zoom lunch that kind of thing, have lunch together. Or maybe it is normal for people to arrange catch-ups and stuff like that. So you want to align yourself with these norms also, Maybe you can push a bit of the boundaries, but largely still align with that.

Andrew: I think one part of the culture is communication styles. So what communication styles have you observed?

Jeraldine: Could you share a little bit more detail?

Andrew: For example, do they hop onto a meeting or they all prefer email or do they gossip at the pantry? I’m trying to quantify this word “culture” a little bit more.

Jeraldine: Okay. Culture is such a broad word, but since you brought up the point of communication styles, it could be simple things like looking at do they prefer Zoom or Google Hangouts? Do they communicate on Slack more or WhatsApp kind of thing? So it’s about the channel and also the way people write emails and stuff like that. You can get a sense that there’s a formal or informal kind of culture. 

Andrew: Is it appropriate to send an email after 6pm, for example. Some culture allows that, some culture will frown upon that so we need to identify all of these. 

Jeraldine: Some culture celebrate that!

Andrew: You know in Gmail you can schedule your email, right? I wrote this email at 5pm but I scheduled it at 9pm. 

Jeraldine: Don’t do 9pm. 9pm is too obvious. You must do like 10.17pm. 

Andrew: Okay, okay. So it looks like more organic, more natural, right? Putting yourself on a line, do you say that you encourage that? 

Jeraldine: If that’s the culture and they celebrate and reward that and you don’t want to sacrifice your hours, that’s one of the ways that you can go about… 

Andrew: Before we move on to the next thing, is there any other thing about culture that we should look out for, off your mind?

Jeraldine: I guess for me, when I think about culture, I think about this quote: the fish rots from the head. So culture to me is something that is defined by the leadership because people will recruit people who are similar to them. Correct? Typically, we like people who are similar to us. We recruit people who are similar to us. So if I really don’t get a good sense of the culture, I would just look on top and I’ll see what are these leaders like and then from there, I will be able to understand how things are shaped within the organization.

Andrew: A fish rots from the head. 

Jeraldine: That’s a quote. I don’t know if it’s really true that a fish rots from the head?

Andrew: We got to fact check that. 

Jeraldine: Yeah, we got to fact check that but it’s a common quote. 

Andrew: So the idea is that it’s from the leadership. So when you go into a company, do you identify the leaders, including the non official leaders, maybe the influencers, gatekeepers? 

Jeraldine: I try to look at the people who are in the company for the longest time and I try to look at the leaders of the companies, people who are managing teams as well just to get a good sense of who they are, what they are like and then from there, I will be able to get a good sense of the culture and what generally the office environment is going to be like. 

Andrew: Sometimes, the person with the title might not be the decision-maker. How do you approach something like that? 

Jeraldine: What do you mean by that? 

Andrew: For example, we talk about influencers or people who have an influence over other people’s opinions but they might not be the CEO or even the directors and people maybe crowd around them, for example. Do you do that? Do you identify people like that? 

Jeraldine: Yeah, of course! Because when we talk about the concept of power, it’s not really about status and rank. Some people have… there are different kinds of powers and some people have… maybe I don’t know the correct word, social power. Perhaps it’ll be good to also look for these people and try and figure out what makes them do well and try to learn from them. 

Andrew: Let’s talk about bosses. We’ve spoken about interacting with our colleagues, but how do you manage your boss? We’ve heard that term, but how do you actually do it? 

Jeraldine: I think that when you’re hired by someone, it’s really your responsibility to find out what makes them tick and how to best work with them. Before I join any company, I try to research the boss. I will ask common friends, common connections and I try to read up on them and stuff like that. I even go to the extent to find their Carousell profile and see their reviews.

Andrew: Carousell! If they are selling things on Carousell, you can see if they are good or they low ball.

Jeraldine: Very interesting story was that before I joined Salesforce, I was being hired by this guy and then I was thinking like oh no, I don’t know much about him. I can’t tell his personality that well. So I went to google him and stuff. Then I found his Carousell’s profile and then the comments were so good and I was thinking like wow, if you just sell a $30 item and he’s so nice, that means this person is nice. Who you are is how you treat people basically. So I took that as a good testimonial and turns out he was really a great guy to work for. 

