Money Stories: Hadassah (Ride Free Fearless Money)

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Money Stories: Hadassah (Ride Free Fearless Money)

BLOGBillie Simmons

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Image of Hadassah Damien from Ride Free Fearless Money

Money Stories is a new series designed to start the conversation about how being LGBT+ has affected our financial lives and hopefully help people feel inspired to talk more openly about money! Share your stories with me at

– Billie

Hadassah Damien is a professional strategist, award-winning queer artist, entrepreneur, facilitator and educator. She founded Ride Free Fearless Money, an iconoclastic blog and finance consulting firm, in 2015 with the mission of stabilizing progressive communities by empowering people’s relationship to money. 

Ride Free Fearless Money helps individuals, partners, business owners, organization leaders, and cooperatives to create actionable and equitable financial strategies. Damien shares writing and online courses, collaborates in strategy sessions, and facilitates online trainings and workshops.

Ms. Damien is Brooklyn-based, with deep roots in working-class Western NY. She puts the values she inherited both into practice and under microscopes in her work. She has an MA from the CUNY Graduate Center, an Honors BA from the University of Toronto, her professional training and work is in communications, civic technology, and human centered design, and she’s an Accredited Asset Management Specialist from the College for Financial Planning.

When was the first time you thought about money?

The first time I thought about money was early on, as my parents made it clear to me we didn’t have much of it. The message was clear: be frugal, make things last, use what we have, creativity is more important than new gadgets, and you’re not getting new stuff so don’t ask. On one hand, these are (mostly) great values and I’m grateful they were instilled in me because they’ve lead me to be able to easily save money and not get stuck in cycles of consumer debt. On the other hand, the purpose of money isn’t to be freaked out by it and save all you get for a rainy day. Currency is meant to be a tool for exchange. My learnings later in life were about balancing rainy day preparation — which is important for those of us without financial safety nets — with using the other money I have.

What was your “aha” moment with money?

I always knew money meant the power to make decisions — I just thought for a long time I’d never have that power and would have to get creative with my decisions. But, in my 30’s, I started challenging myself to think about money as a tool, rather than simply a limitation or source of stress. That got me curious and wondering how it worked – and lead me to be willing to take what felt like risks at the time with various investing methods, because I understood them a lot more.

Once I understood it, I learnt what felt risky because it was so, and what felt risky because it was new, and could work around that. Investing can feel freaky because it’s not everyday you sit down and go “how can I make some money for my future?” but a nice boring reliable recurrent investing plan is one way you can go from precarious to prepared for the future. For folks who experience marginalization in everyday life, or who have historical inequality behind them, this can be a real game-changer. 

How has being LGBT+ impacted your relationship with money?

As a white cisgender lesbian, I haven’t experienced direct discrimination based on being queer, but for a long time I felt very alienated by status quo culture — hetero, middle-class, kahki-wearing white people. I didn’t see all the energy and passion I experienced in my creative, radical, queer life reflected by the status quo, so after trying out a day job and having a terrible boss and experience, I tapped out and worked lower-paying jobs in community. I also decided that I would never end up in a situation ever again where I had to suck it up to a cruel boss because of money — I saved an emergency fund, strategically built up all kinds of skills, freelanced on the side of other freelance, and picked jobs where the culture was intentional and cooperative. It was great; wonderful people, and excellent learning – but at some point, I realized I needed to make more money or I was going to struggle to support myself, forever. 

Queer and progressive people can build amazing businesses because we are more likely to be aware that domination culture is part of the problem, and now I work as a business and experience strategist, human-centered designer, and facilitator with organizations. I’ve made it my work to make work not suck, to center people by design, and help money not to be scary.

What are your financial goals for the future?

As a financial coach and consultant, I’m always asking others this question!! My goals include buying a home in the next year or so and paying the hell out of it so it’s paid off and I’m FI by 50 (I’m 41 now). I watched my mom grind away working low-paying jobs until she was 70 and I am highly motivated not to live that way, so another goal is to make enough money to be easily able to help her, give back, and have money to hit my goals. 

Favorite LGBT+ business (online or IRL)?

Ride Free Fearless Money is my personal brand, where I blog all about how money works from an intersectional and progressive perspective, as well as workbooks, courses, and classes. Let’s Talk About Money is the consulting I do with organizations, schools, foundations, etc:

Otherwise, my favorite queer business was the queer-owned local coffee shop that closed recently, so my 0.02 is to go support your local queer-owned brick and mortar business because they are struggling right now!

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Billie Simmons

Co-Founder, Chief of Staff at Daylight