101. Striving vs. Thriving in Midlife: How to Stop Chasing and Start Living

In today's episode of The School of Midlife, we dive into a critical question for high-performing women in midlife: When is enough enough? Many of us find ourselves caught in the cycle of constantly striving for more—more success, more accolades, more achievements—but at what cost?

As high achievers, we often feel like we’re almost there—whether it’s a financial goal, a physical milestone, or even the approval of others—but somehow, that feeling of fulfillment always seems to slip through our fingers. Why is that?

This episode unpacks the internal struggle many women face in midlife as they try to balance ambition and contentment. We'll explore:

• The never-ending pursuit of more: why we keep moving the goalposts and how it impacts our happiness.
• The myth of "doing more" and why adding to your to-do list isn’t the solution.
• The importance of defining your version of success and learning to say "enough" without guilt.
• How we were raised to follow a checklist of societal expectations—and why it’s time to break free.
• Practical advice on how to live the life you actually want, right now, instead of delaying joy and fulfillment for some future date.

We’ll also touch on the game-changing ideas from Die With Zero by Bill Perkins, which challenges us to prioritize experiences over accumulation and how embracing this philosophy has helped many of us in midlife stop living for the next milestone and start living for today.

If you're ready to rethink what success means, let go of the "good girl" checklist, and take control of your midlife, this episode is for you.

LINKS + MENTIONS:

