1,000 Days After Quitting Corporate: 5 Things I Know Now
by Lauren Rosalanko
At 29, after 2,748 days (or 7.5 years) in Corporate America, I walked away.
My initial intention was to run a one-year experiment. I would give myself the chance to reset and learn if I could or even wanted to continue my entrepreneurial path while living in NYC.
More than 1,000 days later, I’m still self-employed, earning multiple income streams on my own terms, and living my version of the American Dream in Brooklyn.
I quit for many reasons, here are a few:
I wanted to return to fully remote work that I got a taste of during the pandemic
I wanted control over my time and what I worked on
I wanted to pursue a passion of mine: helping more women with their personal finance foundations
I wanted to eventually make more money and not be capped at a salary
Over these 1,000 days, I’ve learned that so many people stand exactly where I once stood: knowing they want more but are unsure of how to take the leap.
If that’s you, I offer five things I wish every aspiring solopreneur, freelancer, or consultant knew as they set off on this path.
Know what you spend before your quit
Most people think the first step to self-employment is figuring out how you’ll earn. It’s not. The first step is knowing how you currently live. Before I left my job, I calculated what my life cost in real numbers. No judgement.
Here’s what you should know to get your current budget:
Your monthly, quarterly, and annual spending
Your “necessities number” (housing, utilities, groceries, health insurance, transportation, phone, other essentials)
Your existing obligations (subscriptions, loans, recurring expenses)
Your lifestyle patterns that are tied to having limited time: takeout, convenience shopping, delivery
These numbers aren’t meant to scare you. When you understand the numbers, you have something to work with. I’ve found that financial anxiety often isn’t about the money itself, but rather it’s about the uncertainty. Clarity will help you find calm so that you can make smart choices.
Savings = Investing in future you
If you can plan ahead even a little, you dramatically increase your odds of staying afloat once you leave. This also can give you some space to breathe and recover from burnout, something a lot of us underestimate. You don’t have to drastically change your lifestyle in every way.
Some things I did to save and reframe:
Label your savings mentally. When you save $7 by skipping a latte, don’t just think, “I saved $7.” Reframe it to, “I just paid $7 to future me.”
Use your credit card points and miles like cash reserves. Travel, flights, or even just groceries can be covered during your early months. I like to say I am a “reformed points hoarder.” I saved a lot of points, always waiting for the best deal. This served me well once I quit to have a reserve fund to continue traveling!
Open a high-yield savings account. You can realistically earn 3-4% on money that’s just sitting there. We love passive income!
Create your Quit Plan
Most people choose one quit date. I recommend two:
Quit date #1: the ideal date (often timed around bonuses, vesting, PTO payout, insurance coverage, etc.)
Quit date #2: The realistic but still empowering date (if the ideal one shifts)
Next, ask yourself some operational questions:
Have I used my health benefits?
How much does COBRA cost?
What are my other options for coverage?
Do I have an FSA balance to spend down?
Will unused PTO be paid out?
What happens to my commuter benefits?
Am I walking away from a bonus payout?
Knowing these answers shouldn’t trap you in a job you don’t love. Understanding the details can free you from surprises. Quitting is never going to be perfect, but it’s powerful to be prepared.
Rewire your brain to get creative with budgeting
When you leave a safe, cushy salary, you’re trading money for time. More time lets you redesign your life on your terms.
Here are a few mindset flips that supported my savings:
Delivery vs. Cooking: You used to pay for time. Now you have the time. Grocery shop, cook, meal prep. Your wallet will thank you!
Travel Flexibility: Tuesday flights at 6am are suddenly on the table and are usually half the price.
Subscriptions: Cancel most of them. If you really miss them, you can always get them back, but this is a major money sink that most people don’t even think about.
Micro-housing hacks: Pet sit or house sit while you travel for free or discounted stays. Sublet your own place if you’re planning to travel for longer periods of time.
Free joy:
NYC museum free days
Your local library - many free resources beyond just books
Donation-based fitness
Walks, workshops, and community events
NYC, ironically, the most expensive city in the world, is full of free things. Take a look at what’s available near you and I’m sure there’s a lot you’ve overlooked! Remember, this phase isn’t about total restriction. You’ve got your time back so spend it wisely and your money can stretch further than you expect.
You don’t need a fully formed business to make money
I don’t recommend jumping straight into building a company the day after you leave your job. Transitioning out of corporate life is a big emotional and physical shift. You may need rest and that’s totally ok! About two months after I quit a wise woman asked me if I took time to not be productive and recover from burnout. I realized I hadn’t and wish I had given myself a bit more time.
Instead, start with income that’s simple, low pressure, and instantly confidence-building:
High-yield savings interest (again, passive income!)
Survey sites or focus groups for easy gift cards or small payouts
Babysitting, pet-sitting, tutoring can be flexible and dependable
Ad hoc project work with no long-term commitment
Whether or not you’re drained by corporate life, these small income streams can feel surprisingly energizing. They don’t have to be forever, but they’ll help you regain momentum, flex into your newfound autonomy, and build trust in your ability to support yourself.
The Real Lesson: You’re more capable than you think
Leaving corporate isn’t just a career decision, it’s a psychological one. It asks you to believe you can build a stable, meaningful life without a company telling you who you are or how much you’re worth.
I’m here, 1,000 days later, living proof that you can.
If you are contemplating a leap into freelance life, consulting, or entrepreneurship, know this: you can do this thoughtfully, safely, and successfully. And you don’t have to do it all alone.
Want more insights like this?
Lauren is a financial coach and the founder of Points for Change. She helps millennials build a Quit Plan, get out of debt and optimizing credit card points. Outside of work she enjoys traveling, yoga and fostering kittens.
If you're navigating a career transition, starting a business, or simply wanting to feel more grounded in your finances, Lauren brings both lived experience and professional expertise to guide you.
Work with me! Points for Change offers an 1:1 personal finance coaching. You can sign up for a free 20 minute intro call to decide if coaching is right for you.
About Onward
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Learn more at onwardbenefits.com.
