Flounder Mode #1: A newsletter about consistently failing upwards
Embarking on a biweekly journey to share all I've learned on software and life
Hello! My name is Jesse and I’m a software engineer. I’ve worked previously at Gusto, and currently at Cocoon.
This is a newsletter about some of the learnings I’ve made about work and life over the years, that I would like to pass onto the public.
If you find this content interesting, feel free to subscribe!
Hello! My name is Jesse and I’m a software engineer. I’ve been in the industry for about 8 years: I spent the first half of my career at Gusto, and am currently at a startup called Cocoon.

I’ve been fortunate to have learned a lot in my career so far, sometimes by choice, and sometimes by mistake. Many of these learnings have come as part of the roles I’ve played at work. For example, about a year ago, I was promoted to the role of a Staff Software Engineer. This role has taught me a ton about the nature of how EPD organizations work together.
Recently, a few of my colleagues have asked me for some pointed advice about certain situations and their careers. I felt I had a lot to say and advice to give.
When I thought about what advice I wanted to give, it really was just all of the lessons I’ve learned through the strange experiences I’ve had, and the people who felt like it was worth investing in me.
I felt grateful while reflecting on this. But the more I thought about it, the more I wanted to pay it forward as much as possible. It would be quite remiss if I didn’t try to share some of this advice in a more public format.
So this is it: the start of a long journey to try and explain to you some of the most impactful things I’ve learned about life and work. My goal is to include general lessons that have helped me personally, and maybe some more technical posts that I would find useful from the lens of a software engineer.
I am committed to writing a something every two weeks or so (I already have a queue of ideas!), and am excited to start sharing some of the many things that live in my head. I hope you come along this journey with me 🐟
P.S. I chose the name “Flounder Mode” not only because it was punny, but because this is how I personally feel sometimes in this industry: a fish out of water, trying to figure out how it all works. I would like to think this is a more common feeling than publicly stated on LinkedIn. But being a fish out of water can be a good thing, because it means you have a unique perspective on most situations, which is the most valuable when you least expect it.