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins

1:1 Coaching with Laurie

Group Coaching: Gap Year

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Transcript

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In today's episode of the School of Midlife podcast, we're talking about knowing your number. We're talking about knowing when enough is enough so that you don't just keep working for the sake of working with not a lot to show for it. So stay tuned. Welcome to the School of Midlife podcast. I'm your host, Laurie Reynoldson. This is the podcast for the midlife woman who starting to ask herself big life questions. Like, what do I want? Is it too late for me? And what's my legacy beyond my family and my work. Each week we're answering these questions and more. At the School of Midlife, we're learning all of the life lessons they didn't teach us in school and we're figuring out finally what it is we want to be when we grow up. Let's make midlife your best life. Hey friends, it's Laurie. Welcome back to another episode of the School of Midlife podcast. I am so happy to have you back here today. In today's episode, we're going to talk about knowing your number, understanding when enough is enough, and essentially trying to figure out what is it that we are striving for at this point in our lives? Because if you are like most high performing women, you've had a pretty damn successful life up until now. You've, you've done amazing things. In the workplace, you've done amazing things at home, and there is still this niggle, there's still this feeling that for some reason we still need to be doing a little bit more. I don't know if you can relate to that or not, but I've been having a lot of conversation with friends and clients lately, and it just feels like there is this, Ever present need to do more that, yes, what we have done to this point is it's great. Yay us, but there's this feeling that we must keep pressing. We must keep moving forward. We must keep striving and achieving so that we can somehow, I guess, arrive at a point in the future when we will finally know that enough is enough, right? That we have finally met the number that we think we should have in our 401k so that we can retire. We will finally see the number on the scale that proves to us that we look good enough to wear a bikini on a beach vacation. We'll receive something from our, I don't know, our kids college, or maybe they land their first big job. And that will somehow prove to us that we have been good parents. We have, as high performing midlife women, we have this, I don't, I'm not going to call it a problem, we have this issue of Continually thinking that we need to be better, faster, smaller, richer, like Everything that we have done up until now is, is fine, but we still have this internal desire, this internal drive, this internal voice that tells us that we have to keep going, that where we are right now isn't enough for us. If you're anything like me, you might think. Well, in order to figure out what I'm supposed to do next, I just need to add a little bit more to my to do list. I mean, for, for years, I used to think that the life that I was looking for was on the other side of another checklist. Oh, I just have to finish these 15 things and then I will finally feel like I am successful or that I am fulfilled or I, I will have that ever present happiness that, that, that kind of settled joy that I expect to find, you know, that fulfillment, satisfaction. And I learned a while ago, actually, that That's, that's not actually how this works. You don't need to add any more to your to do list. I mean, I, I would always tell myself that I would feel a certain way after the next promotion, or after I reached the next milestone, or completed the next endurance event, or whatever the next thing was in my head. And certainly, once I did, Get that promotion or reach the milestone or finish the event. There, there was always this sense of pride and accomplishment because I, I had done the damn thing, but I'll tell you, it was almost always fleeting. It was never that whole life contentment or calm. The, the joy, the happiness, the fulfillment that I was looking for. It was, it was almost like that, those feelings of satisfaction and fulfillment. And they, they just continued to escape me, like I couldn't quite get there. So in my mind, okay, then I'm just going to need to add more to my to do list or I'm going to need to work harder. So I was in this constant cycle of. Working harder, adding more to the to do list, running further, taking on more projects. I, I was living every single day like I was crazy busy. And even worse than that, I was wearing that crazy busy as like a badge of honor. Kind of like, look at me, look at how important I am. Look at how busy I am. And I was equating my busy ness with worth. I was equating that busy ness with success. look at me. Look at how important I am that no one else can do this job this way I can't delegate or hand things off because I can do this the best and on some level I feel like I am proving my worth because look at how much I've been doing and I'll tell you what I filled my time with people And activities, and to dos, if anybody needed help with a project, I would take it on. If anybody needed someone to stay late at work, I was always there to do that. I had this underlying desire to have the highest billable hours every month, which is so stupid. I mean, yeah, as an attorney. You are judged at the end of every year on the number of hours you bill, you know, there's, there's a minimum number that you have to reach and bonuses are, are arguably tied to the number of hours you bill, but not really. I mean, yeah, you might get a couple extra thousand dollars if you overbill, but. At least in the law firm setting where I was, the real cherry on top, the, where you would get the most bang for your buck. That was bringing in new business and it had nothing to do with how many hours you build on that file. It was how much business can you bring in, spread it around and keep bringing more business in because you, you did better with origination fees than you did actually just doing the rote legal work. You certainly, you had to bill your minimum billable hours, but anything above that, I think it, it felt better to me than it actually looked on paper. I mean, I, I wasn't getting anything out of it. and I know that I'm not alone in that because as high performing midlife women, we seem to think that we're going to find the, Fulfillment that we're looking for, or the satisfaction that we're looking for, or the feeling of worthiness or enoughness. This kind of ties back to what I talked about in last week's episode. Episode number 100. Yep, we've made it. 100 episodes. This whole idea that until we change our mindset, about ourselves, that it doesn't matter how much we do, it will never be enough. Women, and I've done it, and my clients do it, my friends do it, but this, we all have approached life with this idea that I'll finally find that happiness and fulfillment and satisfaction, all the things that I'm looking for, in the next project, or the next job, or the next marriage, or the next fill in the blank, because we all have different lists, and because we haven't found it yet, then we go back to that, call it a good girl checklist, or the success checklist, or the adulting checklist, Whatever you want to do, but the, the checklist that we were raised, that you go to school and you get a job and you buy a home and you get married and you raise a family and you get promoted and, and you stay the course and at every junction, you get to. Put a little check mark by the thing on the checklist, the thing that we seem to think is the most important for us to feel valued, for us to finally feel the way we thought we would feel. And we're doing that because we thought it was expected of us. I have a question to ask you though. Which is if we've already done everything we were supposed to do, you know, that go to