City Diaries: Navigating Self-Employment + The Creative Process


Today marks my third week of self-employment. It’s a decision that’s been over a year in the making. A leap of faith that I’ve taken to commit to my own professional and creative freedom. And yet, this is the first time I’m finally sitting down to properly acknowledge it—to be free…to create. I waited 365 days for this moment, and yet, it’s taken me 16 days to even open a new post draft.

Why? I’m not entirely sure, but I have plenty of analogies that attempt to explain how I’ve been feeling the past couple weeks.

In angsty moments, I’ve equated my feelings to the final scene of Like Crazy. You know, the part when they’ve spent years trying to make a long distance relationship work. And finally when they’ve overcome the challenges of transatlantic immigration, when their “happily ever after” seems possible—same country, same loft apartment in LA—something doesn’t feel quite right. The struggle has taken too much of a toll on the relationship, and their love isn’t quite the same anymore.

Now, since that reference may be a bit too dramatic/obscure for the common passerby, I have a more realistic comparison I’ve been using in small talk and text exchanges with friends. This one’s a bit more relatable—understood by anyone who has racked up their fair share of $15 late cancel fees from ClassPass now and again.

Enter: The Workout Analogy.

In this instance, my lack of writing/creating/doing can only be compared to trying to go back to the gym after an extended period of being sedentary. Barre? Dance? Yoga? But WHY would I go when I can use the extra hour to drink wine in bed instead? I’d like to think we’ve all been there. And as hard as it is to workout when you are in the zone, it feels down right impossible when you’ve fallen out of it. And being honest with myself, I fell out of the zone—my creative zone—a long time ago.

How? Well for starters, this has not been an easy year. In fact, it's been the most challenging period of my career thus far. It’s tested my limits in all ways—mentally, emotionally, and even physically. In case you were wondering, stress hives are a thing—thanks WebMD! The past year, and especially the past 6 months, I’ve been clocking triple time. While working full-time as an Associate Director at a paid social agency, I was building my consulting business Walk-Up Digital on the side, while simultaneously diving head first into teaching digital marketing at General Assembly.

And where did writing for 5th Floor Walk-Up fall into the mix?

The same place my time for cooking, working out, date nights, seeing friends, and general sanity went. Temporarily put on hold...only finally being reintroduced into my life in the past couple weeks of my newfound freedom.

In my transition to self-employment, I straddled (and let’s be honest, am still straddling) the line between total elation…and compete dejection. My thoughts have alternated between the unwavering belief that I will one day own a Lifestyle Empirecapitalized because it’s my new favorite thing to say when people ask “so what do you really want to do when you grow up?”—and the illogical conclusion that by quitting my job, I will inevitably become destitute, forced to sell all my belongings on Poshmark (luckily I’ve had some past success), move out of my 5th floor walk-up and in with Craigslist roommates (note: my actual worst nightmare), and become a barista while I beg Corporate America to take me back. Honestly as I type it out, this whole scenario really doesn’t sound that bad after all. I would be v. minimalist while serving up some mean matcha lattes.

As I look back on the past year—finally reemerging from the fog and becoming a fully functioning human again—I wouldn’t trade this time for the world.

I wouldn’t take back the Friday nights spent alone in the dimly lit corner of my favorite vegan restaurant, nursing my third glass of wine while writing business proposals. Or undo the complete and total public meltdown I had on 6th Avenue after missing my early morning yoga class since I’d been up until 3am the night before working through a consulting project. Note: interestingly enough, a girl in yoga pants hysterically crying on the sidewalk at 8am phases ZERO New Yorkers. Or take away the moment I introduced myself to someone at a networking breakfast and they casually responded, “Oh yeah, my mom sent me your website and said I should read!” What!? I’m in with the You-Should-Read-This-Love-Mom emails now!? That is next level and I am still processing.

Or the day I closed my first deal, sent my first invoice, and direct deposited my first consulting check—earned 100% on my own. Definitely, wouldn’t take that back. And I physically can’t, because I cashed that ASAP and finally bought those Gucci loafers everyone’s been knocking off.

…only kidding :) I would obviously rather spend my hard earned money refurnishing my apartment.

But the irony of it all is, in my search for creative freedom, I became temporarily paralyzed when finally presented with its reality. And that paradox is just the tip of the iceberg. Because if the past 2 weeks are any indication, I can tell you this whole "working for myself” thing is going to be one hell of an adventure, and I plan to share the ups and downs with you on this blog.

So, I guess this is my long winded way of saying: hi, again 👋 I’m here.

And while I’m still in the process of finding my footing, I’m excited to be back and can’t wait to create more goodness on 5th Floor Walk-Up.

Thanks for sticking around.

P.S. This is my first official entry of what I’m calling “The Fire Escape"a new section of my site that will be dedicated to any and all life musings from myself and possibly some of my favorite New Yorkers, too. More soon.