Andrew: Most people would go on LinkedIn, but you took it a step further. Of course you still checked out LinkedIn, but there’s always Carousell. 

Jeraldine: Because LinkedIn is what people want to show sometimes. But then Carousell is like… I don’t know whether you can fake reviews but I don’t think so. 

Andrew: You don’t really have any incentive to do that unless you are Carousell power seller or something. But it kind of gives you a sense of how that person is like.

Jeraldine: Or you can even check with common friends, stuff like that. But of course, take everything with a pinch of salt as well because sometimes when people say negative things, it could be your own biases. So just take it with a pinch of salt. 

Andrew: Just like a restaurant with bad reviews does not mean that the restaurant is really bad. Some reviews might be fake and you just take it with a pinch of salt. 

Jeraldine: Correct. 

Andrew: So you get to know your boss better. That’s number one, before you join a company. 

Jeraldine: You need to understand someone before you know how to work with them and I’m sure that a good boss will also try to understand you so they know how to adjust their management style to align with you as well. So it’s a mutual process kind of thing. A lot of things would depend on your manager. Your success in the company, things like your happiness level in the company as well so it makes sense to invest a little bit of time to try and learn more about them, learn more about what they are like, learn what they dislike. 

During the interview, I always ask people what defines an A-player to you in a company so that you know what are the things they look out for. And even with that, it doesn’t mean that what they is what is real because some people don’t really understand themselves as well. So you have to validate that and one of the ways could be looking at people they have promoted. People who they… or we can ask certain questions like what was the worst hire you had? That kind of thing just to uncover like what makes them tick and all that, so that you can adjust yourself accordingly to work well with them. 

Andrew: So during the interview process where they ask you “do you have any questions for me?” and that’s where you ask “who do you consider to be an A-player in your company?” That’s one. 

Jeraldine: Maybe not who, but how do you define. What do you define as an A-player in the team.

Andrew: So you know what’s really important for them? 

Jeraldine: Yes. Correct. 

Andrew: Okay. And what’s the second question that you’ve asked? 

Jeraldine: Sometimes I may ask this question, but not all the time: what’s the worst hire you had? 

Andrew: Worst hire. And you’re asking this question… what are you trying to find out from this question?

Jeraldine: To see if we are a fit because if his answers for A-players is someone who works till 3am every day… 

Andrew: Who would say that? Honestly, who would say that… or they might say it in a different way. You got to pick it up. So from your own experience, could you give examples? How do you identify the personality traits of your boss and how do you work with that kind of personality? 

Jeraldine: You mean in the interview?

Andrew: After you’ve joined the company. 

Jeraldine: Oh, after you joined the company. 

Andrew: So there are three parts. I think number one is, before you join, you will check out Carousell and LinkedIn. During the interview, you literally ask them questions because you are given an opportunity to find out more about the person and the company. Now you’ve joined the company. How do you build this relationship further with the boss? 

Jeraldine: So your question is how do I read that person or how do I build that…

Andrew: How do you work with the personality? 

Jeraldine: Let’s say for example you know this person is a little bit more anxious, then you want to make sure that every time they ping you on Slack or Chatter or email and stuff like that, you reply more timely, right?

Sometimes, you don’t get it right straight away. I remember this time I had my new boss from my previous company ask me, “Jeraldine, do you know what’s the difference between email and WhatsApp?” Then my answer is “oh, WhatsApp is on the phone and email is not.” He was like… “No! WhatsApp is like… I want more quicker replies. Email is like you can take your time” and I am like oh okay. I never thought of it this way. So then I would ask that what’s your expected SLA (Service-Level Agreement). 

Andrew: This boss is direct and honest. I mean, some bosses might keep it to themselves or they expect you to know. And then how do you find out then? 

Jeraldine: It takes a lot of observation. It’s going to be very hard for me to tell you. It depends on that person, looking at the characteristics and stuff like that. But you are right to say that. You can also look at the kind of way they interact with other employees. Is there someone they particularly don’t like? Then you can try and figure out what about them they don’t like, and then try to stop embodying… try not to embody those kind of similar traits and behaviours because it really takes a lot observation, because nobody’s going to tell you that I’m a micromanager. 

