This question was originally asked on Quora . The following answer was selected and re-published by Forbes .
You don't get over the fear. You run towards it, with your knees buckling.
Two years ago I was looking at this very question with hopes and fears, while sitting in my corporate office.
I had been crippled and paralyzed by fear for six months while contemplating this decision.  I finally jumped both feet. And I've been surviving for two years. How did I get over the fear? Reasoning didn't work. Introspection about my happiness needs was necessary but not sufficient. Evidence of success from my outside endeavors were not convincing. The only one thing that got me over the fear was through finding an experience from my own past to build an analog from.
I'll explain. It's a story about a waterfall.
I'd been wanting to be an entrepreneur for almost a decade. In undergrad I graduated as a Computer Science major. During the last six months of school I went to career development counseling, sharpening my resume and interview skills. There, for the first time in my life, I ran into a an interesting type of person. When it was everyone's turn to ask each other "what's your goal?" mine was to find a good job at an important company. His, he said timidly, was to become an entrepreneur and learn to start a business. My ignorance and the way he expressed himself made me pity him. What a misguided career path. He "must have" given up on job prospects earlier than necessary.
I didn't know myself then.
For the first six months out of Waterloo University, I was unemployed. Their statistics mention that nearly everyone finds their first credible job within the first six months of graduation. I made that year's statistic. It took me six months of hunger and debt to find my first job at an enterprise company. And another 18 months to study my way in my spare time into Microsoft.
I paid off my debts. And I lived like a hermit, saving money. I didn't know why.
It was a contract job. And Microsoft contracts legally cannot be longer than a year without three months of bench time. So after a year, I had to take a three month break. This was early 2008. I spent two weeks playing games. Then I got bored and spent the rest of the three months coding a toy project. It turned into, what I later learned was called, a startup.
It was manically exciting and lonely as hell.
Friends started distancing themselves from me, because I seemed to not take my former (and their current) work seriously anymore. I was too deeply absorbed by my idea. It was addictive. It was joyous, exciting, incredibly stimulating, and lonely at the same time. After three months of isolation, I decided I couldn't handle the level of manic and lonely excitement anymore. I decided I had achieved the mental release that I had set out to achieve, and that I didn't know the next step. I certainly didn't know how to commercialize my idea. So that night, in Seattle, I bought a one way ticket to Europe for the next morning. I went to a sports store and bought a backpack, an alarm clock and a pair of new shoes.
I backpacked through 22 countries in 80 days. Alone. For the experience of being alone.
Backpacking took me through completely unexpected experiences that I never imagined would come to my rescue later. The 11th country on my list was Bosnia and Herzegovina. I stayed with a local family in Mostar city, where the old bridge (Stari Most) is located. The bridge stands over the river at a height of an 8-story building. (Heroic) people are known to jump from its edge into the river for a display of courage. It captivated me for some reason. I don't have a fear of heights, but when I walked over it, a strange sensation came over me. As if someday I would have to do this jump. I felt crippled. For the first time in my long journey, I was shaking in fear.
I think subconsciously I was connecting the dots that my consciousness couldn't connect.
The next day, our local host took me and a couple of English, Australian and French hostel-mates on a tour to the Croatian border. He introduced us to Plitvice Waterfalls, a gorgeous area just past the Croatian border. We swam in the water. A couple of guys went up some of the waterfalls and dove into the water. I thought they were absolutely mad. How do you know there are no rocks in the bottom? You could break your freaking head!
I didn't even attempt it.
Then we went for a little hike down the river stream. It was a beautiful sunny day. The host was jokingly flirting with our French companion, saying the only thing in French that he had learned was "Tres Jolie!" and the Aussies and Brits were walking ahead, planning their next adventure. I was in this beautiful and magnificent place, empowered and liberated by my independent travels, and yet ... absolutely miserable. There is no other word to describe the state in which you feel that you're missing once-in-a-lifetime opportunities. And I was miserable because I had come all this way ...
I had come all this way to discover that I was a coward.
Along the way we came across one last waterfall. We had seen it from the bottom, but took a way around to arrive at the top. I was so struck by fear again that I couldn't even remember whether the bottom was rocky or clear. I was shaking again. Then to my surprise, everyone of my companions started taking turns running towards the cliffy edge and jumping off into the unknown. First our host, then the five guys one by one, then the French girl. Then, there was me. I stood up there for what seemed like 30 minutes (I was later told it was only a few minutes) staring my certain death in the face.
I was embarrassed, looking at the accomplished, encouraging and happy faces on the other side of the river. I was angry at myself for not being courageous. And worst of all, I was stuck. Turning around just didn't seem like an option. The only two options were to stay in suspense forever, or to jump.
The suspense seemed more difficult to tolerate. I had to find a way to induce in myself the desire to jump. So I started thinking: why am I afraid? Because there could be rocks down there and I could land on them with my head. How likely was it? I don't remember. But seven people had just successfully jumped off in front of my eyes, landed and crossed successfully. And they were looking at me and the bottom of the waterfall from the opposite side, telling me that it was going to be okay. So it's probably not as risky as I perceive it. Why should I do it? Because if I don't, I'll regret that moment for the rest of my life.
