High Performance

How To Know When To Quit Your Job And To Take The Leap

BY Carrie Yang

The Must-Read Newsletter
For  Every                                Woman


Start Your Week With

We all have ambitious dreams for our future lives.  And for the most part, we do our best to find a career, a partner, and a lifestyle that helps us achieve what we want.  However, as humans we grow, we learn, and we change. Thus, we often times realize that our current situation simply doesn’t contribute to the life we want anymore. Sometimes the answer involves 

“I really want to start a business. Is now the time to do so?”

“I no longer enjoy going to work anymore.  Should I quit and try something else?”

“This relationship isn’t making me happy. Should we end it?”

“I really don’t like the industry I’ve worked in for 10 years. Am I throwing everything away if I try something else?”

“Should I risk what I have now to pursue the unknown?”

I bet most of us have asked ourselves some variation of these questions before and perhaps even considered taking a “leap” into a different job or career, out of an unhappy relationship, or into something completely unknown. I definitely have, and I’ve made four major leaps in the past 3 years. How did I do it without fearing the unknown and without any regrets?  That’s what I’m sharing with you, so you can also take leaps and fly high.

Leap /lēp/: the act of intentionally changing any aspect of your life in pursuit of circumstances with greater alignment with your values, goals, and aspirations. Often times involving risk and the unknown… and may even prompt you to quit your job and pursue a new future.

Reflecting back on the last three years, I’ve taken four major leaps, each having been the most impactful decision of my life and never regretted a single one.  I studied and worked all the way through college to get into medical school, got in and didn’t go. Instead, I took a sharp turn into the finance world. In less than a year, I quit my cushy institutional finance position and joined a food delivery start-up company called Chef Shuttle running their marketing without any prior experience. A year later, I left Arkansas, my residence of 19 years without any connections and friends and moved to New York City. I found a position heading up the marketing for TUSHY, a progressive bidet start-up with immense potential, and found my home and finally a place I belong in NYC. And recently, I took the biggest and hardest leap of all… leaving an amazing team and my favorite city on Earth to go to Texas to grow Sniffle, a health-tech company from scratch.  

I’ve made the decision to leap with confidence and have never looked back. How? I made these decisions with conviction after answering a few honest questions. Uprooting my life in NYC and moving to Texas was my hardest leap, and I’ll walk you through these questions and show how I decided it was right the right move for my future. Apply these questions to your own crossroad and deciding whether to quit your job, start your own company, and take the leap. 


What have I learned about myself in my current situation?

What things have I learned I like?

What things have I learned I dislike?

What do I want to have more of?

What do I want to explore?

I absolutely loved TUSHY, the team, and the work I was doing leading the marketing. Then, a (still very) risky opportunity to start a health-tech company in Dallas, TX arose, and I had to decide to leap or to stay. I asked myself the WHAT questions and found these answers. I loved my life in NYC, my role, my team, and the leadership and technical skills I’ve learned. However, I didn’t have a leadership role in the company that allowed me to make core decisions. I wanted to explore technology marketing, mobile apps, and learn how to build a company from the ground up. Most importantly, I wanted to go back to my healthcare roots while combining my passion for marketing.


Why do I love what I love about my current situation?

Why do I dislike what I do in my current situation?

Why do I want more of what I stated in my answer to the previous question?

In answering these WHY questions, I learned that I loved my position at TUSHY because I loved my co-workers, the freedom to carry out my ideas, and most importantly my life in NYC. However, my dislikes about the position at TUSHY, while limited, were unlikely going to change in my current position. I also realized that I wouldn’t be able to gain more of what I wanted if I stayed, which was medical tech.


How do I put myself in a situation to get more of what I like?

How do I explore more of this?

How do I put myself in a situation where I don’t have to do what I dislike?

The answers to my HOW questions further confirmed what I wanted more of couldn’t be found at TUSHY. In order for me to grow to a position with more decision-making power, in the tech field, and contributing to medicine, I had to depart from TUSHY. By the time I came to HOW, I knew that I had to leap to Sniffle in Texas.


When I make this leap and it fails, is there a way to win? This question means if things don’t work out in an ideal way, will I still gain something from this experience?

Am I in a better position than I was before even if things don’t work out?

Am I more self-aware than I was before, so I can leap even further this next time? If a win can be a win, and a failure can be a win… then leap.

This WHEN questions are perhaps the most important when deciding to leap. This question determines whether the risk is worth the leap. Leaping is taking calculated risks and while the risk is there, the reward can be greater.  I asked myself, “If Sniffle Health failed, would this leap still be a win?” The answer was an absolute yes. Even if Sniffle didn’t work out, I would have learned how to launch a tech company from name to logo to creating the overall brand, marketing strategy, and everything from the ground up! Also, having had held the position as the Chief Marketing Officer of a tech company would elevate my career even if Sniffle Health failed in a few years. Even if this leap “failed” I would still win.

Ask yourself these questions, and you may be surprised at how ready you are to quit your job, start that new company… to take the next leap. If signs are pointing to leap, leap.

You have to take action. You have to leap.

This is the hardest part… the physical and mental act of leaping.  Life is short and to live it without enjoying it and challenging yourself is just a shame. It’s scary how easy it is to get comfortable and to stop growing due to the fear of the unknown and the risks involved in leaping.  However, by asking yourself some key question about the deeper reasons behind leaping, you’ll have the conviction that you’re making the right decision. There’s a lot of merit in the term “leap of faith” since there are always unknowns, but when you’ve determined that even a “failure” is a win, then the odds are in your favor. When the leap is literally a win-win, what is there to lose?  



The must-listen podcast for ambitious women
working on their businesses and careers.

the bossbabe podcast



Pour your favorite latte and join us for honest conversations that take you behind the scenes of building successful businesses, achieving peak performance and learning how to balance it all.

Currently creating the woman I want to be. Excuse me if I become extremely protective of myself, my time, and energy.


Do you have what it takes to create YOUR OWN ONLINE BUSINESS?

we think you do

Get project next