Parachute Moments: How to Trust Yourself When You’re Step
Nov 26, 2025
[Ep 22 of the podcast]
One of the many times I made a truly bold move, quitting a great job at a great company, I felt like I was stuck at the edge of a cliff with a parachute. A cliff where there was steady career growth, financial security, and no change. But I was also feeling very confined in my role and totally at odds with the changing culture of the organization. I couldn't make a move. But I kept looking over the side, unsure. Am I ready to jump? I don't know. All of the voices in my head were screaming, what are you doing? Do you know what you're doing? I hate it here. I want to go. I want to stay. What if my parachute doesn't open?
Spoiler alert. I did take the jump. My parachute opened, and I never looked back. But here's what I learned: Fighting through the fear of taking a big, bold leap is important. It doesn't have to be a stop sign. Fear can be a yellow light, a warning: Slow down, check direction. Make sure you're going where you should be. Or it can be a green light. Proof that it's time to move towards something new.
If you've been waiting to feel fearless before you make your move, this episode is your wake up call. Today we're rewriting the story on fear.
There are different types of fear. Some of them good, some of them not so helpful. Fear often shows up as a compass, as intuition, survival instincts. Fear can be great. It sharpens our senses. When we feel unsafe, we get those gut feelings, the hairs rising on the back of our neck, the urge to avoid dark alleyways, getting a bad sense of someone and knowing you should stay away without knowing why. It's fear's job to keep us alive and alert for hundreds of thousands of years. It's served us well. But sometimes, just sometimes, fear overreacts.
Fear shows up on the edge of growth. When we're standing on the edge of personal or professional expansion, when we're about to grow to step into a new role, start a business, leave a relationship, or chase a new dream. Fear whispers, “What if?”
What if I can't do it? What if I fail?
What if I get bored of it?
What if others laugh - if nobody likes it? If nobody likes me?
What if I end up alone?
It's dramatic, the fear. The more we listen to those fears, the less we trust ourselves. Fear keeps us comfortable in doing what's safe, in staying where we are, in doing what's known, what's considered normal. Maybe you've had that parachute moment too, when you could see something that you wanted, but the leap to get there feels too big. If you knew that your parachute would open and everything would work out beautifully, what big change would you make in your life?
Everyone feels fear, even confident, capable people. Especially confident, capable and successful achievers. The bigger your goals, the more fear is going to show up. You have more to lose. When I decided to leave my job, I didn't know if I'd regret it or if the bold leap would be a big mistake. But that internal voice saying, “There's more, there's something different for you. There's something better. It's a better fit” grew louder and louder. And instead of falling back into the comfort of the money, the safety, the security, the title, I listened.
And that's when growth began.
I see this all the time with the women I coach - the belief that confidence should come before the action. When in reality, confidence is something that you build through action. That's how you get it - by making those first small steps, you build self trust. You build that self confidence. In order to achieve new results or big change, you have to be willing to move forward despite that fear.
A very common response to fear of change, fear of growth or expansion, is to make no decision at all. Feeling unsure, needing more time to think, living in this confused state about what you want. “I don't know” is often cover for “I'm afraid to make a decision. I'm afraid to move forward.” Maybe it's scarier to move forward than it is to stay in the same place?
During my parachute moment, my fear of change was showing up as feeling stuck. I was feeling unhappy. I was paralyzed by indecision. I was confused about what I wanted to do because I was telling myself that I didn't want to walk away from a job. Even though I had outgrown it, I didn't want my life to fall out of favor. It was scary. It's normal to feel scared, though. But I still needed to figure out how to move forward, right? I couldn't just live in this indecision forever.
So, I worked with a coach to help me figure out what was going on. Because I had a lot of confusion around my situation. And sure enough, within a few months with my coach, I was unstuck.
I was on board at a new company. I was on to the next chapter of my life. It was magical, really. But every bold move that we take carries risk inherently.
We weigh the comfort of what's known and safe against the possibility of something better, the possibilities of something greater. Yeah, it may not turn out perfectly. It may come with a few obstacles that are difficult. But what's the alternative? A life that's half lived and safely mediocre? I don't recommend taking huge leaps like quitting your job with no money saved. But I recommend making a plan to make a change.
There are a few people who may never feel fear. They are so comfortable in living a wild and full life - a bold life. Or maybe they don't feel fear because they're staying too complacent - too comfortable.
Maybe they’re just repeating old patterns, living inside a safety bubble. And while safe and stable sounds good on paper, for many people, safe and stable is not the same as fulfilled. Bold living, the kind that brings joy, adventure, meaning, fulfillment will always require courage. You only live once, and life is meant to be lived. So where in your life are you playing it? Too safe, maybe too comfortable. Maybe it's an area where you're settling for good or worse, when you could be making it great.
Great success often feels like a ceiling for us. The higher we climb, the less fear we should feel when making bold changes in our lives. Right? Wrong. I don't think fear of change ever really goes away. In fact, there are a few reasons why. The more success we have, the scarier it becomes. The higher we climb, the further the fall. But as we near the top of one goal, we often find ourselves asking,
“Is this what I came for?
This is it?
