What Three Years of Living in New York City Has Taught Me About Being A Boss Lady

Turning twenty five this year, I fully expected it to be a complete unraveling of myself, assuming a quarter-life crisis was on the horizon. As hard as I have been pushing myself to grow, no growth has felt like enough, often wondering when it would finally be my season to bloom. Yet somehow, and in some ways, the air felt different this year of living in New York City. It felt more favorable than before as if all of my efforts at loving myself more, being kinder to my inner child, and working on finding balance, instead of stressing over the hustle, finally came to fruition.

This year has landed me jobs so uniquely different from the ones I was used to. I’ve also had the freedom to say no to some of the ones that didn’t suit me any longer. I somehow found myself affording the word “no” more than I ever have in the past. What shouldn’t be surprising, is how when we finally say no to the people that do not value us or our work, and we hold ourselves to a higher standard, better, more quality work comes along.

Still, there are nights where I am kept up wondering where else I can improve, shaming myself for not doing more, but fortunately, they are less this year. I’ve learned that shame and guilt do not work for me as motivators. Being able to give myself breaks and allow for slower growth has had a far larger impact than I could have ever imagined.

What Three Years of Living in New York City Has Taught Me About Being A Boss Lady

The “Boss Lady” Narrative is Toxic.

I read an article recently about a woman who was struggling in her “amazing” job, where she “knew” that it was a real “Boss Lady” position, but she felt like there was something off, where there was still more she could be doing. The writer who responded immediately destroyed the idea of how being a “Boss Lady” is the ultimate goal to strive towards. The hustle culture pressures people to constantly be moving, forever unhappy with the speed of their progress, assuming that if they’re comfortable, that means they’re not doing enough. So the writer replied,


Forget whether or not you’re good at your job (which is a very ego-driven fixation) and forget whether or not you’re objectively “strong enough” or “smart enough” or “confident enough.” Who is watching and measuring? Who is strong and smart and confident most of the time? No one. These things are illusions. We’re all insecure and dumb and afraid, because we’re animals. Trade in, “Am I enough?” for, “Do I deserve to be happy?”

I think you do.

– Heather Havrilesky on the Ask Polly column

This struck me the hardest. As I transitioned to being my own boss after college, that boss became a real asshole, unwilling to advocate for the things I did right, nor take into account needing time to heal from traumas I have experienced. It was as if there was some external source that was shouting in my ear, telling me I have to do Something Big. “I don’t care what it is, but it’s gotta be big!” It would say. Nothing was ever enough.

One, giant list of grievances against myself.

Just the other day, I forced myself to write out every single thing that morning I had already managed to make myself feel guilty about/over from the moment I woke up til now. As I began to catalog the bigger things i.e. not getting up as early as I had wanted to, not having enough healthy food to make for breakfast, working at a messy desk, the smaller bits began to bubble to the surface.

They began revealing the inordinate amount of self-hatred I was harboring. I had made myself feel guilty for taking too long to sit down to work in the same moment I was making myself feel shame for not cleaning up my breakfast before sitting down to work. It was exhausting to read back that list, and frustrating that I could have managed to type out such a full list of grievances my mind already had against itself in less than two hours of functioning.

I made myself feel guilty for not doing the things on my to-do list almost as often as I made myself feel guilty for doing things on said list, just not as fast as this external voice felt was necessary. These crazed markers of success weren’t realistic, nor were they based on what normal human beings could accomplish in a day. It wasn’t a new revelation, simply one I’ve striven to actually pay attention to more, especially when that obnoxious, demanding voice comes to the surface.

Productivity is not a measure of self-worth.

My entire identity and purpose felt as if they were riding on how productive I was that day. That angry, inner voice loved to shout about all the things I was doing wrong, ironically enough so, where I was completely unable to take a step forward to fix it, in fear of being judged. By who? This strange, shitty voice? Other people? I truly can’t tell you.

