Reflections from a Quitter

I quit my job 3 months ago. Here's the truth on how it's going.

Three months ago¹, I logged into work for the last time.

I’m remote, so the ‘drama’ around a last day isn’t what it used to be. No packing up my desk, no long lunch with my team, no romping around the office with nothing to do but to say goodbye to everyone, having my sweet ego gently stroked (I’ve always left a job that I’ve chosen to leave on good terms, what can I say?)

Instead, my last day looked like me, alone in my office bedroom, typing up loose ends and getting everything into a nice, shiny Notion doc for the team. I lost access 3 hours before I was supposed to², and the hour-long ‘handoff’ meeting my boss scheduled ended after 10 minutes.

And then I was done.

As soon as that call ended, I started sobbing. Relief? Fear? Sadness? Reality slapping me in the face? All of the above, perhaps?

Since then, each day, I’ve tried to show up as best as I can, more or less.

So, how has it actually been going?

Three months in, and that’s still a hard question to answer. My one-liner, so far, has been: I’m happier than I’ve ever been and less stressed than I’ve ever been, but also less sure of my future and more broke than I’ve been in a long time.

It’s going well in the sense that I feel great. My brain feels like it’s fully mine for the first time in a long time, I’m decently rested, and for the most part, my stress levels are nonexistent. I’m fulfilled, I’m feeling creative, I’m getting to chat and hang with people I want to chat and hang with, and I’m overall enjoying life.

I’ve run two half-marathons, attended a writer’s retreat, and recorded my first ten podcast episodes. I’ve written a lot, signed a new copywriting client, and have landed on a loose strategy to start to go after clients in tech.

I’ve spent a lot of time chatting and connecting with folks, and have been settling into this season of life, which is another way of saying: I’m moving slowly, but that’s intentional.

I’ve spent most of the last three months with less of a plan and more of an intention: be realistic, but also don’t try to have the answers all at once. Take small steps each day, talk to interesting people, and chase ideas down as they come. That’s led me to reclaim my impulsivity, and I’ve enjoyed the permission to continue to do so.

This has allowed me to stay curious and take some pressure off of figuring it all out. I can ‘build in public,’ which is having a moment, and see what sticks. When I’m in the right mindset, this feels right and aligned. But sometimes, I lose patience, or panic, or get in my head about not having more ‘done’ by this point.

I haven’t figured out exactly what my ‘offer’ is, or how I’ll make ‘the big bucks,’ and sometimes I feel like I’m floundering. I write something, I get a little traction, I keep going, and it fades. I sometimes can’t believe that three months have already passed me by, and I’m terribly worried that I’ll wake up one morning and feel like I’ve wasted this time, time I know has an expiration date. The expiration date is fixed, based on my savings, but I also know that extending that date relies on me and my ability to ‘make this work’ (whatever that means…).

If I’m being honest, I’m also feeling very broke. I’m not at Cannes or going to Spain this summer. Heck, I might not even make it to a beach that’s not in New York City. I think about every purchase I make, justifying the hit that means my savings will take.

With my new client signed, my freelance income now just about totals a third of what I was bringing home from my last full-time job. I’m grateful for the small extension to my expiration date and to be able to dip into savings just a bit less.

I know I don’t need my old full income to survive. I’m not yet earning enough on my own to cover all of my expenses, but I’m getting closer. Still, there’s a part of me that wishes I were already there, that I could skip this uncertain bit and jump to the part where my savings can stay where it is, where the expiration date becomes a moot point. At the very least, I wish I could say I was closer to that dream.

It’s annoying (at best) to have to think about money at every turn, to not buy myself the perfect pair of summer clogs or my kid a croissant every time we pass by the coffee shop, but there’s also a level of gratitude that comes from being able to choose to have these as worries. I’m not in survival mode, and I know that it would take a lot for me to get there, even if that means re-entering the workforce.

I also have been hit with a bit of a realization: chores are still chores, and quitting my job didn’t magically make them all get done more quickly, nor did it make me enjoy them more. On the contrary, with so many irons in the fire, I find it’s been more difficult to stay on top of the laundry, dishes, and all the other things at home I thought would magically get done once my time was mine. But when the chores do get done, it feels easier and less urgent (even if, in actuality, I am more behind). I think that’s where I get to see the benefits of my time being mine.

I do have this strange feeling of knowing that, for the time being, there’s just certain information that’s not my business. Instead of trying to peek at what isn’t visible yet, I’m spending my time on what feels right. All I can do is show up every day and hope that I’ll get to see more of the path as time goes on.

I’ve noticed a personal shift that I’m going to carry forward. With what hasn’t seemed like much work, I feel like I’m a bit more confident and sure of myself. I’m defaulting less and less to what I think others want to hear, and it’s getting easier to stand firm in my beliefs. I think this is a shift that happens for many as they settle into their mid-30s, but I think all of the risks I’ve taken (and those that wait for me ahead) have almost expedited this process.

Living more closely aligned with my truth has made all of this feel easier. I don’t have to flip a switch to ‘play’ confidence, it’s just becoming a bit of a default. Conversations with others have felt easier; meeting people and connecting isn’t something I really have to psych myself up for, and talking about the things I’m doing doesn’t feel like it’s wrapped in embarrassment anymore.

I have a lot to show for these last few months, but I also acknowledge that I’ve taken the first chunk of my time off slowly. Intentionally slowly, but still, slowly.

I didn’t jump into cold outreach or force myself to create a stringent offer. I haven’t been holding myself to any sort of cadence for posting or chatting or anything else. That has served me well in these first three months, but I’m also getting to the point where I know it’s time to pick it up, even if just slightly.

This summer, I’ll be looking for ways to be more focused in how I talk about the work I’m doing — freelance writing, my work here on Substack, and yes, the work I’m hoping to do in tech and with founders. I also know that talking about it broadly isn’t enough.

The next big thing I need to chew on is the oh-so dreaded outreach part of being self-employed. I don’t want to get too deep into it, because this is an essay on its own, but the number one reason I’ve dismissed being self-employed in the past is having to be responsible for finding clients, for popping up in people’s inboxes unannounced, and putting myself out there.

But it has to be what comes next, I am starting to feel and know that deeply. I’m unwilling to reach the end of my runway and regret not reaching out to more people. I’m also unwilling to just grin and bear it. I’m committed to actually enjoying this process³.

Other than that, what lies ahead is still mostly unknown. I’ll keep walking the path, keep experimenting, and maybe I’ll finally accept I’ll never be caught up on laundry.

1. and some change

2. Look…time zones are hard, okay? They restored the essentials when I called it out.

3. Again, I have more to say (and some really helpful reframing a new bud shared), but I’m saving that for another essay.