
After years of reading J.L. Collins blog and reading all about Chautauqua, I finally got serious and signed up for the June 2019 Chautauqua in Stratford-upon-Avon.
I wrote this post to describe my experience with this event.
For anyone curious about attending Chautauqua, you can read up on it here.
What is FI Chautauqua?
FI Chautauqua is a seven day personal finance retreat started by J.L. Collins that is held in different locations around the world, bringing together a small group of like-minded people to talk about financial independence (FI).
It’s attended by about 30 people with 10 hosts/speakers. The number of people and seven day duration is such that you are able to get to know everyone, both attendees and speakers. There’s a good mix of planned activities along with lots of free time.
One of the things that attracted me to this event was the fact that it was small, somewhat fluid agenda in an interesting place. Of course it goes without saying that there’s also the idea of bringing together like minded people go share ideas.
Shameless Name Dropping
Chautauqua is planned, coordinated and hosted by the best in the biz:
- Alan and Katie Donegan from Pop Up Business school
- J.L. Collins – The man the legend…
- Mr. 1500 – Carl from 1500 Days to Freedom will take your phone when you’re not looking and take pictures of dinosaurs.
- Mad Fientist – Brandon the guitar and synth-playing Mad Fientist
- Millennial Revolution – Bryce and Kristie will teach you the ways of digital nomading
- Montana Money Adventures – Jillian will help you through your transition into FI.
All of these folks are accomplished bloggers and their reputation speaks for themselves. Then there’s Alan and Katie. There’s a lot that goes on behind the scenes. The planning, coordinating, making sure everyone arrives, has a room and of course making sure everyone is fed! Alan and Katie put out a tremendous effort to make all this go smoothly and they made it look easy.
Getting ready to go
Prior to attending I listened to the Choose FI podcast and read a number of other blog posts by past attendees. I’d recommend this if you’re planning on attending so you can have the right expectations.
Chautauqua is not an intensive, all day long activity packed seminar. There are speakers and structured activities, but it’s also intentionally designed to have lots of free time between these activities to allow you to spend time with the other attendees and hosts.
There are three Chautauqua’s to choose from in 2019 (all sold out), one in the UK and two in Portugal. Past Chautauqua’s have been held in Equador and Greece. Future ones will likely be in new locations. Do some research after you sign up as you will have time to get out and explore.
Here are my thoughts after attending
Reasons for attending
There are a number of reasons people choose to go to Chautauqua. Here are some that I came up with between myself and talking to other attendees.
- Validation – Most people find out they are doing just fine but there’s still a desire to share your journey and experience with others to get validation that you’re on the right path. Chautauqua is good for that.
You can share your personal finances with others or during your one on one if you choose. Or like me, you can just bring up where you are in conversation and gather other thoughts or ideas that may help you on the path to FI.
- Tactics – in this context, tactics are what I would consider the steps people take to reach FI. Different types of investing, real estate, starting a business, and geographic arbitrage are just a handful of topics that were regularly talked about. There was some discussion of these things during presentations, but the conversations with individual attendees were also quite valuable.
- Strategy – most of the presentations focused on this aspect. The long term planning, mindset, and goal setting to not only get to FI, but to do so without sacrificing your happiness or sanity.
- Friendship – Finding other likeminded people was a major driver for attendance. You are the average of the five people you hang out with most. Make friends with fellow Chautauquan’s and you can greatly increase your average.
Had I not gone, I never would have met Tae and Monnica from Financial Tortoise. They started their blog around the same time I started Forging Finance. Also, I wouldn’t have met JT who got me interested in pursuing real estate investing.
- Learn from others – Between the speakers/hosts and attendees you have a wealth of experience and knowledge. The presentations are good as are all the individual conversations. Combined there is a wealth of information. Bring your laptop/tablet/pen and paper and take notes.
The hosts do a great job in making themselves available for chats. It’s a great place to learn from others and bounce around ideas.
Focus on FI (not so much RE)
This revelation came about starting on Day 1. The focus among attendees was on financial independence and not necessarily retire early. In this context, I’m referring to retirement as a “do nothing, binge watch TV” retirement as opposed to retiring into another more fulfilling job or pursuit.
Speaking with others I validated my own thoughts on this subject. The general consensus was that if you are in job or career that you don’t like, the objective should be to find something more meaningful to replace that job as opposed to gunning for an early retirement so you can sit back and do nothing.
FIRE Community
Everyone in attendance comes from other places, mostly from the United States, but there were people from Canada, UK, Romania, and Denmark.
Everyone I spoke with said that no one in their “circles” knows about FI, the blog or any of this FI stuff. By circle I mean friends, family, colleagues at work and acquaintances.
Individually, outside of Chautauqua, we all seem to be in our own FI bubble. The blogs, podcasts, books are all appealing to the folks at Chautauqua but our family, friends, colleagues, and in some cases even spouses are not on the FI bus.
Gathering at Chautauqua provided that validation that there are real people out there that subscribe to FI, and have successfully retired or moved on from a job they didn’t like to something that was more meaningful.
Journey to Financial Independence
The attendees all come from different places and backgrounds. Some have their own business, some have sold their business and retired, others worked or work in corporate jobs, saved and invested. Some arrived a FI through real estate investing.
The point here is that not everyone arrived at FI in the same way. There are multiple ways to go about it. Getting together at the same place and talking about lessons learned in conjunction with daily presentations by the speakers drove home some important lessons.
Happiness on the way to FI
One of the most important themes at Chautauqua is the idea of not trading down happiness in order to get to FI.
I’ll borrow a graphic from Montana Money Adventures presentation. The first graph shows what a lot of us think about the FI journey. You sacrifice happiness and other things to hit this FI threshold, then you assume happiness will drive straight up.

