I have been following Massimo Pigliucci's work for a long time and I consider his thoughts very valuable. Indeed, we share the same interests and the same approach: philosophy, science, and rationality with a non-dogmatic flavour. What differs is the role (not necessarily the commitment): he's a professor and writes books; I am "only" a journalist and a newsletter author, which means I write short and trivial articles — sometimes, like this one, about his work. What also differs is the order in which we came to those interests. I started out studying philosophy and moved later toward science, ending up as a science journalist. He started out as an evolutionary biologist and became a philosopher afterwards.
Then, in 2017, he published How to Be a Stoic, and he surprised me. Philosophy, as I had learned it, was an academic discipline — or, more accurately, a bundle of academic disciplines. It was not something a layperson could go to in order to find out how to improve their life. That book showed me that I was wrong.
So I settled into a division that seemed clean enough. There is a philosophy that analyzes and challenges our concepts and our thinking — and asks questions like what knowledge is and how we might get it — and does so as a specific and sophisticated discipline. And there is a philosophy that helps you live. Two different creatures with a common ancestor and some traits in common, but that live in different territories.
Now he has proved me wrong a second time. How to Be a (Happy) Skeptic takes an epistemological tradition and shows its relevance for a philosophy of life. Because Stoicism is a "complete" system, with physics, logic, and ethics — but the most relevant part (at least for us, but also in the Hellenistic period) is the ethics. Skepticism is the other way around: the core is the logic, i.e. the answers to the questions of how I must think and what I can know.

First of all, some housekeeping on the terminology, because the modern meaning of "skepticism" is quite different from the ancient one, and quite derogatory. Today a skeptic is someone who simply doesn't believe: the climate skeptic doesn't believe in human-made global warming despite scientific evidence, the vaccine skeptic doesn't believe in the effectiveness of vaccines, again despite scientific evidence, and so on. But the Greek skeptikos meant inquirer. A skeptic was not someone who had decided in advance to withhold assent, but someone who kept looking, on the assumption that the answers already in hand may be useful but are not the final ones.
Pigliucci wants that word back, and he wants it for a specific reason. He had practiced and recommended Stoicism, but as we said Stoicism is a system, and like any system it presents a risk. This risk is named by Simone de Beauvoir in her memoirs, in a passage Pigliucci quotes: that from a philosophical system people derive an obsessional attitude, endowing their provisional patterns with universal reach. The risk is to stop asking whether it is right.