My dad is one of the most generous people I’ve ever known. And the thing is, I probably don’t know the half of it. But I do remember seeing him push a tv on a cart down my elementary school hallway & learning he was donating one to every classroom. I remember he’s the one who took me shopping for Toys for Tots every Christmas. I remember he’s the one who took us through a drive-thru on Christmas Eve so he could give a big tip to whoever had to work that night. I remember walking up & down Walmart aisles with him to give away gift cards. I remember in high school when he heard one of my teachers needed a new bike for his commute, he left a brand new one on his front porch to be found the next morning, never knowing who had left it there. He keeps paychecks rolling for his employees who are sick & can’t show up for work. 

He sees people—not their issues. He recognizes we’re all the same— people trying to show up for our families & lives. He sees the reflection of God in people’s eyes.

my dad, my little sister, & me circa 1991

Privilege has been a dirty label to me for a long time.

Because even growing up where privilege was used for good, giving in secret is easily outshined by conspicuous wealth. And when your focus is the opinions of others, whether real or imagined, privilege can feel like a heavy weight around your neck. It’s why when a guy in high school half jokingly said I was going to hell for being rich (how’s that for Biblical humor?), I wanted to crawl in a hole instead of just laughing it off or punching him in the face.

That’s how the lie found its way into my veins. You are spoiled & selfish & naïve. You don’t have a story of substance. Nobody wants to be around someone who’s been given everything.

my dad, my sister, & me circa 1995

No matter how many toys I donated or how much I gave away from my closet, I felt guilty. It’s why I gave away our couches—but it turns out when you just turn around to buy new ones, the guilt hangs around. It didn’t take my therapist two minutes of listening before she looked me in the eye & without an ounce of sugar said, “Your guilt is because you aren’t giving to be like God—you’re giving to not look spoiled.”

I always had examples of people in my life who held privilege in one hand & service in the other. But because I was embedded in the lie that I couldn’t be both, I pushed privilege away, ignoring the gift I had been given & letting the lie steal my joy. I was so focused on what other people might think. It’s why when my dad bought me a Lexus, I parked farther away in the parking lot so maybe people wouldn’t see me get out of it. I got all squirmy & tried justifying myself when someone made an innocent comment like nice car!

What my dad intended as a gift of generosity, I snubbed as a poor use of money. I’ve missed a lot of generous moments, with him especially, because I couldn’t distinguish between accepting lavish love & being spoiled rotten to the core.

my dad at the cliffs of dover circa 2005

I just really like this picture of him on the Cliffs of Dover.

Two things had to take place for me to destroy the lies I’d believed my whole life.

First—I had to stop caring so much about what other people may or may not be thinking. It’s ridiculous to give so much brain space to other’s opinions—especially those not in your inner circle. This is my life. Say it with me– MY life! When we chase the rabbit of pleasing everybody else, those minutes of our lives are lost.

Second—I starting looking for more humans who were covering the world with Joy. I watched Kristen Bell change the lives of twenty teachers along with their present & future students—all through Instagram. I watch Jen Hatmaker rally her troops to gather new shoes to pass out with her church to their homeless community every winter.

The lie said I was missing a story of substance because I’d been given everything. For maybe the first time, I started understanding the universal truth– the only things anyone is given are tools. It’s up to each individual to decide how she uses them.

my dad, my mom, collins, & emma just after emma was born in 2016

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  1. Crystal McDonald on November 1, 2018 at 2:44 pm

    Love this. What a sweet reminder! Thanks for sharing! ❤️

    • Jenna Winegeart on November 5, 2018 at 8:47 pm

      Love you, Crystal Dawn!

  2. Jess SG on November 2, 2018 at 2:05 am

    Love this Jenna. Major heart check, thanks. ❤️ And your dad sounds like an inspiring man.

    • Jenna Winegeart on November 5, 2018 at 8:47 pm

      He really is! Thanks for reading, friend!

  3. Ginni on November 6, 2018 at 2:22 pm

    Beautifully written Jenna!! Thank you for sharing! And I love reading about all of the generous opportunities that your Dad took!

    • Jenna Winegeart on November 7, 2018 at 5:59 pm

      Thanks, Ginni! It was pretty neat to look back on it all.

  4. Al Lowrance on November 6, 2018 at 8:58 pm

    Your writing is definitely inspired. It’s a privilege to enjoy your Blog . In the short period that I’ve had the blessing of knowing your dad, his generous nature has been obvious from the start. Thanks for the reminder to use our God given “tools” instead of wasting time gauging them against imagined scales.

    • Jenna Winegeart on November 7, 2018 at 6:00 pm

      Thanks so much for reading, Al! I’m so glad for the friendship the two of you have (or I should say the four of you). And I can’t wait to hear about NYC! Have so much fun! Thanks again for reading– come back soon!

  5. Shelly Stasney on November 20, 2018 at 4:08 am

    I’m so glad you came around. I had a mindset that money was the root of all evil but thanks to a lot of podcast listening I’ve learned that it is one source of being able to do a lot of good in the world. I no longer feel dirty for wanting to have money. I have big plans for who I want to give it to! I’m sure your father did too! Love this story. Thanks for your vulnerability and sharing.

    • Jenna Winegeart on November 21, 2018 at 3:22 pm

      Thanks so much for your insight & feedback, Shelly!

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