In reality this second graph is how you should go about it. Life is short so it makes a lot more sense to make the most of your time rather than gunning for this thing you think will take you to success.

Of the people that attended, a few were early on the FI path, some well along, and some were retired. Of the people that had retired, some had gone through a difficult, if not confusing transition from work life to retired life. They enjoyed the early retirement, the freedom, and the reduction in stress. But it only took a few weeks or months for boredom or depression to come along. Chautauqua is a great place to learn about the transitions that come after financial independence.
In fact, this was one of the major themes from presenters at Chautauqua. The idea that FIRE is not the goal in and of itself, but instead you use FI as a tool to follow your true passion (assuming your day job is not your true passion….).
What I Took Away from Chautauqua
As you can imagine, there is a lot to take in. If you’re like me, you’ll come away from something like this with a ton of actions to follow up.
Here are my main actions that I took from Chautauqua.
Values – write down your values, write down what is most important to you. Try free writing and not concerning yourself with grammar or sentence structure. Go at it for a while and see what comes of it. Do recurring themes come up? Family, free time, travel, health?
Find the recurring themes in your values and structure your life and goals around those things. You’d be amazed at what you discover.
Mini-experiment – once you’ve defined your values, you should start to re-establish your dreams, wishes, etc. through experimentation. So if you’ve discovered you would like to start a business, selling a product. Try and sell that product now before it’s even made. Don’t waste time creating a website, manufacturing, etc., see if people are willing to buy it in advance of it being finished.
Another angle here is the idea of a mini-retirement or sabbatical. Get to a place where you can take off a month, six months or maybe a year. Experiment with retirement and use that time to figure out what works for given your values.
Transitions – prepare for transitions long in advance. If your goal is retirement, then start thinking about what that retirement looks like well in advance. Start becoming the person you need to be to truly enjoy that retirement. If you start years in advance, the transition will be much smoother.
Frugality – a lot of people equate the FI path to some measure of frugality, even extreme frugality. Align your measure of frugality with your values so your journey to FI does not come at the cost of happiness, meaningful work, or following your dream.
If you’re going to Chautauqua….
Here’s what to bring
- Clothes – this all depends on where it is, but in general the crowd is casual. No jackets, ties or formal dress is needed.
- Electronics – don’t bring work, but do bring what you need to take notes, write, reflect.
- Overall mindset – this is not an intense conference from 8 to 5 every day. That being said, my day was full from the time I stepped out of my room in the morning until I went back to my room in the evening. Come with the vacation mindset but also be ready for lots of activity and lively conversation.
Here’s what to expect
The first few days consist of getting to know your fellow Chautauquans and hosts. There’s plenty of time to eat, drink and relax and get to know everyone.
J.L. Collins will kick things off with a presentation on the first day. After that there is at least one speaker per day in the morning. The rest of the day will consist of free time and one on ones.
One on ones – prior to attending, you get to decide which host you would like to meet with one on one. Chances are you’ll have time with everyone, but the one on one guarantees that you’ll have at least an hour (if not more) with a host of your choice to have a discussion on whatever it is you want to discuss. The one on ones are confidential and can be a good time to assess your path to retirement, help decide what’s next, or just bounce around ideas.
Food -The food is amazing. Pace yourself and expect to maybe gain a little (or a lot). It’s worth it.

Sleep – I probably averaged 4-5 hours a night. Being with such a great group of people made it tough to break away.
Between the free time and planned activities there’s quite a lot of opportunity to take in the surroundings. Depending on where Chautauqua is located there are likely many things to do in that area. The last day of Chautauqua is a free day so you can plan a day trip in advance if you like.
Given that there was so much information thrown around during the week, I actually chose to stay around the hotel and try and capture what I learned.
Parting Thoughts
The magic of Chautauqua is that you have a small group of like-minded people that assembled for a seven day retreat in an exotic location to meet other people and talk about financial freedom. Yes there are presentations and scheduled events along the way, but the real deal is getting people together long enough to make meaningful and lasting relationships.
One of the things that jumped out was that Chautauqua is not so much about tactics such as which investments to buy or how much cash to save. Even though there were plenty of conversations on those sorts of things, I thought it was more about the overall FI mindset, aligning your values with your objective of financial independence while at the same time avoiding the pitfalls of sacrificing your happiness to achieve FI.
If you’re interested in attending, I suggest you sign up on their mailing list so you can hear about when tickets become available. The organizers announce the dates and venue a few weeks before the pro-bloggers get the word out. I signed up a couple of days after that initial announcement and made it just in time before the whole venue was sold out.
Don’t over think it, just go!

This is a wonderful post about Chautauqua! Your closing line of “Don’t over think it, just go!” is the best advice. I was still overanalyzing the opportunity and logistics while John pushed the submit button. There were so many highlights, and the people were the best part.
Way to go John! It was well worth it
It’s funny but I hear your voice as I’m reading this. Ha! It was a pleasure to meet you. Wish we could have met your better half too. Glad you came and be able to talk shop with my husband. It’s hard not to think of blowing things up when we think of you! Great write up Brian. Summarizes Chautauqua UK-2019 amazingly.
Thanks, I enjoyed our talks as well.
Brian, It was an absolute Pleaure meeting you at Chautauqua. This post is a great summary of what was a life changing event. Keep up the work pal.
Thanks, can’t wait to hear your podcast!
So thoughtful and comprehensive. This is the article I was looking for when I was researching Chautauqua! It will be of great use to future Chautauquans. It was great meeting you!