# CHAPTER 8: How to Pack Your Parachute – The Art of Preparing for Your Boldest Leap
Hello everyone, it's me again! How are you all doing? Today I will continue to walk with you and review CHAPTER 8 of "Cultivating Audacity read online," and let me tell you, this chapter feels like that moment right before you jump off a diving board—when your toes are curled around the edge, your heart is pounding, and you're asking yourself, "Am I really going to do this?"
Well, friends, that's exactly where we find our author in this chapter. She's standing at the precipice of change, and she's about to teach us something profound: before you take the leap, you need to pack your parachute.
## The Story: When Life Forces Your Hand
Picture this. It's 2003, and our narrator is living a double life. During the week, she's a producer at ESPN, working on SportsCenter news coverage. On weekends, she's a sideline reporter, doing about twelve games that fall. She's stiff and uncomfortable on camera—her improvement is slow, almost painfully so.
Now, here's where it gets real. One of her trusted supervisors pulls her aside and delivers some hard truth: "You are never going to be good on air if you continue producing." He explains that she needs consistent on-camera repetitions to see real gains. It's time to make a decision—go all in on reporting, or stay safe as a producer.
What does she do? She backtracks. She chooses the safer path. She chooses producing. And honestly, who can blame her? Producing was her established success, her security blanket. Then she takes leave to give birth to her first child, and two and a half months later, she returns to producing because she needs that stable income.
Her first assignment back is coverage of a sensitive story with veteran reporter Shelley Smith—a nine-time Emmy Award winner and a dear friend. Shelley, who had once brought her six-year-old daughter on assignments, urges our narrator: "Bring the baby."
So there she is, with her ten-week-old son Lukas, flying from Colorado to Phoenix and then to Los Angeles, covering a murder case involving a college football player. The baby is screaming on flights and in cars. Lukas is keeping her up all night, and the quality of her work is suffering. The assignment has no end date, and she's bouncing from city to city, exhausted and overwhelmed.
Finally, she breaks.
She calls her boss and cries, "I can't do this." That same supervisor who told her she needed consistent on-air repetitions a year earlier now hears her admit that she needs to leave the unpredictable schedule of a field producer for something she and her husband can plan around.
And here's the pivotal realization: working on games as a reporter meant having a schedule months in advance. If she became a full-time live event reporter, she could plan childcare well ahead of time. It made sense to go all in on becoming a reporter.
As she prepared to jump, it was time to pack her parachute.
## What Is a Parachute, Really?
Now, this is where the chapter transforms from memoir into something deeply practical. Our author asks: what does it mean to pack a parachute?
A parachute, she explains, is not a ripcord—it's not an escape hatch to bail when fear and doubt creep in. Instead, packing your parachute means compiling all the things you need to set yourself up for a safe and softer landing as you embark on a new journey.
Think about it. Before anyone takes a scary jump out of a plane, they don't just leap willy-nilly. They prepare. They check the equipment. They have a plan for every possible scenario.
The same principle applies to audacious living.
The chapter walks us through four specific barriers—the same ones we've been exploring in previous chapters—and shows us exactly how to pack for each one.
## Barrier One: Fear
What are you afraid of? Really, truly afraid of?
For our narrator, her fears about going on camera centered on embarrassment and judgment. She knew she wasn't good. She hated the sound of her voice and her delivery. It was humiliating to be bad at a job in front of colleagues who were consummate professionals. She suspected viewers—and maybe even friends and colleagues—would judge her performance unkindly.
But here's the packing strategy for fear: write down what you're afraid of. Catastrophize it. Go all the way to the worst possible outcome. Then ask yourself—how likely is it that you'll really reach that end? Will you truly die destitute and alone? Or will the outcome, even in a poor situation, fall short of complete ruin?
Our narrator was indeed an awkward reporter when she began. She was embarrassed. Some friends and colleagues did judge her. But she survived. And she worked to get better. Eventually, she thrived.
The fear doesn't disappear—but it loses its power when you face it head-on and realize you can survive the worst-case scenario.
## Barrier Two: Time
Chapter five was all about time and the urgency fallacy, and that theme comes roaring back here.
Our narrator's producing position had been urgent—she'd receive a SportsCenter assignment and head to the airport in a day or two. With a newborn, producing at a high level while also pursuing on-camera improvement was nearly impossible. The lack of notice made childcare arrangements a nightmare.
But reporting came with a schedule of games months in advance. Suddenly, time became something she could budget, plan, and control.
The lesson here? Clearly define what is important to you and allocate time accordingly. Create a time budget. Put it in your calendar and stick to it—even if that means finding four fifteen-minute slots per day. Don't let the urgent always take over the important.
## Barrier Three: Money
What's your money story? This is a question that runs deep, touching on childhood, habits, and beliefs passed down through generations.
Our narrator was lucky. She had a frugal upbringing, and her ex-husband was a saver. They never fought about money. Matt was supportive of her move to reporting—after all, he didn't want her leaving him with a baby on zero notice! They ran the numbers, knew it wouldn't be comfortable, but were confident that slight adjustments in spending would allow room for this change.
The parachute packing for money means finding balance between earning, spending, and saving. Recognize your strengths in your relationship with money. Can you trade money for more time or energy to pursue your goal? Should you tighten spending elsewhere to reallocate funds toward your dreams?
Write down how much you spend pursuing your goal and look for balance. If you're putting a lot in and not getting much in return, it's time to recalibrate.
## Barrier Four: The Inner Critic
Oh, the inner critic. That voice that whispers—or sometimes screams—all the reasons you shouldn't take the leap.
