The Pep Talk I Finally Gave Myself | How to Encourage Yourself

There was a time when I could give a pep talk to practically anyone. A child who didn’t make the team, a friend going through a divorce, someone questioning whether she was good enough for the job, the relationship, or the next chapter—give me ten minutes and a reasonably comfortable chair, and I could probably have her believing she was capable of almost anything.

I was a very good cheerleader for everyone except myself. When it came to my own life, apparently the woman with the pom-poms had gone on an extended leave of absence. I could remind everybody else how strong they were, how far they’d come, and how one bad day didn’t mean they had a bad life. Meanwhile, I’d look in the mirror at tired eyes, gray roots, and a bra that had seen better centuries and think, Well. Things appear to be deteriorating rapidly.

It took me a surprisingly long time to realize something that should have been obvious: the voice I was going to hear most often for the rest of my life was my own. Perhaps it was time to make her a little nicer.

Apparently, I Was Already Wearing What I Was Looking For

The revelation did not arrive during prayer, a retreat, or some profound moment of self-reflection. It arrived while I was looking for my bra.

I was late, naturally, and had torn apart half the bedroom trying to find it. Drawers were open. Clothes were everywhere. My room looked like the aftermath of a Kohl’s clearance sale. I searched under the bed, through the laundry, and inside that pile of clothes I’d apparently decided wasn’t clean enough for the closet but wasn’t dirty enough for the hamper. You know the pile.

Finally, I caught sight of myself in the mirror and realized I was already wearing the bra. There are moments in a woman’s life when all she can do is stand very still and reconsider the choices that brought her here.

Then I started laughing—not a polite little chuckle, but the kind of laugh where you have to sit down because you’ve just spent ten minutes searching for an undergarment currently attached to your body. Somewhere between the laughing and wondering whether this was the beginning of my eventual decline, another thought occurred to me: Maybe I did this in other parts of my life too.

Maybe I spent an awful lot of time looking for things I already had. Strength. Resilience. Courage. The ability to begin again. I kept thinking somebody else was going to hand those things to me when I finally needed them. What if I’d been wearing them all along?

I Had Plenty of Evidence

The more I thought about it, the more ridiculous it seemed that I questioned whether I could handle hard things. I had raised eight children. I had survived school projects, carpools, stomach bugs, teenage heartbreak, missing permission slips, emergency costume requests announced at 9:47 p.m., and approximately four million loads of laundry.

There was the time one of my sons arrived at school only to discover that his little sister’s Dora the Explorer underwear had attached itself to his gym shorts in the dryer and accompanied him to sixth grade. Then there was the school essay one of my children lovingly wrote about me, which included the touching observation, “Every day when I get off the bus, Mom’s on the couch with her Oprah and her wine.” Boxed wine, thank you very much. Accuracy matters.

And yes, there was the afternoon I drove halfway home from teaching CCD before realizing I’d left one of my children in the church parking lot. He got a ride home. Eventually.

The point is, I had accumulated decades of evidence that I could improvise, recover, laugh, apologize, regroup, and keep going. Yet whenever a new challenge arrived, I somehow treated myself like an untested applicant for the position. Are you sure you can handle this? At some point, I should have been able to respond, Have you SEEN my résumé?

The Cheerleader Finally Needed a Pep Talk

I think women become so accustomed to encouraging everyone around us that we forget we’re allowed to turn some of that kindness inward. We know exactly what we’d say to someone we love. We’d tell her she doesn’t have to have everything figured out. We’d remind her of everything she’s already survived. We’d tell her one mistake doesn’t erase years of doing things well. We’d probably make her something to eat.

But the conversation changes when we’re talking to ourselves. Suddenly we’re less patient and less forgiving. We expect ourselves to know better, do better, recover faster, and preferably accomplish all of it while remembering why we walked into the kitchen.

I’m trying to change that—not by standing in front of the mirror shouting affirmations at myself, because I’m fairly certain the dog would call someone, but in a much simpler way. When I catch myself thinking, I don’t know if I can do this, I try to remember that I’ve said those words before. Then I remember what happened next.

I did it scared. I did it tired. Sometimes I did it badly, sometimes I had help, and sometimes I changed the plan entirely. But somehow, I kept moving. Maybe encouragement isn’t always telling ourselves, You’ve got this. Sometimes it’s saying, “You don’t know exactly how you’re going to do this yet, but you’ve figured things out before.” I trust that voice much more.

I’m Keeping the Pom-Poms

I still love being the person who cheers for other people, and I hope I never lose that part of myself. There is something wonderful about reminding someone of what she can’t quite see in herself yet. But I’ve decided there should be room in the cheering section for me too.

Not because I think I’m invincible. Good heavens, I once lost a bra I was actively wearing. We have established the limits of this operation. I simply know myself better now.

I know there will be days when I’m confident and days when I question everything. There will be plans that work beautifully and others that collapse somewhere between breakfast and lunch. There will be times when I need my family, my friends, my faith, and people who love me enough to remind me who I am. But I’m no longer waiting for someone else to provide all the encouragement.

I’ve lived enough life to know something about the woman I’m cheering for. She’s fallen down before and gotten back up. She’s laughed at herself and started over. She’s carried more than she thought she could carry and discovered that asking for help doesn’t make her weaker.

And apparently, she’s capable of doing all of that while wearing the bra she thought she’d lost.

I’d say that’s worth cheering for.

🐞 Stay Awhile…

If you’re not quite ready to leave the porch, here are a few more paths you might enjoy wandering down.

If your own inner narrator could use a little more grace…
→ Overcoming Negative Self-Talk: Finding Honey in the Hundred Acre Wood

If life has thrown you some unexpected curveballs and you’re now traveling down a new path…
→ The Unexpected Joy of Starting Over

And if you’re in the mood to shop, even for just a bathmat…
→ Home Goods is Playing Games With Me

🍃 Come Find Your Spot

If this story reminded you that we’re all still learning how to move through the world with a little more grace, I’d love to welcome you as a Cottage Friend.

I’ll send you my free Welcome to the Cottage letter series—five little notes filled with humor, hope, and gentle reminders that you’re not walking through life alone.

Think of it as saving your own spot here at the Cottage.

🍃 Come Find Your Spot

The porch light will always be on for you! 🐞