This is all there is?
This is what I dreamed of.
The house, the job, the stability.
So why isn’t it enough anymore?”
And then once we get there, something feels missing. We are looking for something more. That's fear disguised as restlessness. We may enjoy the fruits of our labor when we're reaching the top of a goal, only to find that we're still ambitious for more or maybe something different, only to discover that our new life goals for the future no longer seem to line up with the present that we've created.
Maybe you want to slow down, get off the corporate treadmill, live a freedom lifestyle, but you're wondering how to get there? Or feeling stuck in the confines of the success that you've already created and already achieved.
How can you leave now?
Well, we create these ceilings for ourselves. We put a glass ceiling on our growth because we're scared. We're scared to lose, we're scared to change. We're afraid to blow up the cookie cutter lives that we built for ourselves. It seems impossible to tear down success at this age and start over now, right?
We've been conditioned to believe that we only get so much. We only have so much joy, and too much success, or too much ambition is greedy. We tell ourselves, “We should be content, I should be happy, I'm doing too much, I'm too ambitious. Why can't I just relax?”
I mean, I've asked myself some of those same questions, but here is the truth: I like growing, I like striving. I love experiencing life in new ways, pushing myself, learning, creating. My ambition isn't a flaw, it's my nature. I also don't need to blow up my life to make bold changes. Maybe living a more adventurous life for you means committing to doing one big travel trip a year. Maybe for me, I need four. Maybe for someone else they need an RV and no job or home to think of. But perhaps you can start that creative business on the side instead of blowing up your financially secure job. Or maybe you're exactly ready to blow it all up, open up an Etsy business and see the world by RV. More power to you if you are. But know yourself and ask yourself, in what areas of your life are you ready to stop settling for enough, just enough, or just good, and step into more?
Sometimes we know exactly what needs to change, but we're just unwilling or unready to do it. Real change requires an identity shift. Leaving a relationship might mean being single. Maybe you don't want to be single, but you don't want to be in the relationship. Leaving a job might mean redefining your worth outside of your title. What are you if you're no longer a director of such and such? Those transitions feel terrifying because they dismantle who we think we are. The stories that we told ourselves about ourselves. Sometimes we're afraid to lose those. We're afraid of being judged, of failing or being misunderstood. We don’t want to feel lost! But remember, the will to live differently must be greater than the fear stories that we're telling ourselves about what could go wrong. What story are you telling yourself about who you are, about your identity? And how's this story holding you back from becoming who you want to be? What would your future self say about how you're living today?
It’s time to turn your fears into fuel. There are a few steps that you can take to get yourself on the right track to move forward through fear.
Step 1: Name it out loud.
What's the thing you want to change but haven't because of fear?
Say it. Write it. Name it. List all of the things, whether it's leaving a job, starting something new, or setting a boundary. What are you afraid of? Clarity breaks the spell of fear.
Step 2: Reframe it.
Find the story underneath. What are you telling yourself about yourself? About your story? About your perceived limits that are holding you back? Make a list of these. Maybe it's, “I'm too old to change careers. I'm afraid I'll fail. I'll be alone forever. I've always been this person.
I have to be there for whomever. My family and friends will think I'm crazy.”
Are these thoughts true?
Are they overly dramatic?
Understanding our fears can show us what our internal blockers are. By neutralizing or reframing those internal stories towards the positive, or even towards the neutral position, we can open ourselves to the possibility of change. Saying to yourself, “I'm too old.” Can become, “I can build on all of my strengths and experiences to do something new.” “I'm afraid I'll fail,” can be reframed as, “It's natural to be afraid. It's natural to fail. Sure, I'll make some mistakes, but I can fail fast. And I can learn from each mistake. That's how I grow.”
Step 3: Detach from the story.
So ask yourself who you could be. You might think, “I've created this story about who I am, what my limits are, what my life should be like. And I'm afraid to lose some of it. Who am I without this job title? What would my life look like if I didn't live in a nice home with a nice car? If I didn't have this job?”
Your worth isn't attached to the labels that you've carried. Your circumstances aren't always meant to last a lifetime. Sometimes you're meant to do things for a reason or for a season. But very few things are meant to last a lifetime. Ask yourself, “Who would I want to be instead? If I could be anyone without the ceilings that I've created for myself. If I could do anything, be anything, make a life of my own choosing?” From this day forward, detach from the story that you think you should have in favor of the one that you want.
Step 4: Take the wheel.
Take control of your life before someone else does it for you. Move with the fear. Don't wait for it to vanish. Don't wait for the self confidence. You gain that self confidence and trust by moving through fear. Because courage isn't the absence of fear, it's action in the presence of it. To talk through it, get a coach who can help you work through the confusion and mental blockers, around your negative thoughts, and concerns. Around your worries.
Step 5: Challenge the fear.
Ask yourself what is the worst that could happen? And then what's the best that could happen if I do it anyway?
Dear bold Ones, Fear is proof you're playing big enough to matter. So don't run from it. Run, walk, crawl towards the next thing.
Stay connected with news and updates!
Join our community and get access to exclusive resources.
We hate SPAM. Don't worry, your information will not be shared.