in: Career, Career & Wealth, Podcast

• Last updated: March 20, 2022

Podcast #674: How to Land Your Dream Job

Chances are, you’ve got a job right now. Chances are even good that you have a pretty decent job. But there’s also a good chance that you often desire something more from your work life. Not just a better job, but the kind of job you’ve always wanted. A dream job.

Whether you’re currently employed or not, my guest today has concrete advice on how to turn your longing for a dream job into a reality. His name is Ramit Sethi and he’s a personal finance expert, the owner of I Will Teach You to Be Rich, and the creator of the Find Your Dream Job program. Today on the show, Ramit explains why finding your dream job, even in our current economic environment, is entirely viable, as long as you understand that this pursuit is a skill like any other. He then walks listeners through what the average job seeker does wrong, and what the skill of landing your dream job actually involves, beginning with knowing which of three career seasons you’re currently in. We get into why you shouldn’t just look for an opening with the same job title that you have now, but should figure out what your dream company and dream role look like instead. Ramit shares the 10-second test you should do to determine if you’ve got a winning resume, and what you should put in and take out of your resume as well as your cover letter. We also get into how to prepare for and ace a job interview, including how to answer the infamous “Tell me about yourself” question, as well as other sticky questions like why you’ve been out of work for a long time or were fired from your last job. We end our conversation with considerations to think about if you’re contemplating changing careers to a completely different field.

If reading this in an email, click the title of the post to listen to the show.

Show Highlights

  • Why don’t we believe that the dream job is possible?
  • Aren’t we still in a pandemic? Why shouldn’t we just settle for the career we have?
  • Does career fulfillment only come through entrepreneurship? 
  • How do you figure out what your dream job even is?
  • The importance of knowing which career season you’re in 
  • How do you find jobs these days?
  • What should people really be doing with their resumes?
  • The lowdown on cover letters
  • How to prepare for a job interview 
  • Quitting your current job without burning bridges 
  • How and when to make 180-degree career changes

Resources/Articles/People Mentioned in Podcast

Connect With Ramit

Ramit on Twitter

Dream Job Course

Listen to the Podcast! (And don’t forget to leave us a review!)

Apple podcasts.




Google podcasts.

Listen to the episode on a separate page.

Download this episode.

Subscribe to the podcast in the media player of your choice.

Listen ad-free on Stitcher Premium; get a free month when you use code “manliness” at checkout.

Podcast Sponsors

Click here to see a full list of our podcast sponsors.

Read the Transcript

If you appreciate the full text transcript, please consider donating to AoM. It will help cover the costs of transcription and allow other to enjoy it. Thank you!

Brett McKay: Brett McKay here and welcome to another edition of The Art of Manliness podcast. Chances are, you’ve got a job right now. Chances are even good, you’ve a pretty decent job. There’s also a good chance that you often desire something more from your work life, not just a better job, but the kind of job you’ve always wanted. A dream job. Whether you’re currently employed or not, my guest today has concrete advice on how to turn your longing for your dream job into a reality. His name is Ramit Sethi, and he’s a personal finance expert, the owner of I Will Teach You To Be Rich, and the creator of the Find Your Dream Job program.

Today on the show, Ramit explains why finding your dream job, even in our current economic environment is entirely viable, as long as you understand that this pursuit is a skill like any other skill. He then walks listeners through what the average job seeker does wrong and what the skill of landing your dream job actually involves, beginning with knowing which of the three career seasons you are currently in. We get into why you shouldn’t just look for an opening with the same job title that you have right now, but you should figure out instead what your dream company and dream role look like. Ramit shares the 10-second test you should do to determine if you got a winning resume, and what you should put in and take out of your resume as well as your cover letter. We also get into how to prepare for and ace a job interview, including how to answer the infamous, “Tell me about yourself” question, as well as other sticky questions like, why you’ve been out of work for so long and why were you fired from your last job. We end our conversation with considerations to think about if you’re contemplating changing careers to a completely different field. After the show’s over, check out our show notes at

Alright, Ramit Sethi, welcome back to the show.

Ramit Sethi: Thanks for having me.

Brett McKay: So we had you on the show back in April to discuss… Because the pandemic was starting, what people do with their finances to get ready for this unprecedented time that we went through, and we’re still going through. Before we talk about what we’re gonna talk about today, we’re gonna talk about jobs, I’d love to… What’s your take? This was back in April. How are things… How are you seeing the financial landscape now that we’re nine, eight months into this pandemic.

Ramit Sethi: For people who have good jobs, for people who have savings, and certainly for people who have investments, many of them are doing financially better than they used to, which is confusing and surprising for a lot of people. In what world could you imagine that the stock market would have one of the best years in history during a global pandemic? Unfortunately for people who don’t have jobs, or have lower incomes, no savings, and certainly no investments, things have not turned out as well for them, and I think there’s a lot of disproportionate trouble that’s being placed on lower income employees across the country. So what we talked about last time was overreact, overreact. It’s better to overreact than to under react. And there are a lot of people who listened to what we talked about and reached out and said, “Hey, I’m so glad that I started to put away more savings.” They may still have a job, some of them may have lost it or may lose it next year, but at least they know that they have savings. And then for the people who did that and passed that first step of playing defense, they followed their plan in step two and then step three they went on offense. For those people who have invested, many of them have seen tremendous gains, which is great financially for those people.

Brett McKay: Well, so let’s talk about what you’re thinking about lately. So in April you were thinking a lot about the pandemic, what people can do to get financially ready for that. Lately you’ve been thinking a lot about helping people land the job of their dreams, get good jobs. Why’s that been your focus lately?

