There are moments in life when we stand before an opportunity and quietly ask ourselves a question: What if I fail? What if they say no? For many people, those questions are enough to stop them before they ever begin.
They never apply for the job, start the business, write the book or pursue the relationship. They never step onto the stage. Not because they lack talent or because they lack opportunity.
But because they are afraid of failure. Ryan Leak’s story challenges that way of thinking. A motivational speaker, author and executive coach, Leak has built much of his message around an unusual idea: failure does not have to be something we run away from. It can become fuel for the journey ahead, but long before he became known for talking about failure, he created a wedding story that would change the direction of his life.
The Wedding That Took Two Years to Plan
Ryan Leak had a dream, but it was not initially a business dream or a speaking career. It was a wedding. For two years, Ryan secretly planned what would become one of the most extraordinary surprises of his life.
His girlfriend, Amanda, had no idea what was coming. Ryan studied her Pinterest boards. He paid attention to the weddings he had attended as a groomsman. Ryan observed the details that made weddings special and quietly put his own plan together.
Ryan wasn’t simply planning to propose; he was planning what would happen after she said yes. On June 7, 2013, he finally got his opportunity. He proposed to Amanda.
She said yes, but that was only the beginning. Almost immediately, Ryan revealed the secret he had been carrying for two years. Family members and friends were waiting.
A wedding dress was ready, and stylists were prepared. Everything had been arranged. The proposal would be followed by a wedding, and the couple went from engagement to marriage the same day.
Their remarkable story attracted widespread attention and eventually went viral, but beneath the excitement of the surprise wedding was a lesson Ryan would carry for the rest of his life.
He had taken an enormous risk and planned something that could have gone terribly wrong, yet he discovered something important about risk.
You cannot experience an extraordinary outcome without first being willing to face an uncertain one. That realisation made Ryan begin asking himself a much bigger question.
“What Would I do If I knew I couldn’t Fail?”
The wedding forced Ryan to think differently about fear. He realised that many people do not actually fail because they tried. They fail because they never try.
Before they even take the first step, they calculate all the possible reasons they could be rejected. They imagine the embarrassment, people laughing.
Then they convince themselves that avoiding the attempt is safer than pursuing the dream. Ryan wondered what would happen if he removed that fear from the equation.
He asked himself. “What would I do if I knew I couldn’t fail?
The answer came quickly. He would try to play in the NBA. There was only one problem. Ryan had not played college basketball. For most people, that would have been enough to dismiss the idea immediately.
Ryan Leak in a podcast
But Ryan decided to pursue it anyway. He documented his attempt to make an NBA team, knowing that the odds were overwhelmingly against him. This was not a carefully calculated career move.
It was a test. Could he chase something that appeared almost impossible simply because he wanted to discover what would happen if he tried?
Eventually, he got his answer. He did not make the NBA.
He failed. But something extraordinary happened. The failure did not destroy him. It taught him.
When Failure Became Fuel
Ryan could have looked at the experience and concluded that he was foolish for trying. He could have said, “I told you so.”
He could have allowed the rejection to become evidence that he should never dream that big again. Instead, he began to see the experience differently.
The NBA dream had failed, but the lesson had succeeded. His attempt eventually became the inspiration for his bestselling book, Chasing Failure.
The very thing he had been taught to avoid became the foundation of his message. That is one of the great paradoxes of life. Sometimes the door that closes teaches us more than the door that opens.
There are times rejection develops us more than acceptance.
Ryan did not become an NBA player, but his failed attempt helped him discover another platform. Today, he uses his experiences to encourage individuals and leaders to think differently about failure, courage and personal growth.
His story reminds us that failure is not always the opposite of success. Sometimes it is part of the journey toward it.
The Fear that Keeps Us Stuck
Think about how many dreams have died because someone was afraid of failing. A young person wants to start a business but is afraid nobody will buy.
Someone wants to apply for a better job but assumes they will not be selected. A writer wants to publish a book but fears criticism.
An entrepreneur has an idea but is terrified of losing money. Someone wants to ask for forgiveness but fears rejection.
The tragedy is that we sometimes treat the possibility of failure as though it were worse than the pain of never knowing what could have happened.
But what if failure is not the monster we think it is? What if failure is simply information? What if it tells us what needs to change?
Strengthens our character, redirects us, teaches us humility or introduces us to another path? The Bible reminds us that “a just man falleth seven times, and riseth up again” (Proverbs 24:16).
The emphasis is not that the righteous person never falls, but that failing does not have to be the end of the story.
Failure Is Not Your Identity
Perhaps that is the lesson we need most. You are not your failed business, or you are not the mistake you made yesterday.
Failure may be something you experienced, but it does not have to become who you are. There is still another chapter, and sometimes, the thing you call failure today may become the very experience that prepares you for tomorrow.
So take the step, make the call, submit the application, start the business, write the book, pursue the dream, and if you fall, get up because the goal is not to build a life in which you never fail.
The goal is to build a life in which failure never has the final word. As the Bible says, “weeping may endure for a night, but joy cometh in the morning” (Psalm 30:5).
Ryan Leak did not get everything he wanted. He did not become an NBA player. However, that failure gave him something he could never have received if everything had gone according to plan.
It gave him a story, a message and a mission. So the next time fear whispers, “What if you fail?”, perhaps answer with another question: ” What if trying changes my life?” Because sometimes, the greatest risk is not failing. It is never trying at all.
