#24: The Messy Middle - Embracing Challenges and Navigating Your Way to Success

Ever feel like you're stuck in the middle of a chaotic mess while chasing your dreams? That's the "messy middle" - a crucial stage where challenges arise, resilience is tested, and growth truly occurs. Join me in Episode 24 of the Calm Entrepreneur podcast as I shed light on understanding and embracing this often-overlooked part of any journey to success.

Discover practical advice on how to navigate the messy middle with confidence and determination. We'll discuss setting smaller, achievable goals, embracing the process, cultivating a growth mindset, and so much more. Plus, learn the importance of being kind to yourself, building a support network, remaining flexible, and celebrating progress along the way. Don't let the messy middle hold you back - tune in and learn how to persevere through any endeavor with grace and grit.

Chapters

• 0:00 Navigating the Messy Middle
• 15:04 Navigating the Messy Middle

Transcript

Corinne O'Flynn: 0:00

Hey there, my name is Corinne O'Flynn and you're listening to the Calm Entrepreneur podcast. I am a USA Today bestselling author, non-profit executive and organizing nerd with over 20 years experience running my own small businesses. I teach entrepreneurs, solopreneurs and small business owners like you how to organize your business, find more time and deepen your alignment practice to experience more calm and confidence every single day. If you're looking for that intersection between practical business advice and spiritual goodness, then you're in the right place. So sit back, relax and let's dive into this week's episode of the Calm Entrepreneur podcast. Welcome, welcome to the Calm Entrepreneur podcast. I'm your Corinne O'Flynn, and this is episode 24.

Corinne O'Flynn: 0:50

Today, i wanted to talk about the messy middle and I wanted to talk about it within the context of success and how we view success and how we approach our work, because I think it is something that happens in every facet of our lives, no matter when we embark on something, and it's definitely something that I have experienced and also we talk about in author land, and I think that this is one of those things that's just universal. It's something that I think everybody understands, but I think that we don't give it enough attention for how important it is, just like a story unfolds, with an introduction and then the rising action and the climax and the resolution. Our lives and our careers follow similar arcs. There's the spark of inspiration, right, then these initial steps, and then the hardening of whatever it is that we're doing with experience, and then the final accomplishment, like the achievement of the goal. And yet the focus often lies on the beginning It's where the energy is raw and uncontainable or the end, where there's all the glory and the achievement and everything is shiny and bright. But the true substance of any journey, professional or personal, lies in what is really less frequently spoken about, and that is this messy middle. And the messy middle is often the longest period of any kind of endeavor, right? It's this grueling period between the initial spark of inspiration and the final result. Right, and the final stage of this middle's place is the realm where challenges are encountered, where problems are resolved, where our resilience is developed and tested. It's the stage where everything seems foggy and the finish line looks like this mirage in the distance.

Corinne O'Flynn: 2:52

Understanding and embracing this messy middle is critical to achieving meaningful and enduring success in any endeavor. And not just achieving success, it's actually achieving the wherewithal to persevere, because if we don't learn how to carry on, we'll never achieve any goals right, and that has a lot to do with patience as well. But it's really important, i think, to understand the messy middle, because the concept of the messy middle is something that is, like I said earlier, it's truly a universal concept. It's something that we find in everything that we do, and it comes in when we're learning a new skill, right, like building a new company or starting a new podcast, you know, from strengthening personal relationships and pursuing fitness goals, or you know, just about anything that we want to do, from inception of the idea all the way through to completion, requires the ability to persevere through that messy middle. And it's it's we call it the messy middle, because it's not the easy middle, right, it's this, it's the doldrum middle, it's the middle, so it's something that it's where the shine has has has come off of it, right. It's where everything feels a little bit droopy and we start to have doubt and we start to worry if we made the wrong choice or if we should pivot or if we should quit. And I think that you know the journey to any end point is rarely a straight line from start to finish. It involves a labyrinth of trial and error and success and failure and circling back and pivoting and learning and iterating, and I think that that is that is something that we probably should talk more about, because I think that we focus too much on the the edges of of that spectrum of achievement, and I think we're all familiar with what it feels like to be stuck in the messy middle.