Ramit Sethi: It’s funny, for both of our audiences, I’d be willing to bet that over 90% of them have a job. And if you ask people, “What would your dream job be?” it’s actually really interesting to hear their answers. A surprising number of people will say, “Well, that doesn’t exist, there’s no such thing as a dream job.” And I asked them this recently, and that’s what they told me. And when I start to dig into why, many of them say, “Well, nobody around me has a dream job. This person hates it, this person has a terrible boss, this person is underpaid.”, which really reveals that if you have never seen something, you don’t think it’s possible. But I do, I’ve seen it. I’ve had a dream job. I have my dream job now, even though I run my own business.

And the reason that I’ve been getting more and more interested in this is that we spend most of our lives at a job. Many of us have good jobs, I’m not talking about if you have a terrible job, that’s very clear that you should probably make a switch if you can, but it’s really that tricky middle where you have a job that’s okay, but you don’t like your boss, you’re not respected or you’re not paid what you should be. And the final reason I got really interested in this is that finding a dream job is a skill. And this is a classic misconception, a lot of people think there are no dream jobs, or it’s not for people like me, I didn’t go to the right college. Well, it turns out that finding a dream job is a skill. Just like lifting or riding a bike, it’s something that can be learned. And when I started teaching people how to do it, ’cause I learned it myself, suddenly they started to land dream jobs. That’s why I’m talking about it now.

Brett McKay: Well, there’s some people, I mean, listening, just like, “Okay, dream job, that’d be great, but this is a pandemic, companies are laying people off, etcetera, etcetera. I should just settle for whatever job I can get if I’m out of a job.” What would you say to those people?

Ramit Sethi: I think that that’s a fair critique. You know what, there are times where it’s an employer’s market, and there are times when it’s an employee’s market, and that is an important consideration when you are looking for a job or when you’re negotiating your salary. And in certain industries right now, for example, if you are a waiter, yeah, it’s definitely an employer’s market. That means that your power is lower, but I also think that when people say that they say it flippantly, without really understanding the dynamics at play. You know why I say that? Because people have been saying that for the last 10 years. In one of the best employment markets in history, I heard people saying, “Well… I should just be lucky to have a job.” Well, guess what? If you say that when things are good and you say that when things are bad, maybe it’s not about the economy, maybe it’s actually about your mental mindset.

So a better way to approach it is to say, “Have I developed the skills to, number one, identify what even is my dream job?” That’s number one. That’s a skill. We can talk about that. Number two, do I know how to avoid the typical things that people do to find their job? Like spending years updating a resume and then submitting it through some random website, black hole of doom, and then just sitting back and waiting. That’s not how winners get their dream job, that’s how average applicants get it. So the reason you hear me getting passionate about this, is that there’s a much better way to identify what your dream job is and then to land it.

Brett McKay: Gotcha, and those skills can come in even more handy whenever it’s an employer’s market, ’cause you can get the best deal you can get, even if the deck is stacked against you.

Ramit Sethi: Exactly. Your competition doesn’t know this stuff. You know, again, let’s just take, if you asked the average person, “How did you find this job, or how are you gonna find your next job?”, I can tell you exactly what they would say. They would say, “Well, one day at work my boss finally said something that I just really didn’t like. I went home, I decided I need to update my resume.” That’s the first thing everybody does, they update their resume. So when they update it, what are they doing? They’re just randomly adding some chronological fact to the resume, which is totally meaningless. And then what do they do next? They go to some website, they search for the same job title they have today, the one that doesn’t necessarily make them happy, but that’s all they know, and then they post their resume and they sit there and wait. And they do that for two weeks. They check in, maybe they got a couple of hits, maybe not. They wait another two weeks, and then after two, four, six, eight weeks, they get demoralized and they say, “You know what? This economy sucks.”

But what have they done? They did what they were taught, which is do 1.25 inch margins on the resume. Again, who cares? They submit it through a website, basically delegating their job search to some computer algorithm, and then they sit back and wait passively. And that’s why when people think about a job, they don’t think about a dream job. But that’s not how top candidates do it, and that’s why I really wanna emphasize the skills that I learned, the things that I taught, so that other people can land jobs that pay them well, that give them flexibility, that let them have responsibility.

Brett McKay: One question I have for you is, I’ve watched your career since when you were a blogger, like in 2005, and you had your Ramit’s Kickass Guide [laughter] that I bought for five bucks. One thing I noticed about you, a lot of people in that space, when they’re giving advice or offering programs to help people, it’s usually about starting your own business. Like, you gotta be an entrepreneur, if you work for another company you’re a sucker, you’re a sheeple, and you teach people how to start companies. You’ve done that, we’ve talked about that, but you also say, “No, if you want a job… Like, you work for a company, not own a… Be an entrepreneur, that’s okay too.” So how do you figure… Like when you’re talking to someone, they’re thinking, “Well, should I just keep being a company man working for another company, or should I strike out and be an entrepreneur?” How do you… What do you tell that person? How do you help that person figure out what they should do?

