You are currently viewing Demolishing Comfort Zones: The Skydiving Surprise (Part 2)

Demolishing Comfort Zones: The Skydiving Surprise (Part 2)

Welcome back!

Don’t you just love it when someone tells you a story and draws you in?

You let go of reality, visualize every detail, and imagine that you were there.

It was practically like you WERE there.

And then they stop short.

It’s over.

They actually have the nerve to leave you hanging!

Stunned man
What? Are you for real?

Yeah (sheepishly), I did that last time.

I’m glad you’re giving me another chance!


Let me catch you up

So, if you were with me last time, you know that we were talking about all of the growth that can happen when you move from stretching your comfort zone (which is a cool thing) to demolishing it altogether (which can be even cooler).


Leaving your comfort zone behind is about:

  • pushing yourself beyond your limits,
  • realizing you are capable of more than you think,
  • and getting to know yourself better along the way.

It’s about the joy of asking “what if,” and trying… and persevering.

The word “persevering” always reminds me of:

If at first you don’t succeed,

skydiving is not for you.


… Maybe I should have saved that for another time. If you missed part 1, you’ll see why in a minute.

Ok so while pushing, learning and persevering sound cool, I know what you’re thinking.

Let me just stop the ride right now and address your big question; it’s the elephant in the room.

Elephant rug by bed
Aww! 😍 But, no.

Are you saying I have to jump out of an airplane to get out of my comfort zone?

The answer: No!

The follow-up: But am I saying you should consider it?  YES!

I’ll tell you why later.


Here’s more of the story

It was almost our son’s 18th birthday and his sister, dad and I decided to gift him with his childhood dream of skydiving.

With a twist.

After years of saying he could do it alone, we decided to surprise him by jumping WITH him.

It’s all about the family unity thing I shared in part 1.

The funny thing was how quickly my husband and daughter agreed to the idea.  I couldn’t believe it!

It was like they only needed someone to plant the seed and then they were in.

Makes me wonder what else I should be asking them to consider!


So, thanks to our daughter’s awesome research, we chose a place that had a great safety record, a lot of discounts, and a view of TWO incredible places from the air:  the skyline of Chicago and beautiful Lake Michigan.

Chicago skyline
We could get an entirely new view of two of our family’s favorite spots.

Skydive Windy City Chicago was totally game with the surprise idea, even though it meant secretly signing our lives away in advance and trusting that our son would agree to do the same when we arrived in person.

It seemed like a safe bet, considering he’s been wanting to jump since age 2.

I sent a letter to our son’s doctor to let him know the REAL reason we scheduled an appointment: A required pre-jump heart check that needed to be submitted beforehand, not the sports physical my son thought we were scheduling.  When we got there, the receptionist, who was in on the whole thing, gave me a knowing smile.  Dr. Nick checked him out and gave me the “ok” sign when our son wasn’t looking. He was into the idea and it was fun being in cahoots!  Plus we got a sports physical out of the deal.

Our son’s birthday was on a school day so I secretly emailed all of his teachers a couple of weeks ahead to make sure he wouldn’t be missing any quizzes or tests. They work hard and I didn’t want to take them for granted.  But they were all very excited and excused the absence.

Ahh, the conniving.  It was great!

Because I was serving in the Life Enrichment department at a retirement home at the time, I joyfully shared our plans with the residents.  Every new piece was discussed and imagined at length.  It was so much fun to be co-conspirators with them!  They thought it was crazy and loved every minute of the conversation, asking about it for weeks. This is a population that very much loves adventure!! 

JOY TIP:  Ask a senior citizen about adventures they enjoyed or always dreamed of.  You’ll learn a ton and improve their day.

When “Grumpy Edna” told me about her motorcycle adventures, she became a different person, and kissed me on the cheek!

Elderly woman
This isn’t Grumpy Edna. I just love this picture. I have to believe Grumpy Edna is having adventures in heaven!

At last!

The night before our son’s birthday, we could hardly contain our excitement. 

We had to work so hard to keep it from our faces.  I am surprised our eyes didn’t bulge right out of our heads. 

It was torture.  Wonderful torture.

