Fearless Coaching

“I’ve been slowly checking off all the adjustments we outlined together, It’s been an incredible process: I’m already seeing some awesome returns… I feel really fucking powerful.” – LE 

“I can’t believe how many questions you answered for me and how clear and simple you made things seem. I feel super motivated and excited about our saving goals!” – KF, filmmaker

Ready to transform your skills, capacity, and relationship to money? I’m here.

I work with individuals, partners and couples, and small business owners. For some, one-off co-creation sessions get you what you need — and for others, recurrent sessions move you forward towards bigger goals.

When and how can we meet?

Sessions are available: Mondays 10am-10pm EST,  Tues – Thurs 6:30p EST – 10:30p EST, and Sundays 1p EST – 10p EST. You’ll choose the time that works best for you when you book.

We can meet in person in Brooklyn, NY or via a Zoom video call. You’ll get an address or link in a confirmation email you get after you book the session.

When you book your first appointment, you’ll be invited to fill out a coaching intake form. From the info in that, you’ll be given optional customized prep work for the appointment. I recommend booking an intake at least a week out so you have time to do any prep work and ruminate on the work beforehand.

What happens at an appointment? What’s the approach?

My coaching practice is informed by design thinking, agile, an asset-based and trauma-informed approach, and compassionate communication.

Sessions consists of strategic, laser-sharp, compassionate financial education and strategy development customized to you.

Based on what you stated you want to focus on, I use an agile approach to identify and prioritize the most valuable problems to solve, and we focus in on those. As we go “down the list” of what you want to work on, we’ll spend a little less time on each thing. Expect to leave with a customized resource list and action steps document, and a set up spending, savings, or debt plan. Oh, AND with lots of ideas, excitement, and hopefulness. 🙂

I honor intersectionality, want you to have stability, understand artist, freelancer and DIY priorities, and hold progressive values at the core of my work. If you’re here, I LOVE that you are already thinking ahead, it’s only going to increase your successes!

Do you want to make sustainable plans for a budget, a large savings goal, or a job transition? Want to work through money with a partner or finances from your family? I am awesome at:

“Thank you so much for the awesome session — I have been flying high and talking about it all day. I honestly feel less afraid (not yet quite riding free fearless money) and I can’t wait to put your tools and suggestions to work. I already started!” — Emmett F., queer musician & digital storyteller

Session Options

Learn more about coaching packages and sessions below, then book your time and get started!

Individuals: Self-Guided Training

Starting your Budgeting or Savings planning? Stressed cuz you have debt and yet want to save money? You may be best served in a self-guided two hour online course, which is about 1/3 the cost of 1:1 coaching, and covers basics of getting yourself a spending plan you can succeed at.

Individuals: TO BOOK A 1:1 APPOINTMENT

An initial 90-minute strategy session is $175, with sliding scale available ($79-$245). Ongoing one-hour appointments are $110, or less within a package. [more info]


For romantic, platonic, or business partners (up to 3 people), a two-hour session is needed to cover allllll the things there are to work on.

  1. Click here to fill out a coaching intake form
  2. Book a date on the calendar & confirm your appointment here
  3. [more infoTwo hour intake appointments are $245, with sliding scale available $295-$165.

Small Business owners: TO BOOK A 1:1 APPOINTMENT

  1. Click here to fill out a coaching intake form
  2. Book a date for your initial intake appointment here,
  3. [more info] 90-minute strategy appointments are $175, with sliding scale available ($79-$245). Ongoing one-hour appointments are $110, or less within a package.
  4. BONUS: Get access to the Hacks Lab library if you book coaching package!


For community groups and larger organizations (4 people+) the customization needed to cover what you want looks like: having an initial planning meeting, workshop/session development and delivery, and follow-up custom documents. Since that can be a medium amount of work or a LOT, these sessions start with a deposit and we’ll negotiate the cost depending on the depth you want.

  1. Click here to fill out a coaching intake form
  2. Book a date for your initial intake appointment here,
  3. [more infoCustom workshops are $595-$1,500+ and include pre-planning and customized content.

“With Hadassah Damien I gained the skills and perspective I needed to stay calm and focused to make smarter financial decisions.  It was as advertised – judgement-free real talk informed by life experience. I can’t think of a better form of self-care than to give your financial life the attention it deserves through Ride Free Fearless Money. I have a plan for what to do with my finances – which means I can dream bigger dreams than I thought possible.” — S.G., nonprofit lawyer.

If you loooooove testimonials or want to read some interviews with me, check them out here.

I’m rearing to go! I’ll book a one-off session intake appointment here: