My History with Charitable Giving
You’re probably wondering, who’s the type of person that has a goal for giving away $1M to charity? Probably some do-gooder who served in the Peace Corps, I bet.
I’m sorry to disabuse you of that notion, but that certainly isn’t me. Charity was never a big part of my life and I wasn’t really a volunteer for non-profits except occasionally helping out in a soup kitchen for a year or two.
For most of my life, giving my hard-earned money was difficult, and I never particularly enjoyed it. Over time, giving more significantly has gotten easier, and I’ve learned better how and where to give, but it took a long time to get here.
The advantage I have is that I always gave some amount to charitable causes since I started my career in 2011. That’s given me a lot of practice with giving to see what works for me and what doesn’t. It’s similar to how ten years of consistent investing like a Boglehead builds your confidence in investing.
Growing Up
I grew up in a family that went to church every Sunday and it was drilled into me from an early age that tithing is important. For the heathens out there (I’m one myself now), that means giving 10% of your income back to the church and metaphorically to God.
That meant for every $5 of allowance (it was probably less), I should give $0.50 back to God. And with an cheerful and gracious heart of course! To state the obvious, my five year old heart was not always so gracious and cheerful to split with my hard earned $0.50. But I did it.
I also do remember a funny little story about how when I was a small child, there was a major hurricane (maybe hurricane Andrew?) and I told my mom that I wanted to give my allowance to the Red Cross to help the hurricane people. I think I wound up on the phone with someone from the Red Cross. They didn’t actually take my money but sent me some tracking maps of hurricanes and the whole vibe I got from my mom and the Red Cross lady was “aww that’s cute kid. We don’t need your piggy bank money, but that’s so cute of you.” I wasn’t thrilled with that response.
In high school and college I had some side jobs. I believe I still did some small giving, but nothing major.
Early Career
After college, I got my first job working in insurance for MegaCorp. That’s where I started building my giving muscles, albeit slowly over time. I began giving regularly to some humanitarian organizations like Water.org and Compassion. I also started giving through my company’s charity match program. If you work at a large company, see if they have a charity match program. It’s a good way to get started and make your donation go further.
Even back then, it was difficult to figure out where I should give to. I tried not to overthink it and gave to a couple of charities that I felt were doing good work for the world.
On a practical level, I approached the transactions of giving the same way as investing. I decided what charities I wanted to give to and I set it on autopilot either through monthly credit card charges or through payroll deduction with my company’s match program. I highly recommend this approach because you avoid having to renegotiate with yourself and make a decision for each donation. Laziness FTW.
Pursuing FIRE while Giving
During this time, I was also heavily influenced by some of the early FIRE bloggers like Mr Money Mustache, Early Retirement Extreme, Living a FI, and the book Your Money or Your Life. I never really enjoyed having a job and fully appreciated that fact during my years working in a grocery store in High School. Also, the vision of financial freedom and not having to worry about finances was enticing.
While some of my other young coworkers spent their money on fancy cars that needed premium gas, I was investing towards my financial independence as well as giving about 10% of my salary to causes like the United Way. By living well below my means, I was able to pursue both goals.
Sure, I could have saved and invested that 10% instead of giving it to charity and maybe even given MORE now or reach financial independence slightly sooner, but as many have found, there’s no prize for who gets there the fastest. Also, there are needs back then that needed funding back in the early 2010s. Giving more in 2025 is useless to help that.
At this point, on the other side of FI, I am proud that I continually gave throughout my journey to FI. Zero percent of me wishes I had a larger slightly larger investment account now, by being a stingy bastard, instead of giving it during the last decade to great charities and building my “giving muscles.”
Now that I’m FI, it’s much easier to give larger amounts now, not because I have a lot more financial resources and am work optional, but because I’ve had 10+ years of practice giving. Over those years, I’ve learned some good lessons and have gotten more comfortable with the act of giving and letting go. I think that’s an under appreciated skill that takes time to develop.
You can’t go from never investing to suddenly investing $10,000 into VTI at a time. In the same way, you can’t go from giving nothing for your whole life to writing $10,000+ checks to charities one day just because you have the money.
Learning to give Effectively
In 2014, I was learning more about the Effective Altruism movement. I don’t consider myself an “effective altruist” these days, but I do like their focus on making sure giving is done in a way that has a high impact per dollar.
Through that, I learned of the charity GiveDirectly which does direct cash transfers to the poorest of the poor. They’ve been leading the way in showing the research on giving cash directly vs. other forms of giving (like a donor choosing to give a goat or school uniforms). Giving cash directly to people in poverty empowers them to use it for whatever will improve their lives and the lives of their families.
I still give to GiveDirectly today and it’s the main charity I give to in my global giving allocation.
The Transition to FI
Between 2020 and 2023, I was reaching the threshold of being financially independent. If I had to put a date on it (and I don’t really care to) I reached financial independence at the end of 2023.
We all remember 2020 and it was clear that Covid was going to hit our communities (locally and globally) hard. The Greater Rochester United Way was a leader in my community to meet the pressing needs such as the huge increase in demand on local food pantries. I decided to make a bigger gift than I’d ever done before and sent $10,000 to the United Way. later that year, I gave another $10,000 and began to view the United Way as my primary vehicle for helping Rochester and the region in a broad way.
I’ll write about this more, but I see my local United Way as similar to an index fund for community giving. By giving to my United Way, I’m pooling my giving with everyone else in the community who gives to uplift the community in a broad way. The United Way does the vetting of individual nonprofits to make sure my gifts go to effective charities that are truly helping the community. As just a taste, my United Way helps fund:
Domestic violence shelters
Camps for kids with epilepsy
Food pantries
Big Brothers Big Sisters
I love the United Way. I think it’s a great way to give effectively and be completely lazy about it, which I love! It feels very similar to throwing money at VTI/VTSAX and calling it a day. Laziness FTW.
Finding my Focus Area
During this time of transitioning to FI (2020-2023), I found the specific area and charity that I connect deeply with and am passionate about. That area is multimodal transportation and making our cities and communities more walkable, bikeable and less car-dependent.
The quick story is that I am no longer allowed to drive for medical reasons. Because of this, I suddenly (and involuntarily) had to go car-free a number of years ago. I decided to buy a bike for the first time as an adult and get a bus pass so that I wasn’t stuck at home. These days I am car-free for medical reasons, but let me tell you, having zero car-related costs is a huge boost to your FI journey!
Through that experience, I got involved with my local bike/walk/transit advocacy group, Reconnect Rochester. I love their mission of making Rochester a place where everyone can get around safely regardless of whether they own a car. I’ve gotten actively involved in the organization and donate significantly to them. I love supporting them and being actively involved (not just donating) has enriched my own life as well and given me another great reason to get out of bed in the morning.
Accelerating Giving Post-FI
Between 2020 and 2023 I started experimenting with giving larger, five-figure amounts and getting more actively involved in the United Way and Reconnect Rochester. This has been a great success and has encouraged me to give more as I’m able.
Now in 2024, my goal is two-fold:
Give more in 2024 than I have in any other year
Give in a more structured way
My 2024 goal is to give $60k to charitable causes and to try out a framework, similar to an asset allocation, for giving in a more structured way with a real “giving plan.” I think intentionality is a guiding principle here.
My hope is that at the end of 2024, I’ll have a better idea about how to give effectively in a structured way with some lessons for how I can do even better (giving more and with greater impact) in 2025 and beyond.