Ramit Sethi: Well, first of all, I completely disagree with the idea that a lot of entrepreneurs throw around, and that is the idea that you can only be successful if you run your own business, and if you work at a company, you’re a loser. I don’t agree with that. I have worked at a company, I’ve had a W2 salary. I employ many employees, my co-workers, and I think that there are lots of benefits to working at a company. You can have a bigger impact together than you could do it alone, you can have stability and benefits better than you can have alone, and on and on, you can learn skills more than you can learn alone. What I will say is that there can be a time and a place to have a job, or to be an entrepreneur, or to do both of them at the same time. But I really dislike this idea that is shared, mostly by entrepreneurs selling an e-book, that the only way to be successful is to have your own business. That’s not true. What I would say is, in order to build a rich life you want to be challenged in what you do, you wanna feel some ownership and you wanna build an asset. Now that asset can be a business, that’s great, it can be a stock portfolio, which I talk about in my book. So let’s remember that most people who become millionaires do so through a W2 job.

I wanna say that again, because this is very counter-intuitive, although it shouldn’t be. Most people who become millionaires do so through an ordinary W2 job. They build a 401k, they build their savings, and that’s how the majority of millionaires get there. Now, you can define rich however you like, but let’s stop stigmatizing people who have jobs. Let’s instead say, “Okay, I’m not gonna settle for a fine job, I wanna get a dream job. So I’m gonna learn the skills, I’m gonna apply to the right companies. I’m gonna spend extra time upfront, I’m gonna get paid really well because I’m really good at my job and I’m building my skills. I’m gonna become indispensable, but I’m not gonna feel guilty about working there. And if I decide I wanna start a business, I can do that on the side. And eventually, if I wanna go full-time on that business, I can do that as well.” That’s exactly what I did with my own career.

Brett McKay: That makes sense. That’s how I’ve done it too and, yeah, I’m with you. I think it’s so dumb when people just knock on people who work for companies, ’cause I know lots of successful people that they’ve been a career person their entire life.

Ramit Sethi: Yeah, and I also think it’s a little short-sighted when entrepreneurs say that, because what are you gonna do when one day your business grows enough that you want to hire employees? Suddenly you’ve basically labeled every one of your employees a loser. It’s just disrespectful, and it’s just not good strategy. I love my co-workers, I pay them well, I have excellent benefits for them. They all work remotely, they have since day one, and I respect them. I couldn’t do what I do without them. So I don’t think we should stigmatize people who work at a company. I think that there are times and places where you may wanna start a business, but a lot of people don’t. It’s perfectly okay, let’s work on finding a dream job for you.

Brett McKay: Alright, so let’s talk about the skill of finding a dream job. You say this is a skill like any other thing, like riding or lifting weights. And you say the first thing that people have to figure out and learn is, how do they know what a dream job looks like for them? So how do you do that? What’s the process like?

Ramit Sethi: Okay, so there’s this concept I wanna introduce to people called career seasons. This is a new concept that is exclusive here to I Will Teach You To Be Rich. So there’s three different seasons that we’ve identified in people’s careers. The first one is growth. For people in the growth season, that means you want to take on more work, you wanna be paid more, you want a higher a salary, you’re willing to put in extra time, but you wanna know that there are rewards. This was very much me in my 20s. I didn’t mind working on Saturdays and Sundays, I didn’t mind taking on extra responsibility, but I wanted my career trajectory to be vertical. I wanted to be learning a ton, and I did. That was growth for me in my 20s.

The next career season is something we call lifestyle. Now, anyone who has had children may know that, hey, at certain points you decide you’re not willing to work Saturdays and Sundays, and you actually need and want to prioritize something outside of work. This could be children, it could be an elderly parent, could just be a hobby, travel. Fine, that’s lifestyle season. And the third one is something we call reinvention. Think of the lawyer who’s finally fed up and decides, “I wanna be a beekeeper.” Awesome. You wanna switch jobs, job titles, or even entire industries. Okay, with each of those career seasons you need to use different skills to find the right job for you.

So suddenly, everyone listening, I wanna challenge you. What career season would you say you’re in? Are you in growth? Are you in lifestyle? Are you in reinvention? You can only choose one. It’s possible, you know, everybody wants to start saying, “Well, I wanna make more, but I also wanna prioritize my lifestyle.” Pick one, because it determines the most important jobs you’re gonna look for. And I’ll tell you exactly how this works. When you go out and you start searching for the perfect job title and the perfect company for you, if you are in… If you’re in growth season, you’re gonna be examining this company and you’re gonna look at people who work there, you can look them up on LinkedIn, and you’re gonna see have they been promoted frequently. If the answer is no, and they stay in the same position for nine years, that’s probably not the right company for you, so you can eliminate that off your list. If on the other hand, you go and you find a company in your lifestyle season and in reading interviews about their company, you realize, “Wow, they each work 60 hours a week and they’re on call three times a week.” Easy, discard.

But suddenly, instead of simply going and typing into a computer, “Marketing coordinator”, you have a totally different lens to look at these companies and evaluate them through. So rather than ending up with 50 companies where you just blindly submit your resume, you really wanna end up with about 5-10. And you wanna be as specific as saying this, you wanna say, “I wanna work for a B2C company based in Seattle that has between 1-15 employees, and I want my job title to be marketing coordinator or program coordinator”. Okay, beautiful. Once you are that specific suddenly there’s only about 15-20 companies, and you can really start to make a plan to network into those companies and to create a beautiful resume and cover letter that will attract their attention, versus saying, “I wanna help people”, and then just rifling your resume out to everybody on the internet.

Brett McKay: Alright, so that first step though is figuring out what phase in your career you are.

Ramit Sethi: Yeah.

Brett McKay: I guess it means…

Ramit Sethi: What career season.

