3532: The Grace of Failure (Or, How to Avoid a Midlife Crisis) by Dr. Kelly Flanagan on Personal Development
Optimal Living DailyMarch 18, 2025
3532
00:10:26

3532: The Grace of Failure (Or, How to Avoid a Midlife Crisis) by Dr. Kelly Flanagan on Personal Development

Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com.

Episode 3532:

A life well-lived isn’t about achieving every childhood dream, it’s about evolving into who we’re meant to be. Dr. Kelly Flanagan reflects on how his plans have changed over the decades, revealing that failure is often grace in disguise. By embracing who we truly are rather than who we thought we should be, we create a life that’s both authentic and fulfilling.

Read along with the original article(s) here: https://drkellyflanagan.com/the-grace-of-failure-or-how-to-avoid-a-midlife-crisis/

Quotes to ponder:

"It’s easy to plan a Hollywood life, but it takes some growing up and a lot of self-acceptance to gladly choose a life that is a little more ordinary."

"Growing up isn’t about getting what we want; it’s about giving in to the best parts of who we are."

"A true self is a constantly emerging self. A good life is an always evolving life."

Learn more about your ad choices. Visit megaphone.fm/adchoices

[00:00:00] Before we start, please check out our new podcast, Good Sleep. Have you ever noticed how a calm mind can really set the stage for a good night's sleep? That's the idea behind our new podcast, Good Sleep. Greg, our host from Optimal Relationships Daily, is here to help ease you into a peaceful night's rest with some positive affirmations. And these affirmations aren't just comforting, they can help ease anxiety and nurture positive thoughts, setting you up for true good sleep.

[00:00:25] So press play on Good Sleep tonight because a good tomorrow starts with a good night's sleep. Just search for Good Sleep in your podcast app and be sure to pick the one from Optimal Living Daily. This is Optimal Living Daily, The Grace of Failure or How to Avoid a Midlife Crisis by Dr. Kelly Flanagan of drkellyflanagan.com and I'm Justin Malik.

[00:00:48] Welcome back to Optimal Living Daily or the OLD podcast where I read to you from some of the best blogs I can find and get permission from, mostly covering personal development and minimalism on this show. But we cover other topics in the Optimal Living Daily podcast network. That includes a bunch of other shows, definitely follow or subscribe to those if you like this one. Just search for Optimal Living Daily and all of them should pop right up. But for now, let's get right to it and start optimizing your life.

[00:01:17] The Grace of Failure or How to Avoid a Midlife Crisis by Dr. Kelly Flanagan of drkellyflanagan.com 40 years ago today on December 14th, 1976, I was born. Since then, nothing has worked out as planned. And that is a saving grace. You see, if I had become what I planned to be on my fifth birthday, I'd be a firefighter right now.

[00:01:46] As a boy, I was enthralled by the heroism of it. But now, I have a bad back and I hate thrill-seeking and I go out of my way to avoid third-degree burns. Courage comes in many forms. Sometimes we plan for one kind of courage, but we end up having to find forms of bravery more consistent with who we are. By my 10th birthday, the Chicago Bears were reigning Super Bowl champions and I planned to be a running back at Soldier Field like Walter Payton.

[00:02:15] But I'm slow, relatively small, not very strong, and I don't like people bumping into me. For me, bruises rank right up there with third-degree burns. Sometimes it's important to accept that our idealistic plans will be altered by our very realistic limitations. If I'd become what I planned to be when I was 15, I'd be a trial lawyer right now, just like Tom Cruise and a few good men hammering away at Jack Nicholson.

[00:02:44] The problem is, I don't like conflict or courtrooms. I'm not sure what I think about Tom Cruise anymore. It's easy to plan a Hollywood life, but it takes some growing up and a lot of self-acceptance to gladly choose a life that is a little more ordinary. A decade ago, I planned to build a life in the bustling Chicago suburbs.

[00:03:05] The problem was, by the time I was 30, I'd forgotten the little one inside of me who loves quiet and slowness and forested paths and towns where everyone waves to each other. Often when we're young, we plan to grow up into something big and flashy, but sometimes growing up is really about growing young again, reclaiming who we've always been, and living the way we're wired.

