Planning mistakes podcast

There are huge planning mistakes that may be costing you your future.

Planning is the roadmap that gets you from where you are now to where you want to go.

If you don’t plan right, you’re in trouble. You won’t end up where you want.

I’ve narrowed down the most common and costly planning mistakes, and I’m sharing them all in this episode.

Listen to this episode to see if you’re making any of these planning mistakes and what to do about it.

Here are the best resources to go along with this episode:

Full Planning Mistakes Episode Transcript

Welcome to the Design Your Dream Life podcast where it’s all about designing your life on your terms and now your host, Natalie Bacon.

Hello my beautiful friend. I want to start off and say, happy anniversary. We have made it a year together. This is so much fun. We are a year in and it flew by and I think I have grown more in the last year and it’s been my best year ever and I am so glad and happy and appreciative that we’ve been doing this together and that you have been with me this whole time. It has been so fun for me. I remember a year and a half ago when I had planned to start a podcast and it took me six months to actually do it based on where I was in my business. And it just was something that I remember thinking was going to be so challenging and something I didn’t know how to do and very difficult and all these things, right? And now a year later, it’s just a system and a part of my business and I am obsessed with it.

So whatever it is that you’re thinking is going to be really difficult, it probably will be at first, but then it’ll be totally worth it. I, uh, was just posting an Instagram story. If you follow me @NatalieRBacon, you saw this where I said that I just took a strength training class and it was so difficult. So I’m hyper mobile, which means that like my arms hyperextend I’m very flexible. I’m really good with the dance classes. I love hip hop, I love yoga, but where I need the most work is to build muscles.

So I am starting to do that at this new club that I belong to and it’s very challenging for me. Very, very challenging. But I am doing it anyway and I just wanted it to give a nod to you and say that whatever it is that you think is going to be very challenging probably will be, but it’s like a year from now I’m going to be so much stronger. It’s going to be great. I’m going to be so happy that a year before, which would be right now that I actually started doing this. So it’s super fun.

That has nothing to do with anything we’re talking about today. Today we are talking about planning mistakes and I am coaching and teaching in Grow You right now all about time management and productivity. So Grow You is going so well. That was another thing that I started that took months to do and build the framework and the groundwork and it is totally worth it. We are rocking it out. Like if you are in Grow You, love you. I’m so glad you’re in there. It’s been so fun, but I did not anticipate that it was going to be so much um, coaching around planning and it makes sense when I think about the deeper reason for why we plan.

It really does make sense why there’s so much drama around it. So we’re going to talk about that today. But what I specifically want to talk about with you are the three categories of planning mistakes I see and then all of the specific things that I see people doing wrong in each of those categories. And my hope is that you can identify where there’s gaps in your planning system. So that you can change the way you plan and get the results that you want. And I’m talking about planning using your calendar here. I’m talking about planning your time, right? It’s kind of like the time management and productivity all under the umbrella of just planning your life, living a life of intention.

And the first category of mistakes that I want to talk about is the technical part of planning. So this is like the actions that you take to actually plan. And there are several mistakes that I see a lot in this category. And the first one is not scheduling time to do the planning. So I plan Sundays, I like Sunday evenings and I often spend one to two hours every Sunday evening looking over my calendar, making sure that it’s up to date, making sure I have all my projects on my calendar, blocked out in timeframes. I really spend a lot of time doing this and the time that I’m spending planning is on my calendar.

Now, this is not an enjoyable experience. It’s very tedious, but I do it anyway because it sets me up for success. So if you don’t have some sort of block on your calendar to plan things out, you need to put that time, create that space because it’s like sharpening the saw before cutting down the tree, right? It’s that prep work.

You need to actually sit down, look at everything, follow the planning process. If you are new to planning, listen to my um, planning practices, Best Planning Practices podcast episode that will help you do the actual tactics of planning.

The next mistake that I see is not using a digital calendar. I get it. You want to write things down? Great. You can have that as well. But a digital calendar is something you can sync on your phone and you can pull up at any time and make adjustments to and it will make your life easier and whatever is simpler and easier is whatever your brain will do. I use G calendar. It’s just the Google calendar. It’s totally free. I highly, highly recommend it. I always have it up in the background. I’m constantly looking at it, making sure everything’s blocked off appropriately. My planning, the act of planning is so integrated into my day to day life that it is not only a habit, but it’s like the parent of my life.