Brett McKay: Yeah, and I can see that being tricky, ’cause there can be some people who are in their 20s, and there might be the pressure to like, “Okay, I want growth” Like, you’re supposed to get growth, but they really, they’re like, “No, I just want a nice career where I get a steady paycheck. I don’t need much”, and that can be… And you might go for the growth ’cause all your friends are, and then you find out, “I’m just completely miserable in this job.”

Ramit Sethi: Yeah, I mean, look, you and I both know this is true in life. As you and I have taken different paths from many people around us, we both realized early on we were probably influenced by people more than we care to admit. But as you build the skill of really knowing yourself, you start to realize what’s important to you, and I realized what’s important to me. So it’s normal that we would be conflicted. It’s normal that most of us are influenced by the people around us, we’re social animals, but it is really important to get crystal clear about your career season. Because I’ll give you another example. If you’re in lifestyle, for example, and you decide, “You know what? I’ve gotten the taste of working remotely, and I don’t ever wanna have to go back to an office.” Okay, listen, first of all, I completely understand that, ’cause I’ve worked remotely for 15 years and I love it. I’m never gonna do a commute. So how do you apply that to your job search? Well, here’s how. First, when you are seeking companies out to see if they might be your dream company, you’re gonna look and see do they offer remote work.

If they do, that’s a definite yes, I’m gonna apply there. If they say “No”, or “Maybe”, you can still apply there, but in your cover letter from day one, you wanna emphasize, “Hey, I understand that you’re based in DC, but I’ve worked remotely for the last 18 months. I’m proficient in SalesForce, Jira, Confluence, and if this makes sense for both of us, I’d like to continue working remotely.” So from day one you’re emphasizing what is important to you, versus randomly applying to companies and then at the very last minute when they make you a job offer, you say, “Well, I’d actually like to work remotely.” and they’re like, “No, that’s not the way to do it.” So as you can see, knowing who you are and what you value up front, lets you be completely transparent with these companies that you’re seeking and working with to find your dream job.

Brett McKay: Yeah, and that’s something to keep in mind. ‘Cause they’re doing… They’re transparent with you, they’re telling you exactly, “Here’s what we’re looking for in a quality candidate”, and you can do the same to them. You’re shopping for them, just as much as they’re shopping for you.

Ramit Sethi: Well, I’m glad you said that. That’s one psychological difference between top candidates and everybody else. So average applicants, they walk into a job search or certainly an interview, and they believe that their job is just to answer questions. That’s really what most people think their job is in a interview. That is wrong. Top performers know that they are doing something completely different. First of all, they’re discerning, they are interviewing companies as much as companies are interviewing them. And when they walk into, for example an interview, they’re not just there to answer questions, that’s table stakes, they’re there to communicate their three key messages. “Doesn’t matter what you ask me, I’m gonna get one of my key messages into that answer. Doesn’t matter what you say, I have a story and I’m gonna make sure that I tell that amazing story.” So this is the difference. There’s so many subtle differences between top performers and average applicants, and like you said, average applicants just walk in and they just… They take whatever companies are on a website, they search for random job titles, they don’t think that they have a network, ’cause they didn’t go to some special college, but top performers do it very, very differently, and that’s how the job game is played at the highest levels.

Brett McKay: Alright, so how do you find… Where do you go to find jobs these days, ’cause when I… I don’t know, I haven’t looked for a job in almost… I don’t know. How long has it been? 12 years, 13 years. So I have no clue where you would go to find a job. So like what’s the… Where do people usually go, and why is that not a great idea, and what’s a better thing to do?

Ramit Sethi: Well, the typical way that most people look for jobs, is they go to any one of a number of job search websites. And what’s funny is they take the job title that they currently have, the one that is making them wanna look for another job, and then they go and type in the exact same job title. So here I am, I’m a product manager, and I’m unhappy at my job ’cause I don’t like my boss and I hate Excel, and I go over to some website and I type in what? “Product manager”. Why do we do this? Why would we perpetuate the same job title that’s making us unhappy? Well, the answer is, that’s what we know. So a totally different approach is to first say, “Okay, number one. What career season am I in?”, and to get crystal clear about that, to understand the implications. Two, is to start looking at dream companies.

So there’s a whole methodology we teach, but I’ll give you the short version here. You can go on sites like LinkedIn and you can find other people who have a similar title, or maybe an advanced title of what you have, and you start to look at the companies they worked for. I did a video on this in the program, and I was, I think, a marketing manager. So I started sorting by companies with this many employees, B2C, etcetera. And I found some really interesting things. I found a woman who was a marketing manager previously at Disney, and I was thinking, “Wow, Disney is a phenomenal company. That wasn’t even on my radar.” I added it to my spreadsheet where I was tracking everything. I started looking for more dream companies, that’s the first thing. You wanna have a list of approximately 15-20 dream companies.

The second thing you wanna do, is you wanna find your dream role. So it’s one thing to say, “I wanna work at Disney.” Great, but now we wanna identify the dream role. So how do you do this? Most of us only know the job titles that we know, a product manager, product manager. But when you start to actually look through people’s careers, you start to actually leverage your network. You can realize there are tons of other jobs out there that you may have never considered. For example, the difference between program manager and product manager. The pay can be a $15,000 or $20,000 difference, and the work can be very, very different, just with one word being different. At this point, you’ve now got 15 or so companies that are very interesting to you. You’ve also got a couple of job titles that you are really excited about. You look at the job descriptions, you’re like, “Yes, that gets me excited.” Now you’ve got the raw ingredients to begin a really effective job search.

Brett McKay: And what’s the next step after that? Is it like… I mean, most people… I imagine most people be like, “Well, okay, my next step is just send out resumes and cover letters.”