We have a unique way of driving ourselves into the ground and shouting all sorts of negative shit around our heads so that it’s impossible to actually listen to our kinder inner voices when they tell us what we really need. I previously didn’t allow myself to write because it wasn’t making me any money, because it didn’t fit with my Boss Lady plan. I wasn’t willing to start a project that had been years in the making, out of fear of not following through, or worse, no one caring. My perception of what I could be doing and what I should be going after were so skewed, it made complete sense that I was extremely anxious day in and out.

It has taken three years of living in New York City to feel as I am finally doing more than just surviving here, and that I have to continuously put in the work to keep it that way. High rent and “hustle over everything” attitudes can make it easy for people like me to say yes to work that isn’t right for us, all in the name of grabbing ahold of anything to continue to exist here. New York City makes it easy to fall into these traps, where we blink once to find ourselves two years in and unable to come up with the name of a single, large client that they can feel proud about working for.

Part of me feels embarrassed to admit this, but another part has to remind myself that maybe, this is my inner Boss Lady talking, cultivated from absorbing too many Instagram posts about only sleeping when we’re dead, or “inspirational” talks that leave a person feeling worse than when they first hit play. Because right in the past few months, I have worked on jobs I am proud of, started on a new project I can excitedly talk about, and finally accept that I am allowed to not feel like suffering is the only place I feel most comfortable. These three years were some of the hardest I’ve had, only now feeling like I’ve gotten ahold of my footing here, but happy I’ve held on.

How living in New York City has shaped me.

Living in New York City has provided a beautiful, chaotic backdrop to my deepest lows, but also served as a catalyst for some of my greatest moments of clarity, this year being no exception. I made the leap to find an apartment with my boyfriend, and experienced the back-breaking work of lugging each and every piece of furniture and plate down three flights of stairs from my old apartment and three flights of stairs up to my new one.

Yet every morning when I shuffle out of the bedroom and across the hall to the bathroom, I’m immediately struck with how much light pours through every window. The bathroom’s all-white walls absolutely glow, my office becomes bright and enticing. The living room has a soft glow in the afternoons, where I’m happy to transition to my laptop to keep working when my office’s morning light grows dim. It’s a big, beautiful apartment that I’m still in absolute disbelief came about from three terrible photos of the same room on an old listing I kept circling back to.

I also get to share it with someone who I truly do not understand where he came from, in the best of ways possible. Sometimes I feel redundant when I explain to him how I’ve never had a significant other so compassionate and respecting of my choices and shortcomings before. I’m able to love him with my entire heart, never once being told I am too much. There is a mutual respect, something I never quite realized I craved so deeply, and hadn’t come close to before.

Autumn in Central Park

I don’t know if there will ever be a point where I’m free of these unnecessary guilt trips, but this year has been about being kinder to myself. There’s a little less shame-spiraling on my schedule for the day, and a little more of actually doing the things I want to be doing.

This past fall I proved to myself just how hard I could work to live, filling my calendar with long hours and constant commuting from NYC to Connecticut and back, sometimes several times in a weekend. Through this, I learned that being productive and finding purpose can sometimes bring about two totally different results. In the spring, it has been about seeking jobs that are empowering and respectful of what an actual living wage is, having the courage to turn down work that has been soul-crushing to free up time to continue seeking out work that feels good.

The struggle of wanting to be productive while also finding purpose.

The key is finding balance and understanding that our lives exist in seasons, where sometimes we do need to put our big girl pants on to grind to get the experience, full schedule, and paychecks. But as often as we do that, it’s also extremely important to fully examine what it is we’re truly after, pay close attention to that, and fight that Boss Lady voice that tries to tell us it’s not worth it, or you’ll go broke in a year, or no one will give a shit. The hardest lesson I’m learning and re-learning is that if we care enough about it, chances are, there are plenty of others that will as well.

I am creating again, this time putting myself out there to include more than just my voice. It can be hard to remember that unpaid projects I truly love working on could one day become my main source of income. Projects where I fall into bed, exhausted and fulfilled with the work I’ve done, while feeling energized to continue to contribute to the next day. Until then, I remind myself that I’m finally doing work that feels just right, and that’s far larger than any check could be.

What Three Years of Living in New York City Has Taught Me About Being A Boss Lady

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