$40,000 to $200,000+ in 5 Years: Don’t Quit Your Day Job with Cinneah El-Amin

Katie: Welcome back, #RichGirls and Boys, to The Money with Katie Show. I'm your host, Katie Gatti Tassin. And today we are going to talk about something that started with good intent, but has almost surely gone too far. The demonization of the nine to five, the glorification of the multifaceted side hustler, and the work-for-yourself revolution, with all of the flexibility and independence and often ignored frenetic context-switching and accompanying insecurity. 

I saw a Medium article the other day about a woman who wrote about her nine sources of income in lieu of a 9–5 job that really ran the gamut. And I couldn't help but find myself feeling anxiety on her behalf as I read about her schedule, because it wasn't a collection of passive or semi-passive sources of income. It was stuff like “reselling my clothes” and “teaching group fitness classes,” incredibly active tasks that take time, planning, forethought, you name it. Something that I can verify personally, since I have done both of those things for money in the past. And of course it is possible that she just loves all of these things, all nine of these things, and has built an efficient system for including all of them in her schedule in a way that's manageable, but I couldn't help but think, Jesus Christ, that is a lot of context-switching for any given week. And she didn't outright say it, but I got the impression, by the way she was writing about it, that her collection of side hustles cumulatively made less than her full-time job did, by the way she discussed the trade-offs between, you know, working her job and quitting it and now doing this.

So it wasn't like this abundance of context-switching and variety seemed to be generating either excess ease or excess income in her life. And again, that's not a problem, but if you are quitting your full-time job to do a small collection of other things for money with the express hope that it'll either a earn you more or be less stressful, I fear that neither one of these assumptions is necessarily accurate. And there's no shortage of articles of this kind. This was certainly not the first time that I encountered something like this, and they really seem to gain traction for some reason during the global panini, because man, our generation is obsessed with the side hustle, with shirking the 9–5 in favor of working for yourself.

And I get it, because I did that and I do it too, but I'm almost certainly projecting here, but hear me out. I think the glorification of side hustling—so, you know, working part-time on the side of working full-time, or establishing alternative streams of personal income, has definite upsides, but wow, it's also extremely chaotic. I remember working full-time for one company while working part-time for another and teaching fitness and doing Money with Katie simultaneously. And to put it lightly, I don't really look back on that period favorably, because of the amount of exhaustion and anxiety that stemmed from constantly shifting gears and keeping all these different plates spinning for unrelated things made me feel drained all the time and constantly plagued by that feeling that something is slipping through the cracks right now.

So I was only able to maintain that level of output for between 12 and 18 months before my mental health seriously started to deteriorate and I had to make changes. So that period that I'm describing—it still included full-time work. It wasn't just a collection of side hustles, but I think it was an accurate representation of how challenging it is to split your focus among multiple things over the long term. And to a degree, I think it goes against our nature as humans. Most of us have not evolved to multitask and context-switch effectively without allowing other important areas of our life to suffer, or creating what I call “browser tab brain,” which is that feeling like you've got too many tabs open in your mind and you can't close any of them, but they are making you run more slowly, right?

So put simply, working for yourself is not necessarily better than working for someone else, if it means you're just cobbling together a bunch of unrelated and unpredictable sources of income that require your active involvement. And maybe it's a generalization, but I always found working 9–5—I still do, so I suppose I still find it that way—to be manageable and maybe even a little boring sometimes, with spurts of excitement and crunch. Majority of the time though, my biggest complaint was feeling like I was being underutilized or that I was out of the action rather than the opposite. I didn't often feel stressed by full-time jobs. At least the majority of the time. Sometimes there'd be stress, but not often, regardless of which company or which role it was. So I've worked for three different big companies, like tens of thousands of employees and one startup, now a couple hundred employees, and the startup—surprise, surprise—is the only place where I've ever consistently felt accountable and in charge and like extremely challenged in my own autonomy. Most of the big corporations were kind of the opposite because the diffusion of accountability with having hundreds of people in your department meant that I was not often solely responsible for anything of consequence, and the amount of other people working on any given thing usually meant the workload wasn't too demanding on my level of personal responsibility. 

This is obviously subjective and anecdotal to my experience, but I'll never forget discussing the merits of working full-time with a friend who had recently quit her job at our corporation to pursue her side hustle full time. And this will always stick with me. She said with a 9–5, you can phone it in some days, you can take time off. You can leave your work computer at home. You can take half a day on Friday, not even think twice, but now I feel like every single thing I do has a direct and immediate consequence. There's no phoning it in anymore. There's no real difference between my weeks and weekends. And there's nobody to guide me. And at the risk of oversimplifying, working for yourself sometimes paradoxically provides less flexibility and diminishes your ability to only work when you want to, because your output directly affects your revenue. Unless you've set up something entirely passive. In which case, please call me. Some people will almost certainly thrive from that thrill and that sense of importance. Others will be surprised by it and find it jarring. And I think if we're going to promote the merits of working for yourself, we have to do so honestly and acknowledge the pitfalls. We must set expectations, honestly, because sometimes working for yourself is a breeze. But most of the time it is objectively more challenging and more of a roller coaster than having a 9–5 is. So if your hope in quitting your 9–5 job is to take a cruise down easy street, you might want to think twice.

