Money, Anxiety, Work

Last Thursday, I spoke on the intersection of money, stress, and entrepreneurship for a Plutus Voices event in NYC. Here’s the text!

I want to take you on a little ride with me. First, imagine this: I’m a fresh associate in an ill-fitting polyester suit working at an investment management firm. It’s 2009, the market is bottoming out.

Our clients are firing us like mad. Back then, clients had to fax us a letter to terminate us as their manager (there was no such thing as Docusign). On a really bad day, in what felt like a perfect allegory about working in investment management at the time, we were getting so many client termination faxes that the fax machine literally burst into flames.

Good times. Anyways, how’s your job?

I’m Amanda and I run a business called Invested Development, where I teach women to invest.

The Plutus team asked me to come and talk today about the intersection of money, stress, and entrepreneurship. So, I am going to talk about my journey, how I began in the corporate world and why I made the shift to self-employment — SPOILER: it’s because my corporate job sucked.

So let’s portal back to 2008, when I began my career in investment management. After making it through a massive round of layoffs during the recession, I was promoted to the role of Investment Counselor. This was a client-facing position and it was a coveted role at the firm. I worked directly with high-net-worth clients. It was a great job for a young woman and I learned a ton being there. But I also kinda fuckin’ hated it.

The firm I worked at was rigid. Hours were not flexible, and they were long. And these weren’t easy hours, either. Our clients were angry and took it out on us. So many yellies. 

As Investment Counselors, there were about 200 of us, and only a handful of women. I was basically always and forever backstroking through a sea of bro. [Makes exaggerated backstroking motions.]

As the years passed, I grew really tired of this job. I had enough money, for which I am so grateful, but helping the rich get richer wasn’t it for me. And I despised the firm itself. The hardball attitude they encouraged wasn’t congruent with my significantly more, ahem, lax take on the importance of the work we were doing.

And then, there was always an unspoken understanding about the firm: They would pay well, but the rules of working there—like the 6:30 am start-time and the ten-hour day—were non-negotiable. And if you don’t like it, well, then, nobody is keeping you here. [Gesture towards the door like an uncompromising asshole.]

But such a Faustian bargain, even when it’s openly understood, is impossible for so many: Working mothers. Single parents. People who need to take care of family members, which is a responsibility that overwhelmingly falls on the back of women. People with disabilities or those living with mental health illnesses. I could go on. Many of my direct colleagues and all of my managers fit a predictable Don Draper formula: they were overwhelmingly white, male, and had a wife.

I personally dealt with sexual harassment and misogynist attitudes that absolutely affected my pay.

I was also drinking heavily outside of work and money was basically falling out of me. Looking back, I see how unhealthy the extremes of my life were. I struggled then (and I struggle now) to have a healthy relationship with alcohol, in a similar way that I know others have disordered relationships with eating, shopping, sex, money, and food—and I know firsthand these tendencies can be exasperated when you hate your every day.

[Allows people to JUST SOAK in that lil moment of unexpected vulnerability!]

More than 30 million people are entrepreneurs or self-employed in this country.

According to the Women’s Business Enterprise National Council, the number of women-owned businesses has increased by 58 percent from 2007 to 2018, compared to small business growth overall, which increased by only 12 percent. 58% growth versus 12% growth. Hmmmmm [gently strokes chin].

Interesting. One the one hand, this statistic may show that women are smilingly creating work that gels with their schedule or they have these really witchy, intuitive ideas that they know would make great businesses: These are what the study calls “opportunity entrepreneurs.”

Compare that to what are called “necessity entrepreneurs;” those who want to find quality employment but who cannot. The report says that “higher unemployment rates, long-term unemployment, and a much greater gender and racial pay gap led women of color to start businesses at a higher rate out of necessity and the need to survive, rather than a desire to seize a market opportunity.”

In a way, I am a necessity entrepreneur.

I am part of this statistic. Traditional work did not work for me. I had a good idea and a deep knowledge that I could turn into a business, yes, but if I’m being honest, a huge part of the reason that I made the shift to entrepreneurship is because I was scared to switch over to another job, at another firm, just to deal with the same ol’ shit.

For me, it is ultimately a blessing. I am mostly happy. But let’s be honest: Entrepreneurship is a slippery little fish.

But the switch to entrepreneurship, often done for freedom from one type of life, can itself end up being a cage; and comes a whole other set of anxieties.

And hey, I don’t have the time, today, to list them all! Instead, I thought it’d be fun to choose three anxiety-inducing elements of self-employment that I personally meet with mixed results: Something I’m good at, something I’m conflicted by, and something I have little control over. I’m going to lay forth all my problems so the real experts can come up here and gather me. [Points to Real Experts/Speakers 2 and 3, Jamila from Journey to Launch and Kara from The Frugal Feminista.]

First, let’s start with something I’m good at: 

Managing the flow of money in my business.