Ramit Sethi: Yes, [laughter] that’s what most people do. See, most people jump ahead right to the end in everything they do. With personal finances, the first question, they come to me, they’re like, “What do you think of Bitcoin?” I’m like, “What? What are you talking about? You’ve jumped way ahead.” Same with lifting, they go to someone who’s been lifting for 15 years and go, “Hey bro, how much you bench?” That’s not the right question to ask. Okay. We should instead be asking, “What strategies do you use to show up at the gym three times a week?” That’s a good beginner question.

Before you jump to updating your resume, we wanna go slow to go fast. So at this point, we have decided, “You know what? I think I like the idea of being a program manager at Disney and Guitar Center and one other company.” So we start looking at these companies, we also start leveraging our networks. Why do I say this? Because you have no idea if a program manager is a good job title for you. You also don’t really know what it’s like to work at Guitar Center, you’ve just seen some stuff online. This is a key difference in what an average applicants do versus top performers. You want to reach out to people through LinkedIn, through email, or through your own network, and we have the exact word-for-word scripts in the dream job program. And you wanna be able to speak to them for 15 minutes and say, “Look, this is where I currently work. This is one of the reasons that I’m looking to change. I would love to get your input on your career. Why do you make the decisions you make? And what do you like about your job? And what has surprised you?”

Imagine you talk to five people who have the job title that you are interested in, just five for 15 minutes. How much more would you know? You’re gonna hear people tell you stuff like this, “Well, you know what, this is an awesome title. Most people who do this job for three years then switch over to product manager.” “Oh, that’s really interesting. I didn’t know that” Or someone’s gonna tell you, “You know what? This company’s really good, but you should be aware that everybody works on Saturdays.” “Oh wow, that’s really interesting.” Okay, cross it off ’cause I’m in lifestyle. Not interested in that.

You’re gonna get intelligence that you can never find on LinkedIn or publicly. And actually, people are very happy to do this. It’s just called an informational interview, you just have to know how to ask in the right way. So suddenly you’ve narrowed it down from 15 or so companies to about five, you’ve got a really key job title. Now, finally, you are ready to create a very targeted cover letter and a very targeted resume. And I want you to notice one thing, Brett. I want you to notice that people who started their job search at the same time as you did two months ago, they’ve already submitted their resume to 50 or 60 companies. So you might feel like you’re behind, but they’ve gotten very few responses, you’ve done what we call front-loading the work. You’ve put that work in. You’ve gone slow to go fast, and now you have five exact companies and job titles. You know exactly what’s going on at those companies, ’cause you actually have relationships with internal employees. Now you are ready to begin applying and your hit rate is gonna be way higher than everybody else.

Brett McKay: Well, speaking of resumes, I think a lot of people… You said the first thing people usually do is like, “Oh, I’m going to update my resume, ’cause I hate my job”, and they just…

Ramit Sethi: Yeah, don’t do that.

Brett McKay: They add one more thing and then they make sure the margins are tidy, or whatever. So, you laugh at this, ’cause obviously that’s not important. So what should people be doing with a resume to make it stand out, and with keeping them… So I’d love to get your input on this. With all these companies using artificial intelligence to scan keywords and resume to suss out applicants. What’s that look like today?

Ramit Sethi: I want everyone who’s thinking of looking for a dream job to pull out your resume, close your eyes, and then look at it for 10 seconds. That’s it. Put a clock there, 10 seconds, and tell me in one sentence who that person is. If you can’t answer that, you don’t have a winning resume. This is what we call the narrative behind your resume, and it’s that 10-second resume test that we just did. When you look at most people’s resumes, this is the average applicant, they put their college, they have a whole bunch of chronology. Average people love putting chronology. First I did this, then I did this, two years ago I worked at this company… Nobody cares.

What you need to do, and what is most important is, what is the narrative of your resume? Let me give you an example of what my resume was early on. You looked at it for 10 seconds. That’s it, ’cause that’s how long a hiring manager will give you, 10 seconds, and instantly you would say, “Oh wow. This is the technology and psychology guy who really knows marketing.” Now, what could your narrative be? It could be the performance marketer who can drive 10,000 leads a month, profitably. It could be the organizational leader who has managed turnarounds over and over again. Doesn’t matter, your resume is yours, but it should be crystal clear within 10 seconds. Your margins don’t matter, the font you use is largely irrelevant. Chronology is not that important, much more important is removing the jargon and communicating the key outcomes that you drove at the company you were working for.

Brett McKay: So you don’t need to put you’re proficient in MS Word or…

Ramit Sethi: Yeah, just delete it. [laughter] I’m so glad you said that. It’s funny. I do like to keep people to one page, or maybe two if they have a very long career. But it’s funny, when I go through people’s resumes with them, and I did this in the course, I actually re-did resumes so you can see the before and after. It’s funny, as I go through it line by line, it’s often the case that you can delete 30-50% of what’s in a resume right off the bat. And that can seem intimidating, because the first thing people do is they worry, “Well, what am I gonna put on there?” But actually what that does is, it allows you to have the room to speak even more about the important things. For example, do I care that you’re proficient in Word? No. Instant delete. Every word needs to earn its way on to the page. However, if you can tell me how you coordinated and collaborated with three other members of your team to improve conversion by 18% in 12 months, hey, take five lines in your resume to write about that, I wanna know every detail.

Brett McKay: Alright. So, yeah, think of your resume as a story then. And look at when you’re applying for your job, look at what you did at your current job or your past job and think what were the high points in the story, that little mini story of my career, and I’m gonna highlight that.