Corinne O'Flynn: 4:55

It's often characterized by feelings of ambiguity and self-doubt and this constant questioning about whether or not we've made the right choice. And it's when the initial excitement has gone and our energy starts to like roll and it's not necessarily constant or consistently high or consistently low, and we just kind of roll with this like this nebulous, i'm not sure right, and then reality sets in. But it's also the place where growth happens, it's where character is built, it's where skills are honed, it's where lessons are learned And it's where we truly begin to understand ourselves and our capabilities and then push beyond them right to really test what it is that we've got to see and challenge ourselves if we can get where we want to go with the tools that we have right. And so it's really important, i think, to embrace this messy middle, and the first part of that is recognizing that it exists, right, and that's just the first step, because next, and perhaps the most important step, is learning how to navigate it without losing sight of the goal, because I think that that's something that gets harder and harder, i think, as we, as humans, move through the life that we're living, because, with technology the way that it is now, and expectations the way that it is now, it's almost as though we're not allowed to ruminate and percolate and sit in the stew of exploratory time in the messy middle. But we have to. We need to look at it as an opportunity, right, it's this play, it's the testing ground, it's where we adapt and it's where we learn to pivot as circumstances change, and we learn to evolve in ways that we never thought possible. You know, it's where perseverance grows And it lays the foundation for the next endeavor, because it's one of those things, like you know, experience arrives just after you need it. But once you have that experience, you've got it for the next time right, and you won't have those experiences if you quit, when things get boring or when things get sluggy, or when they get foggy and they feel like we're never going to finish. So we have to persevere And I think that part of navigating the messy middle is to look at it like you know, look at it like it's an opportunity.

Corinne O'Flynn: 7:13

But it's also about breaking down that goal and looking at things in smaller pieces so that the middle part doesn't last forever, which is, i think, really important. I think that's why we chunk down the goals. I think that that's one of the biggest probably you know pro tips that we can take to kind of mitigate the biggest pain points of what it feels like to be in the messy middle, because it can be overwhelming when it feels never ending, and so if we don't learn how to power through, we're going to have burnout and we're going to abandon our goals. Right. But when we split things into smaller achievable targets, that can make the journey feel less daunting because we are hitting milestones, and so we shorten that span of what feels like this messy middle. And I think that in the process of doing that honoring that the messy middle exists and looking at it as an opportunity and then breaking our goals down into chunks to trick our minds into thinking that the messy middle are shorter we actually are cultivating a practice of patience and self-compassion, because it's not about instant gratification, right. Nothing nothing is nothing that's worth doing comes in that way, and it's more about really embracing consistent progress.

Corinne O'Flynn: 8:29

Mistakes and setbacks are inevitable and they don't need to be roadblocks. They can be valuable learning opportunities And if we treat them as such and remember to be kind to ourselves in the process, that's, i think, the path through. And this is not actually just limited to like tangible goals, like projects with our work. Right, this is everything. This is self-development, this is personal development, this is learning new skills, but it's also learning how to handle our emotions. It's developing our emotional maturity, and all the things in our life need to be framed against the willingness and the understanding of dealing in the messy middle.

Corinne O'Flynn: 9:10

By only focusing on the extremes the start and the end of something we run the risk of romanticizing the journey. Right, we fail to appreciate the value of that messy middle, because we now know, right, this is where the magic happens. But I think that When we focus on the extremes in that spectrum, which is the beginning and the end, that's kind of like living your life on Instagram, looking at somebody else's fabulousness But there's nothing wrong with sharing your successes But nobody really talks about what it looks like in this log, or you know what I shouldn't say? nobody, i think that few people do, but that number is growing, i think because we're kind of releasing our hold on this unrealistic aspiration of this perfection, of this beautiful, sculpted and staged kind of life. I think that that's a refreshing change for me, but it's something that I'm definitely leaning into.