I fear that this obsession with side hustles does two things that make things worse for people, and particularly young people. Number one, it pressures people to monetize their every hobby. This is something I feel guilty about encouraging from time to time, honestly, because it did work out well for me, but I realized there is a bit of survivorship bias here. And I often don't talk about all the side hustles I had that did not become lucrative businesses. Hint: There were a lot of them. I actually highlighted some of them in a blog post about wasted effort that I will link in the show notes. But when I visited my parents in their retirement community, I noticed something important and different. These people who are in a different generation than I am have tons of hobbies that bear no prayer of monetization. They garden, they golf. They putz around on their pontoon boats and they sit outside and they look at birds, they do crossword puzzles and they read, and these are things that I almost can't fathom most of my generation engaging in, in any meaningful way. I actually forget the last time I did something that I couldn't either justify as indirectly productive…like even a walk is accompanied by a finance podcast, with the thought that that time should be spent learning something I can turn into content. And there's nothing wrong with being productive. But I have recognized in myself an inability to turn it off.

And I fear it is a bit of internalized glorification of life-hacking and monetizing everything into oblivion at the extreme sacrifice of ever having any true leisure time for the sake of just having leisure time. And number two, it makes people place an undue emphasis on the idea of working for yourself. Nobody is more acutely aware of their responsibility to their employer than someone who just spent 15 minutes on Money Twitter. Those people will have you believing that your employer has you in handcuffs, chained to the furnace in the office boiler room. 

Now make no mistake. I completely understand the fear and the uncertainty around having a single point of failure in your earning, like one job source or one source of income. But most people throughout most of history have only had one source of income. Most people are always living close to the edge in that way. It's not unusual to work only one job. In fact, I downloaded US census data to fact check this, because I was curious how prevalent it is. And fewer than 10% of the population has more than one source of income. There's certainly something to be said for establishing multiple sources of income, but the “millionaires have seven sources of income” stat is often misrepresented to suggest that your average millionaire is running seven different side hustles, and that's just not the case. I think of a family friend who's worth millions of dollars, and he is mostly earning money right now on residual deals from the past that are still paying him. 

So being a hardworking go-getter is great, but don't let someone guilt you into becoming an Uber-driving, Facebook Marketplace-reselling, moonlighting Etsy retailer against your will, because you're trying to hit seven individual streams of income. And sometimes I have to remind myself of this. If you lose your job, you will get another one. It's not worth stressing yourself out about finding a second or third source of income. If your first one is relatively stable and you've got enough saved to support yourself, if shit hits the fan—hell, even traditionally unrelated sources of income can be impacted by the same market or economic forces as evidenced by March, 2020, when my full-time airline job and my part-time fitness job were both threatened overnight by the same thing. I thought I had my bases covered 'cause I was thinking, oh, if I get laid off because people stop flying, I'll just have this backup job that I can scale up and generate more income: easy. But then I was swiftly reminded that both travel and boutique fitness are things that people do in groups with discretionary income. And I was not as safe as I thought. And I guess you could point out my initial flawed logic here that neither travel nor high-end group fitness is recession-proof. So my founding thesis that because these two things are unrelated, they'd be affected in an uncorrelated way—that was flawed to begin with, right? But to that end, Covid-19 taught us a valuable lesson in general: that we're not as in control as we'd like to feel. And stacking our income deck with random revenue generating activities at the expense of our own time and happiness may just be giving us a false sense of control. And what drives the need for control? Fear and scarcity. 

I didn't realize how much this fear impacted my outlook and my sense of security until I talked to my friend Bridget. She's @BridgieCasey on Twitter and Instagram; she's a Canadian personal finance writer, and she laid it out for me straight. She said your irrational fear of losing everything you have stems from our collective cultural obsession with scarcity that just erroneously motivates people to work harder than they need to. She was like, you've already got half a million in the stock market. You're fine. You've already won. Now I know that that's a very privileged perspective, having already reached that point in my investing life, and you might be like, well, that's great for you, asshole, but I'm nowhere close to that, so your newfound comfort is completely useless to me. But her point is interesting as part of this larger conversation around fear and scarcity-based hustle. Sure, it's effective to some degree, if it means it's going to push you to earn more, but at what cost and to what end, and are we doing this in a way that's efficient and gives us the highest ROI, or are we just hustling aimlessly? It's inefficient and it's counterproductive when it encourages favoring a bunch of small fluctuating sources of income that require independent management to one big source of income that's relatively predictable and manageable, and dare I say, scalable. Just because your 9–5 job can be taken away—and sure, one source of income is dangerously close to none sources of income—it doesn't mean you should preemptively give up that one source of income. That doesn't mean there's something wrong with that one source of income. And so often I think we underappreciate financial freedom in favor of our relentless pursuit of financial independence.