[00:03:31] By the time I was 35, I planned to write a little blog for a handful of therapy clients interested in working directly with me. It seemed arrogant to hope for anything more. Sometimes our plans are too big, but just as often, our shame makes our plans too small, admonishing us for dreaming big, calling it conceit. Yet, our plans get to be exactly as big as our love for ourself, our people, and our world.

[00:04:01] Now, here I am, the big four zero. Now, I've got new plans, bigger plans. I've got a new book coming out in March, a second new book I'm going to give away for free to those who preorder the first book, and I've got all sorts of hopes and plans for all of it. Yes, I still make plans. We have to. Plans propel us forward. Yet, today on my 40th birthday, I find myself hoping none of my plans work out.

[00:04:28] It would have been a disaster, particularly for people in burning buildings and the Chicago Bears, if I had become who I wanted to be when I was five and ten years old. Likewise, when I'm 50, I don't want to be who I planned to be at 40. A true self is a constantly emerging self. A good life is an always evolving life. Growing up isn't about getting what we want. It's about giving in to the best parts of who we are.

[00:04:57] Slowly, over time, as we begin to glimpse them, cease to reject them, welcome them, embrace them, live them. Growing up is about learning how to listen to the voice of grace, which is whispering within each of us all the time, nudging us in a particular direction for today. That, I think, is the challenge of turning 40. This birthday makes you want to look backward or forward. However, the question it begs of you is,

[00:05:26] can you stay focused and look deeper into the now? Can you live today as authentically as possible, so your days will eventually take you somewhere you ultimately want to be? A couple of weeks ago, my oldest son looked into the now as we crossed a bridge in our hometown, far outside the bustling Chicago suburbs. Someone we didn't know had just waved to us in passing. The son had just said, and with more than a little awe in his 13-year-old voice, he observed,

[00:05:53] twilight over the river here is beautiful. I'm not sure how many years I have left, but I've only one plan I'm planning on keeping. I'm going to keep looking at now, I'm going to keep listening for the voice of grace, and I'm going to keep trusting that if we do this, the twilight over our lives can be beautiful too. You just listened to the post titled,

[00:06:20] The Grace of Failure or How to Avoid a Midlife Crisis, by Dr. Kelly Flanagan of drkellyflanagan.com, and I'll be right back with my commentary. Thank you to Cozy Earth. Cozy Earth products are designed to transform your five to nine, the time that matters most, into the coziest sanctuary. Seriously. With Cozy Earth, my bedroom now is my personal retreat. With Cozy Earth's bamboo sheet set, luxury starts where you rest. These sheets are buttery soft,

[00:06:48] keep me at the perfect temperature all night, and I feel like I'm sleeping in a five-star hotel. And the bath sheets are a game changer. They're huge, super absorbent, and super soft. Now here's what I love most. They offer a hundred-night sleep trial and a 10-year warranty on all Cozy Earth bedding and bath products. Try them risk-free, but I'm pretty sure you won't be sending anything back. Luxury shouldn't be out of reach. Head to CozyEarth.com and use my code OLD

[00:07:17] for 40% off sheets, towels, pajamas, and more. If you get a survey after purchasing, mention you heard about them right here on the podcast. That's 40% off at CozyEarth.com with code OLD. Sanctuary awaits at Cozy Earth. Thank you to Dr. Flanagan. I could definitely relate to this one personally, especially in my college years. I was all over the place trying to figure out exactly what I wanted to do.

[00:07:45] From the outside, it's actually pretty obvious, but where I went to school, there wasn't a business major. That was an obvious choice for me. So I was trying to figure out where I fit in. I went into the school undecided, then changed to a computer science major, and then changed universities. Then my major changed to computer information systems, all the way to sociology for some reason, accounting, and then finally landed on business. A very strange path,

[00:08:15] but what Dr. Kelly said in this made perfect sense to me. We've all had those childhood or later dreams, mine mostly hovering around being a musician. But then we discovered parts of ourselves that maybe we didn't fully appreciate before. For me, while I did enjoy performing to an extent, the real fun was marketing the band, building the website, selling t-shirts and CDs and so on. More the business side of it. But sometimes we're afraid to say

[00:08:44] what we really want out loud because it seems too unrealistic or too big. But really, the worst that can happen is that things don't work out exactly as planned, which, as Dr. Kelly points out, might be the best thing anyway. So good stuff to think about today. Thank you for being here and listening every day. Have a great rest of your day and I'll be back tomorrow reading to you where your optimal life awaits.