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Beyond the 9-to-5: In Conversation with Chelsea Fagan

Chelsea Fagan’s videos are credited for making me finally understand stocks — no small feat, since both economics teachers and my dear parents had been unsuccessful at cracking my skull. With just the right number of pastel pillows and aesthetically pleasing plant combinations, her YouTube presence combines an impossibly chic visual appeal with deep cuts into the intimidating world of budgets, credit cards, and investing.

All very inspirational: naturally, I rolled out of bed 20 minutes before the interview and failed to get out of pyjama trousers before logging on, feeling like the absolute opposite of the accomplished woman I am about to call. Outside of being YouTube’s honest, feminist financial voice, Chelsea Fagan is the founder of The Financial Diet (TFD), a Manhattan-based, all-women media company dedicated to talking about money: what it does, how it intersects with our lives and social structures, and how to best cultivate a relationship with it.

One technical mishap later, we rolled into a conversation about TFD’s 2021 vision. Fagan’s followers on Twitter are familiar with her frequent updates on TFD’s workplace policies, and I was curious to learn more about flexible work-from-home and 35-hour work weeks from the perspective of a CEO. Fagan’s voice lit up, and I could sense palpable pride in her tone. ‘Before COVID we had a very flexible work-from-home policy where employees were only required to be in the office three days a week. We had a relationship to work-life balance that I think was already […] skewed more towards life than many employers, especially in media.’ Pre-COVID, TFD employees enjoyed ‘Summer Fridays’ in addition to flexible remote-work arrangements, and Fagan noted that neither productivity nor company revenue dipped.

However, she is hesitant to exaggerate the impacts of her workplace culture experiments. ‘The model that we have, which is essentially having leadership that feels very strongly about these issues and makes these choices, is unfortunately not very scalable, because quite frankly a lot of employers don’t feel that way.’

Fagan has made no secret of her politics: she supported Sen. Bernie Sanders in the 2020 Democratic primaries, and our conversation frequently circled back to systemic ills in American capitalism. On the subject of exploitation, she does not mince her words. ‘Especially when you get to large corporations and, of course, publicly traded corporations, their loyalty ultimately is to their shareholders and their bloated executive packages, it’s not toward their workers. And in many cases their workers’ interests can be diametrically opposed with what is profitable.

‘[…] I do believe that when implemented properly, a lot of these practices are very good for the health of the business. My business […] operates this way and it’s been fantastic for the overall health and sustainability of the project, but I know that it doesn’t scale. I think the answer in a much broader sense is, of course, worker empowerment [and] unionisation. It’s really grassroots, and unfortunately I can’t do that for every worker in America, but I hope that by, in a very small way, setting an example, at least in our own industry of media, we can start to shift the narrative a little bit.’

Why run a business helping individuals get good at money, if the problem lies with an entire system rigged against much of her young audience? Fagan says that this dilemma is ‘the tension at the core of everything we do.’ Referring to TFD’s expansion into Spanish-language content for Latino communities and her experiences working with underprivileged individuals, she adds a game metaphor for explaining American society’s unspoken financial pain. ‘As the game in which you’re operating becomes more and more rigged and more and more difficult, it’s very, very hard to put too much of the emphasis on individual choices and individual responsibilities. You don’t want to get into […] victim-blaming someone if they happen to be in a tough financial situation, because the majority of what determines our financial outcomes in the US is the family to which we’re born and the circumstances to which we were born.

‘Most of wealth is inherited and poverty is very difficult to escape once you’re in it. Especially as the communities […] get more and more marginalised, it’s quite frankly very difficult to to find the right balance between personal responsibility and social awareness.’ Nevertheless, her work has convinced her that individual leveraging power through financial literacy is meaningful. ‘If I had to sum up the ethos of how we frame this information and how we communicate to our audience in a soundbite, it would be to say: the game that we’re playing is rigged. All of us are playing a rigged game here in the United States when it comes to building our financial stability, there’s no way around that. However, while we’re playing this game, it is in your best interest to play the best game you can possibly play.’

