Life Planning: How to Close the Gap Between Wanting and Achieving
with Dr. Lisa Marie Bobby, PhD, LMFT, BCC and Courtney De Ronde, CPA, CEO and co-founder of Forge Financial & Management Consulting and author of Planning to Scale
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It Was Never a Discipline Problem
Good life planning isn’t about more willpower. It’s about closing the gap between what you want and what you actually achieve, and most of the time that gap is a planning problem.
You know what you want. You’ve been working hard at it, too. And somewhere along the way a quiet story started up: maybe I just don’t have the discipline. Maybe the dream was wrong. Nobody ever taught us the mechanics of turning a big vision into an ordinary Tuesday, and that missing piece gets mistaken for a character flaw remarkably often.
My guest is Courtney De Ronde, the CEO and co-founder of Forge Financial & Management Consulting, a CPA with more than 20 years in practice, and the author of Planning to Scale. Her framework was built for business owners, and I have been part of her Scaling Leader program for years. Reading her book, I kept thinking: this is exactly how planning a life works for the rest of us, too.
We got into the three horizons of a plan and why most of us are wired to handle only one of them well, the hillbilly fire pit story about a vision that wasn’t clear enough, why we want a three-year vision to be true right now, visionaries versus doers, how to set a vision for each area of your life, the Apple Maps approach to separating vision from strategy, telling a dip from a cul-de-sac, and the brilliant plan that broke her partners’ trust.
“We give up on our vision instead of shifting our strategy.” — Courtney De Ronde, CPA
Moments from this episode
Episode transcript
Dr. Lisa: What if the reason that you feel like you’re not getting traction in your life and you’re not moving forward and the things that you want so badly are simply not coming into fruition has nothing to do with your lack of motivation, discipline, willpower, or even vision.
Courtney: We give up on our vision instead of shifting our strategy. Oh, and and sometimes that’s because we have intermixed them and we we can sometimes get caught up in what we’re doing and forget that we’re doing it to get to a certain place.
Dr. Lisa: That is actually a really common mistake that many of us make. I know I have. Because nobody teaches us how to actualize the things we want, especially when those dreams are big.
Courtney: We aren’t all good at all of the parts of the process that are needed to close the gap between where we want to go and what we actually achieve.
Dr. Lisa: And so on today’s episode, we have a very special guest, Courtney De Ronde, who specializes in exactly this and who teaches people a framework that she uses all over the place. successful leaders, organizations, entrepreneurs, business owners who have big dreams, you guys, how to finally bridge the gap between where they are, what they want, and what they actually have. And she is here today to teach you the system.
Courtney: Our methodology covers these three different parts of the planning process. the long-term, the annual, and the implementation because it requires intentionality to close all three. And most of us aren’t wired to instinctively close all three.
Dr. Lisa: And if this is your first time tuning in, hello and welcome. I’m your host, Dr. Lisa Marie Bobby. I’m a psychologist, a marriage and family therapist, a board certified coach, and I just love being here with you every single week in service of your growth, your love, your happiness, and your success. And one of the reasons I’m so excited about today’s episode is that whatever you want, if it’s a change in your career, if it’s a change in your relationship, if it is a change in yourself, the process that you’re going to learn about today is the way to make things happen, things you can feel, not just ideas anymore. And my guest is one of my all-time favorites, Courtney De Ronde. She is a superstar. I have been a fan of Courtney’s for years and years, and it is such a treat to be able to share her teachings with you.
She has done so many things, but most recently, she is the author of a new book, Planning to Scale. Courtney,
Courtney: thanks so much for having me, Lisa. Yay. So, Courtney,
Dr. Lisa: planning to scale goes into so many different dimensions of how to make a business work, but what I found so fascinating as I was reading this is all of the different ways that these same ideas can apply to our personal lives. So take us into this maybe by telling us a story of something that exemplifies the need to plan the outcome that you want to experience and maybe what can go wrong when you don’t have that even on a personal level. Yeah, absolutely.
Courtney: So um I’ll give you a story. I share this story in the book and and a lot of my clients remember this story. I think it’s a great way to understand what we’re talking about. Um during COVID, I had this vision like a lot of people did to spend some time outside with my family, right? We’re all kind of cooped up and I wanted to spend some time outside with my family and I was envisioning, you know, like s’mores over the fire pit. And so I mentioned this to my husband and he um set out building a fire pit. And so he spent a couple days at the farm uh like full days fabricating this fire pit. And I was trying to imagine what in the world is he doing? And he came home.
He was very excited to present to me for my Mother’s Day gift, this fire pit, which all of my friends and clients know this as the hillbilly fire pit because aesthetically it is not pleasing. It is very hillbilly. It is from made from an old tractor wheel and it’s uh very rustic, very wellb built, very well fabricated. He, you know, welded things on there. He spent a lot of time making this fire pit. And so what does that have to do, you know, with what we’re talking about? Well, I had this vision for what I wanted, but I wasn’t clear enough with him about what that needed to look like and feel like. and he went out and took a strategy, a how of building it. There’s all kinds of strategies that we could have done. We could have went um to Home Depot and purchased one. I could have ordered one from Pottery Barn. We could have built one from, you know, Pavers.
Those are all strategies that would have gotten me to this reality of being able to have s’mores. But I wasn’t clear enough with him that I wanted to have s’mores in an aesthetically pleasing way, something that fit in with our backyard. Right. Yeah. And that happens to us across our lives in so many ways that we have an idea of what we want, but maybe we don’t get clear enough about it to align other people to it. and other people start to take action doing things that might be very well and good but misaligned from getting us where we’re going. And so we end up falling into this gap of what we want and what we what we actually achieve. That’s just one of the way strategy is one of the ways. There’s all kinds of places that we can fall into this gap.
But but that’s what we’re talking about is, you know, having clarity about what we want, aligning with the people who will help us get there, about how and and then really having activity that we do that supports us in really achieving it, right?
Dr. Lisa: Ugh. See, Courtney, this is why I was so excited to talk with you because I think that in some ways it’s so easy to make a plan. And now there’s it’s also true that people can struggle with with clarity, right? Like where do I want to live? Do I want to have a kid? What kind of job? What kind of career? Right? And and so these questions need to be answered first and that is its own process. And then there’s so much support around creating the vision, the mood board, cutting the pieces out of the magazine, like putting them on the billboard, right? And imagining the outcome that you want. But then there’s like this empty space around how do you actually make it happen? And I think so much frustration that we can all relate to of wanting to have these outcomes and feeling it clearly.
It’s not that you’re not like motivated, but the actual mechanics of moving things around in order to create this desired outcome is I it’s it’s not known, right? Like, how do we do this? And so, you’ve spent so much time teaching business owners how to create a business vision and then, you know, move move the pieces on the board to get there. What do you see as being some of the biggest obstacles that either business owners or people in their own personal lives just don’t even recognize? So, say you mentioned communication as one of them with a hillbilly fire pit, but what are the other usual suspects that get in people’s way? Yeah.
Courtney: So, another very usual suspect is what I refer to as capacity. Do we have the bandwidth, the time, the energy, the resources to actually do what we want to do? That is another very common place that people fall into this gap between what they want and what they actually achieve. Um, yeah, I
Dr. Lisa: I think that’s me. I do that. Okay. I’m like, it’ll be great. And then I’m like, oh my god. But
Courtney: right, it was like we once we So let’s assume that we are clear about what we want. Yeah. And I know you’re right. You’re absolutely right, Lisa. Some people have a struggle getting clear about what they want. They they are more instinctively actionoriented and they just want to go do stuff. They’re not really sure how it fits with their long-term picture. But let’s assume just for for the people who have that clarity about what they want. We often think visionwise um in this longer term horizon three to five years out this is where I want my life to be this is where I want my business to be this is what I want my family to be like my health whatever domain of life you’re thinking about we think long term and as soon as we get clear about what we want it’s hard for us to unsee it and then we want it to all be true right now. Yeah.
And a long-term vision cannot be achieved right now, but we want it to be because we’ve seen what we’re going for. And so, we really overestimate what we can accomplish because our our brains just want to close this gap between what we now see that we want and and what we want to be true. And so that’s very common is that we think in big long-term visions and we try to execute on them in short time frames that are not realistic based on the energy, the time, the money, the resources that we have to actually do it and and the solution is that we have to actually sequence it out over time.
