Taking the leap (realistically)

Anna Bao
5 min readAug 13, 2021


You’ve probably heard different versions of the phrase “take the leap, and the net will appear” or seen images like the one below circulating in today’s social media. The idea is simple: if you want to change “what you are today” to “what you want to be in the future,” you take the leap of faith; the call to action is to jump. I’ve received this advice to “jump” before, though never wanted to blindly follow it. I wanted to gain certainty around the right timing and situation to “leap.”

Upon a closer look, I began to question a couple of things:

  1. Why do I want to take the leap in the first place?
  2. How big should my jump be?

I also was skeptical about the “magical” net, leading me to the question:

3. Can I freely trust-fall and still get back on my feet if my jump fails?

When I most recently “jumped” from working as a startup employee to full-time entrepreneurship, I tried to evaluate what went well in my past experiences where I took the leap. By sharing my insights here, my hope is to demystify this phrase and provide you with considerations so that you can realistically take the leap and find (or build) your net.

Taking the leap

The definition of taking the leap is to go for something unexpected or take the chance on something, whether it be professional or personal. When taking the leap, I’m deviating from typical inertia by introducing uncertain variables into my path. When these new variables collide, they promote potentially good and potentially bad consequences to happen at a faster rate than normal; hence, diversifying the opportunities and therefore the paths forward. I know this sounds like physics class, so let me more clearly make the analogy through two personal examples of taking the leap.

I first took the leap when I was a freshman at Rensselaer Polytechnic Institute. That time shed light on what a 4-year college experience at a predominately engineering college would look like for me. I quickly began to understand that the social and career prospects weren’t aligned with my priorities nor my strengths. My reason and motivation for transferring reached a point that led me to consider taking the leap.

I landed on Cornell as the school I’d focus my transfer efforts on, or my energy to jump. Cornell was larger and more diverse in its course offerings. I was unaware of the opportunities I’d have at the time, but I knew if I increased my options of majors and mentors, I could accelerate my learning. Similarly, I was likely to expand my career path prospects. As a result of this transfer — the leap — I graduated with a major in interdisciplinary studies and a variety of classes, like biomedical engineering, food science, and business management, Upon graduating, I landed my first job at a corporate rotational program.

In a similar way, I took the leap from corporate to the startup world. With a few years of work experience, I continued to hone in on my awareness of my own development and learning. I was dissatisfied with the slow timeline of corporate life, and couldn’t see myself being fulfilled in the role. I didn’t know where I should jump to, but a leap became imminent.

Although risky, and sacrificial in short-term benefits, I took a 3-month role working for Techstars, a venture accelerator. I urgently made this leap with nothing lined up afterwards because I was driven by the hope that it would increase my options, and therefore my odds of determining the next job for me. This 3-month role program provided me with the opportunity to learn from 10 different companies across 10 industries. Further, I realized that I saw myself supporting startups in the early stages. I ultimately found a role as the first product hire.

The pillars of a leap of faith

I can point to courage and confidence as the pillars that support any leap of faith. Courage causes the action and confidence leads to the reflection that fuels your next, larger jump. Both of these characteristics, however, take time to develop and get stronger with repetitions.

Preparing for my own leap of faith actually started as early as middle school, when I advocated my way to the honors program after voicing an interest in an advanced level class to the principal. My naivety and passion contributed to my courage then. Years later, I cultivated my confidence when traveling for an overseas externship with a 12 hours layover in Tokyo, and increasingly evolved into a combined 5-week solo trip in Eastern and Central Europe.

Fast forward to today, and without the confidence gained from my previous experiences, I wouldn’t have taken my current leap of faith in founding and building Kleido — a marketplace platform that allows for real-life career exploration for high school students by facilitating conversation with young professionals.

Through my exploratory experiences, I’ve learned that I’m passionate about aligning the incentives of these two groups of people in a more accessible and beneficial way than what exists today. My hope is that Kleido introduces another variable for its students and helps them see their options more clearly.

The net

While hoping that there will be a net that magically appears when you leap helps lower the fear, realistically you’re going to be leaping into a pitch black hole. What helps is knowing some definitions and structures of the net, its potential to extend, and your own ability to expand the net.

When taking the leap in schools and work, my nets were defined by the credentials and network of the academic institution and the company I worked at, respectively. When building Kleido, however, I leveraged the nets from my background and proactively created my own structure using communities like Propel, Day One, and Transcend Network: all while learning as much and as fast as possible from internet resources and other members. I find reassurance in these growing communities and networks as I continue to grow.

The phrase, “take the leap, and the net will appear” is easier said than done. There is never the just right time and situation, and the most effective leaps always rely on some constructs of intentional support. It’s not a decision to be taken lightly, and realistically, it takes a combination of urgency, awareness, courage, confidence, and planning.



Anna Bao

Not the best writer, but have a story to tell. Currently building Kleido.co, a career exploration platform for high school students.