What does your inner critic say as you prepare to take your audacious leap? Practice recognizing those messages as unrealized fears, not facts. Separate them from yourself. Thank them and move on.
Our narrator says "thank them" because when you acknowledge them, you're not trying to push those thoughts down—you're letting them surface and choosing not to follow that path.
When she transitioned to being on camera, she hadn't yet fully separated her inner critic from her own voice. But her mindset as a former collegiate athlete was a great help. In athletics, no one is "good" when they start a new sport. It takes mistakes, losses, and failures to become proficient. Just as she had worked consistently as a volleyball player to be a little bit better each time, she knew she would need the same patience on air.
She quieted her inner critic as often as possible and focused on incremental steps to improve.
## Building Your Front Row
This might be my favorite part of the entire chapter.
"No one does it alone," our author writes. "Who are the people who want to see you succeed without jealousy? I call those people my front row."
Your front row should consist of individuals who genuinely want to see you thrive—family members, close friends, mentors, and peers who share your aspirations or have experience in the areas you're pursuing. They not only cheer you on but hold you accountable.
Our narrator has multiple front rows. She works out with two friends—Holly and Nicole—every Monday, Wednesday, and Friday. They have a text chain peppered with "Don't forget to sign up for class" and "Are you both coming tomorrow morning?" If she doesn't show up, they don't let it slide. That's her fitness front row.
Her personal front row is made up of friends she confided in first about her divorce. She felt like a failure, feared judgment, and carried huge shame. It took almost a year to tell anyone that she and Matt had split. She flew to New York and cried with three friends she'd known since her teens. Gradually, she told her four brothers one by one, each time fearful. But they all supported her, asking, "What do you need?"
Matt, her ex-husband, is in her parenting front row. They made a pact to skip the drama and present a united front to the kids. Without the pressure of marriage, they became better friends.
Building your front row is about finding people willing to talk you off the ledge of uncertainty and imposter syndrome—even when you don't want to hear it. You can be comfortable failing in front of that squad because you've witnessed their failures and triumphs too.
## Choose Your Front Row Wisely
But here's the crucial counterpoint: it's equally important to recognize who should NOT be in your support circle.
A woman once asked our author after a keynote, "Is it possible to have a back row?" She laughed, but it was a good point. There are those who shouldn't even be allowed in the room.
Be careful of the well-meaning fearmonger. Potential saboteurs have their own reasons for trying to talk you out of changing things up:
- They don't want you to be hurt or disappointed - They have anxiety about making changes in their own life - They're jealous of your chutzpah and afraid your success will diminish their accomplishments - It's comfortable for you to stay the same because they fear your relationship will change - They project their fear of failure onto you
You may love your mother, but that doesn't mean she belongs in your front row. Parents' own experiences with risk and adversity shape their attitudes about risk-taking in their children. They may want to shield you from pain or prioritize safety over exploration.
When faced with well-intentioned discouragement, approach with empathy but also assertiveness. Communicate your feelings. Explain how their pessimistic words impact you. Express your need for positivity and reassurance.
You don't want a room full of yes-men when taking bold risks. You want friends who have your very best interests at heart without competition.
## The Final Preparation
The chapter closes with a powerful warning: beware of getting caught in the cycle of packing and repacking your parachute indefinitely, wanting it to be perfect.
It will never be perfect. You will never have all the answers. But you are ready. You have everything you need. You have done the work examining your barriers. You have a plan for each obstacle. It's not a perfect plan—but it will do.
None of this is set in stone. You have identified your front row.
The "right time" is not coming, so don't wait for it. Waiting doesn't work.
This is the right time. Right now.
The next step is to take the leap.
Let's go. Turn the page.
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## Reader's Impressions & Star Rating
Wow. Just... wow. This chapter hit me right in the gut in the best possible way. What I love most about this chapter is how it balances the deeply personal—our narrator's raw, honest story about crying to her boss, about bringing her newborn on assignment, about the fear of judgment—with the universally applicable. We've all been there. We've all stood at that precipice, terrified to jump, clutching our excuses and our fears like lifelines.
The concept of the "parachute" is brilliant because it reframes preparation not as procrastination but as wisdom. It's not about waiting until you're ready—it's about preparing so you can jump when the moment comes. And the "front row" concept? That's going to stick with me for a long time. The idea that we need to be deliberate about who we let into our inner circle, who we allow to speak into our dreams, is something we don't talk about enough.
This chapter also does something I deeply appreciate: it doesn't promise that everything will work out. It doesn't say you won't be embarrassed or judged or scared. It says you'll survive it. And sometimes, that's the most powerful message of all.
⭐⭐⭐⭐⭐ Rating: 4.9 / 5 Stars
The only reason it's not a perfect 5 is that I wanted even more specific examples of how to have those "critical conversations" with people who don't belong in your front row. But that's a minor quibble. This chapter is a masterclass in preparing for audacious living.
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## Next Chapter Prediction
Based on the cliffhanger ending—"The next step is to take the leap. Let's go. Turn the page."—I predict Chapter 9 will be all about THE JUMP. We've packed our parachute. We've built our front row. Now we actually have to leap. I expect we'll see our narrator's continued journey into full-time reporting, including the challenges, the failures, and the wins. I also suspect we'll get more examples of people who took their own leaps—like the teacher Brenda who wanted to be an assistant principal, whose story was teased at the beginning of the current chapter.
Chapter 9 will likely be the emotional payoff, showing what happens when you finally do "the thing" and discover that the landing, even if it's bumpy, is survivable—and maybe even spectacular.
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