But most of us, if we don’t think about it that way, if we don’t recognize there are some actually some underlying principles and processes that help us close the gap based on our human nature, we’re just going to instinctively try to do more than we realistically can and then typically get frustrated and abandon those places or get overwhelmed and burnt out
Dr. Lisa: and feel bad about it too, you know, like and I I’m sure that there are other like avatars or reasons why this goes off the rails, which is as as a personal share and I’d be curious, you know, to hear what what your what when I go off the rails, this is what happens to Courtney. But I’ll tell you for me, I am an enthusiast. Like I get so excited about ideas. I’m like, “Yes, that makes so much sense. We should definitely do that.” Um, and even most personal things too, you know, like I I will plan a day that includes uh cleaning out the basement and going and doing these things and yet we’re going to go to a water park, too.
like, you know, and my my husband was like, “No, no, we’re we’re not actually going to do all these things because it’s like being excited and seeing the possibility and but then frequently, you know, I I do bite off more than I can chew and now I have all these obligations and commitments and it’s like h and I I wind up dropping balls, right? I am late to stuff. I let people down. I uh you know don’t don’t follow through with something that I said I was going to because I forgot it in the midst of the 36 other things that I’m trying to like manage. Um and so that’s actually something that I’ve really had to work on is being able to have more discernment around that capacity piece. So, let me just ask you.
I mean, for for other people listening and okay, maybe like me a little bit too, like when it comes to our capacity in our personal lives, how what what do you recommend people do to just get like more realistic about what you can actually do versus what you want to do? Yes.
Courtney: So, there’s two main things. The first one is once you’re clear about what you want and it’s a longer term picture, the first thing you need to do is decide how far you can go on that in the short term. So let’s say you know three years from now I want I don’t know let’s let’s just say I want to I want to quit my job and start my own business in the next three years. That’s my three-year vision. So I need to decide in this next 12 months what am I going to accomplish? What outcome do I want to achieve to get a year closer to that?
So it might be that um by the end of this first year, I need to have obtained some kind of certification that would qualify me to actually deliver the service that I want to to deliver or I need to have a certain number of clients that I’m doing on the side in the fringes, you know, whatever it is, but I need to set a milestone, a benchmark for what I what progress I want to make in the first year. that doesn’t get me all the way to the three years because that’s not realistic, but gets me a year closer to it. So, that’s the first one and just look at this annual horizon, right? The second one, this is the one that most people struggle with uh the most is what do I need to change in my days and weeks and quarters in the way that I implement this?
Because it’s one thing for me to say I want to you know within the next three years quit my job and launch a business and in the next year I want to have achieved the certification to be a license to coach in this you know methodology. Mhm. Those are that’s all still planning, right? At some point I have to say what am I going to do next week, next quarter, next month, tomorrow so that I actually get the certification accomplished and and and these all three of these horizons have to be met. We have to think long term. We have to think one year and then we have to think about days, weeks and quarters. And and if we don’t, we will fall into those to that planning gap in one of those places.
Dr. Lisa: Yeah. Okay. And so that it this is so great because like you’re you’re almost reverse engineering this big vision and breaking it down into milestones, but then even further like in order for this to be true and for me to be making forward progress, what does that progress look like on a a month-to-month basis, on a week- toeek basis? How do I work it into a daily routine? Because otherwise what you’re saying is that this vision remains in the ether is that that we bring it we bring it down into this plane of reality by by the doing of the things today. Yeah.
Courtney: Yes. Absolutely. And so just to like to you know round out that example you might say well this particular certification requires you know I don’t know I’m just making things up 300 hours of coursework and study. So, I need to figure out when am I going to do those 300 hours. And I might say from now on, every Saturday morning from 7 to 9:00 a.m. And that’s probably not enough. I
Dr. Lisa: know. Like, I I need a calculator like 300 hours. Oh my god. You know,
Courtney: I’m going to do this coursework. I have to somehow make it part of what I do.
Courtney: And and people are wired in different ways. So there are some people that think easily of that big long-term vision and it stays kind of out there as oh I’ve got plenty of time to make that happen. Three years is a long time. Eventually I’ll get there. But then they don’t because they don’t ever break it down. There are other people who aren’t quite sure what they want and they are more actionoriented. They’re more executionbased. Yeah. And they will, you know, sign up for a 300 hour course and start taking it without ever having any plan or intention to quit their job and start their own business. They’re just doing stuff. They are studying and they are taking tests and they are spending money and they don’t know what they’re going to do with it, but they’re more on the execution side.
And so it’s not right or wrong, but we have to understand these things about ourselves and be intentional about connecting the missing piece. So if I’m a doer, I’ve got to eventually think, what am I doing this for? Like what’s my right there? And if I’m a visionary, I have to think, okay, I’ve got the vision, but how in the world am I going to actually make this happen? And so, again, it’s not right or wrong. It’s not good or bad. It’s just how we are made, right? And once we understand that about ourselves, we then need to be intentional about filling in the rest of the parts of the process that don’t come as naturally or as or maybe don’t seem as fun or adventurous to us depending on how we’re how we’re wired.
Dr. Lisa: Yeah. How we’re wired. Absolutely fascinating, Cordy. Honestly, like I’ve I’ve never connected with that idea in the same way before that that a a visionary and an actualizer uh have different problems in some ways that can be prevent people from really getting where they ultimately want to go. But that a more actionoriented person, it feels good to just feel like they’re making progress in the moment or doing things in the moment. But that if it’s not connected to a big why, you you don’t really get where you want to go because you don’t even know where that is. And so to have that’s that’s a different level of the work.
Courtney: It’s a different problem. It’s it’s more like drift. That’s how people end up, you know, three years from now in a in a career owning a business that they never really even wanted, right? It’s it’s so it it can happen either way and it’s usually not going to happen both ways to the same person. Like we’re we have ways that we’re inclined, you know, to carry these things out. Um and so just recognizing that there are lots of ways that we can fall into this gap between what we want and what we get. And that’s why our methodology covers these three different parts of the planning process. the long-term, the annual, and the implementation because it requires intentionality to close all three. Yeah. Most of us aren’t wired to instinctively close all three. We might be wired to instinctively close one and then we’ll fall into the gap on one or both of the other two.
Dr. Lisa: Oh my goodness. Fascinating. some of the things that people subconsciously do without even realizing they’re doing it that is creating this this frustration and this like feeling like you can never really get where you want to go either through you know communication and alignment with other people through um not really having a clear vision for where you want to go in the first place just jumping into action or sometimes having a very clear vision without a awareness or appreciation of your actual capacity and the way to translate uh you know forward movement towards a big hairy goal into like what am I doing today? So, these are some of the the problems that are typically standing in people’s way. And so, when you’re working with somebody, maybe a a business owner, even if a personal friend came to you and said, “I feel like I am just spinning my wheels. I am working so hard. I’m not getting anywhere. I’m so frustrated.”
Where do you even begin helping them understand what it is that they’re doing that’s getting in the way? Yeah.
Courtney: Yeah. So, one of the things that we always start with is helping people know their wiring. It’s so all of our team, all of our clients, uh we use three different assessments that help us understand how they’re wired and help them understand how they’re wired. So, this is an aspect of we call it human intelligence. It’s about you know some people might call it emotional intelligence but we use CliftonStrengths Kolbe and the integrative nog and these give us different lenses on the way people are wired or their working style. So we start there to help people understand what parts of this process will come very easily and naturally to them and what parts will be harder and more challenging to normalize that we aren’t all good at all of the parts of the process that are needed to close the gap between where we want to go and what we actually achieve.
So there are parts that come naturally and instinctively and we’ve probably done them over and over and over again and found ourselves back in the same place. Like if we are naturally instinctively visionoriented or um an adventurer or we um we are okay with risk and change and uncertainty, we probably have no problem coming up with big ideas for our vision.
Dr. Lisa: Stop. You’re you’re you’re speaking right to me, Courtney. I could feel it. But yes.