Corinne O'Flynn: 10:11

I resist the high polish in every way. It's not because I'm lazy or sloppy or anything like that, it's just so. Not me, right, it's just not who I am. I think that more people are realizing that that's okay too, that there's actually more of us in that space of the realistic messy middle. When we see that reflected back to us on social media, that's wonderful. But that's what I mean about romanticizing the journey, because if all we ever focus on is the goal and looking at other people achieving the goal, right, like climbing Mount Everest we see pictures of people climbing Mount Everest and you watch the documentaries and you realize, oh my gosh, like the whole messy middle of getting up to the top of Mount Everest is something else, right, it is not a pretty thing, but if we didn't know that, all we would think is that well, why aren't we doing that fabulous thing and taking our picture at the top of the mountain? It's about having this realism, but it's also about balancing optimism in there. I think that we have to temper ambition with patience. We have to understand that it isn't merely about the attainment of the goal, but it's about what we learn along the way. It's the climb. To quote Miley Cyrus, the journey is what it's all about.

Corinne O'Flynn: 11:33

I was talking to my daughter last night and she was actually talking about poetry and an English teacher that she had in high school and the poem about how the take in the road less traveled. I think that's one of those things where it's at least for me it's been misunderstood in a lot of ways because I took the road less traveled and that made all the difference. I don't think what that means is that I took the road that nobody else has taken. I think what it means is that either choice led me to where I'm at right, not that both roads would have ended there, but you are where you're at because of the road you took, and therein lies the gems. You can't get there from here is, i think, the lesson. There You can't look at the other path and say what could have been. You can only look at the path that you took and say that that's what made all the difference, and I think that that's something that is kind of missed in there sometimes. At least, when I talked to my kid about how they were taught that poem and what they discussed in class, so I just thought that was an interesting thing And that's part of why I wanted to talk about this today, because everything you've done has led you to here.

Corinne O'Flynn: 12:54

And it's one of those things like if you had a time machine and you could go back and you could change things, what would you change? And when you really sit down and think about it, the answer in many cases is going to be nothing, because anything you change is going to change everything that comes after. And are you willing to wipe away all the things that happen between then and now? Like, i'm not, and I've been through some dark stuff. So I think that all the roads lead to here and all those roads and that part that led to here if I look at here as the goal, as the endpoint, because I have nothing else to look at Everything happened past, here, right here I am now.

Corinne O'Flynn: 13:36

Everything before here has been the messy middle, so I think it's kind of a little bit of a mindbender when you really think about it like that. I think that's the point. You know, we have to stop looking forward and romanticizing the goal and instead really sit in the moment because, really, like now's, all we have Right, all we get is right now. You know, the past doesn't exist, the future doesn't exist, all we have is this moment. And if, in this moment, all you're doing is looking forward, you're not actually here. And If the thing that's pushing you to look forward is the fact that right now feels like a slog Because you're sitting like up to your neck in the messy middle, then I think that's a reframe that has to happen there, because the messy middle is where it's at. So, cherishing the journey and embracing the struggle in the middle phase Means that not only are you aiming for the destination right, because we're all hopefully going somewhere, but we're also valuing the transformations that are happening in the process. And I think that when we really are mindful of what's happening in that messy middle, it prepares us to handle future challenges right, and that's again personal growth, career advancement, parenting. It's, it's Everything, everything under the Sun, right, it makes everything more realistic, it makes us more resilient and it helps us have a more grounded approach to to life.

Corinne O'Flynn: 15:04

So some tips that I have for How to think through or at least how I think through Really setting into this messy middle and making the messy middle what it's all about. The first one is to set smaller, achievable goals. Like I said earlier, having having an overarching, learned, long-term goal is vital. Right, we have our yearly goals and some people have their five-year goals and And I've shared before that I have given up on the 10-year five-year because I pivot too much. You guys, i change my stuff. But my long-term goals, my one-year goals, my two-year goals you know those tend to feel like the right time frame for me. But within that year to year goal, i have Six month goals, quarterly goals, monthly goals and when I set smaller goals with achievable milestones, that can be really helpful because Then I have these little finish lines that are happening along the way and that makes the messy middle smaller.