And my definition of these two things are different, because financial freedom to me is the point at which the first consideration for any given decision isn't money anymore. When you've bought yourself enough runway to change course without serious consequence. Financial independence obviously is the point at which you no longer need to work at all—you’re work optional, the ultimate flexibility. But the reality is, once you have financial freedom, you've already earned yourself the permission to not live in fear anymore. Congratulations, you have done enough to protect yourself from any major downturns and you are officially going to be okay. Even in the worst-case scenarios, you might not be totally unscathed, but you're definitely not going to be totally screwed either. For example, if you've got, say, an emergency and three years’ worth of spending in the stock market—so pretend you spend $40,000 per year and you've got $120,000 in the market. You have sufficient runway. Even if your portfolio lost 50% overnight and your job went out the window at the exact same time, you would still have a year and a half of technical runway before you'd be out of money. And obviously you wouldn't want to have to draw down on those funds because that would undo your progress from the past. But even if it took six months for you to find another job, you know, you've built up a moat of capital large enough to make sure that you're okay. 

So I think for me, it comes down to this question of, when should you push yourself and forsake balance? And when should you get maybe a little bit more realistic and back off a little bit?  Maybe the ideal timing or approach would be the following: Put the pressure on yourself to side hustle while you climb the corporate ladder until the point at which you've got a sufficient amount of runway. So for example, a net worth that is representative of a few years’ worth of necessary spending, like the $40,000–$120,000 example, and then reassess. Do I still want to work multiple jobs? Do I still want to put the pedal to the metal? Is there anything I'd reassess now that I've reached the point at which I am financially buffered from even long-term worst-case economic scenarios? And I'm just going to come right out and say it. Someone trying to answer these questions would make a great protagonist in, say, a sitcom… TV announcer: Coming this fall. She's a finance radio host side-hustling as a personal chef. Katie: Caller number one, you’re on Money Line. 

Caller: My stock portfolio dropped 21%. 

Katie: You are fuuu…ndued. 

Henah, senior editor: Ever since you started side-hustling, we never hang out anymore. What are you doing Monday?
Katie: Working.

Henah: Tuesday?

Katie: Working.

Henah: Wednesday?

Katie: Working.

Henah: Thursday, Friday, Saturday? 

Katie: Working.

Henah: Sunday? 

Katie: Well, Sunday I have off. So I'll be looking for more work. 

TV announcer: Katie Gatti Tassin, in Money Line. 

Man: Katie, I'm asking if you will marry me. 

Katie: Sshhh. You had me at prenup. 

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If any showrunners are listening, my DMS are open. Anyway, I struggle with that discussion of income scarcity and scarcity in general, because I've seen firsthand the paradoxical positive outcomes that being afraid of losing everything has created in my life. So I'd be remiss not to credit some of my professional success, on some level, to sustained paranoia and fear. But that same paranoia and fear has driven me, at times, to living in a state of agitation and, not infrequently, unhappiness. The impossibility, right, of being present, thanks to just constantly fearing the other shoe's about to drop. And it's really hard to make decisions about the most efficient way to scale up income and proceed forward when you're in that mental state. It's the reason why I caution embracing the side hustle life too extremely, or making any drastic changes. That's why I wanted to talk to Cinneah El-Amin from Flynanced, who is the self-proclaimed “Guide for 9–5 Hotties,” which I fucking love. So Cinneah, welcome to The Money with Katie Show. I'm so happy that you're here. 

Cinneah El-Amin: Thank you so much, Katie, for having me. This is awesome. 

Katie: Absolutely. So to start, I'm curious, just to level set for everybody. Can you give us a quick rundown of your career path so far? 

Cinneah: Absolutely. So I've spent all of my career working in product management. I started working fresh out of college and a one-year graduate program, and landed my first job at American Express, where I was, yeah, the most junior person on the team. I was a senior analyst at that time, but on a product management team. So back in those days, my team was launching the Gold Card. So if anyone has the Gold Card…

Katie: I have the Gold Card, but I got it because it's pink. 

Cinneah: Exactly. So all of those decisions around that product—how it was priced, how it was going to kind of be this new entrance into this like dining-focused rewards card—all of that was the team that I worked on then. I stayed at AmEx a little bit longer, was promoted, became a manager of product development. And then was kind of only working on new product launches at AmEx on their consumer side. It was a really cool time and an amazing first job for me.