Courtney: Yes. And and I’m right there with you, Lisa. I have so many ideas for what I want and I know you do as well. And and so that comes easily and naturally and that’s fun and energizing. And then we fall into this gap because we never or we don’t usually not without some intentional planning and maybe some other people to to come alongside us turn those ideas into plans for next year and then things that we build into our routines for the days, weeks, and quarters ahead. we don’t break it down into projects and milestones and tasks. They stay up here as ideas and and then we get frustrated because we have all these ideas, we can’t get them done and then, you know, other people um are the opposite and they struggle to figure out what they really want. So, like we were talking about before the break, then they end up drifting somewhere.
So, we ground people first in just understanding that how you’re wired is going to influence how you experience this process. And it doesn’t mean that you’re broken or that you’re, you know, you can’t do this. What it means is when we get to the part of the process that you’re not naturally wired for, it’s just going to take more of your energy, right? It’s not going to feel as exciting and energizing. It’s going to be a little more draining. That’s okay. You can do it. But what happens to most of us if we don’t know that about ourselves, we get to that part of the process and we tell ourselves, I can’t see this is the part where I can’t do it. I I don’t know how to plan projects. I don’t know. This is terrible. I’m horrible at this. Right? We have all this stuff that we tell ourselves because we think that that’s true, right? And it’s not.
What we have to learn is I’m not as instinctively wired to do this, so I have to be more intentional about it. and I just have to prepare that it’s going to take more of my energy. And so that’s how that’s where we start with everyone. Yeah. Is setting the stage and normalizing how they will experience the process. That same information can also be really helpful for people in how they insert themselves into their plan, the things that they say that they’re going to do and whether or not that really is aligned with how they’re wired. Um, but really first we’re teaching it and starting there just so they understand how they’re going to experience the process itself.
Dr. Lisa: Well, and and Courtney, I love this so much. It warms my little psychologist heart because we need to have this visibility into ourselves because otherwise, and you know, I I see this a lot like everybody’s out there dispensing advice, right? Like very confidently about the right way to live. And and what I think is always so interesting is that based on who you are and how you’re wired and what your instinctive strengths are, it’s really going to look so different for you. And so just to get a snapshot into what what genre of human are you and what are you naturally good at? So not only can we be um keeping an eye on this is when I’m going to struggle. I’m going to need some support. I’m going to need to be more intentional. how do I manage this?
But also, you know, embracing the strengths like not not only what are you good at, but how do you make it easy to win by using your strengths intentionally? And it’s just, I think, a very positive and empowering way of looking at this because, you know, going back to something that you were were starting to say at the end there, what what I see is that um and I’ve experienced this in my own life, too. You probably have as well, Courtney. But like it can start to feel just so defeating when you’re operating in a way that’s not congruent with your strengths. It’s not going well. You don’t know what you don’t know. It it turns into this like narrative about your worth as a person that can also make it hard to have the confidence and the energy to do what you need to do in order to make it be different.
And so it turns into this like downward spiral also like comparing yourself to other people. Like there’s all kinds of things that can go in there. And so but this the step one of self-awareness as the launch pad for like designing your own path forward I think is just so affirming and empowering. And you guys are the assessments that that Courtney was speaking about. She we were talking about the CliftonStrengths which is spooky. Oh my god. I read it and I was like Jesus these people are watching me. Then uh there was also the Kolbe which is very interesting working styles and then also the NEOG uh the assessment that you recommended the iEQ9 I think it is. So there are different enog tests on the market. I think that of the ones I’ve explored that to me yields the most reliable results.
And also if there’s anybody who’s like enog shinogram you know pop there there’s actually a lot of emerging research from the field of psychology and personality to support the fundamental of of assertations of the enog which is really is just a combination of big five personality traits that that tend to show up in clusters depending on how you’re wired. So there really is quite a bit to it and we’ll link to all of those assessments in the the article for the show. Okay. Courtney. So, so with this this understanding of the self, then where would you walk someone next? I mean, somebody who’s been like, “Ah, nothing’s working.” And how do you start shining a light on here’s something to think about doing differently going forward? So, we talked about capacity, which is fantastic advice, but but there’s more. There a couple other dimensions. Yeah.
Courtney: So once people really understand who they are, how they’re wired, um the next thing we do is vision. So where do you want to go? And so if this is in your business, we talk about six different categories of the business. Um if this is in your life, if you’re not a business owner, think about the different domains of your life. So, in business, we’re talking about how you get clients, what it is that you do, how you do it, who you are as a leader, the results you get, and how you care for your team. But if you’re talking if if you’re not a business owner, you’re thinking about, okay, well, what what is my vision for my life, you might think of domains like your relationships, you know, maybe you could even break it into parenting, um, marriage, or you could just say relationships, you could say your finances, your physical health, your emotional health, right?
So these you look at these different dimensions of your life because if you just said well where do you want to go you know where do you want to be 3 years from now and you didn’t have any kind of buckets to put things into right it can feel like well I I don’t know so having these kinds of um like I said buckets I guess um categories is helpful and you might you might not have a vision for something different than what your current reality is in each category. You might be very satisfied and content with the way you currently get clients or with your current physical health and your vision is not to change it. Your vision is to preserve it and maintain it. Great. But in another domain of life, you might say what I currently have is not working and I want it to be different.
So that’s the first step is just evaluate these different aspects of your business or your life and ask yourself, is there something that I want different? What’s my vision for what this will be like? Amazing. Three years from now. And
Dr. Lisa: and just to share a resource and and Courtney, I know that you you go into this a lot particularly for business owners in your book planning to scale and also the Scaling Leader program. That’s a lot of what you’re doing there. And also just for friends here listening, if you’re thinking about how just to get your arms around the different dimensions of a p your personal life, a very common intervention that we use in a a coaching process, like a life design coaching process, is a a tool called the wheel of life. You could Google wheel of life. Everybody in the world has a PDF. You can download it. It typically organized like a wheel. And around the edges of this wheel, it has common domains. So things like, you know, your exactly what you’re saying, your relationship to your uh partner, parent, your health, spirituality.
And so you can download one of these, but also just spend a little bit of time thinking about are there other domains of life that are personally important to you that might not be personally important to everyone. Like if there’s a hobby that you’re feeling really connected to or if there’s a a a cause that you’re really uh deeply aligned with. And so make it your own. Um, but then you have a framework for going to surround that and asking yourself, how do I feel? You might even consider on a scale of 1 to 10, one is it’s horrible, 10 is it’s perfect. What would I rate myself in this area? So just as a way to kind of like crack into that. Um, but so Courtney, you’re saying that that visibility is very important. First is just that like check-in. How am I doing when it comes to my finances or whatever it is, right?
Courtney: Yes. That’s because we’re we’re we’re trying to look at where do we want to go? So, what do we want to be true? It’s it’s aspirational. It’s future focused. Um that’s your vision. And so, we start there before we get into what’s true right now because sometimes if we start with what’s true right now, we get bummed out and we and we can kind of close off our perspective of what’s possible. So, so we first start with what do we want to be true? um in these areas of our business or domains of our life. Then we say and and where am I starting from?
Courtney: And the reason we do that is so we can chart the path or the strategy is the technical term for how we’re going to get from where we are to where we’re going. And and I think of it like if you were going to put a destination into your Apple Maps, it’s it’s going to pull up where you’re starting from, right? And then so if I put in uh Lisa’s in Colorado so and I’m in Tennessee. So if I was sitting here right now and I put in um to go to Colorado, it would give me a few different routes. And one of them is going to be the shortest distance. Another one is going to be the shortest time. And for whatever reason, the third one is the fewest turns. I guess there’s people out there who plan their trips trying to reduce the amount of turns, right?
Same thing is true for us when we say where we want to go and where we’re starting from. I could get there the fastest way possible or I could get there the shortest number of miles or the least amount of turns. Right? So in real life, this might be I could spend a lot of money and get there faster. That might be a perfect
Dr. Lisa: like a health goal. I could I could start paying a personal trainer $300 a week to sit there and watch me do the whatever.
Courtney: Yes. Exactly. Or I could take a longer path that’s more affordable. So I’m There’s tradeoffs. That’s what we’re doing is we’re looking at all the different strategies, the different how we could get from where we are to where we’re going. You could even say, okay, we’re we’re not even talking about the, you know, the different routing methods on the ways map. We’re talking about do we take a plane? Do we take a train? Do we take a car? Do we take a bike? Right. Yeah. The point is strategies are methods. They’re how we get there. And they can change depending on the resources that we have or the trade-offs that we want to make. The vision where we want to get to generally doesn’t shift and change much. Like we’re getting clear about what we want, but we can hold those strategies a little bit more loosely. We could say, “Well, it could be this one or that one or the other.”