Andrew: Nobody will admit that. 

Jeraldine: Nobody wants to say that, right?

Andrew: Yes, but you realised that the person is a micromanager.

Jeraldine: Everyone said the same thing. “Oh I’m very approachable, I can take feedback and all that.” How do you tell if it’s real? You watch someone else give them feedback and how they respond to it. You don’t like “oh, okay you are like this.”

Andrew: And then you give your most honest feedback then realise you shouldn’t have done that. 

Jeraldine: This applies to everything in your life. Nobody is what they say, it’s about what they do. Observe more rather than just listen to the words.

Andrew: Okay. So observe what they do and you can observe the way they interact with your other colleagues to find out who they really are as a person.

Jeraldine: Yes, correct. I mean, I’ve made that mistake also, of course. Like someone said he is very open to feedback, he’s not a micromanager and I just took it on face value and stuff like that. After that, I realized that’s not the smartest thing to do because nobody will ever say that they are a micromanager or they say that they can’t take feedback. Maybe they don’t even know that they can’t take feedback.

Andrew: Cause there is the… how do you identify yourself? How do you see yourself versus who you really are? How do you set expectations with your boss? Or boundaries… for example, because you talk about that WhatsApp and email example, and let’s say this boss always WhatsApp you after working hours and you want your work-life balance. How do you have a conversation like that? Sounds difficult. 

Jeraldine: Well, this never happened to me. I’m so lucky that all my bosses are pretty much very appreciative… not appreciative but maybe more… they have clear boundaries. But if there’s someone else in this situation like this, honestly I don’t have that much to advise because I’ve never been in that situation before.

Andrew: But how about other areas where you need to set expectations in terms of KPIs or in terms of your working hours, how much time should I spend in office versus going outside to meet clients? How do you set expectations? 

Jeraldine: I think expectation is typically set by the company culture again. What are the other people doing? If other people are doing something then possibly that would be allowed for you and all that. 

Andrew: I’m also thinking that because you mentioned during the process and before you even work at a company, you should find out as much as possible. If it’s not a right fit, then maybe you shouldn’t have taken the job.

Jeraldine: That’s why the interview process is so critical because a lot of people view interviews as “oh, I’m here to impress someone”, but it’s also a two-way thing. 

Andrew: Dating! Back to dating again. You like me, I must like you also. 

Jeraldine: Correct. So it’s a two-way street and just do your due diligence, do your research because the last thing you want is to waste your time to join a company which you know is not right for you and you have to move out of it and do the difficult explanation and stuff like that.

Andrew: Okay, so get all of these done even before you join based on your own criteria which you mentioned at the start of the interview, whatever you’re looking out for that’s the most important to you and this answer really depends on the individual. What is a rewarding career to you? That’s the first thing you talked about as well. 

Jeraldine: Yeah, I guess when I do my introduction, I always talk about building rewarding careers. That goes back to the first question that we talked about. Rewarding means different things to different people, but I guess that for me, it’s really the way I define it like being paid fairly, having that kind of balance, not too much OT (overtime) or anything and then the learning opportunities for growth. Because when you learn and grow, you are future proof because you are picking up the correct skills and all that. That’s really what I define as a rewarding career. 

But of course, there are other elements to that which other people care about. For example, some people really care about the friendships that they make at work, being able to go for drinks and stuff like that, which to me is like a plus. 

Andrew: How do you really identify these deeper things that you are looking out for? Because it does take quite a bit of work. Of course, in your example, you ask them questions, get them thinking. How is the process like for you? Do you journal? Do you sit down and meditate on it? How do you know what you’re already looking out for? 

Jeraldine: It takes a lot of reflection and self-awareness. I had this friend of mine who was lost. At every job she went to, she would be unhappy about something and I just did this table for her which is actually on my blog. This template is on my blog for everyone to benefit from. What are you must-have, good-to-have, and absolutely-cannot-have? Then you just fill in the blanks, write that down. Distance from your house, how critical is that? Are you willing to travel one and a half hours to work? That kind of thing, that kind of questions. 

