“In like a lion, out like a lamb”. If that’s what March stands for, what does February stand for? For my investment portfolio, it meant being nice and calm at the beginning of the month then entering a lion’s mouth by the end. The amount and pace of this drop was significant, something we haven’t seen in years. I published my initial thoughts after the six day drop and I’m sure it’ll be a topic of posts over the next few weeks and take up a good chunk of March’s recap.
Where was I during the month of February? PopUp Business School!
Why would this early retiree even attend a PopUp Business School? Well, for starters I got to hang out with many FI minded people, which surprisingly made up at least 20% of the attendees. We were fortunate to have a local financially independent individual lead the fundraising to bring PopUp to Charleston, SC and to convince Alan Donegan to personally attend. Alan is a special individual and PopUp Business School is a unique achievement. I was in a high-end corporate job and was exposed to many corporate trainers & coaches at the top of their game. Alan is a step above anyone I’ve ever met.
It was amazing to look at the evolution of PopUp. Here’s a corporate trainer & coach at the top of his profession that figures out a funding model for his passion: teaching and inspiring entrepreneurs. Alan and his team raise the cost of training through sponsors and provide a two week course for free to the attendees. In addition to the time spent teaching, I watched all three of his team members spend countless hours of one-on-one time coaching people through their various business or life decisions. I’ll write more about my experience later, but have to share two takeaways from my time there: The first is Alan’s philosophical post on exchanging time for money, asking Are You Willing To Pay The Price? Secondly, my friend Steven wrote this post as part of spending two weeks and how PopUp Business School helped him NOT start a business on his path to financial independence.
Now let’s look at some of the best content I found in the month of February:

I get a lot of questions about healthcare in early retirement. Personally, I’ve wimped out on health insurance in early retirement between using COBRA and corporate insurance from a side gig. Kim at the Frugal Engineers shares her experience with FIRE and signing up for health insurance for 2020.
Lisa quit her job around the same time I have and has been writing more about the philosophy of taking a different path. I often wondered what is enough before I quit, while Lisa reflects on How to (Finally) Feel Like You Have Enough.
I was *always* in a hurry, rushing from one task to the other, and it takes time for that to slow down. Fritz has been retired now for almost two years and talks about the process of slowing down and taking the long way home.
With the stock market drop, I’ve been excited to “buy” since the assets went on sale. I’ve been programmed in me ever since an early mentor told me to “throw money at the bear until it goes away”. Michael Batnick challenges that thought, analyzing what actually happens when you “buy the dip”.
Not all financially independent people pursue early retirement: Doc G gets in depth with Scott Trench, the CEO of Bigger Pockets on the What’s Up Next Podcast about what happens when it stops being about money.
What I’ve Been Reading:
Annie Duke: Thinking In Bets. What happens when an Ivy League psychology graduate makes it to the highest ranks of professional poker? She gets really astute at understanding probabilities and human reactions. This is not a book about poker as much as it’s a book about understanding risk and human psychology. I specifically took away the reinforcement of how to analyze decisions: A bad result doesn’t equal a bad decision. This is important to remember in investing, especially when things turn out poorly. Not everything will work out and just because something didn’t work out, it doesn’t mean it was a bad decision. The same applies to good results, are they because of good decisions or just luck?
I wanted to explore this further and picked up a copy of Fooled by Randomness, a constantly referenced book from this and other sources and am working my way through it.
Want to get notified every time a new post is written? Please subscribe on the right hand side page and don’t miss the most recent musing. Have additional thoughts? Please leave a comment below!
Taleb was easily the most impactful (to me) author I read in 2019. I’ve made my way through The Black Swan and Antifragile and they really changed the way I thought about risk. Fooled by Randomness is on my 2020 list.