And based on my current reality, I’m going to take this one. But I might find out along the way that something’s going to cause me to to shift course. I might I mean, how many of us have ever booked a flight and then had it be cancelled and ended up renting a car and driving, right? Right. Of course, we’ve all been there. That happens in real life with our visions as well. We think we’re going to get there one way and life happens and we end up choosing another way. So that’s the difference between vision and strategy. Vision is where we’re going. Strategy is how we’re going to get there. Strategies can change and evolve. Vision usually stays pretty close. We’re only tweaking or recalibrating occasionally.
Dr. Lisa: Yeah. But Courtney, this is also just so empowering and I think so refreshing because I think that what is usually more true the way that people operate and I know I’ve been vulnerable to this is like okay fine you have a vision and then the first idea that pops into your head or or something that kind of seems like a good idea like this is the way right and especially being in a a zeitgeist right now where there’s a lot of advice around the right way to live is that you’re actually saying that if you really want to get where you want to go, don’t do anything at first and instead just consider 12 different options that will get you to the same place. So again, like if you’re you have a a improved health goal, I want to feel more energized. I want to feel more clear. I want to feel like I have more vibrant physical health.
Is that before you just join a gym, think about that. And and I’m imagining too, this is where some of that reflection on your wiring and your capacity needs to come back in because I’m thinking some of these strategies are probably more feasible than others when you really look at what it would require. Is it true? Yeah,
Courtney: absolutely. Truly, you are spot on. And and I think that you’re exactly right that what happens to us a lot of times is we compare ourselves to other people’s journeys and we think well they’re doing this so I must need to do that. That must be the way that we get there. Right? That’s the way they got there. And they are starting presumably from a different starting place than I am. They may have different resources than I do financially, time, energy, capacity. They might be wired differently than I am. And so you’re absolutely right that the So if we first understand how we’re wired, we second decide where we’re going. Then third, we decide we we figure out where we’re starting from, but then how are we going to get there? It’s a brainstorming exercise. What are the potential strategies I could take? If I want to lose weight, I could um have a surgery. I could take a do an injection.
I could exercise again. Get a personal trainer. Right? Like those are all strategies and they all have different tradeoffs to them. Some of them would be faster and more expensive. Some of them would be very, you know, painful and anyway that that’s what we’re doing first. Yeah. And we aren’t we don’t have to feel like the strategy that we eventually have to choose one, right? And we have to like get to going on it. That’s the second and third parts of the process. But while we’re in this first long-term planning phase, we are brainstorming potential strategies and we just have to know that over time, even once we pick one, we can change it later. We can decide, you know what, this is taking too long and I am willing to spend more money to get there faster and I can change it. I’m not changing where I’m going.
either faster or we can, you know, run out of energy and say, I’m going to take a longer path because I don’t have enough capacity in my life to do this right now. And so, um, that’s the way you should think about strategy. It’s the how and there’s all kinds of different ones that will get you there and they all have tradeoffs and you get to choose and you can also change. Yeah. After you
Dr. Lisa: do well because what what’s coming up for me right now, I just want to run this past you.
Dr. Lisa: I just had this like light bulb moment as you were talking. Um well, one of my favorite books of all time besides yours, by the way, Planning to Scale, uh is is wonderful. It is called um The Dip by Seth Godin. It is everybody within the sound of my voice read this book. It’ll change your whole worldview. But but and it’s a it’s a short book but the basic premise is that um it is very very very important to acquire the ability in this lifetime to understand when are you going through a a rough patch that if you continue to work and and try different things like it’s it’s going to get better. You will get to a different place keep going versus being in a cul-de-sac no matter how hard you work or how fast you run like it’s not going to change.
And the only thing to do is to recognize that and get the hell out of there as fast as you can. And as you were talking about like the strategy selection, what was coming up for me was this idea of I I wonder how often that people are getting stuck or feeling like they’re not making progress with this vision because they’re simply in the wrong strategy and they have not recognized it and they also don’t see that there are many other strategies. And so then they like abandon the vision cuz they’re like, “I can’t do this.” Not even realizing that they’ve just they were in a cul-de-sac with a strategy, not with the idea. Is that true?
Courtney: Absolutely true. And I love that. I haven’t read that book, but I’m going to ask you now. Read it. But I love what you’re saying there, Lisa. And I think that’s absolutely what happens is that we give up on our vision instead of shifting our strategy. Oh. And and sometimes that’s because we have intermixed them and we we can sometimes get caught up in what we’re doing and forget that we’re doing it to get to a certain place. Executing this strategy in and of itself is not the goal. Achieving this vision is the goal. And there are lots of different ways I can get there. But sometimes, and this can be based on how we’re wired, it could be there’s all kinds of circumstances that could cause us to keep circling the cul-de-sac and not realize it or cause us to bail out um instead of, you know, backing up and going a different route.
But I think that’s what’s so important for people to realize. It’s just another gap. It’s another way that you fall into the gap between what you want and what you achieve. This is another example of it. you can fall into the gap because you pick a strategy and you believe that that is the only one you got and if it doesn’t work you just keep slugging away or you give up and then you don’t get there. But that’s not that’s not true. That’s not the way it has to be.
Dr. Lisa: How to actualize a vision in a very practical way that’s related to wiring. It’s related to what you want. It’s related to your capacity, your process and and so so that we have this out in the open. I happen to know that you have been the the agent of transformation in the lives of so many people specifically business owners and entrepreneurs through your different initiatives. So you certainly have as a Scaling Leader program. You also run uh forge an accounting and business consulting.
Dr. Lisa: But so tell us a story of transformation. You know somebody coming in who is not doing any of the things that you are talking about and is like I hate my life and and what you have seen them do differently and the changes they were able to make because of that. Yeah. So I have stands out.
Courtney: Yeah. One that stands out for me. I have a a few clients that I work with privately. Um, so a lot of what we do is in our group coaching program called Scaling Leader, but I have a few clients that I work with privately. Yeah. And I have this client I’ve worked with for probably four years now. And they really attached to the vision and the strategy that we’ve been talking about so far pretty easily. Like they knew where they wanted to go. they had some pretty strong ideas of how they wanted to get there and where they fell into the gap was in the implementation. Um so they would they knew where they wanted to go, they knew how they were going to get there and then the next step is the annual planning. So how far are you going to get next year and we need to break that into projects that we will execute and this is where they struggled.
they didn’t really enjoy the process of project planning as some of us don’t. Now, there are people who love it, but I I am kind of with them in this um realm of I’d really love for somebody else to figure out exactly in more detail what needs to happen now. Um by when and by who and how much will it cost and you know all those details of project planning. But that was the part that they had continued to put off. So, you know, I’ll facilitate sessions with them and then they would say, “Let’s not worry about that together. We’ll do that later on our own.” But then they would struggle to actually do it later on their own. And so then we’d meet again, meet with them every quarter and we’d look at the list and how far did we get? And the number one reason that they were not making progress came back to the lack of project planning.
And so what happened was we shifted our time together where when I meet with them quarterly, we plan the projects together. We do the hard part together with support and space dedicated to it instead of leaving them on their own to do something they don’t really want to do later by themselves. And so I think so so for your listeners, some of you might that might map exactly to you. you’re like, “Yes, I would actually hate project planning and I would need that.” But it might not be project planning for you. It might be something that you’re leaving to your own discipline that is that’s not going to be enough. So Lisa, you mentioned like having a personal trainer. For some of us, we need a personal trainer who will give us the space and support to do the workout because if we don’t have them, we won’t do it.
And so for this particular client, that’s what I was to their project planning part of it. They could they could do project planning. It wasn’t that they couldn’t do it. It was that they didn’t like it. Yeah. And so it kept getting put off and they needed me to give them the space and support to get it done.
Dr. Lisa: Well, and like it goes back to what you were saying though about like the importance of understanding our wiring and our strengths, but also our limitations because it’s like all this stuff could be lined up, but if there is a weak link when it comes to creating an actual plan for what will this look like on a day in dayout type basis, like that’s very important. And and so maybe for people listening like whatever your use case is so to speak to think about where do you tend to drift or not follow through or you know like where does where does it kind of fall apart and the I think the meta message here Courtney is like what are the support systems or are there people you can bring in to help you or other like how do we navigate this rough part of the journey I Maybe is that the right way to say it? Okay.