And then I realized I wanted a lot more money. I didn't want to have to wait for it, right? So I ended up transitioning to another company. I worked at MasterCard, still in a product development function. And then recently made the jump into tech, where now I'm a technical product manager working on a web-based product. So I love to say that I fell into product management, but as I've grown in my career, I've learned that, one, it's a super in-demand skill that I think more 9–5 hotties should learn about, but that two, it definitely gave me, you know, a lot of confidence to be able to chart my own path, in terms of building the career story that I wanted for myself, which was, yep, I've done the consumer-facing thing. I've done the technical thing. Now I'm working on digital products, and this has kind of been my journey as a young product manager in financial services and tech. Start to finish, that encapsulated just about five years. So I've jumped, I've worked at three companies and had four roles in five years. Yeah. I had no formal training, no certificates in product management. I fell into that very first job at AmEx through networking. 

Katie: So that's really interesting, because before I left my role at a tech company to do this, I was a content designer. And prior to that was a product owner. I didn't know any of that stuff existed when I was in college. And I think, for a while, I would look at tech and look at fields like that and say, I don't have the technical skill sets to be doing those things. I think I held myself back for that reason. And I didn't know that you could really study anything and then work your way into the field. So your work—and by your work, I mean your content creation work—what inspired you to take this niche focus in your work? The 9–5 thing, because most of the personal finance creators that I talk to and follow are very much, I think, all about this entrepreneurial lifestyle. And I think that really sets you and your work apart, and makes what you share really relatable for the majority of people who, you know, probably do have a standard 9–5 job. So where did your pro 9–5 point of view come from? 

Cinneah: I love this question. I would honestly say that it's evolved. So when I started Flynance and started showing up as a creator, and—you know, I just saw you posted about this, Katie, talking about your very first post on your Instagram account. Back then, I just kind of wanted to talk about my debt payoff journey. I wanted to talk about travel, because I felt like a voice was missing. I felt like I was being called to kind of add my voice to dispelling this narrative that you have to shame yourself for how you want to spend your money as you are building wealth, as you're paying off debt. As I grew as a creator and really learned what my audience wanted to hear from me, I realized two things. One, I realized that I wasn't giving the people that I was serving the clear steps to be able to do the things that I was doing, like putting all this money into paying off debt and investing and building my net worth, because I wasn't really showing them how I was doing it, which was through my nine to five. 

So at the same time, I'm hearing from people in my audience saying, this is great. I want to do all the things that you're doing. I want to travel. I want to invest more. I want to build wealth, but since I don't make enough money, I try to pride myself on being a transparent and authentic creator. And it's kind of like, what has been possible for me in terms of my financial wins, and the transformation that I've had in my money, is because of my nine to five career. It's because I fell into this in-demand career path, which—I love what you just said. I had no idea product management even existed when I was in college. I fell into this, and then realized, wow, I can make a lot of money with this. I can continue to build transferable skills every year that I'm in this career path; this idea of a product manager is becoming more and more mainstream, right? So all of this was kind of happening at the same time. And that's when I really kind of felt like, all right, there's a need for this that I need to be speaking to other working women like me, who may not have ever had this blueprint to say, how can I take this job that I have and turn it into the lifestyle that I want?

So that's kind of what I just started doing. I just said, okay, I'm just going to start telling you guys what I do. I get the question all the time. “What do you do? How do you make money?” And that's when things just totally went off. Like I went viral many times over, doubled my following in a month. It was insane. 

Katie: I remember, because you hit a hundred thousand followers and then three weeks later had 150,000. And I was like, I'm going to need to take a page out of your playbook! But okay. I'm curious if you get pushback from people, and if you do, what kind of pushback do you hear from people about anything that you're kind of creating about? 

Cinneah: Absolutely. So, you know, I call my followers nine to five hotties, and I want to say this because I think this is like spot on for what we're talking about. This term popped in my head around the same time that I would feel like I was seeing a lot of content that was really demonizing the 9–5 job. So I love this idea for this episode, because that's really what inspired me to start talking about, not just talking about 9–5, but like putting some respect on other working women like me, who are just like, put some respect on our names, right? Like there's nothing wrong with having a nine to five, and many of the entrepreneurs and creators that I follow, many of them started working in 9–5 jobs, well-paid 9–5 jobs at that, that allowed them to have the money to be able to put into a business, to be able to put into working capital, to be able to put into real estate investments. 

So it's like, why are we acting like everyone should just wake up one day and become like an online entrepreneur? And it's just roses and butterflies? That's a lie, right? So I think the biggest pushback that I get is, you know, I think I get some fair criticisms around some of my content being a little bit too aspirational for people, right? So we talked about this, my career journey. I've made incredible leaps and bounds in my career in just five years of working. But at the same time, I've also grown my salary four and a half times. I've doubled my total compensation in one year. Like my very first job working at AmEx, that first year that I worked, I only made $48,000. Now I make well over $200,000. Like that is…

Katie: Which, by the way, can we just pause to be like, A) that's amazing. B) bless you for saying it. I'm so tired of people being hush hush and cagey about how much money they make. We have to talk about the numbers that are out there, because someone listening to this could be like, uh yeah, that sounds okay. It's like, well, if I know that I can make over $200,000 with five years of experience, that might push it past “that sounds okay” to like, “oh, this is actually worth the time and effort to look into.” So anyway, I digress, but thank you for the transparency. 

