What I Learned From My First F.I. Meetup

What I Learned From My First F.I. Meetup

Hello friends,

I’ve got some fun news!

I went to my first ever ChooseFI meetup in New York City and it was interesting.

If you don’t know what ChooseFI is, you can read more about them here.

They have local groups scattered around the major cities of North America.

Living near NYC, I thought it would be a fun idea to go to one set up by Dan.

Dan, if you’re reading this, are you essentially a magnet that draws us all together? Are you the Nick Fury of the New York FIRE Avengers?

meetup pic meme of nick fury saying I'm putting a team together

What Do I Wear?

I didn’t know what to wear and was torn between my usually Jack The Dreamer outfit, or a more “New York City-esque” button-up office shirt and jeans.

The Dreamer Outfit

meetup pic of jack wearing his thai garb
Making Tamagoyaki in Tokyo (eggs)

I had a hunch that, given the 6:30pm meetup time in the Financial District/Wall Street area of NYC, everyone would be coming out of work and arriving in their business casual outfits.

Erring on the side of safety, I went with a button-up and jeans.

My girlfriend also said that I look good in a button-up and jean so I should wear them.

And in order to get the best of both worlds, I should wear my Jack The Dreamer Thai mountain man jacket on top.

I thought about it but it felt off, so I opted for just a button-up and jeans.

My lesson from this is to be pretty much be yourself.

Dress how you want to dress and be comfortable.

Wear what makes you feel good (and maybe confident too?).

I remember seeing a picture of Mr. Money Mustache giving a keynote at FinCon and he was wearing a red plaid button up and jeans.

Mark Zuckerberg gives presentations in a t-shirt.


So in the end, wear what you want to wear, taking into consideration the social norms, and adjust accordingly.

I think FI has a much more self-aware community of people who realize that you don’t need to dress up to prove anything to anybody, because you have F-U money in the bank.

Next gathering, I’m aiming to wear my Jack The Dreamer garb.

Trying To Be Frugal AF

I felt that if I spent a good amount of money on this trip, I’d be a hypocrite because I write about frugality, saving money, smart money moves, and overall my experiences getting to financial independence.

With that in mind, I tried to be as economical (AKA Frugal) as possible on this trip into NYC.

I made 3 little sandwiches of only turkey breast and organic lettuce to bring on the trip.

I didn’t even add mayo because my family didn’t have mayo, and buying a tub of it from BJ’s was like $6.70.

So I made a dry sandwich.

Transparency: I didn’t spend any money on making these sandwiches because my dad bought the ingredients.

I filled up my 40 oz water canteen because I didn’t want to buy a bottle of water when in the city.

At the train station in the suburbs, I paid $21.50 for a round-trip ticket to Grand Central Station in NYC and back.

When in NYC, I walked the 1 hour and 15 minutes from Grand Central station to the bar where we were meeting.

This helped me save $2.75 from not taking the subway.

Before I even went to NYC, I’d set in my mind that I was only to going to get one beer and that was it.

I’m slightly proud of myself that I stuck to that goal.

My cost for a pint of Guiness in the Financial District? $8.50 + $1 tip = $9.50.


Dan, the organizer, was so nice, he got me a beer after I’d finished mine. Thank you Dan, you da best! 👍

After the meetup, I paid for the subway to get back because I didn’t want to walk the hour and a half back to Grand Central.

Cost of Subway? $1. I had a subway card that my girlfriend gave me with some money on it so I only had to add a little bit more.

Total cost of going to this ChooseFI meetup: $32.

That’s not too bad. The train accounted for 2/3 and the beer for 1/3.

I Almost Didn’t Go

Because I’d never been to any Financial Independence (FI) meetup of any kind, I didn’t know what to expect.

To be completely honest, I was on the verge of not going.

I had this notion, “I already know about FIRE. I read the books. I read the blog posts on Twitter. Why the heck would I want to go meetup with people to talk about what I already talk about on Twitter? I can save the money if I don’t go.”

I’m Glad I Went

Long story short, I’m glad I went.

I was initially hesitant before going into the bar but remembered that FiMeOuttaHere’s experiences with the FI community at FinCon was positive so I went in with a positive mindset.

What I liked was the laid-back and down to earth vibe of the group.

It felt liberating to talk about numbers, plans, goals, and aspirations knowing that everyone was trying to help support each other.

It felt nice to be around people who “get it” because I sometimes struggle to explain FI to my friends and family because they either don’t understand it nor do they want to understand it.

The force of several decades of society’s consumeristic inception is strong.


I felt included.

This was a group that shared roughly the same values (F.I.) and because everyone came from different backgrounds and perspectives, the insights we shared helped it not feel like an echo chamber and more like a mind-growing group discussion.

The Meetup Helped Broaden My Horizon

Robert Kiyosaki, author of the Rich Dad, Poor Dad series, once said that going to seminars, conferences, and these sort of gatherings, might not provide you with hardcore data and facts to “fill your cup” but it can help you increase the size of your “cup” so that it can hold more content later.

In a sense, it’s not about filling your mind, but expanding it.

I tried to go in with low to no expectations and as open a mind as possible, because I can get very close-minded sometimes and think that I know everything.

Boy, has this ignorance cost et so many opportunities to grow in the past.

I’m trying to learn from it.

I also realize that if we are to truly grow in this world, we need to do and learn things that expand our mind’s capacity to learn and grow.

Everyone was super friendly and inclusive (more adjectives: warm, down to earth, and inviting).

We all introduced ourselves and remembered each other’s names.

I noticed that the age range was around 25-45 years old, with the majority of the group skewing toward the 25-35 age range.