Courtney: Absolutely. Yes. Absolutely. So the more we understand about our wiring and our behavioral patterns and our history and our track record and then set things up to counterbalance them or to support them, the more likely we are to get through this gap. Yeah. But I think so often we think, well, if I just were more disciplined, if I just, you know, put my head down and get to work, like, I can do this and I’m just going to, it’s me, I’m the problem, and I just need to buckle down and do this. Always do that. Yeah. And that’s probably not the reality of it. Or it’s just not sustainable. And and I think for most of us, if we think about the vision we have for our lives and our businesses, they’re bigger than what we have the capacity and the capability to do on our own. Yeah. And and that’s great.
Like we can achieve more together than we can alone, but we have to be willing to enlist other people in the journey with us and not feel like that’s an indictment on our capabilities or skills or character because we can’t do this all ourselves. And so accepting that sometimes we need additional space, additional support, additional resources, additional gifts and strengths of other people to get to where we’re going. That’s a good thing. That means you have a big vision. Um it requires more than just you.
Dr. Lisa: Yeah, that’s so good. And and to make it a collective effort, you know, let let other people into your process and and I would imagine especially in in personal realms, maybe being part of theirs, right? I mean that that you need somebody else’s help to um actualize what needs to be done in a specific area, but how could you also bring your strengths to someone else’s process in a really uh nice and complimentary way? That’s so beautiful.
Dr. Lisa: Courtney, can I ask you a question before we we wrap up? and and apologies if if this is personal or maybe maybe you have an example that you you shared in your book, but I would be so curious to know um you know you’ve done so much work on yourself and I know that you’ve invested a lot in your own development you know your own wiring your own capacity and over the time that that I’ve known you you just give the impression of being one of these almost supernaturally competent people right where you and you’ve been able to do so many things that are genuinely impressive. I’d just be so curious to know did you at some point recognize something about yourself in terms of your process? Are you aware of of operating or perhaps capacity that you were like oh okay I need to recalibrate here if this is going to be different for me personally.
Courtney: Yes. Uh well, thank you for your kind words, but I most of my success has come from learning from the mistakes I made on the way to that success. So, um but I would say, you know, one of the things that as I reflect back on, um a big shift for me was recognizing that I am inclined to take action. So I on the CliftonStrengths I lead with execution. Um, and so I can get very clear about what I want, how I want to get there, and move into execution mode. And and as a leader, as a business owner, as a mom, a wife, you know, as a person interacting in the world full of people, I can sometimes forget the relational aspects of change or of planning or execution. And so one example that stands out for me is um my first step as CEO of the firm that we split it off from. I was I became the CEO of this firm.
I had this brilliant strategy to split the firm. I presented it to my partners. It made sense financially for everyone. It made sense um from a logistics standpoint. I thought it was just so smart. and I presented it and the it was on a Zoom call and my fellow partners were just shocked and dismayed. We didn’t even vote on this proposal. They were so hurt and the trust was broken and I was stunned and I thought this is so smart. This makes so much sense. But I hadn’t considered the people and the relational work that was necessary to present such a proposal. And so that that moment that was in 2020 that is when at first I thought well I’m not cut out to be a leader. I should just quit. A and thankfully I had an executive coach who encouraged me that that was not the case and that I could actually learn a lot.
I could probably learn more from this mistake than most people will learn in a decade because that’s how big of a mistake it was. So I set out to increase my understanding of human intelligence of people and of what is required if you want to move forward in something aligned. That that strategy ended up being the right strategy. We had a unanimous vote to do it two years later, but there was a lot of work that happened in between to rebuild trust and to develop relationships. And so for me, that was the biggest one. And for some of you, it might be the opposite. You might be great relationally and you struggle to pull the trigger and actually get something done. Both have their challenges. All of these things have challenges.
And I just have learned that the more I understand about myself and the people around me because we are humans dealing with humans, the easier it will be to navigate these things that that require relationship and alignment and human involvement.
Dr. Lisa: Right. H Courtney, thank you so much for for sharing that story. Um and and what a powerful lesson and so much humility also you know that that the idea would not was not wrong. It was a good idea but that there were all these invisible factors around it that that needed to be seen and then managed in a really intentional way and that it gave you visibility into um work that you needed to do. Right. And that is so true for all of us. You know, even just hearing you talk, I think that I’ve um made so many mistakes in the opposite dimension. I’ve I’ve overindexed relationships to the degree that it’s been to the detriment of being able to get things done. And I think everybody listening has their own combination of stuff.
And so this is also though I I think a very important takeaway from this entire conversation is that when it comes to creating a vision and moving from where you are now to where you want to be, it isn’t just about time management and schedule blocking and all of these things. It really requires this deep self-awareness and self-nowledge and this really fearless ability to understand how we are operating in the world in a um reality based way so that we can uh just start making changes on deeper levels. That is really where where the work is and and I think your story that you just shared is such a powerful example of that. So thank you. Yes, my pleasure. Yeah. Well, Courtney, it is such a delight to spend this time with you. This has been really such such a pleasure for me and I know that our listeners have been like, “We want more Courtney in our lives.”
So, so of course the book Planning to Scale, the author is Courtney De Ronde. You can find that everywhere, particularly if you have entrepreneurial aspirations. Go check that out. But but Courtney, before we let you go, tell us more about the other things that that you do to support people in their lives and their businesses because it’s kind of a lot.
Courtney: Yes. So, uh, so I am the co-founder and CEO of Forge Financial and Management Consulting, and um, most of our team is helping small business owners and nonprofit organizations get visibility on their financials. And so, uh, a lot of our team are CPAs and adviserss. And so they’re working in the financial realm with our clients. And then we the management consulting side of the practice is where I get to spend my time uh which is primarily that group business coaching and leadership development program called Scaling Leader do a little bit of private consulting as I mentioned and um and one-on-one coaching but the the bulk of it is um guiding leaders every quarter through the tools that they need to solve the problems that come up as they grow and scale their organizations.
Most of the clients we work with are service-based businesses and they came up, you know, through their careers as experts, expert therapists, expert accountants, architects, attorneys, financial adviserss, uh, physicians, and eventually they became leaders and business owners, but weren’t necessarily equipped with how to handle all of that. And so each quarter we teach them different um practices and tools that help them figure out what’s going on here and design solutions to solve it. And I I always tell people, you know, these things don’t mean that you won’t have problems. Um it means that you will recognize them more quickly and know how to solve those problems. But like I said before, anytime we’re working with people, there will be challenges. And so that’s what we’re helping um helping our clients to do.
Dr. Lisa: Amazing. Well, thank you so much. I just personal share I that I have been participating in your program, Courtney, for the last several years. I’ve gotten so much out of it. Um and exactly that, you know, being a therapist, totally different thing than being a business owner. And so it’s been very instructive. Would encourage anybody to check it out. So Scaling Leader is that the website scalingleader.com. Scalingleader.com.
Courtney: Yes. And then the book um the book is Planning to Scale that. So you can go to planningtoscalebook.com um or you can order it on on Amazon. We have audible, Kindle, and hard copies there as well. Um I will mention too, if it’s all right, Lisa, that um in the book at the end of each chapter, there are tools that you can download for free at planningtoscalebook.com/tools. So um you know if you if you read the book and you want to start building your vision, your strategy, your project plans, all of those tools are available for free at planningtoscalebook.com/tools to help you actually implement what you’re learning through the pages of the book.
Dr. Lisa: Amazing. Courtney, it has been such a pleasure. Thank you again so much for spending this time with us today. Well, it’s my pleasure, Lisa. Thanks so much for having me. Thank you. I’m so genuinely thrilled to be able to introduce you to someone that I just love so much and that I have personally had the opportunity to learn so much from it feels so meaningful to me to be able to bring Courtney to you. So, I I hope that you enjoyed her as much as I do. She is truly a gem and one of the kindest people you’ll ever meet. But, you know, she has so much to share and and I hope you heard this part. Like, one of my biggest takeaways that honestly landed inside of me a little bit differently today, even though I’m very familiar with Courtney’s work and I’ve even heard some of these stories before. She was talking today. I was like, “Huh?”