Ramit Sethi: Yeah, and take out anything that doesn’t support that story, it doesn’t add to it. Your job, again, this is a really subtle reframe, average applicants think their job is to communicate the chronology of what they did. Again, nobody cares about your chronology. I don’t need to know that you were born under a palm tree. I don’t know, I don’t care. What I do wanna know; who are you? What’s your narrative? And then everything on that page should support that narrative.

Brett McKay: Alright, what about cover letters? What’s the state of cover letters in 2021?

Ramit Sethi: Cover letters are good. They are a great opportunity for you to tell a little bit more about the key highlights on your resume and expand. Don’t just repeat, that’s a common mistake people make, they just repeat what’s on their resume. Look, I already saw your resume. Okay. This is how hiring managers work. They look at your resume for 10 seconds, if they think you’re worth it, they go over to look at your cover letter. If they don’t think you’re worth it, you’re instant delete. That’s it. That’s how it works, and I think a lot of people would be surprised. They expect, “Oh, I spent all this time on this resume. I deserve at least five minutes of consideration.” Hiring managers are literally getting hundreds or over a thousand applications per job.

You have 10 seconds, so you better make sure that every word earns its way on the page. Now, as for cover letters. This is an awesome opportunity to tell a story. Tell them why you are excited to apply for this role, tell them who you have spoken to, who works there or worked there, and tell them why they got you excited. Write your name dropping here because you’ve done your natural networking. Tell them why you are looking to make a change now and what you can contribute. And of course, as I mentioned, if you’re in lifestyle, this is a good place to mention that you’d like to work remotely, but you can deal with that when the time is right. If you are looking to… You want X, Y, Z, you may want to mention it early on. For example, “I’m very interested in contributing to the role and to developing my skills.” Mention that, tell them that you are eager for growth. That’s what you do in a cover letter.

Brett McKay: And should people… Like I mentioned earlier, I’ve been seeing these companies use more and more of these artificial intelligence to scan through resumes and discard. Should people write the resumes for robots, or they just should keep doing what they usually do?

Ramit Sethi: The ultimate goal is that if you go through the dream job program, your job is not even being handled by these AI-type bots. When my students get jobs, the best way that they get them is their resume gets forwarded by someone internal to the company. Now, that’s ideal, that doesn’t happen every time. But we show you how to find people at the company, how to do informational interviews, and if they like you, remember a lot of people want talent, they wanna work with great people. So if they like you, they’re gonna say “Hey, send me your resume. I’ll make sure it gets in to the hiring manager.” This happens over and over and over again. So that’s ideal.

If that can’t happen, if you simply cannot find an in to the company, yeah, you can submit it through the front door. As for should you write for AI? In general, no. You should write to make sure that you are communicating your key narrative. That, if you are searching for a product manager role, well, you definitely need to use the words product and management, and you need to use ROI and prioritization. Those are obvious, but aside from that, you should not be depending on AI to save you. Do not delegate your career to an algorithm, that is a classic mistake people make.

Brett McKay: Alright. Let’s say you’ve done all the stuff, you’ve thrown in the resumes, the cover letters, sent them out. Now you’re getting called in for job interviews. I guess, and a lot of them now are remote. They’re doing via Skype, or whatever. You mentioned earlier that a lot of people just go into a job interview thinking their job in this job interview is to please the employer. Like, “I gotta say all the right things. There’s a correct answer, and I gotta know what the correct answer is.” You don’t wanna do that, so what’s a better way to prepare for a job interview?

Ramit Sethi: I want you to know your three key answers, your three key messages. So for example, let’s take my earlier resume narrative. I was the technology and psychology guy who was very good at marketing. Okay, so guess what? One of my key messages needs to be that I love understanding human psychology when designing marketing systems. And so if they ask me, for example, “Why do you wanna work here?” Okay, or, let me ask a better question, “Tell me about yourself.” This is the first question you’re gonna get in an interview. I would say 75% of candidates go off right here, they get it wrong from the first question. When I ask you, “Tell me about yourself”, I do not wanna know that you were born in this hospital, and I do not wanna know that you love Kicks cereal. Nobody cares, right? I’m not your mom, I’m not your dad, I don’t wanna know about your childhood. You need to have three key messages. So I might say something like this, “Well, as you can see from my resume, I’m very interested in technology and psychology, and I’ve used those interests to be able to drive measurable results in marketing. For example, at the last company that I worked at, we took a Facebook ad system that was performing okay.

And I looked at the data and I said, “Something is missing here.” I went out, I interviewed over 300 people. I built a system to incorporate their feedback, and eventually I learned that we were missing one qualitative factor, it never showed up on the spreadsheets, it only happened because you had to get in there and talk to them and understand their psychology. And when I fixed that, along with my team, we were able to drive a 28% improvement in conversion. That is why I’m very excited to work here because I know I can learn more from Acme Corp, but I can also contribute what I’ve developed previously.

Brett McKay: Right, so you continue that narrative.

Ramit Sethi: Exactly. So everything should fit together, and remember, I did not tell you anything about what type of food I like, and all that stuff, irrelevant, but I walked in there prepared, I knew my narrative, everything flows from that. And that hiring manager, noticed what happened in that answer, first of all, it was a story, it was not jargon, like, “I like to collaborate, I like teamwork,” nobody cares. Tell them a story, make it compelling, which means you need to practice ahead of time, and make sure that it is concise, typically I would say 30 to 45 seconds, and you’re watching the body language of the interviewer. And you can even do these little verbal drops, you can say, “If you’d like I can go into that in more detail,” but the key thing that we took away was, “We need to interview our users.” That’s a beautiful little verbal drop where the hiring manager might say, “Yeah, can you tell me how you did that?” And then you have permission to go deeper into that story.