Corinne O'Flynn: 16:03

And again, embrace the process right, understand that the journey toward anything significant involves these up and downs. It didn't it. You can't get there without the middle. So, embracing the process of learning and evolving and growing. You know, instead of avoiding challenges and like we don't, we can't avoid the challenges We have to look at them and say, well, what's the next challenge and how am I gonna get through that and how am I gonna Overcome that and what am I gonna learn here? right, that's, that's what I think embracing the process of really living in that middle looks like. And, of course, my next, my next tip is my favorite thing of all time Cultivate a growth mindset.

Corinne O'Flynn: 16:43

Right, adopting a growth mindset can significantly impact how you navigate through the messy middle. You know, believing in your capacity develop, to develop new skills, to learn and to improve is Is everything, because it means that there isn't a failure. It means that it's you know, you have that experimental mindset. If you will, and When you have a setback, it's not a measure of your worth, it has nothing to do with you, it's this thing that you're embarking on. So, growth mindset, growth mindset every day, a growth mindset. If I could hand things out like that at Christmas, i'd give out growth mindset to everybody, because That's, you know, the world needs a whole lot more of that.

Corinne O'Flynn: 17:25

And my next, my next point, is to practice Self-compassion, right, like be kind to yourself. The journey through the mess of the messy middle. It's becoming a tongue twister, you guys. The journey through the messy middle can feel fraud, with what looks like failures and what looks like setbacks, you know, and instead of dealing with ourselves Through harsh criticism, we need to practice compassion for ourselves. We need to recognize that it isn't about These ups and downs. The ups and downs are inevitable. They have they. We can't get to the to the goal without them. They're not an indication of our personal flaws, right, they're just part of the experience and they're a normal thing.

Corinne O'Flynn: 18:11

In fact, if you had a goal that had absolutely zero setbacks, that that'd be kind of weird, don't you think? like, what would you have learned in that thing? Like it's cool to have something that you can do with your eyes closed, like, yeah, i can, i can fold laundry like nobody's business, but that's, you know, that's not a goal That's worthy of, of Persevering through. Like the things that are worth doing are gonna have that messy part, and I think that that's something with with practicing self-compassion, you know, it becomes really important. And And alongside that is develop a support network, having people around you that understand and Speak your language about the perseverance and about the personal journey and about this need for support Can be invaluable, and it's especially helpful if You have a group of people and I talk about this in many episodes, about having like a mastermind or an accountability group or some kind of peer group with other people who are also embarking on journeys of their own, because then you can support each other and you can, you know, bounce ideas off each other and then Lean on each other when stuff starts to feel like it's you know, go on nowhere.

Corinne O'Flynn: 19:20

Remain flexible. We need to make sure that we are able to pivot when pivoting has to happen, and sometimes pivoting doesn't mean pivoting away from a goal. It could be pivoting on your method. You may need to have a new strategy, try something out that you wouldn't have done before, which you could get those ideas from the brainstorms, from your peer group or your mastermind. Or maybe it's about pivoting the timeline. Maybe it's about elongating the timeline or shortening the timeline or cutting out a few steps and taking corners a little more tightly than you might have before, or widely. Flexibility can be added to any aspect of the things that we're doing, and it's often the key to moving forward when we encounter roadblocks during this messy middle And again celebrate progress.

Corinne O'Flynn: 20:12

The idea of breaking things up into smaller goals is all about being able to celebrate the milestones out along the way. So regularly acknowledging and celebrating the progress you've made is a really big deal, and this is something that I had to really embrace. It wasn't something that I did, naturally, and my mastermind group has made that a thing. Whenever we share the stuff that we're doing, when we hit a milestone and I think all of us tend to we share what's going on and what we've achieved And we're just listing off the things that we've done and we're going on to the next thing. Inevitably somebody else in the group would be like excuse me, pause right there for a moment And we have a moment of applause and cheering for this thing that. Did you forget how hard that was two weeks ago? And here you are, you're done and you're just going to move on Absolutely not. So celebrate your progress and share your celebrations with other people and bring other people in when you're working on something, because they can boost your motivation and they can help you and you can lean on them. But it's also it shortens that messy middle because you have little baby finish lines along the way.

