20 Things I've Learned After Breaking Up With My 9 to 5

And lessons I'll continue to learn for the rest of eternity

I spent most of my life on the safe path, chasing society’s ideals of success. At 32, I had everything I thought I wanted—a successful career, financial independence, my own home—but instead of feeling happy and fulfilled, I found myself grappling with a profound sense of emptiness and a nagging question: “Is this it?”

I was anxious, disembodied, and discontent. I was also overworked, suppressing my creativity, and out of alignment with my values. On the one hand, I considered myself a queer, anti-racist feminist. On the other hand, I felt complicit in upholding systems that harmed the people that I claimed to love and protect. I was out of integrity, and I was curious about what I could do when I let go of old attachments and limiting beliefs and, instead, started trusting myself.

Faced with the choice between staying on the safe path or venturing into the unknown, I decided to embark on a journey of self-discovery and leave my job without a plan¹. I’ve been out of corporate for 18 months now, and while it’s been one of the most challenging and confronting things I’ve ever done, it’s also been the most rewarding. I want to take pause to reflect on what I’ve learned (and continue to learn) on this journey². Many of these might be unique to my experience, so take what works and leave the rest.

Here’s what I’ve learned/am learning/will continue to learn forever and ever.

1. I am enough, even without a fancy job. Like many, I have a deep-seated belief that my enoughness comes from what I “do”. But my achievements have diminishing returns, and the dopamine I get from climbing and striving never seems to last. It’s not easy, but I'm trying to detach my sense of worth from what I accomplish. I remind myself that I am worthy, simply because I exist.

2. Discomfort doesn't mean I'm on the wrong path. Carving a new path is uncomfortable and sticky, and when we're in that space, it’s easy to believe that we made the wrong decision. But being uncomfortable isn’t necessarily a bad thing—rather, it means I’m hitting a growth edge and shedding old layers. There's nothing to fix or change, and I just need to sit with it.

3. Choose the path of curiosity over fear. I used to make all my decisions based on fear—fear of not having enough, of being judged, of ending up in my mom’s basement. This past year has meant following my curiosity no matter how silly it seems, and it’s led me to places I never could have planned for. Elizabeth Gilbert writes, “Curiosity is an impulse that just taps you on the shoulder very lightly and invites you to turn your head a quarter of an inch and look a little closer at something that has intrigued you.” Follow that.

4. Nothing is as urgent as it seems. Urgency culture is relentless. It’s also largely manufactured, rooted in capitalist and colonial ideologies. We can choose to push back on the demands. Leaving my 9 to 5 has given me perspective on what’s important and reclaim my agency in how I spend my days. I know this is a privilege, but it’s something I want for all of us.

5. I was addicted to external validation, and I no longer want to build my life around it. It feels good to receive positive recognition. But there’s something unhealthy about designing your entire life around the hopes that a middle-aged white man named Mark is going to tell you you’re doing a great job. Why do we care so much about Mark?! I’m trying to shake that pattern, and instead, do things because they feel good to me.

6. We can stop giving a sh*t about what other people think. We allow our lives to be ruled by what a few people might think about us, and truthfully, we usually don’t want to end up like those people anyway. I no longer want to mask, compartmentalize, or suppress parts of myself to make others comfortable. They will either love the fullest expression of me, or they won’t.

7. We can create our own definition of success, one that's self-determined and self-sustaining. I am working to release the notion that success is solely defined as more money, status, power, followers, land, etc. Instead, I’m trying to look at success as being in alignment with my values. Things like integrity, creativity, and healing. Sounds simple, not easy.

8. Quitting is cool. You can quit things, even if you’re good at them. You can quit things and change your mind later. You can quit things because you don’t want to put up with the bullsh*t anymore. It doesn’t make you weak or ungrateful. It just means you know what you don’t want. Also, quitting what isn’t working will create space for what does. For me, that meant having more time to explore writing and art, which I wouldn’t have done otherwise.

9. It’s okay to start over again…and again and again. I used to so be afraid to change courses, scared I was wasting time or people wouldn’t take me seriously. I now realize that I can always pivot if something isn’t working—whether it's related to a job, newsletter, branding, or anything else. We learn a lot this way and it keeps things interesting. The real ones who resonate with you will keep showing up, no matter how many times you begin again.

10. Carving your own path is a process, not a destination. I struggle with this one, thinking that one day, I’ll finally just arrive. But living a life off the beaten path is inherently creative, with no final landing place. Repeatedly, the universe reminds me to stop trying to control the outcome and embrace what’s thrown at me. Gotta enjoy the ride.