Brett McKay: At what point do you start discussing compensation, do you discuss that during the job interview or after you’re offered a job?

Ramit Sethi: Typically, after you’re offered a job, but you can drop in little hints about it early on. So for example, at the end of the first interview, the interviewer will say to you, “Do you have any questions for me?” You better have some questions. If you’re making a decision on your career, you better be intellectually curious about this company. You might say things like, if you’re in growth career season, you might say things like, “One of the things that interested me about Acme Corp is the potential for growth, and at my last company, people tended to stay in the same position for over five years, I’m really looking for a more dynamic environment, one where there’s opportunity for promotion, for learning new skills, ongoing training, can you talk to me about how Acme trains and grows and develops its employees?” Okay, that’s a real question, that’s a question that shows you are serious about this role.

And guess what? If their answer is, “Oh, we don’t do that, we don’t train anyone, you’re on your own,” then you should say, “Thank you very much,” and once the call ends, you should cross them off the list ’cause they do not fit your growth season. But if they do, you’ve let them know from the first interview, “Hey, I’m interested in this, I’m here to grow.” And so when it comes time for the negotiation, which will be after they make you the offer, you can say, “As we discussed in our first interview, I’m interested in growing my career, I’m interested in growing my results, my compensation and my responsibilities, so I appreciate the offer you’ve made, I think we’re close, but I’d like to discuss negotiating this offer now.” That’s how you do it.

Brett McKay: So you negotiate after you get the job offer and… Well, let’s talk about people who are looking for a job ’cause they’ve been unemployed for an extended period, and I’m sure you know this, that’s one of the most debilitating things that can happen to someone because it creates this vicious cycle; people see you’ve been out of the job market for a long time, you become sort of a pariah a little bit, and then you just get depressed and unmotivated to keep applying for jobs ’cause you… It’s like, “What’s the point? I’m gonna get rejected.” So, any advice for people who’ve been unemployed for extended period and they’re trying to get a dream job?

Ramit Sethi: Yeah. Well, first of all, I have a lot of compassion for people who have been laid off. I have to tell you, I’ve been laid off, that does not feel good. And if it’s been for an extended period of time, like you said, it can be really mentally debilitating. With that said, I think the best thing that people can do if they are in that situation is, number one, learn the skills of job hunting. Again, if you got laid off and you go right back to doing what everyone else does in hiring or looking for a job, you’re just competing with tens of millions of other people, and with just a little bit of work you can learn how to do things differently. That’s number one. Number two, if you get to the interview, which I’m confident you will when you use the right skills, have an answer for the question that’s the elephant in the room. The hiring manager undoubtedly is gonna say, “I don’t see anything on your resume for the last 18 months, how do you explain that?” You need to have an answer for the most common questions in your interview. If you look at your resume and you really are honest about it, what are the common questions somebody might ask you? If you job hop, they’re gonna say, “Why are you a job hopper?”

If you have jumped from one industry to another, they’re gonna say, “What do you actually wanna do with your career? You just look like you’re doing whatever job’s in front of you.” And if you’ve been out of work for 18 months, they’re gonna say, “What were you doing for the last 18 months?” So I want you to prepare for this, because the best place to prepare is before you go in for an interview. One answer you can say is, “I took some time for personal reasons, and now I’m excited to get back to work.” And one of the reasons that Acme Corp is so interesting to me is that… Pivot right back to your key message, that’s it. You addressed their question, you took some time for personal reasons, and now, boom, pivot right back to your key message and why you were excited to contribute to Acme Corp. That’s it. Hiring managers want to know, when they ask that question, they’re not looking to do a, “Gotcha,” they’re not looking to trick you, what they want to know is, “What happened? And what are you doing about it?” And the longer your career goes on, the higher your chances are of being laid off or being fired or making a mistake. It happens to everybody. What’s important is you admit it or acknowledge it, and then you have a plan for what you are doing going forward.

One last thing on this, if you were fired and they ask you, “Why did you leave your last job?” Don’t lie. Never lie. Tell them, “You know what, when I joined that company, I was excited about X, as I started to get deeper into the role I realized it wasn’t the right fit for me. Unfortunately, my performance slipped, my manager tried to correct it, but I wasn’t able to deliver the results that I had committed to, and I was let go, and I wanna be really transparent about that, and over the last six months here’s what I’ve done, number one, I joined a new training program, number two, I looked back at what I did and I painfully examined the three key areas I could have improved, and number three, X, Y, Z.” Hiring manager hears that and says, “Wow, that’s someone with a lot of self-awareness, and they’ve made a plan to correct what happened in the past.” So whether you’re laid off or fired, it happens, right, I understand it. Have an answer, and then pivot to what you are doing about it and your key messages.

Brett McKay: One thing I like you just said there, that was kind of subtle is, if you are unemployed, don’t do nothing. There’s something you can do, if that means doing online training or getting extra continuing education, do that, ’cause that will look like, yeah, you actually maybe got better while you’re unemployed.

Ramit Sethi: Exactly. Remember, you set the frame, you set the frame, this is so important. When you walk into an interview, it’s not like they can see into your soul, they’re not gonna be able to tell that, “Hey, you’ve been pretty down for a couple of months,” all they can see is what you tell them. And while I wanna emphasize you should always tell the truth, you don’t have to tell them about all of your emotional roller coasters that you’ve been on, instead focus on what you’ve done in the time being.