So the the takeaway is that being stuck or when things feel hard or you’re not moving forward, it does not mean necessarily that you need to get grittier or try harder or like double down or you know something about you like maybe you need to back up and think about where you want to be like on a macro level and that maybe just maybe you are pursuing the wrong strategy. Maybe there are a lot of different ways to get where you want to go and the one that you have been trying is not actually the best one. Not that it couldn’t work, but given your unique combination of gifts and strengths, maybe there’s another one that is better for you. Or maybe there’s a better support system. Maybe you need to have some other people on the boat to help fill in some of the gaps. Right? We all have strengths and beautiful things and we all have some limitations.
and knowing what those are and being able to to partner with people who have complimentary strengths is such a gift. It this all comes back down to having a clearer understanding of yourself, even our communication patterns, right? Like Courtney was talking about that as well. And so this all boils back down to us, who we are, what we know about ourselves, and then how we make decisions accordingly. And so could not encourage more the you to check out everything that Courtney has to offer includes Scaling Leader including the book Planning to Scale. But if you’d ever like a partner to get under the hood around some of that personal development and self-awareness work that is exactly the type of thing we do at my practice Growing Self. And you are invited to do that work with us if you’d like to stop spinning your wheel.
start creating the life you want that is based on a deep, deep, deep understanding of who you are in a very selfaccepting way. We’re not trying to change you. We want you to be more of what you are. And if you want to partner to help you make that happen, head over to growingself.com. You can uh tap the button like get connected, schedule a free consultation with one of the experts, licensed therapists who specialize in coaching psychology, very very unique, and book a free consultation to explore what getting some support for this growth might look like for you. All right, you guys, that’s it for today. Thanks again so much for tuning in and I’ll be back in touch with you soon with another episode of Love, Happiness, and Success.
What to take with you
Stuck isn’t a character flaw.
When the gap between what you want and what you achieve won’t close, it’s almost always a planning problem, not a discipline problem.
Plan on three horizons.
A three-to-five-year vision, a 12-month milestone, and weekly implementation. Most of us are wired to handle only one well.
Know your wiring.
Visionaries stall because ideas never become tasks; doers drift because tasks never connect to a why. Either way, the hard part just takes more energy.
Change the route, not the dream.
Your vision should stay steady. Your strategy can change whenever time, money, or energy shifts.
Check for cul-de-sacs.
Before you abandon a goal, brainstorm at least three other routes. You may be stuck with a strategy, not with the idea.
Stop leaving the hard part to willpower.
Find the step you keep putting off and get support for it. Needing help means your vision is big.
What we cover, in order
- What is a life plan? (It has three parts)
- Why do good plans stall?
- How do you plan your life when you’re wired the way you are?
- How do I plan my life, one area at a time?
- How to plan your life: separate the vision from the strategy
- Should I give up on my goal or change my strategy?
- How to create a life plan you’ll actually follow
- Why reading this article probably isn’t enough
What’s in this article
Not at all. Courtney’s framework was built for business owners, but everything here applies to personal goals: a career change, your health, your relationships, or a dream you’ve been carrying for years.
If a goal has stalled, check the route before you abandon the destination. Most of the time the strategy is the problem, not the vision, and not you.
No. They’re helpful mirrors, and I’ve linked all three at the end, but the real point is to notice which part of planning drains you so you can plan for it.
That’s a very common starting point, and it’s not a failure. Start with the Wheel of Life exercise in this article, and consider talking it through with a coach.
The video is at the top of this page, and the full transcript is organized by chapter above the article.
Life Planning: How to Close the Gap Between Wanting and Achieving
You know what you want. Maybe it’s leaving the job that’s slowly draining you, or building the business you’ve been sketching in the margins of your notebook for three years, or finally feeling strong and energized in your own body. You’ve been working hard at it, too. And somewhere along the way a quiet story started up: maybe I just don’t have the discipline. Maybe the dream was wrong. If that sounds familiar, here’s the answer I want you to have first. Good life planning isn’t about more willpower. It’s about closing the gap between what you want and what you actually achieve, and most of the time that gap is a planning problem, not a character flaw.
I say that as a psychologist and a coach who has watched this play out more times than I can count, in my own life and in the lives of the people I work with. Brilliant, motivated people get stuck all the time. Not because something is wrong with them, but because nobody ever taught them the mechanics of turning a big vision into an ordinary Tuesday. That’s exactly the work we do in life coaching at Growing Self, and it’s why I was so excited to talk with my friend Courtney De Ronde on the podcast this week.
Here’s the honest truth, though. Most people who come to our coaching practice with this frustration have already read the books. They’ve made the vision board. They’ve bought the planner with the pretty fonts. The problem isn’t information. The problem is that you’re trying to see your own patterns from inside them, which is really hard to do alone. What I’m going to share in this article is real, and it will give you language for what’s been happening. But the part where you actually do it differently, next week, with your real calendar and your real energy levels? That’s the work my team does with people every single day.
Courtney is the CEO and co-founder of Forge Financial & Management Consulting, a CPA with more than 20 years in practice, and the author of Planning to Scale. (Full disclosure: I’ve been part of her Scaling Leader program for years.) Her framework was built for business owners, but as I read her book I kept thinking, this is exactly how life design works for the rest of us, too. So let’s get into it.
What Is a Life Plan? (It Has Three Parts)
A life plan connects the life you want in the future with what you actually do this week. In Courtney’s framework, that means planning on three horizons at once: a long-term vision, an annual milestone, and implementation. Miss any one of them and you fall into what she calls the gap between what you want and what you achieve.
- The long-term vision. Where you want your life to be three to five years from now, in whatever area you’re thinking about.
- The annual milestone. How far you’ll realistically get in the next 12 months. Not all the way there. One year closer.
- Implementation. What changes in your days, weeks, and quarters so the milestone actually happens. Courtney says this is the horizon people struggle with most.
What struck me most was her observation that most of us are naturally wired to handle only one of these horizons well. We handle that one beautifully, fall into the gap on the other two, and then conclude that the problem is us. If you’ve ever made a long-range personal plan that looked gorgeous on paper and then quietly faded by March, you know exactly what she means.
Figuring out which horizon you tend to skip is one of the first things we look at with a new coaching client. It’s almost impossible to spot on your own, because the horizon you skip is, by definition, the one you don’t think about.
Why Do Good Plans Stall?
Most plans stall for a handful of predictable reasons, and none of them is that you’re lazy. The two Courtney sees most often are a vision that isn’t clear enough to guide the people helping you, and an honest overestimate of your own capacity.
She tells a story I can’t stop thinking about. During the pandemic, she mentioned to her husband that she’d love to make s’mores around a fire pit with the family. He disappeared to the farm for two full days and came home, beaming, with her Mother’s Day gift: a fire pit he had welded out of an old tractor wheel. Very sturdy. Very well made. And, as her friends and clients lovingly call it, the hillbilly fire pit. Her vision was fine. It just wasn’t clear enough for the person helping her to choose a route that fit it, because what she actually wanted was something that looked nice in the backyard. Sound like anyone you know?
The second reason is capacity. Courtney described something I’ve felt my whole life: once you get clear about what you want, you can’t unsee it, and suddenly you want all of it to be true right now. So you try to execute a three-year vision on a three-month timeline, with the time, money, and energy you actually have. Then you get overwhelmed, burn out, and abandon the plan. And usually you feel bad about it, too.
I’ll raise my hand here. I’m an enthusiast. I have been known to plan a single Saturday that includes cleaning out the basement and a trip to the water park, and my husband has been known to gently say no. When I overcommit, I drop balls, run late, and forget things I promised. That isn’t a character flaw, but it is a pattern, and I’ve had to build real discernment around it. (If this is you too, you might like my episode on how to get out of your own way.)
There’s research behind this, by the way. Psychologists studying the planning fallacy found that people consistently underestimate how long their own tasks will take, even when they know similar tasks have run long before (Buehler, Griffin, & Ross, 1994). You’re not uniquely bad at estimating. You’re human, and so is everyone else making a plan.
How Do You Plan Your Life When You’re Wired the Way You Are?
You plan your life by starting with self-knowledge. Courtney begins every client engagement by helping them understand how they’re wired, because the part of planning that drains you is exactly where you’ll be tempted to quit. Knowing that ahead of time changes everything.