Cinneah: Absolutely. No. Yeah. I think it's so important, especially for the people that we serve. So, you know, I think that's some of the biggest pushback that I get, is just like, you know, this is unrealistic. Like, people can't make these kinds of jumps that you've been able to make. I think there's some fairness to that, right? Like as a content creator, I think, you know, we're often balancing keeping up with these algorithms, but also just creating content that we know people want to see, right? Like I think someone is more likely to sit and watch a video of someone talking about, “Hey, I went from $48,000 to $200,000 in five years. Here’s how I did it,” versus “Here's what I do in my nine to five.” Like, no one cares. 

I would say, beyond that, one of the challenges that I am consistently trying to overcome as a creator, right, is that I'm not a career coach. And I don't seek to be. I'm not a recruiter. So I actually have no power on getting people hired. So what are the limits that I can do as a creator, as someone that is putting out all this great information that obviously people want and need, especially in times like this? But then how do I actually direct them to real resources, to real individuals who can help make those decisions for them? I think that's probably something that I'm also still continuing to work through. Like I've talked about everything from, you know, budgeting to debt management to travel hacking, to now talking more about careers. And I think with that, it's like, you know, as a creator, I always want to make sure that I'm not just putting out free smoke, but actually helping people with my content. Like I'm not just trying to put out a bunch of pieces of content, just making people feel either good or bad about their financial situation, but I really want to help people with my content. So I think that's kind of where I'm at right now, is like, okay, great. Like I put out these fire pieces of content, obviously it resonates with people, but what can I do more as a creator to actually guide people to real resources, where they can actually get the help they need, you know?

Katie: Right. That makes a lot of sense. I do think that the visibility, representation, awareness thing, that goes a really long way, because I think until somebody sees someone else doing it, you have, I mean, I think we don't even realize the limits and the boxes that we put ourselves in. Like I used to think all the time, well, I have a communications degree, no one's going to pay me six figures. I'm not worth that. And I think until I saw other people, other women, making multiple six figures doing things, that I thought, “I could do that, like that's not beyond my scope of comprehension or intellect or competence.” You have to see someone else that's done it in order to believe that it's possible for you. So I do think that even with the pushback that maybe this is aspirational, or maybe your path or your success has been extreme, I still think there's a fine line, right, between aspiration and inspiration. And I think for a lot of people, they're going to see that and be like, oh my gosh, I had no idea that was even possible. And that's going to open a lot of doors. 

Cinneah: You're absolutely right. I think that's probably why my content has resonated so much with people, is I think, one, they're learning about career paths that maybe they didn't even know were possible, that they already had skills that they could be working in. Two, I think actually giving people a new way to see how they can break into some of these industries that kind of feel like they're super mysterious, and like, how do I get into FAANG companies? Like what skills do I actually have? And then I totally agree with you. That third point is like, yeah, how many Black women are even talking about this stuff? Like, it's not as common as we think. I really appreciate you saying that. 

Katie: Oh, thanks. Yeah, no, definitely. I think representation is extremely important, because if you don't see somebody that looks like you doing the thing you want to do, how are you going to know that that's possible for you? I think so much of that happens on a subconscious level too. Like I don't think we even realize that we feel those limits until we see someone defying them. And then we're like, oh, wow. So you've mentioned too, like, especially right now—and I assume you're referring to like, the current, you know, economic situation, the job market. It seems like—and I'm not super plugged into the status, so you correct me if I'm wrong, keep me honest here. It seems like the job market is still pretty good right now. I don't know if it'll stay good. But what types of industries and roles do you frequently tell people to pursue, like for a listener that is not engaged with your content yet? Is it all tech? Are there other industries or sectors or types of things that you're consistently kind of like, you know, making people aware of that you're a fan of, or, you know, has that changed this year? Can you give us a sense for that? 

Cinneah: Absolutely. So I love telling my followers to actually start their search in the financial services industry. That's where I started my career. And that's where I think that there is still a ton of growth and stability, even in these challenging times. I think often a lot of us think, oh yeah, I want to get into tech, but have no idea what the barriers to entry are. And I have found, even in my own experience, that the barriers to entry in financial services are often much lower. So say, for example, you're someone who wants to pivot into product management. You might have a faster way of getting your foot into the door of a financial services company, like a Stripe, an American Express, a MasterCard, a Citi, a PayPal, etcetera, getting that experience, getting that title, and then being able to use that and leverage that to go wherever else you want to go. Instead of trying to go straight to a big tech company, where you might be competing with other established technologists who have other experience that can kind of show that, you know, that they're kind of already in that industry.

