You Win Some, You Lose Some More: How to Embrace Rejection


What’s the worst they can say? No?

This phrase ping-pongs around my head a lot when I’m pretending to be brave. I’ve thought of it every time I’m applying for a new job or asking a favor of a friend or sending a pitch to a publication.

There are a few life lessons I keep learning over and over. 1. You have to ask for what you want. 2. Sometimes you won’t get it. 3. Other times you will get it, and it’ll make all the other embarrassing, time-consuming or heartbreaking times when you didn’t worth it.

As a writer, I’m constantly baring my bleeding heart. That pitch that I thought would be the Next Big Idea? Well, my editor didn’t. That other pitch I thought was going to truly change my career? Nope, it went nowhere. Countless versions of “unfortunately” emails trickle into my inbox, and even then I feel lucky that I received a response at all. (Turns out editors are just as good at ghosting as men I’ve dated.) But after reading this New York Times piece, I’ve decided to embrace rejection.

It’s empowering, they say! It’s gritty! Everyone loves the word gritty!

So I set a goal. By my 31st birthday in April, I wanted to receive 50 rejections, 50 “unfortunatelys.” It’s a grown-up version of the “shoot for the moon” theory. Even if I miss, I thought, I’d land amongst some stars, right?

Turns out failing is fun for exactly nobody, but it’s a necessary lesson to, well, lessen the blow of rejection. Like it or (more likely) not, rejection will happen again and probably again and then definitely again for the rest of your living days. It’s now almost spring and so far I’ve written for a new dream publication, am in cahoots with a hotel management company I’ve been wanting to collaborate with, and yes, that editor I adore would like to have coffee this week.

I’m also failing at a greater rate than ever before. I interviewed for a potential dream job, wrapped my head around the idea of moving to New York, before I got – whaddya know – rejected. I was also yanked around by a man who liked me, then didn’t, then sorta did, then didn’t again, as if he were playing Love You, Love You Not with flower petals and my feelings. Rejected. That magazine I told everyone I was going to start writing for had their budget slashed. I’m racking up rejections every day, and though sometimes I want to crawl under the covers, the rewards that accompany a yes are just too good to give it up.

There’s a particular type of vulnerability to getting rejected. It’s personal, or so it seems. I don’t like your idea, I’m not attracted to you, you’re not smart enough for this job. You, you, you, you, you. Though, like most things in life, usually, it’s not about you. In my case, maybe my pitches tanked because that editor already had a similar story in the pipeline or, hell, I don’t know, hadn’t eaten lunch yet.

The only way to get better at rejection? Do it, then do it again. It’s exposure therapy. The more comfortable you feel being rejected, the less you’ll fear it. The more you dive into the deep end, the less you’ll worry about cracking your head open. 

All this rejection talk reminds me of an interview I saw with singer/witch/magical human being Maggie Rogers lately. She’s known for heart-piercing lyrics, which apparently has been a life-long defense mechanism for her. In middle school, she said, she’d tell all of the boys she liked that she had crushes on them immediately. “Because I felt like if he just knows, then no one can hurt me. If I tell the entire world my deepest, darkest secrets, then I’m bulletproof.”

Bulletproof. I like that. Because so often, for every “unfortunately” email, there’s often a “try again!” Every door that closes, well, you know what happens. So I’ll keep at it, winning some, losing some more. Do the same, will you?

Exposure Therapy for Rejection:

  • Remind yourself why you do this. Because you were born to be a – you name it, because you want to find love, because _____ means _____ to you. Fill in the blanks.
  • Take a break. It’s exhausting and disheartening to hear no so often. So take care of yourself and trust you’ll get back into the swing of vulnerable things soon enough.
  • Make a mental note of your Top People. Editors who make your sentences sing, your personal cheerleader friends, that college professor who believed in you more than you did. Appreciate them and lean on them.
  • Read this Elizabeth Gilbert passage often. “Send your work off to editors and agents as much as possible, show it to your neighbors, plaster it on the walls of the bus stops – just don’t sit on your work and suffocate it. At least try. And when the powers-that-be send you back your manuscript (and they will), take a deep breath and try again. I often hear people say, ‘I’m not good enough yet to be published.’ That’s quite possible. Probable, even. All I’m saying is: Let someone else decide that. Magazines, editors, agents – they all employ young people making $22,000 a year whose job it is to read through piles of manuscripts and send you back letters telling you that you aren’t good enough yet: LET THEM DO IT. Don’t pre-reject yourself. That’s their job, not yours. Your job is only to write your heart out, and let destiny take care of the rest.”


BY Megan McCarty - March 12, 2019

Did you know W&D now has a resource library of  Printable Art, Templates, Freebies, and more?

take me there 

Arrow Alone

Get Our Best W&D Resources

for designing a life well-lived


add a comment

  1. Jackie

    March 12th, 2019 at 10:17 am

    Megan McCarty. The timing of this piece was so oddly perfect for me, on the tails of a phone call last night with a guy I’d been seeing (won’t get into the details, but he truly began it with the words “you’re a very nice person” so, I mean, yeah…you know what happened next). I’ve processed it, I’m actually doing okay, but your article was still a very nice reminder for me to read first thing on this Tuesday morning. Thank you for articulating your thoughts on the topic so damn well.

  2. You Win Some, You Lose Some More: How to Embrace Rejection – Business Blog

    March 12th, 2019 at 1:56 pm

    […] Continue reading You Win Some, You Lose Some More: How to Embrace Rejection at Wit & Delight. […]

  3. SnapDragon X.

    March 12th, 2019 at 7:18 pm

    Yes! I love this idea. Life is a crapshoot; sometimes we win and sometimes we’re taken out with the garbage. But we have to keep trying.

  4. Working to Have Fun – Coffee Chalk

    March 16th, 2019 at 7:42 pm

    […] Rejection sucks! Whether it be in your love life, family members, a new (or existing) job opportunity. The only way to get better at rejection? Do it, then do it again. It’s exposure therapy. The more comfortable you feel being rejected, the less you’ll fear it……Ouch, yes,  BUT A much needed “Ouch”. Read about it here: You Win Some, You Lose Some.  […]

Leave a Reply

Your email address will not be published. Required fields are marked *


Why Decorating Your Home Is Good for Your Mental Health

What 10 Years of Blogging Taught Me

The Hidden Benefits of Being Incredibly Uncomfortable

6 Easy-to-Grow, Can’t Kill Houseplants for Beginners

The Golden Rule: A Dream Career Built From Love, Loss and Resilience

Introvert Dating An Extrovert? Here’s How To Make It Work

Tornadoes to Tablescapes: Life Inside the Lifestyle Blog

Black, White and Love All Over

Marriage – A Requirement of Commitment?

Women vs. Women, and a Little Thing Called “Self-Respect”

Homemade Green Tea and Honey Mask

An Apartment of Firsts: A Personal Story

Find Financial Freedom with a Value-Based Budget

Freedom Is Trying New Things and Failing

How to Quiet the Voice in Your Head that Tells You “You Can’t”

Perfectly Imperfect Parenting

Kate’s Picks: 8 Things I Tried Last Month and Loved

Do You Really Need a Flat Sheet? And Other Key Questions About Bedding


Arrow Alone

the latest

Thank you for being here. For being open to enjoying life’s simple pleasures and looking inward to understand yourself, your neighbors, and your fellow humans! I’m looking forward to chatting with you.

Hi, I'm Kate. Welcome to my happy place.

Easily navigate all our recommended products across beauty, fashion, decor, and wellness. 

SHOP W&D Loves ›