She describes two broad types. Visionaries (hi, it’s me) find big ideas easy and fun, but those ideas stay up in the clouds because they never get broken into projects, milestones, and tasks. Doers jump straight into action, which feels productive, but without a clear sense of what it’s all for they drift. Courtney says that’s how people end up three years later in a career or a business they never really wanted. If you suspect you’re a doer, spending some time figuring out what you actually want may be the most productive thing you do this year.
Courtney’s team uses three assessments to help people see their wiring: CliftonStrengths, the Kolbe A Index, and the Integrative Enneagram (iEQ9). I’ve taken all three, and I’ll admit the CliftonStrengths report was a little spooky in how well it described me. I promised on the show that we’d link to them, and you’ll find all three in the resources section at the end of this article. One honest note from my psychologist brain: the Enneagram is hugely popular in coaching, and the iEQ9 is the version I find most useful, but the research base is still developing (Hook et al., 2021). Use any assessment as a mirror for reflection, not a verdict.
Here’s the part I want you to hold onto. When you hit the part of the process you’re not naturally wired for, Courtney says it’s simply going to take more of your energy. Not that you can’t do it. That it costs more. In her words, she just has to “prepare that it’s gonna take more of my energy.” Without that awareness, we tell ourselves, “See, this is the part where I’m terrible,” and it’s a short trip from there to comparison, discouragement, and a painful story about your worth. Discovering your strengths is the antidote.
This is one of my favorite parts of the work we do in coaching. When someone understands how they’re wired, the shame drains out of the room, and we can build a plan that plays to their strengths instead of fighting them.
How Do I Plan My Life, One Area at a Time?
Plan your life one domain at a time. Instead of asking yourself the impossibly huge question “Where do I want to be in three years?”, break your life into areas such as relationships, finances, physical health, emotional health, and career, and set a vision for each one.
Courtney made a point I love: in some areas, your vision might be to keep things exactly as they are. Maybe your marriage feels great and your health is solid. Then your vision there is to protect and maintain it. That counts. In another area, you might look honestly and say, what I have right now isn’t working, and I want it to be different.
In our coaching work we often use a tool called the Wheel of Life. You can find a version with a quick search. Add any domains that matter to you personally (a creative hobby, a cause you care about, your spiritual life), then rate each one from 1 to 10. It’s one of the simplest ways to see what to work on in coaching or on your own.
Notice that Courtney starts with what you want before looking at where you are. That’s deliberate. If you start with your current reality, it’s easy to get bummed out and shrink your sense of what’s possible before you’ve even begun.
Here are a few examples of personal goals written as three-year visions, just to get you thinking:
- Relationships: We have a weekly check-in that actually feels good, and we laugh more than we bicker.
- Finances: I have six months of expenses saved and I stop dreading my bank app.
- Physical health: I have the energy to hike every Saturday without needing Sunday to recover.
- Emotional health: I notice when I’m spiraling and I have people I can call.
- Career: I’ve left my job and I’m running a small practice I’m proud of.
And if you sit with the wheel and realize you honestly don’t know what you want in one or more areas, that isn’t a failure. It’s information. It’s also one of the most common places people start with our coaches, and there’s a whole conversation on how to figure out what you want in life if you want a head start.
Take the free What’s Holding You Back? Quiz and you’ll get a personalized set of next steps.
Take the What’s Holding You Back? QuizHow to Plan Your Life: Separate the Vision From the Strategy
The single most useful life planning skill is separating your vision (where you’re going) from your strategy (how you’ll get there). Your vision should stay fairly steady. Your strategy can, and often should, change.
Courtney explains it with Apple Maps. You type in your destination and your starting point, and it offers you a few routes: the fastest, the shortest, the fewest turns. You could also fly, drive, or take the train. Every option gets you there, and every one has trade-offs in time, money, and energy. With a health goal, for instance, I could hire a personal trainer for $300 a week and probably get there faster, or take a slower, more affordable route. Both are legitimate. You get to choose.
And you get to change your mind. Courtney asked how many of us have booked a flight, had it cancelled, and ended up renting a car and driving. We’ve all been there. Life does that to our plans, too. You didn’t change the destination. You changed the route.
| Vision | Strategy | |
|---|---|---|
| What it is | Where you want to go | How you’ll get there |
| How often it changes | Rarely. You recalibrate occasionally. | Often, as life, money, and energy shift |
| Example | Leave my job and run my own business within three years | Get certified on nights and weekends, or save a year of expenses and go all in |
| When you feel stuck | Ask if you still want it | Brainstorm at least three other routes |
This is also where comparison gets sneaky. We see someone who got where we want to go and assume their route must be the route. But they started from a different place, with different resources, different capacity, and different wiring. A strengths-based approach to your goals means choosing the route that fits you, not the one that fit them.
Should I Give Up on My Goal or Change My Strategy?
Most of the time, change your strategy first. When a goal stalls, the route is far more likely to be the problem than the destination, and walking away from the vision is usually a much bigger loss than trying a new path.
This is where I had a real light-bulb moment during our conversation. One of my favorite books of all time is The Dip by Seth Godin. Its premise is that you need to learn the difference between a dip, which is a rough patch that gets better if you keep going, and a cul-de-sac, which is a dead end no matter how hard you run. What hit me was how often people are in a cul-de-sac with a strategy, not with the idea, and they abandon the whole dream. (Tacy wrote a lovely piece on staying persistent with your goals if this one’s landing for you.)
Courtney put it perfectly:
“We give up on our vision instead of shifting our strategy.”
Executing the strategy was never the goal. Getting to the vision is the goal, and there are lots of ways to get there.
There’s good science behind being thoughtful about what you let go of. Research on goal disengagement and reengagement suggests that people who can release truly unattainable goals and redirect that energy toward new ones tend to report better well-being (Wrosch et al., 2003). The skill isn’t never quitting. It’s knowing what to quit. Usually, it’s the route.
A few questions to ask when you feel stuck:
- Is the destination still something I genuinely want?
- Have I brainstormed at least three other routes, even ones that sound a little wild?
- Is this route a poor fit for how I’m wired, or for my capacity right now?
- Am I copying someone else’s route because it worked for them?
Here’s the thing about cul-de-sacs: they’re really hard to see from inside the car. You’ve been circling so long that the circle starts to feel like the whole world. That’s one of the most valuable things a coach on our team does. We sit in the passenger seat, look at the map with you, and help you tell the difference between a dip worth pushing through and a route worth leaving.
How to Create a Life Plan You’ll Actually Follow
To create a life plan you’ll actually follow, reverse-engineer it. Start with a three-year vision, decide what you’ll realistically accomplish in the next 12 months, then decide what that means for your calendar this week. Here’s the full sequence Courtney and I walked through:
- Know your wiring. Visionary, doer, or somewhere in between? Which part will drain you?
- Set a vision for each area of life. Three to five years out. Some visions are about keeping what works.
- Look honestly at where you’re starting. Time, money, energy, and support.
- Brainstorm strategies. At least three routes, each with its trade-offs.
- Choose a route and a 12-month milestone. One year closer, not all the way there.
- Build it into your days, weeks, and quarters. This is where plans live or die.
- Get support for the part that drains you. More on this in a moment.
Courtney’s example made it concrete. Say your three-year vision is to quit your job and start your own business. Your first-year milestone might be earning a certification. And if that certification takes 300 hours of coursework (I did the math on air and needed a calculator), the real question becomes: when, exactly, are those hours happening? Tuesday and Thursday evenings? Sunday mornings? Sometimes building the one habit that moves the others is what makes the whole plan possible.
Research strongly supports getting this specific. In a large meta-analysis, people who formed implementation intentions (concrete if-then plans such as “If it’s Tuesday at 7pm, then I open the coursework”) were meaningfully more likely to reach their goals than people who simply intended to (Gollwitzer & Sheeran, 2006).
This translation step is where most plans quietly fall apart, and it’s also where the right support makes the biggest difference. Our coaches help people turn a vision into a calendar they can actually live with, and they adjust it with you when life happens. It’s a big part of what we mean by coaching for personal growth.
Why Reading This Article Probably Isn’t Enough
I want to be honest with you about something. Everything Courtney and I talked about is real, and it works. But I’d be doing you a disservice if I let you close this tab thinking that reading it was the work.
