The biggest risks are often the quietest decisions – that email you finally send, that conversation you stop postponing, the moment you choose to move forward instead of being comfortable.
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Many people know what opportunities they want, but many are unwilling to take risks. Promotions may seem out of reach, and important conversations often never happen.
These moments are not just about opportunity; They are about trust. At some point, you you have to trust yourself Or keep waiting for the right time or someone else’s approval. The best leaders act even when they are not completely sure.
I learned that lesson firsthand at a critical juncture early in my career.
My own “now or never” experience came in my mid-twenties when I worked in Hollywood. I arrived early to an awards show and saw Steven Spielberg drive down the red carpet. I told the woman I was talking to that I would love to meet her someday. She immediately replied, “Why not tonight?”
His question took away every excuse. I had access. I was already there. The only obstacle was my interpretation of risk.
During dinner, I came up with a plan. If I had avoided eye contact with security at the entrance where the celebrities were sitting, and walked confidently, I probably would have looked like I belonged in that section. I kept asking myself: Am I someone who simply sees opportunities, or someone who pursues opportunities?
After passing the guards, I went straight to Spielberg. We talked for two minutes.
Research on regret shows that inaction lasts longer than action. By the end of 2025, studies still show 76% people regret missed opportunities, while only 24% regret their actions. Psychologist Albert Bandura says mastery experience The best way to build self-efficacy. Confidence comes from taking action.
The conversation didn’t change my career; However, it changed the way I saw and continued to see myself. That moment became proof. This proved that proximity without action means nothing. Whenever I doubt myself I think about that night.
If you want to understand a successful leader, ask them when they chose action instead of hesitation.
risk asking
Sara Haynes, co-host of ABC’s The View
ABC/Jeff Lipsky
Sara Haynes, at 22, now co-hosts ABC’s SceneMoved to New York City in hopes of getting into NBC’s competitive pageant program. He applied but never received a reply. No rejections, no interviews – just silence. For many beginners, that silence feels like a signal to wait.
One morning on the train he saw a man with an NBC bag. He saw her again the next day and the next day. Every time, she wondered: Should I say something? Would it be weird? Will I look stupid?
The third time he saw her, he felt more hesitant than taking the risk. He called it a fork in the road. “I’m more afraid of regrets than failure,” she told me in a personal interview. That thought changed everything. Not knowing became scarier than being embarrassed.
He followed him to Penn Station and stopped him. She asked, “Do you work at NBC?” He did it. Gary Quinn handed him his card and offered him his resume.
That introduction led to the interview she was hoping for.
Contacting him was only the first step. Being ready for delivery was all that mattered. As she said, “By getting that interview, I knew I’d sell the rest. I knew I was enthusiastic. I was working hard. I just needed that interview. And finally, that was the moment I thought, ‘It’s now or never.’ Not even ‘why not today’, which sounds very positive. It was either do it or else.”
He didn’t show fake confidence. He just took a decision.
Self-confidence Often comes from the verb, not before it. Haynes didn’t wait until he felt ready. She took a step forward and got ready.
how to ask
1. Decide before contacting. Before you ask, know exactly what you want. Is this an introduction? an interview? A new assignment?
2. Lower the emotional stakes. Good leaders keep rejection as a part of who they are. University of Chicago 2018 Study found that people routinely underestimate their willingness to help others when asked directly. In other words, the odds are often better than we expect.
3. Be direct. Strong requests are clear and to the point. Skip long explanations and respect the other person’s time.
4. Be prepared to follow through. Before you ask, ask: If they say yes, am I ready?
build momentum around doubt
Diane Farr, lead actress and director of CBS’s Fire Country
Courtesy of Dianne Farr
diane farr, lead actress and director of CBS fire countryIt was soon discovered that the greatest risks were not always external. It is internal.
When we spoke, Farr didn’t pretend that negative voices disappear with success. He described it as familiar. The difference, he said, is the reaction. “My best weapon against the negative voice in my head is to come in the side door every now and then,” she shared.
Instead of debating the doubt, she creates momentum around it.
That philosophy extended beyond the audition. At one point early in her career, the actress bought a bar, moving into a completely different kind of performance. This was not a creative risk. It was financial, operational and reputational. Owning a business means that uncertainty is no longer theoretical. This was reflected in payroll, customers and daily decisions.
He later sold the establishment, allowing him to focus on auditioning and building a reputation in the entertainment industry. Bar’s experience expanded his tolerance for ambiguity. He learned that risk is about participation.
Be it business or entertainment, his approach remained consistent:
“If I hit three side doors, one of them is going to work.” Multiple paths lowered the emotional stakes. Optionality reduced fear.
Over time, the internal question changed. It was no longer “Am I capable?” But “When will I use what I made?”
Farr rejects the idea that self-confidence is innate. She added, “I don’t believe anyone is born with courage.” “I think courage is something you grow; you have to grow it. You have to water it. You have to give it sun. You have to give it oxygen.”
Risk tolerance is built through exposure. Every detail expands the identity. Every decision strengthens self-confidence. Self-doubt does not go away. It subsides as evidence accumulates.
Farr added a final dimension. Environment matters. “There will be people who will support the negative voice in your life, and there will be people who will support the ‘let me just try’ voice, and friends are better off listening to the ‘let me just try’ voice.”
The biggest risks are often the quietest decisions – that email you finally send, that conversation you stop postponing, the moment you choose to move forward instead of being comfortable.
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How to become comfortable taking risks
- View risk as practice, not a one-time leap. Treat every effort as an opportunity to get better.
- Don’t tie rejection to your identity. A failed attempt is merely information. Leaders who handle risk well don’t confuse results with self-worth.
- Make side doors. Taking more than one path reduces risk and helps you keep moving forward.
- Prepare evidence before you need it. Self-confidence increases through small, repeated experiences. recent research Emphasizing “inhibitory learning” it was found that exposure not only reduces fear in the moment but also helps individuals form new safety associations that weaken the original fear memory and improve long-term resilience.
Opportunities do not make leaders. Let’s decide.