Corinne O'Flynn: 21:24

And my last tip here is something that it was probably one of the best pieces of advice that I've ever received, and it was from another author and it had to do with authoring, but it's a universal piece of wisdom And I, like whenever I'm asked what's the best advice you've ever received, or, you know, share one piece of wisdom with a group of people. It's this let go of urgency, let go of this sense of urgency. The urgency isn't real. It's something that we are projecting from within And it's this rush toward the end and it forces us to speed by without really engaging in the process. But it also causes so much unnecessary stress, which can lead to burnout. But it also it bypasses patients And I think that we lose sight of the work And I think that that's dangerous.

Corinne O'Flynn: 22:30

I think that, especially as entrepreneurs and I, like this is one of those things that you know I say all the time you are an entrepreneur, you chose this business, you chose this as your business for a reason, and I don't think it's because you hate it. There's something about this that you love, there's something about this that calls to you, and I think that if we're able to steep ourselves in that and really fall back in love with the work that we do. I think that that will not only help us, you know, in the messy middle, but it really does let go of that sense of urgency. And whenever I talk about this sense of urgency and the need to release it, i'm reminded of a book called The Practicing Mind by Thomas Stirner S-T-E-R-N-E-R, and I will add that link in the show notes, but it's an itty bitty book. You can read it in one sitting. But he tells the story about the value of really sitting in your work and really like letting go of time and focusing deeply and what that does and how that really. You know it makes you a time bender And it's a wonderful thing, but I think that that is the medicine, that is something to really embrace and think on if you struggle with that, if you struggle with the sense of urgency, if you feel like the clock is running out and you're late to the party and there's not enough time for you.

Corinne O'Flynn: 24:10

First of all, let me just tell you, absolutely not Like. You're here at the exact right time. The ship has not sailed. There is room for everyone. There is room for you And there is room for you. Whenever you get there, you don't have to rush, you don't have to stress, you need to arrive bright-eyed and bushy. You need to be like fully hue when you get there, and the only way to really do that is to release that urgency And, i think, fall back in love with your work. That's the way that that happens.

Corinne O'Flynn: 24:49

And so, in an era where success stories are truly boiled down to highlight reels that focus only on the highs and they overlook the lows, i think it's really important to remember the value of that messy middle and the fact of the messy middle. And when you are looking at somebody who's achieving a goal and you're saying, oh, i want, they're doing something that I want to do, instead of looking at that goal and having any negative thoughts about, well, i'm so far behind, i haven't even started. Blah, blah, blah, blah, blah. I challenge you to look at what they've achieved and imagine all the things that it actually took to get there, because some people do share, like the steps, how I got here, but a lot of people don't. And I think that we get really stuck up in that FOMO thing and that feeling that we're never gonna get there because we just we're doing it wrong. And I think that that's a really good exercise to do.

Corinne O'Flynn: 25:50

If you say somebody doing something that you wanna do or something that's like what you wanna do, or they're experiencing joy in an achievement and you wanna have an achievement in something that you wanna do, that's not even what they did, but something completely separate for you. Imagine if you were there filming the documentary and the end scene was all that got posted on their Instagram, for example. Imagine what the rest of that nine hours of documentary footage looked like, and place yourself in those scenes, because that's really where it's all happening. Because I think it's really important that we don't see the messy middle as something to endure. Instead, i think we should view it as a vital stage to engage with and to learn from right. It's not just the road to success, but it's a journey in its own right and it's full of lessons to learn and skills to acquire and experiences to savor. So the next time that you find yourself in the messy middle, i urge you to stop and don't try to rush through it, because I think the messy middle is where life happens right. It's where growth occurs, and I think that that is where success actually and truly takes shape. So that's all I've got for you this week.

Corinne O'Flynn: 27:10

Thank you so much for listening. I'll check you out next time. Remember, part of being a calm entrepreneur is developing the systems, habits and know-how that lets you know that you are the one in the driver's seat. You get to choose how you run your business and you get to choose how you work. So you got this. I hope you enjoyed listening to this episode of the Calm Entrepreneur Podcast. I'm Corinne O'Flynn and if this episode was valuable to you, please head on over and rate and review. Wherever you consume your podcasts. Please subscribe so you'll never miss an episode. New episodes go out each week on Tuesdays and I look forward to hanging with you again. This is Corinne signing off. Have an excellent day.