The decision to make accessible financial media her life mission was an intensely personal one for Fagan. In video essays, online articles, and public talks, she frequently harks back to her own money-troubled young adulthood. Rarely can anyone talk about sinking credit scores and being arrested for debt with such refreshing clarity, and it’s clear that Fagan has moved past financial shame. ‘I’m someone who went from experiencing pretty substantial poverty early in my life to becoming more financially stable, and it’s not an exaggeration to say that having money and financial security is like playing with a cheat code in life. It’s very difficult to get over that hump when you’re on the other side of poverty or not having enough. But ultimately, it is not going to help you and it’s not going to help your family if you abandon the game and just say, “well, I’ll never win.” I understand that; I think that’s a very human reaction and it’s very, very hard to find motivation to make the right choices when you’re working with so little. But you’re still better off making those better choices.

‘And in the meantime, especially [for] those of us who do have financial privilege, we can walk and chew gum at the same time. We can advocate for people to improve themselves in terms of their financial literacy and the choices they’re making, and simultaneously advocate for better policy and for better social responsibility with regards to quality of life.’

Where and how do we find the capacity to ‘do both’ — seek both individual and systemic change — at the same time? I ask Fagan about ‘selling-out’ for graduate jobs and ethical conflicts in careers choices. She isn’t familiar with the phrase: Fagan dropped out of college in 2010 to start her career and never obtained a degree. Nevertheless, is it possible to balance the pursuit of financial wellbeing with values?

To Fagan, the answer depends on who you are. ‘I do believe that as people achieve higher and higher levels of financial stability and freedom themselves, it becomes something of an ethical obligation to […] do whatever you can to make sure you’re not just getting on the hamster wheel of hoarding money for yourself.

‘Quite frankly, especially at elite universities, many of the most privileged children who come from wealth and really would have a lot of options will often go to extremely high paying jobs that are probably pretty detrimental to society. That’s not good, but it’s understandable if people’s central values and self worth […] is centred around how much they have and how much they can afford.

‘And then on the flip side, especially in more progressive circles, you have the opposite pressure […] which is to do something that is true to your values but perhaps will keep you trapped in a cycle of poverty, because a lot of these jobs that are very important are also terribly paid. If you have a massive debt burden, which you likely would if you’re coming from an elite school and you didn’t come from a wealthy background, you could be signing yourself up for a pretty hand-to-mouth life for some time and not be able to do any of the things that you would want to do, like maybe own a home […].

‘So I don’t think there’s a right or wrong answer to the choice of how you position living up to your values versus achieving financial stability for yourself, but I will only say to people who are […] struggling financially, who come from a disadvantaged background, [and] who don’t have a lot of resources: you do not owe purity to anyone. You are allowed to prioritise your stability. You are allowed to prioritise your financial security. And you don’t have to explain that to anyone.

‘It’s often the people who have the financial security who are going to really drill down on someone for opting to do the same thing. But I will say again: once you do have financial stability, resources, and choices, I do believe that if you care about living in a more financially just society, that it is an ethical obligation to some capacity to make sure that you’re paying that forward.’

We return to the emphasis on life beyond work, and Fagan believes that such a shift can also be value-based. ‘It is important to remember too that your nine-to-five job is not the only place that you can have an impact on the world around you. You can have a job that is stable and allows you to live a functional life, and with your additional time you can do things that are contributive [to] building the community around you and helping improve the situation in which you’re operating; it doesn’t have to always be through your job.’

In terms of the future of work for Gen-Z, Fagan, a self-proclaimed millennial, is cautiously optimistic. ‘When it comes to the concept of work, we have seen over the past century that human productivity has increased by leaps and bounds. A lot of that is a result of our ability to synthesise our human capabilities with all of this technology. We’re producing more than ever, but we’re still stuck in a very old-fashioned concept of what it means to work; it’s really about an arbitrary number of hours that was decided a century ago.