And then in terms of roles, I mean, I love to talk about product management, because I mean, the product management industry has completely exploded even in the five years that I've been working. And why I love to tell people about product management is because there really is no other role, I think, that can allow you to easily get into a technical field to really get to some of those higher-paying—because it is a strategic role—without really any prerequisites. Like there are really no prerequisites to becoming a product manager. There is no, “Oh, everyone has to be PMP-certified to be a product manager.” That's not true. And I try a lot in my content to push against this narrative. If you want to invest in those types of certifications and that kind of learning, by all means do it, but you don't need it to become a well-paid product manager. Like I don't have any of those things as part of my background, I don't have any technical certifications, networked my way into product management, and learned on the job. And that's what's allowed me to build this career. 

And I also have a lot of nine to five hotties who follow me who have worked in probably like customer service, like executive assistant roles. I love to tell them about program management, because they have all of the skills of being a program manager, and don't even know that by simply switching the way that they talk about themselves, as they show up in these job interviews, as they craft their resumes, that they could be getting $30,000, $50,000, $70,000, a hundred thousand dollars more in income by just now showing up as a program manager and not an executive assistant. Like even just like the language that we use to talk about our skills and talk about the work that we've done. I think that is kind of also what I'm trying to help put into the ecosphere. Like there's plenty of jobs out here, and I definitely agree with what you said about, like, the job market is still hot, but I think the biggest gap is that so many of us feel like, well, do I even have skills to get some of these jobs? Yes! But like, when have you taken that time to kind of reflect and say, “Hey, I actually have a lot of these skills that they're looking for in program managers, like, why don't I just start to show up as a program manager?” And use that to your advantage, to get to those big obnoxious bags that we all deserve. 

Katie: Those big obnoxious…I love you. I'm sitting here grinning, because I just know there's someone listening to this that's an executive assistant, that's like tired of making what she's making or he's making. And I can just like feel the wheels turning preemptively. So I just love how actionable that is. And the note on the financial services industry in general. So I guess in a nod to that person who may be listening, who's like, “I want to make $200,000,” what would you tell someone who was frustrated with their current compensation? Maybe they are in a field or a role that's not highly paid, or maybe there's something else going on there. I know that is kind of a generic question, but I think I want to give somebody that actionable step of like, where should they begin if they know that they're frustrated, they know they want to make more—where's the best kind of starting point? 

Cinneah: I think the best starting point is to start where you already are, start at the company where you already are. So if you are in a role where you feel like you're being underpaid, overworked, and your skills are underutilized, start to have those conversations, one, with your immediate manager, to kind of understand, like, okay, I feel like I want to grow in my career here. Let's start to connect me with other hiring managers at the same company that I can talk to and kind of understand what they're looking for. Right? Like, companies want to retain talent, especially in a job market like this, where companies small and wide are completely being purged of their high-performing talent. So if you're one of those people who you're getting these good remarks, right? You have great reviews, performance reviews, every time they come around, use that to your advantage and start to see who else is looking for people like you with your skill set. What I've already said is that many of the jobs that we want, we are going to learn on the job how to do them. 

So I think a great example is like someone who is in a very like front office-facing, business-facing role already, start to see, like, do you have product managers at your company? Do you have program managers at your company? Like who can you start to talk to that's kind of more so in the more technical roles at your current company? Start to network with those people and kind of understand, how can I internally make the switch over to more of the work that you guys are doing? I think the benefits of that is you may be able to see an increase in your salary, staying at the same company once you move. Right? Say if you're a marketer now and you move to product management, that may come with a bigger salary because your company may see a product manager as a more technical role.

Katie: Can confirm. 

Cinneah: Exactly. Right. And then I think from there, really seeing, can you continue to grow in that? I think if you've exhausted those options and you just don't feel like you can do that internally, that's when you can start to say externally, okay, based on the skills that I have, what are those jobs that work for me? So I share this a lot in my free content. If you download my free guide linked in my bio, I give you some job titles, but it's really just starting to do that discovery work to say, okay, these are the things that I've really enjoyed in this role. These are the things that I feel like come easily and natural to me. What are the jobs that align with that, right? Like if I'm telling you, okay, you know, I got a lot of hotties who are like, yeah, I have a sales background. Do you know that you could be like a business analyst? Do you know that you could be like a tech sales lead? Tech sales leads make an incredible amount of money, right? Like, you already have those same skills, but you've never called yourself these other job titles, right? 

So that's where I would say start. I would say it's always easier to make an internal pivot, whether that's to another team, whether that's trying to get promoted internally, whether that's trying to like move into another part of your existing organization. Once you've exhausted that, or, you know, like me, you got to a point where you're just like, yeah, I’m making the most money that I can make at this job level. These people are not going to promote me fast enough. So I need to be looking elsewhere. That's when we can start to job hop. That's when we need to start saying, okay, what job titles are out here and what companies are hiring for these job titles, and then just get really focused in on your search.

