Let’s wrap up the 9 to 5 discourse
Because it’s your business.
Happy Monday, y’all!
We’re skipping the small talk this week.
I’ve been sitting on this one for a while, and honestly, it needed to be said. So here it is…
TL;DR 👀
Everybody’s got an opinion about how you should feel about your corporate job. Everybody.
You’ve got the “I quit, and I’m free” camp. You’ve got the “Stop the corporate slander, I love my job” camp. And somewhere in the back, a former coworker all in your business. That’s a different conversation.
Listen.
You don’t have to hate corporate to want something different.
You can be good at the game and be sick of playing it.
You can outgrow a place you once thought was perfect for you.
You can redefine what the dream job even looks like.
You can let go of the vision you had at 22.
Good for you if it’s the 9-to-5 and a side hustle.
It’s okay if the dream job is the 9-to-5.
It’s okay if you don’t dream of working.
You don’t have to love your job for it to serve a purpose in your life.
You can love the grind and hate the politics.
You can pivot out of pure necessity.
You can want to climb the ladder and still wish things were different.
You can get off the ladder and get back on.
You can deprioritize work for a moment, a year, or forever. That’s your call.
You don’t have to quit to reclaim your power.
But if you do quit? That’s your business too.
You can want stability and freedom at the same time.
You can respect the path that got you here and still want to choose a different one.
There is nothing wrong with climbing the corporate ladder, and there is nothing wrong with climbing back down.
All choices are valid. It’s not a zero-sum game.
Because at the end of the day, it’s your business.
The adjustment no one talks about after leaving corporate
Learning to measure yourself without a company.
So, I’m currently in the “I quit, and I’m free” camp that I referenced above; however, it’s not all rainbows & butterflies. One of the things no one tells you about leaving corporate is that imposter syndrome doesn’t magically disappear once your Slack is deactivated.
In fact, for a while, it can get louder.
A lot of people — and yes, I’m including myself — assume the opposite will happen.
How can you not?
You picture yourself working from a cute little coffee shop, answering emails between long walks or workouts, and admiring a mostly empty calendar reserved for “deep work.” No constant pings, no 9 a.m. standup, no performance reviews.
I imagined I’d finally feel like myself again once I was out of the corporate problems that had me questioning my career path, my future, and even my identity.
But multiple truths can exist within the same reality.
While people often tell me I’m “glowing” since leaving corporate, internally, I feel anxiety, along with a mixture of excitement, possibility, and motivation.
Inside a company, you’re surrounded by signals that quietly reinforce your current path. Your manager affirms you’re doing well. The org chart shows exactly where you stand. You’re pulled into meetings where decisions are being made.
There are performance reviews, promotions with title changes, and launches with your name attached. Even the daily rhythm of deadlines, standing meetings, and messages from coworkers creates a sense of structure.
When you step outside the corporate world, you also step outside that scaffolding of external validation.
Then, the truth behind the structure many of us were given — go to college, work hard, climb the ladder, and live comfortably for the rest of your life — starts to look less stable than we were promised.
If Millennials have learned anything from our 5, 10, or 15+ years in corporate, it’s that these corporate signs of validation can disappear in an instant. A reorg. A shift in priorities (which lately have been AI-related). A company navigating economic or geopolitical pressure.
Over time, moments like the ones I mentioned above start to reveal something subtle about how these systems truly work.
When progress is constantly reinforced through shared signals, we learn to read those signals as proof that we’re moving forward.
And because everyone around us recognizes those signals in the same way, they begin to feel objective.
So many of us learned to measure our professional progress through those external markers.
Ironically, the real adjustment isn’t learning how to work outside a company. It’s learning how to measure yourself without one.
The internal signals that you’re moving forward become quieter and more personal: the work you finish, the clients you help, and the ideas you bring into the world.
That kind of confidence — the kind that isn’t tied to a title or a company — takes a little longer to build.
But once you do, it’s a lot harder for anyone else to take away.
Building my website with Claude Code
As many of you know, I am not a designer. I am not an engineer. I am a person who once Googled “how to center a div” and closed the tab immediately.
So naturally, I decided to build my own website from scratch.
Instead of spending thousands of dollars on someone who actually knows what they’re doing, I turned to Claude Code, Anthropic’s AI that, bless its heart, did not once make me feel silly for asking the same question five different ways.
This project is where I truly understood what “vibe coding” means. Because I didn’t have to speak in code. I got to speak in feelings. I told Claude the vibe I wanted for my website, and it responded with... actual working code.
With a very patient, very supportive fellow creator by my side, I started prompting. After Claude asked clarifying questions, I uploaded my brand guidelines. Then, it started spitting out HTML like it was nothing, and we refined it together — prompt by prompt, screenshot by screenshot — like two people assembling IKEA furniture, except one of us knew what we were doing.
Then Claude helped me figure out where to host the thing AND connect a domain I bought three years ago “just in case.”
AI is how we future-proof our careers, and you don’t have to be technical to use it. You just have to be willing to try. Check out my site > https://roxycouse.com/
Take the risk, make the big change
Leaving corporate or taking any big career step can change how you see progress. Rebuilding that internal compass takes time, but it’s also what makes your confidence harder to shake.
That’s it for today! The next issue of That’s a Monday Me Problem drops March 16th — see you then. 👋🏿
if I would’ve said “yesss, and “oh my God” one more time while reading this because you were hitting all of the points that as millennials we have had to deal with in the past couple of years, the need for freedom, the need for loving something and no longer loving it at the same time, the feel of not being able to have to do, as well as entering a time where there is way too much to do!! Thank you for always taking our thoughts and concerns and putting it to paper. Well technically this isn’t paper but you know lol
Yes yes yes 👏 the definition you had of success at 22 does not have to be the same definition you have today!