These are the things where the answer is different for everyone, but there’s no right or wrong. But once you actually define what’s your must-have, good-to-have, and absolutely-cannot-have, when you go to a job, you are more likely to be satisfied because you know that this actually meets my criteria and even if I don’t have this, it’s like a good-to-have rather than a must-have. 

Andrew: So it’s about… we want a lot of things, but you put it under the good-to-have category, you know you can sacrifice that if there are other things that they fullfill in the must-have category. 

Jeraldine: Yes, yes. Correct, and I think this framework you can apply to everything in your life. Back to friends, dating…

Andrew: Absolutely-must-not-have… will be something that’s a landmine and definitely no. What is something that people might put in their absolutely-cannot-have category?

Jeraldine: For some, it could be commute. For some, it could be more like they don’t want too much bureaucracy kind of thing because not everybody thrives well in that kind of environment. For some, it could be like… culture is super important to them because they’ve been burnt badly by the environment which is toxic before so that’s absolutely critical for them. 

Andrew: Unfortunately, you can’t really get that answer first hand but you have to do whatever we just talked about this whole interview which is doing all your research, talking to people in the industry. What if you do not know anyone? Do you reach out to them on Linkedin?

Jeraldine: You can reach out. I’ve done that before I’ve joined my new role. I reached out to people on LinkedIn, asked for opinions and stuff like that. 

Andrew: Someone you did not know beforehand?

Jeraldine: Kind of added like as a first connection, but not like buddy kind of friends and stuff.

Andrew: What do you ask? I might be offered a job in this position…

Jeraldine: Can I learn more about what it’s like? Can I get on a call? Because if you approach someone on LinkedIn and they don’t want to tell you the answer… 

Andrew: Because I don’t know you yet, right? 

Jeraldine: That means something’s wrong! Because if it’s good, It would be no qualms about it right but if it’s bad, they probably don’t put it in writing or they don’t want it to come off from their mouth. That’s one of the hints that I will get. But so far, lucky for my current role, everyone is happy to talk to me and share why they joined and stuff like that so I was able to find out the answers that I wanted and to get a good sense of the environment.

Andrew: That’s a good way to filter because I don’t mind being an ambassador of my company… 

Jeraldine: If I love it. 

Andrew: If I love it, right? You might be my new colleague… hey, join the company! It’s great. I’d love to have you as my colleague. 

Jeraldine: Correct, correct. But if people are like “huh…”, they don’t want to talk about it, then you know something is not right because they don’t want to say anything that could jeopardize their own reputation. That means the thing that he’s going to say is negative.

Andrew: That is a tell tale sign. That is a clue that there could be something there. 

Jeraldine: Does it make sense to you?

Andrew: It makes sense to me. I was thinking about this question because if I don’t know you, why would I want to tell you about my company? 

Jeraldine: Some people can be really closed off. They just ignore the mail and stuff like that. But then if some people really love it, you will definitely…

Andrew: So that tells you something. If somebody is ambivalent… 

Jeraldine: Or they don’t answer at all. 

Andrew: That tells you something but if someone is truly passionate about the company, that tells you something? 

Jeraldine: Yes. No answer is also an answer.

Andrew: So how does passion play a part in all of this? 

Jeraldine: Going back to what I brought that up about passion… like I said, there’s a group of people in this world who are super lucky. They know since young, I want to be a teacher and now, they are a teacher.

Andrew: Like Joseph Schooling! Since young, he knows he wants to swim! How did you know that? Was it 11 years old? How do you know that at 11 years old? 

Jeraldine: Yeah, so it’s really a privileged group of individuals. But I guess for many of us, it’s not like that. So I would encourage people to think of passion as not like… a feeling kind of thing, but more like something that you develop over time, as you get good in something. 

A mistake that many people make is that they will think that if young, I want to be a pilot, for example, that’s the only path that I can pursue which is my passion, like my one true love. But it does not factor into the consideration that maybe people change. Like the kind of girl you like when you are 13 is different from now, right? The same for passion, the kind of things I wanted to do at 13 or maybe 15 even is different from what I want to do right now. 

Andrew: Okay. Let’s say you want to be a pilot but you might have psychomotor problems that might not be suitable for you, for example.