‘I think the broader question is: how do we get to a place where we are not centering our lives around work? It can be an important facet of our personality, of our identity, of our validation and all of those things — I think it probably always will be for certain people — but it shouldn’t be the absolute centre and majority share of your life. And I don’t think it needs to be, because productivity as we’ve seen has skyrocketed, people are producing more than ever, and that’s completely decoupled with their average wages.

‘[In] professional managerial class jobs, if you’re even remotely competent at the job, you don’t need to be sitting at your desk for nine-plus hours a day. You just don’t.’ Her line of argument shaping up around some echoes of David Graeber, Fagan laughs a little as she pictures a potential future that allows ‘automation and technology to […] liberate workers, and to liberate people and to free up more of our time and resources. […] It will only be a net positive for society, because right now we are forcing people to waste not just a lot of their time, but a lot of their identity and a lot of their potential on planting their ass in a chair for fifty or sixty hours a week at many of these jobs, if not more.’

For one last question, I ask that classic aspiring-creative query on the values and limitations of unpaid work. Fagan sees social media advocacy and websites like Glassdoor as having had important impacts on workplace transparency, but also recognizes the internet’s inherent complexity. ‘The internet has had [an] inherent effect of devaluing a lot of work, because so many people can produce it, and a piece of work can be lifted and manipulated and repurposed and reproduced in seconds for all kinds of purposes. It’s not always clear who is the victim of that versus who is the beneficiary of that.’

She raises the example of one of TFD’s recent clients: a young woman whose Twitter video went viral. Her work was ‘repurposed left, right and centre’ by major media corporations, but she received no monetary compensation. Fagan sees more nuance in the story: ‘the original viral video she made no money from, but […] as a result of that virality and as a result of that ability to reach an audience, she has been able since to build a very lucrative career off of that attention. Certainly, it doesn’t work like that for everyone; there are shades of it.

‘We as a company at TFD do not do any unpaid internships […]; people don’t work for us for free. However, I got my career start in media distinctly by working for free, and had […] a similar experience to that young woman who went viral, in the sense that the visibility that that work, and that the internet was able to give me, I was able to [then] parlay to my own benefit and eventually start my own company through it.’

While recognizing the visibility economy’s many possibilities, Fagan makes thoughtful counterarguments. ‘We have to understand that it’s a double edged sword, the exposure and the transparency and the communication of the internet versus the inherently devaluing of it.

‘My biggest piece of advice to anyone starting out in their career is to be an opportunist. Look at everything as an opportunity, [and] weigh it as a cost-benefit analysis in terms of its future possible benefits for you. If you do something unpaid or underpaid, be very clear about why you’re doing it and what leverage it might give you in the future.’

Fagan ends on a resonant and honest note, on-brand as always. ‘Remember that these employers and companies that are leveraging you for free or for very little, they don’t care about you. So use them in the same way: use them for a byline, use them for a connection, use them for a step up.

‘I’m glad I did the things that I did when I was at the beginning of my career because I did leverage them as opportunities. I think having that real opportunist mentality is the only way to square the circle of the simultaneous level of visibility and devaluation that you will find in a digital job marketplace.’

In no way is the tension between individual action and collective problem-solving resolved; indeed, it seems that Fagan does not anticipate such a resolution. We haphazardly survive the ethical chaos of money in an inherently unjust world, hopefully doing all we can to pick the system apart. Such an idealistic, transformative task calls us to analyse employment as an honest tradeoff while imagining identities beyond work. I leave the call with questions still, but more interesting ones for the coming years and decades: how do we balance the need to cope, financially and otherwise, in the present with planning for a radically unpredictable future? What about the looming horizon of climate change? At the very least, I’ll be tuning in to TFD for more advice.

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