Keeping winging it

by Dale Davidson March 18, 2026

A humorous illustration depicting the concept of 'everyone is just winging it.' The scene shows a group of stick figures in various professional attire, like business suits and lab coats, all with makeshift wings strapped to their backs. They're all trying to 'fly' in different clumsy and funny ways - some are running with arms flapping, others are jumping off small stools, and a few are just standing puzzled with their wings. The image is light-hearted, exaggerating the idea that in all professions, people are improvising and learning as they go, symbolizing the universal experience of 'winging it' in a whimsical and funny way.

One hesitation for people who are considering going 1099, or even current 1099s, is the feeling that they don't actually know much, are not an expert, and that they don't "deserve" to be getting the money or respect that they're getting. You are just winging it.

The thing is, so is everyone else!

Oliver Burkeman agrees, and summed up this phenomenon nicely.

"It’s easy to spend years treating your life as a dress rehearsal on the rationale that what you’re doing, for the time being, is acquiring the skills and experience that will permit you to assume authoritative control of things later on. But I sometimes think of my journey through adulthood to date as one of incrementally discovering the truth that there is no institution, no walk of life, in which everyone isn’t just winging it, all the time."

Four Thousand Weeks: Time Management for Mortals by Oliver Burkeman

If everyone is just winging it, you might as well wing it in a way that helps you live the life you want to live.

Want the full playbook? Check out Going 1099.