15 Years in NYC

What it's been like to color my way through the maze of New York City over the past 15 years

It wasn’t much. But it was exactly enough to get started.

I’ve been reflecting a lot lately on the work it takes just to get to the starting line (which is completely separate from the work it takes to actually run the race). As I’ve learned over 15 years, cold starts are hard. Keeping the momentum going is also hard.

I don’t think a lot of people realize how many dead ends you have to hit in pursuit of a goal in order to finally get to the place you want to be. I thought today would be an appropriate time to share this story because I know a lot of people right now are feeling a lot of dead ends and cold starts of their own — whether in their careers, their personal lives, or both.

To stick around in a place like New York City for 15 years requires a near-constant level of vigilance, intentional leveling up, and personal and professional expansion. There’s a reason they’ve got that catchphrase, after all:

If you can make it here, you can make it anywhere.

As it turns out, this so-called “New York state of mind” has a lot of fringe benefits that go far beyond day-to-day survival. It builds resiliency, adaptability, and grit — all of which are incredibly helpful character traits in general, but they are particularly helpful during sea changes times of massive transformation (like we are experiencing right now, in nearly every corner of the economy).

It reminded me of this picture of a children’s maze that my friend Julia Austin shared recently, along with the following two observations:

1. This maze has more than one path to the finish line.

2. The middle is messy but the end is clear.

It doesn’t matter what the mess in the middle looks like. What counts is that you keep holding the crayon and remember where you’re going.

This “messy middle” phase is also what has inspired another recent podcast to emerge, “The Messy Parts” by Maryam Banikarim. She (and every guest on her show) understand this core tenet to be true: The stuff in the middle doesn’t always make sense.

You just have to keep coloring.

A lot has happened over the past 15 years. I’ve gotten to do way more things than I ever would have imagined, and I’ve continued to push down on the buttons of the corners of the city that matter to me.

By year 5, I (finally) had a debt-free income stream. By year 10, I had my first baby. And now in year 15, I’m planting down even more roots by grounding myself in IRL community at the heart of the tech and business ecosystem itself.

That’s not to say NYC has made it particularly easy to stick around. I’ve weathered hurricanes and pandemics. I’ve made friends and lost them. I’ve worked at more companies that have fallen apart than ones that have stayed together. I’ve had two babies who are now enrolled in the NYC public schools system. And I’ve tried on more than a dozen careers while flitting about a half-dozen apartments – including one force ejection due to toxic black mold, which was the only time in my entire trajectory that I feared I might actually need to leave for good.

“Maybe we need to see other people.”

I wrote in a faux breakup letter to the city, dated September 2023. (Because don’t all of life’s strongest relationships have a breakup period?)

But luckily I married someone whose own internal hustle culture mirrors my own. And so, while I’ve worked my way up from “the girl who wants to move to New York” to the acting president of my block association on the Upper West Side, he’s needled his way from a part-time job at the Apple Store in SoHo all the way to Broadway musicals and sound gigs on Saturday Night Live.

It still is not easy. It still is not straightforward. But I think 15 years is as good a time as any to finally declare: I am not letting go of the crayon. (And you shouldn’t either.)

It wasn’t much. But it was exactly enough to get started.

I’ve been reflecting a lot lately on the work it takes just to get to the starting line (which is completely separate from the work it takes to actually run the race). As I’ve learned over 15 years, cold starts are hard. Keeping the momentum going is also hard.

I don’t think a lot of people realize how many dead ends you have to hit in pursuit of a goal in order to finally get to the place you want to be. I thought today would be an appropriate time to share this story because I know a lot of people right now are feeling a lot of dead ends and cold starts of their own — whether in their careers, their personal lives, or both.

To stick around in a place like New York City for 15 years requires a near-constant level of vigilance, intentional leveling up, and personal and professional expansion. There’s a reason they’ve got that catchphrase, after all:

If you can make it here, you can make it anywhere.

As it turns out, this so-called “New York state of mind” has a lot of fringe benefits that go far beyond day-to-day survival. It builds resiliency, adaptability, and grit — all of which are incredibly helpful character traits in general, but they are particularly helpful during sea changes times of massive transformation (like we are experiencing right now, in nearly every corner of the economy).

It reminded me of this picture of a children’s maze that my friend Julia Austin shared recently, along with the following two observations:

1. This maze has more than one path to the finish line.

2. The middle is messy but the end is clear.

It doesn’t matter what the mess in the middle looks like. What counts is that you keep holding the crayon and remember where you’re going.

This “messy middle” phase is also what has inspired another recent podcast to emerge, “The Messy Parts” by Maryam Banikarim. She (and every guest on her show) understand this core tenet to be true: The stuff in the middle doesn’t always make sense.

You just have to keep coloring.

A lot has happened over the past 15 years. I’ve gotten to do way more things than I ever would have imagined, and I’ve continued to push down on the buttons of the corners of the city that matter to me.

By year 5, I (finally) had a debt-free income stream. By year 10, I had my first baby. And now in year 15, I’m planting down even more roots by grounding myself in IRL community at the heart of the tech and business ecosystem itself.

That’s not to say NYC has made it particularly easy to stick around. I’ve weathered hurricanes and pandemics. I’ve made friends and lost them. I’ve worked at more companies that have fallen apart than ones that have stayed together. I’ve had two babies who are now enrolled in the NYC public schools system. And I’ve tried on more than a dozen careers while flitting about a half-dozen apartments – including one force ejection due to toxic black mold, which was the only time in my entire trajectory that I feared I might actually need to leave for good.

“Maybe we need to see other people.”

I wrote in a faux breakup letter to the city, dated September 2023. (Because don’t all of life’s strongest relationships have a breakup period?)

But luckily I married someone whose own internal hustle culture mirrors my own. And so, while I’ve worked my way up from “the girl who wants to move to New York” to the acting president of my block association on the Upper West Side, he’s needled his way from a part-time job at the Apple Store in SoHo all the way to Broadway musicals and sound gigs on Saturday Night Live.

It still is not easy. It still is not straightforward. But I think 15 years is as good a time as any to finally declare: I am not letting go of the crayon. (And you shouldn’t either.)

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>700 subscribers