11. Do things you’re bad at. No one hates being bad at things more than me. Beneath that is the fear of looking dumb and being judged. But growth requires enduring initial clumsiness, and confidence comes from the humbling experience of being a novice. If we want to get good at something, we need to allow ourselves to be awkward and a little bit cringe.

12. Investing in yourself is a responsible decision. I used to prioritize saving as much money as possible for the rest of my life. Not that there’s anything wrong with this, but the future is uncertain, and investing in the here-and-now is important too. My therapist helped me see my self-discovery as an investment portfolio, and this has been a huge shift for me.

13. I was more complicit in oppressive systems than I wanted to see. In corporate, I unconsciously distanced myself from capitalism, thinking I was morally superior or “one of the good ones”. Leaving that environment showed me that my participation played a role in upholding these systems. As Ani DiFranco put it, "Those who sit furthest from the center of power, see it the clearest." No shame, no blame, but I see things clearer now.

14. When we give up power and privilege, we gain access to so much more. Getting off the ladder was hard—I now realize how much of my self-worth was derived from status and wealth. But as I move from “power over” to “power with”, I feel more trust, connection, integrity, and self-love.

15. It's okay to crave a spacious life. The obligation to be in back-to-back meetings, all day everyday, was not sustainable for me. I wanted more space to enjoy my coffee, read a book, and rest when I needed to. As Tricia Hersey writes in Rest is Resistance, "You were not just born to center your entire existence on work and labor. You were born to heal, to grow, to be of service to yourself and community, to practice, to experiment, to create, to have space, to dream, and to connect.”

16. Not having a plan allows for unexpected opportunities to emerge. We live in a culture that rewards certainty, where not having a plan is seen as flaky and irresponsible. But jumping into the deep end gave me space to experiment and find what feels good. It’s like Googling the best bars in the city you’re in, versus wandering the backstreets and stumbling upon a hidden gem you wouldn’t have found otherwise.

17. I don’t want to numb my life away. I used to use work, weed, alcohol, and TV as a means to escape, and I missed a lot of what was going on around me. Leaving corporate forced me to confront myself, sit with reality, and become more embodied. With more space in my life, it’s harder to disassociate, and I feel a lot more of the world’s beauty and pain. It’s uncomfortable, but I also feel more alive than ever. And isn’t that the whole point?

18. Leaving a job is a lot like a break-up, and it's okay to grieve when it’s over. Despite knowing it was the right decision, I spent a lot of time mourning the end of this chapter and the loss of old identities. Shedding parts that once protected you is really f*cking hard. Honor that.

19. Living in integrity ain’t for the faint of heart. This path has been really freakin’ hard. Like, one of the hardest things I’ve ever done. The system is stacked against us, and it will try to pull you back in. I’ve found it helpful to surround myself with good people who are on similar paths and will laugh and cry with me when things get really hard. Having a community to lean on has made the journey a whole lot easier…and way more fun.

20. Life expands as we eliminate the excess. Leaving my corporate job required cutting expenses and releasing my attachment to certain luxuries. It’s forced me to examine what’s truly important and be present with what I do have. In retrospect, I had way more than I ever needed, and I don’t need that much to live a fulfilling life. Redesigning my lifestyle may seem like a loss of freedom, but in reality, I’m freer than I’ve been.

P.S. After I left my job, I took a six-month sabbatical, then started a coaching and consulting practice to help others reconnect to their truth and build values-aligned lives & businesses. If you want to inquire about working together, go here.

P.P.S. I've come to recognize the universal experience of denying oneself in pursuit of external success, of sacrificing our aliveness to chase the illusion of safety. My hope is that this helps at least one person slow down and get curious.

P.P.P.S. I might go back to a 9 to 5 job at some point, and that’s okay.

1. I recognize that there’s a lot of privilege in being able to leave your job without a plan, and not everyone can do this. I am childfree without significant debt, and it took substantial savings to be able to take a risk like this. But it’s my journey, and it’s one I want to share. Generally speaking, I think it’s important for people with privilege to reflect on what it would be like to give some of it up.

2. I want to stress that none of these lessons came easy, and I’m doing the work to heal these parts of myself every single day. This process is a co-created one, and I’ve arrived at these lessons/learnings/realizations with the help of many, many coaches, therapists, friends, books, podcasts, and strangers. Thank you - all of you.