school, get a job, buy a house, everything on the checklist, then why is it we don't feel like we expected to feel? I think one of the biggest mistakes that high performing midlife women make is we're trying to figure out how to make the second half of our lives happier and more fulfilling, but we keep repeating the same patterns of overwork and overwhelm because we keep adding more to our to do list. We keep filling our plate with all of the things for all of the other people in our lives, whether that's our family, at work, our friends in the community. I mean, does any of this sound familiar? I'm sure it does because we do it all the time. It's also why we keep hitting the same roadblocks and plateaus, right? We Receive another accolade, we hit another career milestone, achieve the next big thing, and the first time we do it, we feel so proud. And there is some subconscious level that we believe, you know what, now that we've done this, we'll finally feel like we've arrived. We'll finally feel like we're making our parents proud. We will finally feel like we deserve the promotion or that what we are doing is worthy of approval. But here's the thing, that doesn't happen, right? I mean, yeah, we, we might get some small bonus at work. They might throw a party in our honor. Um, and then when you try and repeat it the next time, that feeling of success, that feeling of approval. Once you reach it, it's gone even faster than it was the first time. So we find ourselves in this constant state of state, a bigger, better goal, and then work damn hard to achieve it and, and, and then actually achieve it and then immediately move on to the next something that's bigger or better. And we do that not because. We feel like there's no getting off the hamster wheel or the treadmill, but we believe that the life we want is on the other side of another checklist or another to do list. It's just that we haven't done all the things that we thought we needed to do. But here's something that you probably haven't thought of. We keep moving the goal line. And what I mean by that is we keep moving the finish line. We keep moving the number that we need in our deposit accounts so that we can retire. We keep moving the top of the job ladder. That we keep climbing because every time we get promoted and we expect to feel a certain way when we reach that goal or milestone, but we don't, so we think we need to do more and it's this constant battle, this constant struggle of more, more, more, and there's no enoughness. There's no feeling like we've arrived. We just keep pushing for more, pushing for better, pushing for bigger. I know I've talked about my favorite quote by Albert Einstein a lot on this podcast, but remember he said that the definition of insanity is doing the same thing over and over and expecting a different result. As midlife women, we do that all the time because we think that that feeling of enoughness is going to show up after the next promotion, or after we start the next company, or after we earn another degree, or more credentials, or have more more letters, after our, our name and our signature block. After we lose the last 15 pounds, after the next milestone, birthday or anniversary, once we retire, we just keep thinking. I'll finally get there when. But because we don't actually understand what it is we're working for, we're never going to feel the way we want and expect to feel by adding more to that to do list, to that checklist. Here's what I mean by that. The checklist was never ours. If we go back to that good girl, success checklist, whatever you want to call it, that was given to us by our parents and society. And as the diligent workers that we were, we just got to work on making that our reality. We just got to work. I mean, most of us worked while we were in college and worked as hard as we could to get out of college as soon as we could so that we could get to work making money because we were expected to earn a degree and then go make some money, right? So we did what we thought we were supposed to do. We went to the best school that we could get into. We studied and earned degrees. We interviewed for a number of different jobs. And we took the one that wanted to pay us the most. So, at that point, we were already in motion on fulfilling the success checklist. But here's the problem with that. It was never our checklist to begin with. We never took a step back to figure out, is what I actually want? My life to be is anything related to that checklist also related to what I want? Because I'm going to tell you that Knowing what you want and and that's what you actually want Not what you've been conditioned to want not what your parents have told you to want not what society tells you to want Not what you should want, but what it is you actually want. Knowing what you actually want is the only way that you can create and live your best life. It's the only way to get It's the only way that you're going to feel the fulfillment, feel the satisfaction, feel the happiness, experience the joy for the long term. Yeah, there might be some quick hits of excitement, pride, but in the long run, doing more isn't the answer. In fact, In my opinion, doing less is the key. So instead of going to that checklist and adding more to it, thinking that you're going to finally feel what you are expecting to feel, instead of doing that, the key is do, do things differently. Figure out what it is you actually want. Figure out how you define success. Figure out if you had the opportunity to live your best life, what does that look like? And then once you know what you want, what success means to you, what your best life looks like, then get busy making that your reality. Fill your time with people and activities that Fill your soul that, that align with that definition of the life you want to live. Make it a priority to take better care of yourself and do that first before taking care of the needs of others. And by all means, stop wearing crazy busy, like a badge of honor. So how do you start doing that? Uh, last year as part of the Your Next Chapter Book Club, and yes, the School of Midlife has a book club. If you don't know about that, I'll drop a clickable link in the show notes so you can learn more about it. But we read books that impact the way midlife women are living their life. And we talk about topics and ideas that will help us live more fully into our purpose and who we're supposed to be and make midlife our best life. but anyway, so last year we read Die With Zero, Getting All You Can From Your Money and Your Life by Bill Perkins. And one of the big themes in the book was that as. Americans, we have this unique ability to work longer than we need to, to save more money than we should. And in the process, we forego making experiences, having experiences, making memories. It's really experiencing life and doing the things that we want to do. We put that off because we think that we have to earn more and we have to save more and we have to pass down a lot of money to our children. And Bill Perkins idea is. Everyone's goal should be to maximize the amount of experiences that we can have at the time in our lives when we can enjoy them, because a lot of people decide, you know what, I'm going to do all these things when I retire and so when they are able bodied and they could actually be going and having more experiences. They spend the time behind a desk to make a bunch of money, to save a bunch of money so that they can have this great retirement. And then they get to retirement and before they know it, they've got a physical ailment or they don't move as well as they used to, or they find that they've put off. All of the things that they wanted to do to save them for retirement. And then they don't have the retirement that they expected to have. My dad is definitely someone who could have benefited by reading Die With Zero. If you've been around the podcast for a while, you've heard me talk about my dad before, but for those of you who haven't, my dad was my