Becoming Dauntless

I got laid off from my last corporate job at 39 weeks pregnant. HR tried to call me while I was driving to my final doctor's appointment before heading to the hospital. While a layoff worked out in my favor, I DREAMED of quitting for years.

Around half of W-2 employees in the US of A want to quit, but are too nervous, according to a 2026 industry job search report. Since my unceremonious departure from the 9-5, I've met many corporate quitters. Some left to pursue their own business ventures, while others crashed out without a plan. Here are the most common regrets I've heard and how to avoid them and become a successful corporate quitter:

“I left my corporate job for more freedom, but now I work longer hours for less money.”

• People selling online courses who claim to work "two hours a day" are not to be trusted when it comes to time investment expectations. Businesses take time, especially during the startup phase (or transition phase if you buy vs. build). Freedom doesn’t mean “less work”, it means managing your time and decisions without external structure. I still work 8+ hours a day, but I don't have to ask a dude named Carl when I can take lunch or stress if my kid needs an early pick-up from school.

“I regret not learning more business basics before I quit.”

• Preparation gaps are easily the biggest regret. Everyone wishes they had learned more business basics, like marketing, sales, or budgeting, before quitting. While you never feel "ready," you can get a taste for your blindspots by doing something low risk, like selling on flipping garage sale finds on eBay, opening an Etsy storefront, or a closet on Poshmark. Selling digital downloads or thrifted clothes doesn't have to be your passion; it's a learning exercise.

“I didn’t expect this level of self-doubt.”

• It's one thing when strangers on the internet tell you that you're making a mistake or that your business idea is dumb. It's something else when those comments are coming from your spouse, parents, family, neigbours or hometown crowd. Few are prepared for that level of emotional resilience. It's why founders almost universally face impostor syndrome, uncertainty, and loneliness, and those that don't probably score high on the PCL-R. There's no shortcut to ameliorating self-doubt (if you have one, share). All I can say is safety is an illusion, cultivate some founder/business owner friends, and get a good therapist.

“I didn’t save enough money before quitting.”

• Financial instability is the top stressor; not the biggest regret, but the biggest stressor. I recommend an F-U fund of 3-12 months of expenses and checking to see when your benefits accounts, like 401(k) contributions, fully vest, so if you walk away, you don't have to give anything back.

If you found this insightful, check out more like this on Substack.

Tech News to Make You Smarter

• OpenAI Might Have Earbuds on the Way. OpenAI is rumored to be developing "Sweet Pea," AI-powered earbuds with a unique behind-the-ear design, aiming to create a truly ambient AI companion. We've covered this before: OpenAI probably doesn’t feel like competing with Meta by putting wearable AI in glasses. Plus, it’s already normed for people to wear their AirPods and talk to them in public. It’s a socially acceptable wearable microphone, and you can offload all the computing to a phone. Whenever I hear about behind-the-ear earbuds, I think of the "Seashell" thimble radios people wear in their ears in Fahrenheit 451. And while I usually like to talk about science fiction becoming science fact, I prefer that the inspo doesn't come from dystopian novels.

• Meta: Reality Labs Layoffs, VR Meeting App Discontinuation, and Dropped B2B Support. If you read that and thought "the metaverse is dead!" go put $5 in the swear jar. Divestment of the metaverse? Not quite. Zuck cut 10% of the Reality Labs team, about 1,500 people, but then also posted job openings for Reality Labs roles, including a Partner Manager. Meta also announced the discontinuation of their VR meeting rooms, spun up during COVID. Finally, a Friday afternoon announcement heralded a stop to selling Quests to business customers and supporting the business services that run on those devices. Overall, Meta cut stuff related to VR and Horizons, but nothing related to glasses and mobile. Shift on the medium of the metaverse and not the metaverse itself.

• Google's Gemini to Power Apple's AI, Including Siri. This is not surprising because the AI behind Siri is...lacking. I am surprised that Apple went with Google as they are a direct competitor, rather than going with OpenAI. Apple is one of the only companies on the planet that could acquire OpenAI, and they already acqui-hired Jony Ives from iPhone design fame for a $6.5B buy out. But Apple didn't bite. Which begs the question, what does Tim Cook know about OpenAI and Sam Altman that we don't?

Saved on Socials

The posts, memes, job postings, and videos that caught my attention this week:

• Finally, a belt that goes with everything (Instagram)

• VR apps to try if you just got a Meta Quest (LinkedIn)

• $240k to work in the office or $120k to work remote? (Instagram)

Recently Played >

What we listened to this week.

• The Will of the Many (Audible). Started listening for the fantasy school, stayed for the magic system and political intrigue.

Overheard on Slack

Enter the chat. What our devs are talking about…

• “The Quest is like the Honda Civic of headsets. The Varjo is like a Ferrari, but if you look at it wrong, it might fall apart.”

• “I’m detached from the realities of corporate life. Is a 10% layoff a lot?”

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