This spring, we’re focusing our energy on community-building – from our recent political action workshop to helping you retool your budget to be less consumption-minded. And being more community-focused means putting your dollars where they can make the most impact: through a community foundation that’s fueled by people in their local region. 

For those of us here in the NYC area, The New York Community Trust is the region’s trusted community foundation, playing a vital role in making life better for everyone, from those struggling to pay the bills to immigrant families and LGBTQ+ communities, among many more. With more than 2,200 charitable funds created to benefit NYC and beyond, a Donor-Advised Fund at The New York Community Trust is the best first step to make a big difference. A DAF works like a charitable checkbook that lets you give tax-smart, eliminate paperwork, and use a variety of assets. Your fund is invested for growth, meaning your money often goes further than through a simple donation.

Level up your giving to the causes you care about with The New York Community Trust. 

What's an extrovert to do when her literal personality type is the most expensive one?

As a 98th percentile extrovert (according to Myers-Briggs and every other personality assessment I've ever taken), I know first-hand how expensive building community can feel — financially and emotionally. Being an active participant in your own life, especially when you live in a major city, often requires spending money — and it's exasperating when you keep shelling it over only to reap so little for your efforts. Whether you're buying your way into the rooms where your people are or putting a little towards trying something just for the sake of it, it can all start to feel frivolous pretty quickly. But I want to offer a different perspective: some of this is simply the cost of showing up.

Before being employed full-time, I only budgeted for my absolute bare necessities (rent, groceries, bills). I didn’t have money to “waste” on trying new hobbies or attending events. Now that I’m in a better position, ridding myself of the scarcity mindset that was protecting me and helping me survive has been a challenge. But, luckily, putting myself out there more and more to help retrain my POV has helped so much. 

And I’m not here to be preachy! If I’m going to ask you guys to do something hard, I’m willing to do it too so, here it goes:

I nearly cried in a figure drawing class recently. Twice. Yeah, you read that right. 🫣

It was $40. My friend had invited me weeks prior, and I was so excited to go. The vibe was relaxed and everyone in the room was (supposed to be!!) a beginner. And yet, their renditions were beautiful. Mine, meanwhile, was a blank page streaked with eraser marks. Nothing I tried was quite “good enough.” 

I literally stared at it for the better part of an hour because I couldn't figure out how to even start. The instructor kept bypassing me to help others and I couldn't decide if that made me feel invisible or relieved. The tears were right there, brimming, because, first of all, I despise feeling inept and mediocre — it’s an eldest daughter flaw I’m working on. Second, I couldn’t help wondering if I’d just wasted 40 whole dollars on this. That’s money I could have stretched elsewhere!

I refused to let my tears fall because, of course, I’ve got that dog in me. But, like...I just wanted to leave.

I kept turning that $40 over in my head on the train ride home. Was it really wasted?

Ultimately, I’ve decided no, it wasn’t. 

And more than that — I think it might be some of the most intentional money I've spent in a while. Not because I learned anything profound about drawing, but because I'm learning, slowly, that the cost of participating in your own life — of trying things, of showing up to rooms where you don't yet belong, of being a beginner somewhere new — is worth budgeting for. It just doesn't always feel that way in the moment, especially when you're blinking back tears over a blank page while everyone around you is basically Picasso.

*****

As a finance media company, we see a lot of talk about intentional spending. “Optimize your budget, cut what doesn't return value, be strategic about every dollar.” And I believe in some of that. You've read enough of my newsletters to know I track my spending, I set goals, I pay attention. But there's a whole category of spending that doesn't fit neatly into an ROI calculation: the cost of showing up imperfectly. Of finding your people. Of being mediocre on purpose, in public, and surviving it. What is the return on investment of finally feeling like you’re allowed to try? Of being in a room full of people who don’t require perfection — just the courage to make an attempt?  

To be clear, nobody is saying go into debt for the sake of belonging or “YOLO.” Simply put, I’m saying that it is just as important to budget for trying new things and being in new rooms as it is for you to budget for the other things that matter in your life. And then, however it goes when you get there, you hold onto this: the point was to show up. The connection you're looking for, the people who will become your people, will come with time and with continued presence. The rooms that don't deliver aren't failures. They're data. They're how you refine the search. They're how you eventually find the room where things just…click. 

I’ve especially been considering this as I’ve tried to get to know more Black queers here in the city. Moving from D.C. to NYC back in February, I'll be honest — I thought I'd be closer to being settled by now, especially as an extrovert who befriends people pretty quickly. It hasn’t been the easiest. There’s certainly been a bit of culture shock. I'm a Black, pansexual woman who spent years in DC, where finding your people, especially in the Black queer community, felt easy. Porous, even. You'd show up somewhere, smile a few times, and someone would talk to you. Easy peasy! You'd become a regular. You'd get folded in. 

Here, getting folks to just talk feels like trying to open clams with my bare hands while wearing stiletto nail extensions. It's simply not happening and the events aren’t free. And yet I keep showing up (within my budget) and am using the data I’m collecting to make each event I sign up for more intention. Okay, so, maybe dance parties aren’t really my vibe (at least not without my girls to join me), maybe I can do a crafting event? Or a group walking event? It’s all helping me refine my approach and try new things while I’m at it! I literally can’t lose.

Thankfully, some meaningful moments I've had recently cost nothing: a random invite to walk in the park with a new friend, tagging along to the grocery store with my neighbor. The most nourishing rooms aren't always the ones you have to buy your way into — and I'm actively looking for more of those. No one is saying you must spend money to build community. I wrote this now viral post for TFD about free ways to spend time with friends because of how strongly I feel about that.

But when the $40 class is calling? Go. Budget for it, show up for it, and let it tell you something. Walking through the door is the win. That's the whole thing. Let go of the commitment to perfection and the survivor's scarcity mentality. Because the point isn’t to be the best or the most popular. It’s to show up so you can be present for the world of possibility that simply being present may offer you — whether that’s data about what’s not for you, or a peek into a world that may just hold your calling or your new best friend. You don’t know! But isn’t it fun to find out?!

Email me at [email protected] if any of this resonates with you. 

I love hearing from and engaging with you all. 

Xoxo

APRIL 14TH: Join us TOMORROW for Your Anti-Overwhelm Approach to Budgeting — a free, live workshop designed to help you build a budgeting system that actually works for your real life (no stress, guilt, or burnout required).

Co-hosted by TFD’s Alexa Claire and Rachel Samara, this session will walk you through how to create a simple, sustainable approach to managing your money—whether you’re starting from scratch or trying again after a few false starts. You’ll leave with practical tools to reduce money anxiety and finally stick to a system that feels doable.

The workshop includes a one-hour presentation followed by a live audience Q&A.

To attend, you’ll need to download Monarch using TFD’s link. Register here.

A quick reminder about one of our most practical resources that you might’ve missed: TFD’s Ultimate Budgeting Guide, created in partnership with our favorite budgeting app, Monarch Money.

This interactive guide helps you identify the budgeting system you’re most likely to stick with—and walks you through exactly how to set it up inside Monarch, step by step. It also includes a 30-day budgeting challenge to help you reset your spending with clarity and intention, not restriction.

All you have to do is sign up for Monarch, and the full guide will be delivered straight to your inbox. If you’ve been meaning to get more consistent with your money, this is an easy, low-lift place to start.

Whether you’re starting fresh or resetting your approach, this is your roadmap to feeling more in control of your money.

The Society at TFD