Brett McKay: Let’s say you get offered a new job, is there anything, considerations that people should take into account when they had to quit their current job, without burning bridges? Do you guys talk about that? Yeah.

Ramit Sethi: Yeah, this is a great question. It’s amazing to me that people think so much about finding a job and they’re so deliberate when they learn these skills, but they don’t think as much about closing out a job that they’ve worked at, and I think that’s a big mistake because I will tell you that I’ve had former co-workers of mine who left and they just did such a beautiful job of transitioning out. They told me ahead of time, “You know what, Ramit, I wanted to let you know that I’ve decided to take another job, I’m absolutely willing to work with you in transition, I do have some flexibility on when I can leave, and my intent is to leave with a new person hired and a full playbook so that they are trained and ready to go, you’re not gonna have to worry about anything.” That is music to my ears, as a hiring manager and as a boss. It also ensures that we leave with a really positive feeling towards each other.

So I’ve sent clients and I’ve sent business to people who have worked with me before, I wanna keep doing that, it’s important. But make sure that if you can, you communicate proactively to your boss once you have an offer. I would not recommend you try to engage in a bidding war, I don’t think that’s a good idea, I think it’s a classic mistake people make, they get an offer and then they go back to their boss and say, “Hey, I got this offer, what can you do?” Your boss might match it for the time being, but you’re first on the chopping block. And honestly, if you’ve gone through the process to find another job, and you are excited about it, take it. Okay, take it. But leave by transitioning everything out, and remember that your boss wants to know that things are taken care of. Your boss, she doesn’t wanna have to worry about, “Oh, is this thing gonna fall through the cracks and what about that vendor?” Do a great job. And as my track coach used to say, “Finish strong.”

Brett McKay: Alright, so don’t burn bridges, let’s not do that. The one thing we haven’t really talked too much about is the reinvention season, any special considerations there? Someone who wants to, they wanna go from lawyer to beekeeper, any special considerations they should take in account that they might overlook in that process?

Ramit Sethi: Yeah, the reinvention season is the least common of all, and that is because the older you get, the more difficult it is to make a complete career shift, it’s difficult for monetary reasons, it’s also difficult for identity reasons. Take that lawyer, for example, who used to dress up in a beautiful suit and have the corner office, and their friends would say, “Oh wow, great, you got that great case.” And suddenly they are a beekeeper, or they’re working at a non-profit, that’s a big identity shift. Now, you will know if it’s time to do reinvention because you’ve probably been thinking about it for years, and you are ready to make a move, money doesn’t excite you as much as it used to, or the reasons you got into that career are not motivating you. A couple of things to consider. First off, talk to people who made a similar switch, find lawyers who switched industries completely, doesn’t have to be to beekeeping, but it can be to anything else, and ask them, “How did you know it was time? What made you even start thinking about this, and what were some of the surprising things you encountered when you first made the shift?”

I remember I spoke to a former NFL player who got injured and had to leave, and he was looking for what to do next, and he decided to get into theater, very interesting transition from the NFL to theatre. And he said that, overnight he went from a celebrated athlete where there would be people, thousands of people cheering him when he went out to play, to being a complete nobody, and that is very, very devastating. Very devastating. So, understand that, what’s it gonna take? What should you expect? Also, think about money. If you are going to have to take a pay cut, this happens sometimes though, not always, you probably wanna start saving in advance, so you at least have some breathing room. And you also want to find out what is the average pay in the career that you are considering? If you’re going from 200 grand to 20 grand, that’s a very, very radical shift, you need to be honest with yourself about whether you can take it. If it’s 100 grand to 75 grand, okay. Sometimes it’s 75 grand to 110k. Great, a lot of industries pay more, but be aware of that. And if you do those things, your transition is gonna be much much more smooth.

Brett McKay: Gotcha. Well, Ramit, this has been a great conversation, where can people go to learn more about your work?

Ramit Sethi: Okay, you can learn all about some of the techniques and tactics that I taught you, you can go to I’ll give it to you one more time, it’s, and we’ll give you a bunch of training and scripts and examples, resumes of how to land your dream job.

Brett McKay: Fantastic. We’ll include that link in our show notes as well. Well, Ramit Sethi, thanks so much for your time, it’s been a pleasure.

Ramit Sethi: As always. Thanks a lot, I appreciate it.

Brett McKay: My guest today was Ramit Sethi, he is the owner of the website, I Will Teach You To Be Rich, they got the dream job program going on right now. You can find out more information by going to his website,, also check out our show notes at where you can find links to resources, where you can delve deeper into this topic.

Well, that wraps up another edition of the AoM Podcast, check out our website at where you can find our podcast archives as well as thousands of articles written over the years. And if you’d like to enjoy ad free episodes of the AoM podcast, you can do so on Stitcher Premium, head over to, sign up, use code MANLINESS to check out for a free month trial. Once you’re signed up, download the Stitcher app on Android and iOS, and you can start enjoying ad free episodes of the AoM podcast. If you haven’t done so already, I’d appreciate if you take one minute to give us your review on Apple Podcast or Stitcher, it helps out a lot, and if you’ve done that already, thank you. Please consider sharing the show with a friend or family member, who you think would get something out of it. As always, thank you for the continued support, until next time, this is Brett McKay reminding you not only to listen to AoM podcast, but put what you’ve heard into action.


Related Posts