There was a little bit of a warming up preamble but once the “FI ice” was broken, so to speak, we chatted about FIRE, our favorite FI podcasts, FI books, FI blogs, rentals, bloggers, Chatuaqua, Camp FI, money, existential life questions, and Brooklynn 😂

Overall the meetup was better than I expected.

It was fun and it definitely helped me to expand my horizons by being around people who I deem as more along the FI track than I am.

Everyone had a story to share and it was interesting hearing how people got started on this mindset.


Fun Questions

Some deep and fun questions that we asked around the group:

“What was your ‘gateway drug’ that got you into FI?”

“What one blog post are you still thinking of that is changing the way you think?”

These were fun questions to think about in a group and to hear other people’s answers and I will attempt to answer the gateway drug to FI one in another blog post later.

What I’m Walking Away With

Up until this point, I had only ever interacted with FI people on Twitter and Facebook groups, and Dan, the meetup organizer,  brought up a good point that “we all met on the internet.”

Suffice it to say, I’d never really heard people talk in person about FIRE and FI and it was quite liberating to be in an environment where everyone shares the common idea of FI and FIRE.

And while we all share this common idea, we all come from different perspectives and backgrounds and have different thoughts as to how we can reach FI and FIRE.

No two people are the same, just as no two paths to FIRE are the same.

Overall, the $32 I spent for this entire trip was well worth it and I now understand more of the allure of FinCon, CampFI, FI Chautauqua, and any other gatherings of the FI minds.

It’s a gathering of the minds, the souls, of kindred spirits and ENERGY.

It’s like when I started doing yoga. I said to a friend at some point, “Why would I pay to take yoga classes when I can do them for free at home?”

My friend responded, “Because isn’t it nice to be doing it in a group setting, surrounded by other people who share your passion?”

My friend had a very good point.


It is much more enjoyable doing yoga together with everyone else in a room than doing it alone at home.

Yes I would be saving money if I did alone, but the enjoyment of group yoga outweighs the cost.

That’s how I’m starting to feel about the F.I. community and its gatherings.

It would be cheaper doing it alone, but it’s much more enjoyable doing it together.

With positivity, constructive insights, and sharing of the collective knowledge, we push each other to greater heights than what we could do alone.

To end with a quote from Nick Fury in The Avengers:

“There was an idea to bring together a group of remarkable people, to see if they could become something more. To see if they could work together, in order to fight the battles we never could.”

That’s how I feel about the FIRE community.

Thank you for reading,

Jack The Dreamer

Get a Free Copy of My New EBook “The 5 Powerful Habits For Financial Independence 

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Seriously though, if you want to see all the fun threads and conversations we have, follow me on Twitter, it’s lit AF there 👌

Jack The Dreamer

I'm a dreamer. But you know what? All the best people are. And if you're one too, join the revolution! My blog is about being financially independent and working towards that goal each and every single day so that we can all start living the life we've always dreamed of! Jack the Dreamer, over and out!

This Post Has 10 Comments

  1. So glad you went! I’ve been to a couple of meetups now and there really isn’t a way to replicate face time with likeminded people.

    1. Jack The Dreamer

      😄 so true! It’s interesting how that works, felt weird to hear these names IRL versus just reading about it lol. Thank you for your comment and for reading 😆

      1. And there are tons of awesome FI folks without blogs that you’d never talk to at all otherwise!

  2. Jack The Dreamer

    OOO yes! Do you think I should go back and add that part to my blog post? (Like do you think people would care about the specifics of: out of the 9 people there, one was a blogger and one was podcaster, one had gone to Chautauqua, etc.? and that it was interesting hearing about FI life from non bloggers for a change lol

    Also, I understand that some might have reservations going to their first meet up if they’re an introvert. But the low-key chillness of it was good.

  3. drmcfrugal

    Awesome. I should go to one of these in my hometown. Looks like fun. I am going to FinCon however. And I think it would be cool to go to a chatauqua in some exotic vacation spot one of these days. Maybe when I am truly FIRE and I can just take off whenever I want. Ha!

    1. Jack The Dreamer

      Haha Doc, go for it! It’s interest meeting other Personal Finance nerds 😋 and we def have to meet at one of these FinCon/Chautauqua’s one of these days.

      Chautauqua’s only a couple of thousand and they let us know months in advance, so it should be do-able! 🔥

  4. Philip Taylor

    Thanks for sharing your experience and for the ways you stayed frugal. Impressive. Reminds me of the frugal trips I used to take to NYC. I want to hit up a FI meetup one day too. I just missed the one here in DFW due to a conflict but I’m excited for the next one. Hope you can make it to FinCon one day, of course. The desire to be around like minded folks and not spend too much money to do so has definitely always been a part of the culture of the event. Look for a scholarship coming out in the Summer. We also have really discounted early bird rates. Hope to meet you at an event in the future!

    1. Jack The Dreamer

      Thank you so much for your comment and for reading, PT! Were your frugal trips to NYC for FI meetups too? Lol. And I def am looking forward to my first FinCon, applied to CFSI’s #FinHealthMatters scholarship contest that just ended. Waiting till the end of this month for the results 😊 there was stiff competition with a ton of good stuff so fingers crossed! Will def keep an eye out for the summer scholarship that you mentioned! Thank you so much for letting me know! 😭 hope to meet you at an event in the future too!

  5. mrhappyfrugal

    My first FI meetup was a ChooseFI group too. After that first meeting I was hooked! It’s funny how awkward it feels to go to a meetup and then you leave with new friends! This community is the best!

    1. Jack The Dreamer

      Haha that’s awesome! It does feel weird to hear words that you’ve only ever read online doesn’t it? Lol. I was like “So THAT’s how they say FI? It really is a great and supportive community. I’m glad you’re now on Twitter to see all the shenanigans we get up to 😆🙈

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