Courtney told a story about a private client she’s worked with for about four years. They knew exactly where they wanted to go and how they wanted to get there. Where they kept falling into the gap was project planning. In their sessions, they’d say, let’s not worry about that now, we’ll do it later on our own. And every quarter, when they looked at why progress had stalled, the answer was the same. So they changed the structure: now they do the project planning together, in the session, with dedicated time and support. That’s when things started moving. It’s a perfect picture of what life coaching does.
Here’s what I love about that story. The client could do project planning. They just didn’t like it, so it kept not happening. Courtney calls this the thing you’re leaving to your own discipline, and it’s the personal-trainer principle. Most of us know how to do a squat. We do a lot more of them when someone is standing there with us. The research on coaching backs this up: a meta-analysis found that coaching has meaningful positive effects on people’s goal-directed self-regulation, performance, and well-being (Theeboom, Beersma, & van Vianen, 2014).
Even Courtney learned this the hard way. As a new CEO, she presented a financially brilliant plan to split her firm to her partners, and they were so hurt that they didn’t even vote on it. She’d skipped the relational work entirely. She thought about quitting. Instead, with the help of her own executive coach, she spent two years rebuilding trust, and the very same strategy passed with a unanimous vote. That’s what achieving your most ambitious goals often looks like in real life.
So if you’ve been waiting until you’re more disciplined, I’d gently suggest that discipline was never the missing piece. Needing support doesn’t say anything bad about your character. As Courtney put it, “That means you have a big vision, if it requires more than just you.”
That’s what coaching with our team actually is. Not lectures and not generic advice, but a real, ongoing relationship with a licensed therapist trained in coaching psychology who’s paying attention to your wiring, your patterns, and your life. You don’t need to be in crisis, and you don’t need to have failed at this five times first. If something in this article landed somewhere specific, that’s your signal. Schedule a free consultation and let’s see if we’re a good fit. We offer coaching at several price points, including sessions with coaches in our practicum program, so there’s a way in that fits your life right now.
We’re not trying to change you. We want to help you be more of who you already are.
xoxo,
Dr. Lisa Marie Bobby
P.S. Not sure which part of the plan is tripping you up? Take my free What’s Holding You Back? Quiz and you’ll get a personalized set of next steps.
P.P.S. To hear the whole conversation with Courtney, including the hillbilly fire pit story and the firm-split story, press play on the episode at the top of this page, or jump straight to any chapter in the clips above.
About this episode’s guest and host
Courtney De Ronde
Courtney De Ronde is the CEO and co-founder of Forge Financial & Management Consulting, a CPA with more than 20 years in practice, and the creator of the Simple ScaleUp System. She spends most of her time leading Scaling Leader, a group business coaching and leadership development program for service-based business owners who came up as experts (therapists, accountants, architects, attorneys, physicians) and suddenly found themselves running a business.
Her book, Planning to Scale, lays out the annual planning process she uses with leadership teams, and every chapter ends with a free, downloadable tool for building your vision, strategy, and project plans at planningtoscalebook.com/tools. You can also find her on LinkedIn, learn more about her firm on her Forge author page, and explore Scaling Leader.
What I appreciate most about Courtney is how generously she shares her own mistakes. If her framework resonated with you and you’d like help applying it to your own life, that’s exactly the kind of work my team at Growing Self does every day.
Dr. Lisa Marie Bobby
Licensed psychologist, licensed marriage and family therapist, and board-certified coach. Founder of Growing Self Counseling & Coaching. Author of Exaholics. Host of the Love, Happiness & Success podcast.
On this episode she brings her own version of the story, including the Saturday that was going to include both the basement and the water park, and presses Courtney on the part most planning advice skips: what happens in the week after you make the plan.
Questions people ask about life planning
Life planning is the process of deciding what you want your life to look like in the future and connecting that vision to what you actually do day to day. Good life planning works on three horizons: a long-term vision, an annual milestone, and weekly implementation.
A life plan is a written picture of where you want to be in three to five years, broken into areas of life such as relationships, health, finances, and career, plus a 12-month milestone and specific weekly actions for each.
Start by understanding how you’re wired, then set a vision for each area of your life, look honestly at where you’re starting from, brainstorm several strategies, choose one, and build it into your weekly routine. Get support for whichever step drains you most.
Reverse-engineer it. Take your three-year vision, decide what you’ll realistically accomplish in the next 12 months, then schedule the specific hours and habits that milestone requires. Specific if-then plans make follow-through much more likely.
Examples include having a weekly check-in with your partner that feels good, saving six months of expenses, having the energy to hike every weekend, building a support network you can call, or leaving your job to run your own business within three years.
Your vision is where you want to go. Your strategy is how you’ll get there. Visions stay fairly steady, while strategies can and should change as your time, money, energy, and circumstances change.
In most cases, change your strategy first. When progress stalls, the route is usually the problem rather than the destination. Brainstorm at least three alternative routes before deciding the goal itself is wrong.
Common reasons include trying to achieve a long-term vision on a short timeline, skipping one of the three planning horizons, working against your natural wiring, copying someone else’s route, and leaving the hardest part to willpower alone.
A useful life plan usually looks three to five years ahead for the vision, 12 months ahead for milestones, and days, weeks, and quarters ahead for implementation.
The Wheel of Life is a coaching tool that divides your life into domains such as relationships, health, finances, career, and spirituality. You rate your satisfaction in each from 1 to 10 to see where you most want change.
CliftonStrengths, the Kolbe A Index, and the Integrative Enneagram (iEQ9) are three that Courtney De Ronde uses with clients. They help you see which parts of the planning process come naturally and which will take more energy.
Yes. A life coach helps you clarify what you want, spot the planning horizon you tend to skip, choose a realistic strategy, and stay accountable when life gets in the way. At Growing Self, our coaches are licensed therapists trained in coaching psychology.
Questions people bring us before they start
Sources cited in this episode
- Buehler, R., Griffin, D., & Ross, M. (1994). Exploring the “planning fallacy”: Why people underestimate their task completion times. Journal of Personality and Social Psychology, 67(3), 366–381. https://doi.org/10.1037/0022-3514.67.3.366
- De Ronde, C. (n.d.). Planning to scale: An annual process to narrow your focus and clear your company’s path for growth. https://www.amazon.com/Planning-Annual-Process-Narrow-Companys/dp/B0H223C49S
- Godin, S. (2007). The dip: A little book that teaches you when to quit (and when to stick). Portfolio.
- Gollwitzer, P. M., & Sheeran, P. (2006). Implementation intentions and goal achievement: A meta-analysis of effects and processes. Advances in Experimental Social Psychology, 38, 69–119. https://doi.org/10.1016/S0065-2601(06)38002-1
- Hook, J. N., Hall, T. W., Davis, D. E., Van Tongeren, D. R., & Conner, M. (2021). The Enneagram: A systematic review of the literature and directions for future research. Journal of Clinical Psychology, 77(4), 865–883. https://doi.org/10.1002/jclp.23097
- Theeboom, T., Beersma, B., & van Vianen, A. E. M. (2014). Does coaching work? A meta-analysis on the effects of coaching on individual level outcomes in an organizational context. The Journal of Positive Psychology, 9(1), 1–18. https://doi.org/10.1080/17439760.2013.837499
- Wrosch, C., Scheier, M. F., Miller, G. E., Schulz, R., & Carver, C. S. (2003). Adaptive self-regulation of unattainable goals: Goal disengagement, goal reengagement, and subjective well-being. Personality and Social Psychology Bulletin, 29(12), 1494–1508. https://doi.org/10.1177/0146167203256921
Resources mentioned in the episode:
- CliftonStrengths (Gallup): the strengths assessment Courtney’s team uses with every client.
- Kolbe A Index (Kolbe Corp): an assessment of instinctive working style.
- Integrative Enneagram Questionnaire, iEQ9 (Integrative Enneagram Solutions): the Enneagram assessment Courtney recommends.
- The Dip by Seth Godin: the book Dr. Lisa recommends on air for telling a dip from a cul-de-sac.
- The Wheel of Life: a common coaching tool for rating satisfaction across life domains, described in the article above.
- Planning to Scale by Courtney De Ronde: planningtoscalebook.com, with the free chapter tools at planningtoscalebook.com/tools.