I think it's very easy to get overwhelmed in the vast sea of hundreds of thousands of open jobs out here. But I think when you come in and really focus and say, yep, these are the two to three job titles that I feel like match my skill set right now. Like I don't need to up-skill, I don't need to get a certificate. Like right now, these are the skills that I have. These are the two or three job titles that I have. Boom, I'm going to hit the pavement. I'm going to use LinkedIn. I'm going to use my network and start to see what companies are already hiring for these roles and just focus my efforts there. I think that is probably the best plan for anyone listening who's really ready to, you know, get hired quickly. 

Katie: Wow. Okay. So I'm amazed, A) because you pretty much described exactly how—and I didn't have the forethought to do this, I didn't know that that's what I was doing as it was happening—but that's exactly what happened to me, is I was in marketing as a brand copywriter, switched teams to become a UX writer, didn't know anything about UX writing and just followed this, you know, followed suit of the principal UX designer on my team, learned a lot for two years, and then moved to Facebook and doubled my salary. So it all took the jump of like going on LinkedIn and changing my title from copywriter, where I never got any recruiter messages, to UX writer, where every single day I was getting recruiter messages. And I was like, weird, because I'm the same person and I have the same skills. And yet this title is…they're just flooding the door. So I love that you took such a generic question and were like, these are the 12 steps, in this order, do it this way. And it'll like, yeah, can confirm that that does work. 

Cinneah: And thank you for giving us your real-life, lived experience to show how possible it is. Because I think sometimes when I'm telling people this, I think they're just like, well, that's just like, too obvious, but I'm like, that's literally how it works. That's literally how it works. And one thing that you just said that I want to call out is, I think, especially, we get really overwhelmed with LinkedIn, but keep in mind, LinkedIn, just like IG, just like Twitter, just like TikTok, LinkedIn has an algorithm. So what did you do, Katie? You gave the algorithm more of what it wanted to see. Yeah, no one's hiring for copywriters. 

Katie: Tell it what it wants to hear, people. 

Cinneah: Exactly. But all these recruiters are already looking for these UX writers. So now we're going to bump Katie's profile up to the top of the algorithm because she's using the language that we want to see. And this is not to shame anyone. If you're listening to this and feeling like, oh wow, this makes sense. Like, yes. And really think about, what are the reasons why we have been consistently told to overcomplicate our career paths is because, I don't know, the powers that be clearly do not want women, especially, to have this kind of knowledge to know, oh wait, this company's not paying me nearly what I deserve. I can go somewhere else. Like I want y'all to fumble me. Like, I’m the prize. I will go somewhere else. And I think back to like, yeah, this was early 2020, right before the pandemic hit, I'm at AmEx, and I'm just like, I need more money. Like there's no way I'm going to be able to pay off all my debt on the same salary. And I remember having, you know, some people in my ear being like, what do you mean you're going to leave the company? Like you have all of these great relationships. And so many people want to see you win. Like, how can you give up that brand equity? And I'm just like, none of that shit is paying my bills. 

Katie: Actual equity, I will give it up for actual equity.

Cinneah: Period! And I really think back to, you know, I have colleagues who are still at those same companies at those same teams; our financial pictures couldn’t be more different. Like, in the same time that they stayed in those same roles and like, yeah, maybe gotten a merit increase or promotion here and there. What, I've like tripled my income, like to the point where I don't think about money, because my nine to five now is paying me enough that I'm not like stressing over the fact that like, I've always been a hard worker. Now I feel like my compensation finally caught up with the amount of work that I feel like I put into my career. You know? 

Katie: I used to tell myself, you know, I’d make $50,000, and I'd be like, this is the least amount of money you're ever going to make. Like, you're a stock that's going up. Trajectory is going up. So, same thing. It's like you're at over $200,000. You're like probably still the least amount of money you're ever going to make, which is pretty cool. There's a great deal of confidence too, in being able to do something as just concrete as like, screw it. I'm going to call myself a program manager. I'm going to call myself a UX writer. Like there is a degree of belief in yourself, and okay, fine. Maybe I don't know everything about it. I'll stretch into it. I think they've now debunked the statistics, so I don't want to quote this too strongly, but how like men will apply for a job if they're 60% qualified, and women won't until they're a hundred percent. It's kind of in that same vein of like, are you willing to believe in your own competence to stretch into things that maybe you're not a hundred percent comfortable with, but are more in line with your potential? 

Cinneah: Absolutely. I mean, what's the saying, you gotta walk around having the confidence of a mediocre white man? 

Katie: Yep. Amen. 

Cinneah: I can't think of a better scenario than going into a job where you're just like, yeah, I can be, I can do most of this. Like yeah. Knowing that you guys are gonna teach me everything else. Like I don't need to be an expert in any of this stuff. It is 2022, sis, you can literally go onto TikTok and learn how to become a UX writer, learn how to become a product manager. Like, like we just got to stop putting these limiting beliefs on ourselves, because it's literally impacting how much money we have. Like it's literally stopping us from getting the big bags. Yeah. If I listened to those naysayers back at AmEx, I'd probably still be sitting in the same role twiddling my thumbs. And now I'm a fully remote hottie and I'm just like, not being micromanaged, making more money than I've ever made. And also still being able to show up as a creator. Like it didn't take me that long to do it. I didn't have to put in all of these years to prove myself. It's like, my average that I've worked at a company is two years, two years, like two years is going to go by fast anyway, sis. Like, you may as well use it to say, well, yeah, in these last few years I've grown my salary by $70,000. Like that's, those are the wins that I want you to have, not, oh yeah, I took on all of this work and now I'm in the same place and I'm not promoted. No, no, no, no, no. That story ends today. 