person. He, he was definitely the parent who I look to for all of the things. Retired from his second career on his 66th birthday because he wanted to maximize his social security benefits. And yes, I said second career because he tried early retirement in his 40s. That didn't stick because he didn't really have an idea of what he wanted to do in retirement and he got a little bored so he went back to work. He retired from his second career on his 66th birthday. He wanted to maximize those social security benefits for a couple reasons. First, because he felt like he had worked for a lot of years and, and he had, I mean, he started working at 16 and worked all the way through, except for that, nine months when the retirement didn't work for him, but he worked pretty much his whole life. And he kind of felt like. He was owed those social security checks. And also he was diagnosed with early onset Parkinson's in his early 40s. So he wanted to make sure that he had enough. Money saved up in his retirement investments and social security benefits to make sure that he could pay his medical bills and retirement. So he wanted those social security payments to be as high as he could get them and he could do that by working until 66. So he postponed retirement. He absolutely could have retired earlier from that second career, but he wanted to wait until he was 66 so he could get. the maximum social security benefits. He retired on July 10th and moved back to Boise at the end of July and he lived with Mike and me for about 5 months because the house that he was building was not yet. Completed and we had a great time living with him for those five months. We did all sorts of fun things in the summer and the fall. And we also talked a lot about what he wanted to do in retirement. He was a big golfer, wanted to golf five days a week. Wanted to get back into snow skiing because he was moving back to Idaho. Wanted to take up fly fishing. He was a drummer in high school and wanted to join a garage band with some old time guys and maybe even write some music for the band to play. He wanted to travel to Europe, because he had never made it to Europe. And he had all these ideas of experiences that he wanted to have in retirement. Well, he retired on his birthday on July 10th of 2015, and then he had a heart attack and died on December 26th of 2015. So those social security checks that he was so worried about getting? Those, those social security checks that you wanted them to be as high as possible. He received five of them. And not only did he just receive five of them, he postponed his retirement and all the things he wanted to do in retirement. Learn how to fly fish, golf every day, travel to Europe, join a garage band. Everything he wanted to do in retirement, everything he was looking forward to. He didn't get to do any of it. If he would have taken Bill Perkins advice, he could have actually spent the last, I don't know, 10 years probably, having the experiences that he wanted to have, making the memories that he wanted to experience. He could have done all of that instead of working full time, retiring at 66 and then dying 5 months later. And that's the thing. I mean, none of us really know if we're going to have a long retirement. None of us know what the quality of our life is going to be at that point. And Bill Perkins says, and I agree with him. And frankly, many of the women who read the book as part of the, our book club discussion agreed that what he's talking about in the book. By reading that book, we have changed the way that we are living, that we are trying to infuse more of those experiences that we want to have right now, instead of delaying them, instead of putting them off. And what I've found with myself and my coaching clients is once you figure out what you want and what your best life looks like, then You actually work less because you understand what you're working for. You understand when enough is enough. You understand what the dollars look like that will support the type of life that you want to live. Because you're already starting to do that right now. You're not waiting until retirement. You're not waiting until the kids leave the house. You're not waiting until someday or this perfect idea that, you know, everything is going to be right and all the stars are going to align. And of course, you're going to know that now is the time to do the damn thing. Spoiler alert, there is no such time that will ever be the right time. You're not going to receive the sign that you're looking for. So I'm telling you, if you do nothing else in 2025, start figuring out what your best life looks like and start living that right now. Stop delaying it, stop putting it off. And frankly, as high performing midlife women, you also need to hear this. You need to have more fun in your life. You need to do things that excite you and bring you fulfillment and joy and things you like to do. Not because your family wants to do them, not because somebody expects you to do them, but because you want to do them. So many of us, when, when I ask my clients, what, what do you want? They don't know and that's not uncommon. Most of us don't know cause we've never been asked and because we've never been asked, we've never actually thought about it. We just, we got to work on that good girl success checklist because we thought that was what we were expected to do. And related to that, we just assume that that's what we should want. I'm not saying that. What you've done up until now that you haven't wanted to do it. But if given the choice, would you want to do everything that's currently on your plate for the next five or 10 years? Maybe, maybe not. Maybe there are some things that you have done in your life that you're grateful to have had the experience, but you're ready for something new. And of course, if you're someone who is trying to figure out what you want to do. Um, with the rest of your life, you know, how do you want to spend the second half of your life? If you're trying to figure out what that looks like, what your options are, how you can get started right now, that's, that's exactly what I do with my coaching clients at the school of midlife, whether that is one on one coaching or in our group coaching program, the gap here, there are a number of great opportunities. Get the coaching that you need. And whether you choose to work with me at the School of Midlife, or you choose to work with another coach, what matters most to me is that you receive the support that you need. Because you deserve to live a life that you love. You deserve to live your very best life in midlife. You have been doing all of the things for everyone else in your life up until now. Isn't it time that you came first in your own life for a change. It's time to figure out what your number is, when enough is enough. And I'd be honored to help you through that process. As always, I am so grateful for your time and your support of the school of midlife podcast. Thank you so much for being here today. And I will see you right back here next week when the school of midlife is back in session.. Until then take good care. Thank you so much for listening to the School of Midlife podcast. It means so much to have you here each week. If you enjoyed this episode, could you do me the biggest favor and help us spread the word to other midlife women? There are a couple of easy ways for you to do that first. And most importantly, if you're not already following the show, would you please subscribe? That helps you because you'll never miss an episode. And it helps us because you'll never miss an episode. Second, if you'd be so kind to leave us a five-star rating, that would be absolutely incredible. And finally, I personally read each and every one of your reviews. So if you take a minute and say some nice things about the podcast, well, that's just good karma. Thanks again for listening. I'll see you right back here. Next week when the School of Midlife is back in session until then take good care.