That night, I could barely sleep.  The excitement had me tossing and turning endlessly.  The minutes dragged.  It was so hard to stop my imagination.  I was wishing for an invisible sledgehammer to the head, just to end the excitement and sleep the time away.

My heart is beating faster just thinking about it right now.  I hope I can sleep tonight!


Author's son opening kidnapping instructions

We started our son’s birthday like we always do, early in the morning, with birthday cake for breakfast and gifts.  The pile of gifts was small.  He didn’t seem to notice.

When he opened his final gift, a “Seek Discomfort” shirt (shoutout to YES theory, we’re catching what you’re throwing down), we asked him to wear it for the day and announced he was being kidnapped for an 18th birthday surprise.

He was shocked.  He was so excited!

But it could not TOUCH our excitement!  Blessing people with surprises is amazing.

We felt like we were going to explode, getting birthday cake everywhere.


We jumped in the car and drove for hours while our son kept trying to guess what the surprise was.
And you know what? He wasn’t even close!

He would never guess this. 

After years of wanting to skydive, it was like he was having birthday brain amnesia, and we loved every minute of it.

It was funny to hear the guesses he kept getting stuck on: Cigarettes and gambling!

man playing poker
Welcome to adulthood, kid.

As we got closer, we started seeing skydiving billboards, so we made him close his eyes from that point on.  The intensity grew.

The butterflies migrated from my stomach to fill my whole body.  I was so fluttery I felt like I could fly away.  No need for an airplane.

We scanned the scenery for any sign of airplanes. 

I thought our stomachs were going to burst.


Finally, we could see the airplane hangar! 

Months of dreaming and planning and scheming had led to this moment.

We were shaking and deep breathing, eyes huge, hearts pounding, guts churning.

It was great. Really!

We stopped the car and our daughter shot this video of the big reveal:


Now, those of you who are especially detail-oriented (you know who you are!) will notice that earlier, I said “Here’s more of the story.”

Mm hmm.

I did not go full Paul Harvey and promise “The Rest of the Story.”

(It’s like being in the 80’s, hearing his voice on the radio, drinking Jolt Cola).

So, next time, I promise, I’ll share every last detail!

JOY TIP: If you aren’t already part of the JOY BITES tribe, subscribe on this page so you don’t miss the ending.

But first, I want to talk about YOU.


Why you should consider skydiving

Short version: Because it’s fun.

And let’s not forget: It feels great to push yourself beyond your limits, realize you are more capable than you think, and get to know YOU better.

Was this message for you?

Here are some questions to ask yourself.  Let me encourage you to leave real space for the honest answers… after all, this is between you and you.

  • Have I grown all I can?  Am I ok with the answer?
  • If I don’t push me, who will?  And whose job is it?
  • What amazing joy-bucket-filling experience could be mine if I persevered?
  • Should I consider skydiving? 
  • Or better yet, do I need to demolish my comfort zone in my own way

If this resonates with you, welcome, my friend… It’s time.

You are in good company. (Well, that’s debatable).

The question for you is, what’s YOUR version of a big growth experience? 

What seems impossible, but would be amazing to look back on, and say,

“I can’t believe I did that?”

Your “skydiving” experience might actually be:

Downloading the couch to 5K app and training for a race

Learning an entirely new language, maybe even sign language

Starting a new business

Moving to a place more suited for you

Offering forgiveness to someone who wronged you

Asking that person you’ve been dreaming of out on an actual date

Starting your first (or next) book

Hiring a coach who can help you turn your passion & purpose into your new profession

Committing to 30 days of thank yous

Calling someone you’re estranged from and beginning with “I am sorry for…”

Dying your hair a different color

Cutting your hair completely differently

Scheduling that medical appointment you’ve been putting off

Skinny dipping

Finishing your high school GED or college degree

Going on a mission trip

Jumping out of an airplane


The list is endless and I would REALLY love to hear what comes up for you!  Please share it in the comments.

I’ll see you next time with the rest of the story… there may even be video!

Go forth and be joyful!

This Post Has 2 Comments

  1. Mom

    Dangling that carrot again!! WE WANT THE SKY-DIVING VIDEO!😂

    1. Robin Shear

      I am laughing so hard right now!
      There are important things to address first!
      But your enthusiasm shall be rewarded. 😘

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