How to Quit Your Job and Still Make It in New York

Working in NYC

I’m not much of a risk-taker. I deadbolt my apartment door even when I just go downstairs to take the garbage out; I added earthquake straps to my furniture to make sure it doesn’t topple over unexpectedly; and yet I quit my stable financial journalism job a year ago to start my own content marketing firm, even though I was living in Manhattan, one of the most expensive areas in the world, and I didn’t quite know where I was going professionally.

In the 12 months since, I’ve learned four important lessons for how to quit your job and branch off on your own, without letting the city eat you alive in the process. So if you want to feel less risky before you put in your two weeks notice, here’s what you need to know:

  1. Weigh Your Opportunities to Make Money Against Your Obligations
    Quitting your job to pursue your passion may be the modern American Dream, but it’s not realistic for many. You have to be fortunate enough to be in the right circumstances, because if you lose your source of income and have kids, a mortgage or many other types of responsibilities, it can be very difficult to keep up.

    So start by identifying your obligations and how you would cover them. In my case, I had rent, utilities, insurance and a cell phone, which isn’t all that much responsibility, but I was also saving for an engagement ring and wanted to keep my current lifestyle of enjoying New York by going out on the weekends, ordering some takeout here and there, etc.

    I knew what I needed to make each month to keep things going the way I wanted and thought I could get there, but I could have done a better job with Lesson 2…

  2. Have Initial Opportunities Set Up Before Quitting Your Job
    It can be very tempting to just walk in to work one day and tell your boss you’re never coming back, but since it can take a while to build up your own business, you’ll blow through your savings or go into debt if you don’t have something set up already.

    In my case, I contacted my old journalism  job (the one prior to the one I was quitting) to see if there would be any freelancing opportunities, tried to get some freelance gigs through my part-time membership at WeWork, and I also started applying to part-time service jobs like at coffee shops. But this was all patchy; I knew I could put it together, but it definitely was not a golden parachute, and I could’ve used more time to set things up before leaving my other job.

    In New York, it wasn’t nearly as easy as I thought it would be to get a service job, because most places want significant experience and a long-term commitment to the job. Luckily, I had an in with a friend at a quick service restaurant, so landing that job gave me a bit of stability as I built out my content marketing business. But if it wasn’t for that connection, I might not have even been able to get a service job anytime soon.

    While it’s important to have to some initial opportunities set up so that you’re not totally scrambling to find work once you quit your job, you also don’t have to have everything squared away, or else you might never make the leap. Know that New York is full of opportunities if you’re willing to put yourself out there, so establish a baseline you’re comfortable with, and then dive in.

  3. Take Calculated Risks
    As indicated above, quitting your job in and of itself should be a calculated risk rather than a wild gamble. And once you’re out on your own, don’t be afraid to keep taking calculated risks to advance your business.

    For example, working part-time at the quick service restaurant was a great way for me to transition from my old job to my new one, but I only kept it for two months. At some point, I had to take the risk of leaving that job in order to gain more work in content marketing. Otherwise, what was the point of starting this new venture? 

    Because New York is so big and competitive, you have to keep taking calculated risks to grow your business. In a smaller town, you could perhaps afford to be a bit more patient and let events unfold naturally, but here, if you’re not making some sort of investment in yourself or your business, you could be left behind.

    Still, don’t stray so far that you can’t return back to a comfortable baseline.

  4. Find a Good Place to Work
    Given how expensive New York real estate is, it seems silly to pay for office space when you’re already shelling out so much for your apartment. But many residences are small and not conducive to productive work, and even if you do have the space, it can get lonely.

    If that’s the case, take the calculated risk of paying for office space, particularly at a coworking space where you can keep costs manageable and still have a professional, yet social atmosphere. I spent far too long getting frustrated in my tiny studio, or bouncing around from coffee shop to coffee shop, and not really doing as much work as I could if I made the small investment to have a good place to work.

What’s Next?
Now that a year has passed, I’ve been able to settle into my work a bit more, establish a better routine, gain good clients, and still keep up with the same New York lifestyle I was living before I quit my job (plus buy the engagement ring I was saving for). 

It’s not always easy, and it’s normal to think about going back to a regular job every now and then, but if you keep things in perspective, such as remembering how lucky you are to live in such an awesome city AND have the freedom to work on your own terms, then it’s an easy decision to keep moving forward.


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