Katie: Or like I'm cobbling together 14 different side hustles that pay me $20 an hour. It's like, I think that's the seven streams of income thing that gets tossed around where it's like, most of us honestly are better off devoting that energy to our actual jobs and doing exactly what you're describing. Thank you so much for being here, Cinneah, this was a blast. 

Cinneah: Thank you, Katie. This is awesome. I absolutely love what you're doing to, you know, just make money more relatable, more fun. And we need that. So thanks so much for having me.
Katie: All right, everybody, to close us out this week, we've got another Rich Girl Roundup. As a reminder, we will take listener questions every month. I'll put out a call for questions on Instagram. So follow @MoneywithKatie if you're not already, and we will pick one that feels interesting and widely applicable, and we'll answer it. As my standard disclaimer, I'm not a licensed financial professional. This is not financial advice. This is “What would Katie do in your situation?” This segment today is brought to you by Betterment, giving you the tools, inspiration and support you need to become a better investor. 

Here's this week's question from Neil. 

Neil: Hi, Katie. My name's Neil, and I'm calling into Rich Girl and Guy Nation from outside Philadelphia, PA. I'm 23 years old. I've recently graduated and I'm mulling over two offers. The first is for a year-long contract with the top company in my industry that pays a third better than a full-time position, with a short commute. The second is for a full-time position that has an hour-long commute, but a little bit better benefits. I've come to ask, when is a contract worth more than the full-time employment? 

Katie: This is a great question. And I think the answer will be a little subjective depending on how you like to work, Neil. I've done both contract engagements and full-time engagements. And I think most of us would generally agree that the full-time employment agreements are better from a few standpoints, like access to a 401(k) and employer matching that you likely don't receive as a contractor, health, dental, and vision insurance. And the sense of long-term security—though, if you're an at-will employee, that may be a perception that's not entirely grounded in reality, but I like that you're highlighting that the contract role pays 33% more than the full-time role, because I think people will find that's pretty common. This is because providing all of those full-time benefits costs money. For example, the Kaiser Family Foundation found the average cost to an employer to provide health insurance to an employee and their family was $16,000 in 2021. This is why I'm such a proponent of universal healthcare, as a side note, and believe it will actually make our economy more competitive, because employers won't have to bear the brunt of ensuring citizens. That 16,000 bucks is considered part of your total comp as a full-time employee, which means it's money that you're not being paid as a salary. 

So if I were weighing these two options myself, and all else was considered equal—and by that I mean I'm equally interested in both companies, in both jobs—I'd probably try to understand what the true differential is between compensation, by assessing the true value of those benefits. For example, how much are you paying for health insurance as a contractor? How does the coverage compare, if you can find out with respect to your deductible and your out-of-pocket maximum as a full-time employee. Putting numbers around it, for example, maybe you’re paid $33,000 more by the contract role and your health insurance costs to provide for yourself are $10,000 per year. Well, you're still coming out net $23,000 ahead. Same with the 401(k). If you don't have access to one as a contractor and you need to use IRAs instead, you can calculate the difference in tax savings. For example, if you're in the 24% bracket and you contribute the full $20,500 to a 401(k), you'll save $4,920 on your taxes, plus any matching contributions you would have received from your employer. But if you're a contractor, you'd have to use an IRA instead, with a $6,000 limit, which only creates $1,440 in tax savings, for a net difference of $3,480 bucks and whatever the match would have amounted to. In this example, though, it's clear that you are still in the black as a contractor, if the pay difference is that drastic. But it'll depend, of course, on the actual numbers, the cost of your health insurance, the marginal tax bracket you're in, and whether or not you actually plan to leverage a full 401(k) plus the employer match and any other monetary benefits you may have gotten from the full-time role.

Being a contractor can have some benefits too, since you're hourly. They have to pay you overtime if they require you to work more. Whereas the salary doesn't typically come with that perk. So thank you for the question, Neil, and I hope that helped. 

All right, folks, that is all for today's episode of The Money with Katie Show. I will see you next week, same time, same place. Our show is a production of Morning Brew and is produced by Nick Torres and me. Sarah Singer is our VP of multimedia, and additional content editing comes from our lovely senior editor, Henah Velez. Sam Cat is, as always, our vice president of chaos, who turns recording a podcast into an obstacle course. And Jojo Beans is our chief of woof. Especially if we are recording when the FedEx man comes to the door.