Then came a near-death moment.
Most near-death experiences I've heard of have been accidents. But I'm convinced that moment felt like dying. A rush of blood flowed in my face and every limb, as if my mind had accepted that my body's will was no longer under its control. I was in my mind. But my body was doing the running. What seemed like someone else's legs ran towards the cliffy edge, and my mind exerted one last command into my weak body to spring out and distance myself from the edge of the cliff in the final moment; a command that didn't even work, because my knees buckled in fear and everything became a sudden blur in the final moment.
I jumped off that cliff. And I did die in that moment. The coward inside of me died. I remember falling for a long 100 milliseconds that was long enough only for a brief thought. And the thought crossing my mind while falling was: "Well... this is it! I have eliminated the version of the future in which I'm a coward. I'll either land on rocks and that's the end, or I'll emerge as someone new on the other side."
I didn't register the impact when I landed feet first in water. In fact I didn't register much of any feeling until I was about 8 feet under water, realizing that I had to swim back up if I wanted my next breath, and for my head not to implode under water pressure. When I emerged on the water surface, I was fighting the flow of the river, completely distracted from my previous fears. And when I finally made it to the other side, everyone started clapping and laughing in jest. "Alright!!! That wasn't so terrible, was it. Let's look for another waterfall ... Next!"
When I returned from the trip, it was October 2008, the peak of US recession. Everyone was being laid off. But these ensuing six months were very different from the six months of unemployment that I endured after graduation. From the recession of 2008 till six months later, I found an incredible project at Microsoft, a graduate admission into Carnegie Mellon University, a senior-level job at a Silicon Valley startup and the girl I married. It's a story for another time, but the common thread for those achievements was the same lesson over and over:
Jump off the cliff and become alive, or spend a lifetime regretting it like a dead man walking.
I worked my butt off in several startups in Silicon Valley while studying in parallel in Carnegie Mellon, and finally against all odds and expectations, ended up at Google. I worked at Google while studying masters at the same time -- Can you imagine walking in the shoes of a person who couldn't find a job for six months, a mere seven years prior, now being handed the keys to (reportedly) the best company in the world?
Once again, I had a lot to lose. This time, it wasn't my life, but it was an amazing career.
After about two years of a satisfying experience at an amazing company, I was once again the miserable man walking like a coward along the river. I had dreams and ambitions. But I had a good life. Heck no, I had a great life. I knew I was privileged, despite hard work, in a world where the next guy doesn't know whether they can keep the roof above his family's head for another year. Why leave this? Why pursue dreams when you're already living a dream?
Encouraging quotes from famous people (across the river) didn't seem to make me feel better:
Were there none who were discontented with what they have, the world would never reach anything better.
Why do we jump off the cliff with our lives?
How do you get over the fear of quitting your job to start a startup?
By realizing that at the height of our success, we live in a cage. The most successful animal in the animal kingdom is the lion living in the cage of a zoo. He gets his every meal, guaranteed and on time. He has no natural enemies. Even diseases and harsh climates are not a concern. Eat. Sleep. Die.
If lions in the zoo could speak, they'd tell you "I don't want this to be it". Reaching the peak of what you thought was success is only the stepping stone to seeing the fundamental ways we make ourselves happy: to hunt; to run in the wild; to have serendipitous experiences; and the very blessing in the experience of climbing new peaks. Once you get to all of your goals in life, including career success, you must be able to let go of your new-found ego and burn the past successes if you want to continue to grow.
Two years ago the following Quora answer gave me inspiration:
The most honest answer is that you probably won't get over the fear. The types of people who make Startups work are the kind of people have a 'feel the fear and do it anyway' attitude and are able to persist despite all kinds of obstacles, emotions and obviously 'the fear'.-
Jim Lawrenson, Quora
You know, I voted for that answer on one of those miserable days when I couldn't live with the coward inside of me. This time, it was only two years ago, or four years after the waterfall story. But then I remembered my own experience from the waterfall that day.
When you're standing on the edge of a cliff, the only experience you can draw on is your own.
So look for the analogs that have worked, and trust them more than the pep talks and stories from others. But perhaps more importantly, assume less in your question:
How do you get over the fear?
You don't "get over" the fear. It's there when you're thinking about jumping. It's there when you're running towards your next goal. It's there when you take a leap; it doesn't even let you feel your limbs. And it's certainly there when you're in a free-fall. But then you do fall, you submerge yourself below the lowest point you could imagine possible, and you somehow figure out that the worst scenario imaginable wasn't the most probable scenario. And after that, you're a new person, encouraging the next guy about to jump, with a smile, from across the river.
And who knows ... afterwards, you may continue to dream about jumping off of the Stari Most.
- I even up-voted Jim's answer as the one that resonated with me the most.