Jeraldine: Or practical realities that… maybe I don’t have good eyesight or something. 

Andrew: Maybe you can’t do Lasik for some reason. But how would you… where do you place your passions? 

Jeraldine: Where do I place my passions?

Andrew: What are your passions in, if I were to ask you this question? 

Jeraldine: Passion is a really strong word so I don’t really use the word passion much for the things that I do. But I guess where I derive satisfaction in my life is… of course, career does play a part in my life satisfaction. The challenge that I get, the learning opportunities that I get… this is really one of the key factors, but there are also other factors that contribute to my happiness as well.

For example, my close friends. Being part of the journey together with them, walking this journey together in life. Family, of course. Things like having my own interests outside of work… reading about the things that I like. Things like going to museums, things like cycling… hobbies and stuff like that. 

These are the things that add meaning to my life and of course the other element that I brought up earlier is volunteer work and being able to contribute to my community or my generation’s lives through content creation. These are things that really gives me meaning and really helps to make my living experience in this earth a lot more memorable. 

Andrew: Any closing thoughts about work that you might have before we wrap up this part of the conversation? Because people are still going to be reading your blogs, they might still be direct messaging you on LinkedIn, on Instagram and they will have so many questions about life, about work itself. Any last words before we wrap up? 

Jeraldine: I guess at the end of the day, it’s really important for you to go back to the question and ask yourself: why do you work? How does work fit into your life? Because that will really clear up a lot of misaligned expectations that you may possibly have from your job and help you to really gain satisfaction out of it. 

Andrew: Okay. Thank you. 

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I have three questions for you. What is one core life principle that you hold? 

Jeraldine: For me, I have seven core values.

Andrew: SAF? 

Jeraldine: That’s what people say every time… I tell you a joke. I was telling my brother… 

Andrew: I feel like drinking water already. Okay… tell me about your seven core values. Water parade… seven core values! Oh my god, the memory is coming back! 

Jeraldine: Care for soldier. 

Andrew: Yeah, loyalty to country. 

Jeraldine: Of course, I admire some of the values that other organizations and people have but I also have my own that are important to me. Of course, love is critical to me and how I define love is… not just romantic love, but something that extends to the family, the community and friends and stuff like that. I categorize that under love itself. Freedom is also critical for me. Being able to have the freedom to make my own choices. Growth. Gratitude… being grateful for the things that I have,which will actually keep me in a positive mindset every day. Achievement, respect and pragmatism.

These are the key values that are important to me and I always tell my audience that value sounds very fluffy, but once you know that you can use that as a basis for almost every decision you’ve made in your life…

Andrew: You also write about finance and investing. What is one piece of financial advice that you think should be shared more often?

Jeraldine: When it comes to finance, everyone like to talk about the sexy topics like Bitcoin… 

Andrew: Crypto to the moon! 

Jeraldine: Elon Musk says and stuff like that. That may catch attention, but it’s not really fundamental. For most people, it’s really getting familiar with the concept of compounding interest. Starting young basically, so that you can let time work in your favour.

Andrew: Which part of your life are you giving additional focus right now? 

Jeraldine: Right now, I’m trying to work on my empathy skills because I think that I want to be a better support to the people around me, be it my close friends, my family, my readers and stuff like that. So I’ve been reading a book about how I can do that a little bit better and how I can be a better listener. Instead of always trying to give suggestion first, it’s really more about identifying emotions, asking questions which I feel that can not only help me in my personal life, but also in my professional life as well. 

Andrew: I would like to ask a bit more about that. How do you build empathy?

Jeraldine: People think empathy is a feeling but that’s not really always the case. Empathy begins with identifying the emotions. It does seem that you look sad… and then you kind of justify emotions for them like “I will be sad too if I were you, because…” and it’s not wrong to feel sad.

So you validate and justify that emotion for them so that they don’t feel that… they don’t feel bad about feeling sad. After that, you can also thank them for their vulnerability. You can ask permission. “Do you mind if I share my perspective?” and stuff like that.

These are some of the ways you can show empathy. So it’s not about feeling sad when they are sad but it’s really more about being present and being there for them and being a better support to them. 

Andrew: Thank you. Thank you so much for the time.