Now, this is not because I am some especially diligent bookkeeper. Instead, it’s for two main reasons:

1. I’ve always had an “anchor client,” which essentially means: I do work that I don’t wanna do for a steady paycheck. When I started this whole business-thing, I bartended for not one, not two, but 2.5 years (!!!) to get up and running. Nowadays, I do financial copywriting on many days of the week. Would I love to quit that job? Of course I would love to frickin’ quit that job. But for me, the trade-off of knowing that I have a steady paycheck is worth it—even though this means that my business growth is just going to be slower.

2. When I work with women entrepreneurs, here’s somethin’ I won’t shut the hayl up about: Save money, even when it feels scant. Do what you can to generate a profit. I see so many entrepreneurs cycle everything back into the business. And I get it!! We want to nurture our babies, our most important investment.

Well, don’t. Here’s the thing. I may not do this forever. And if one day I walk away from this business, you better believe that imma have something to show for it. My business exists to serve me, I do not exist to serve my business.

Next, something that I am conflicted about:

The glorification of overwork within entrepreneurial communities.

Ever seen a meme that says shit like:

“The best thing about being an entrepreneur is you get to choose which 16 hours a day to work.” When I see this type-a thing, I can’t help but think: HOW DEEPLY LAME. But then also, damn it’s kinda true.

Imma start with a wide lens here: A capitalist, and increasingly entrepreneurial, system, intrinsically requires that we “hustle” and “grind.” It’s built into the model. So, I DO NOT blame any one individual for trying to frame hustle as a good thing; people are simply trying to make the best of the reality that they’ve got.

There was a great article in the New York Times earlier this year that defined performative workaholism as a “glorification of ambition not as a means to an end, but as a lifestyle.” It’s hard not to get sucked in, and I am experiencing it as an entrepreneur to a much greater degree than when I worked in a corporate job.

If you spend any real time around entrepreneurial circles what you’ll notice is that there is this obsession with overwork that is so humorless and self-promotional and devoid of nuance; COME AT ME with your “the best goes to those who obsess” Instagraphic. No. For me, obsessing about work is not a way to live a happy life.

This is such a fine line that we walk, the message we send when we celebrate overwork in ourselves. I don’t expect everyone to agree with me here, and that’s okay, but I tend to think we could all be happier if we framed success in a more community-based or even feminine context. (In many ways, I do not like the world that men created, I don’t want to “lean in,” especially if that means leaning into a hierarchal system that when I’m on the top, requires someone else to be at the bottom. Some days, I want y’all to lean the fuck out.)

Ambition solely for ambition’s sake can be the diametric opposite of being thankful for what we do have and for what we have accomplished. Within me, the overwork mentality breeds competition and a culture of comparison AND creates anxiety, financial and otherwise. Like in 2019, I NOT ONLY compare myself to women with better hair or clothes, but to women with more success. I personally think we need LESS of this in the world, not MORE of this.

And let me make it clear, again, that I am no beacon of morality on the matter. I’m confused. Sometimes, I feel aligned. I feel like my relationship with ambition is healthy. But other days, I work too hard and don’t take care of myself AND I CRAVE that SWEET, SWEET external validation. Hey, I’m only human! 

Lastly, something I have little control over: 


I Can’t talk about anxiety and money and entrepreneurship and not talk about healthcare. If I quit doing what I’m doing—it’s because of unspeakable daily loneliness—JUST KIDDING—it’s because of healthcare.

I won’t say too much, except for this: If you believe that healthcare should continue to be tied to a dying traditional employment model and/or marital status, I gently ask that you please consider the fact that this stance is further punishing those for whom traditional employment has already failed. I deserve reasonable access to healthcare. Period.

Thank you, Plutus, for creating a space for us to come and talk about this important topic. I feel better already.



  1. Steveark on December 10, 2019 at 9:42 am

    When you said people faxed you at work I couldn’t reconcile that with your photo of somebody obviously too young to have used that old tech. I’m an irrelevant boomer and still remember when you were a big deal if you got a fax at work on the one fax machine that served 400 people. Who knew the investment community still used them in 2008! Great post, well written and I’m sure well spoken.

  2. DB on December 10, 2019 at 10:38 pm

    Very well put and thanks for annotating with movement cues – I can see you trying to grasp that slippery fish. You’re doing great!

  3. SwiftChat Live Chat App on December 11, 2019 at 7:00 am

    People think entrepreneurship is easy but it is much more difficult than 9 to 5 especially in initial years of business.

  4. Danielle on December 18, 2019 at 9:52 am

    Love this. I am just now breaking out on my own after 20+ years in the same career/field.

  5. vurtil opmer on January 4, 2020 at 4:44 am

    Utterly composed subject matter, thanks for entropy. “Life is God’s novel. Let him write it.” by Isaac Bashevis Singer.

  6. Done by Forty on January 6, 2020 at 8:26 am

    I’ve never leaned towards entrepreneurship, mostly because I have so much trouble spelling it.

    The point about healthcare is such a big one, and something we struggle with in our FIRE plans as well. Tying insurance to traditional work has so many unintended (or hey, maybe intended) consequences.

    Absolutely loved the flow of this piece, too, friend, especially the stage directions. 🙂