Like I just do what’s on my calendar and I know that I’ve thought about it ahead of time and that I trust myself. I’m going to follow through and then that goes to the mistake that I see a lot of people doing, which is the next mistake, which is not keeping the calendar in front of you.

So if you’re doing the actual planning and you’re using a digital calendar, but then you’re not looking at it, it’s not useful. Right? Like I can’t even remember what I have on my calendar for tonight or tomorrow or the next day. I have no idea. I have to have it up and be always looking at what’s coming next. Now this doesn’t mean that I’m go, go, go, go, go. Quite the opposite, right? If you’re doing the planning right, you have that downtime in there. You have that work time and that downtime and that workout time.

Like I had on my calendar today that I was going to the grit strength class. Right? I had um, you know, other things on my calendar like doing this podcast and I have it in front of me so that I don’t have to remember it. I have it synced to my laptop, my desktop and my phone. So make sure you keep it in front of you. The next planning mistake that I see is to not give yourself hard deadlines. So if you are planning and you’re sort of like doing planning the activity and this goes to productivity, if you’re planning the activity instead of the um, the result, you’re not going to give yourself a deadline. And then it’s like being in school and working on the paper without a deadline. And we know we would never finish the paper and turn it in. But for that deadline you have to give yourself deadlines for things and then get super focused during the time where you’re supposed to complete it.

So I know I’m supposed to sit down for an hour and do this podcast. I have my notifications off, I have only my program that I record on in and my mic and then my notes and that’s it. And I’m fully focused and I know that I have one hour to get all of this done. So be really, really strict with respect to your own deadlines. It’s like you got that paper done in school, right?

You have to start giving yourself deadlines and then if you keep missing it, right? Like let’s say I was taking an hour and a half every single week, well then I need to evaluate and start planning an hour and a half, but only do that, making sure that I’m going 100% all in during that hour and a half and it’s not an hour of productivity and a half hour of clicking around and notifications, and that’s what I see most commonly. Okay?

The next mistake is to not plan for obstacles ahead of time. You know that if you have children, they’re an obstacle to you sitting down and recording a podcast. So think of your obstacles ahead of time and think of a way to solve them. We call this in Grow You turning obstacles into strategies. So think of the obstacles, all the obstacles that you can think of ahead of time and turn them into a strategy, right? If you want to have date night with your husband and you have kids, an obstacle would be what are you going to do with the kids? Right? You need to get a babysitter and you can do that ahead of time, right? If you know that you’re always interrupted at a certain time of day or you don’t feel good or productive at a certain time of day, that’s an obstacle. How can you turn that into a strategy, right? So think be forward thinking about your obstacles.

Most people are like, welp, well I have kids, so that’s a problem. Just can’t solve it. Can’t do the podcast. No, that’s not how it works. I promise you. Tons of people have podcasts with children. You have to plan for these things.

The next mistake, Oh my gosh, y’all, I see this so much. It’s saying yes to everyone else before you say yes to yourself. Now you hear this and you’re like, yeah, I get it. I need to say yes to me and do my goals and write them down and put them on my calendar. But then what happens is someone invites you to something or you get an email and you’re focusing on your email and you’re doing all these things and all of that is is other people’s goals and plans. You need to be really focused on your goals and your plans and scheduling out time to look at your emails.

There are so many emails I don’t even open. Okay. I know so many people who will open the emails and then indulge in the email and then write this reply and it’s about an opportunity for their business that they have no interest in. I’m like, why even open the email? Like you don’t have to open your emails. Did you know that? It’s super fun, right?

It’s a particularly people who make it super obvious in the subject line that it’s some sort of promotion or you know, someone wants to do a sponsorship or my favorite is when people who I don’t know at all, like they, I think sometimes that they are going to ask me to be on their podcasts but they’re asking to get someone else on my podcast and I’ve never even met them or talked to them and obviously they don’t listen to this because I don’t have guests or sponsors on the podcast, right?

So you guys get this completely free of ads and without interruption, but it’s super fun for me. I just see that in the subject line. Just delete, right? So easy. So just really think about how often you are saying yes to everyone else and that includes how you’re using your time.

The next mistake is not scheduling downtime, family time, rest time a lot of people in Grow You. Oh by the way, if you want to find out more about Grow You, you can go to I changed that URL. So now there’s like a nice pretty landing page it’s super fun, and you’ll see it there. But what I’m finding is that I’m teaching and coaching on how to be more productive and you know, people are getting how to do the calendaring and plan their results, but they’re not scheduling downtime or family time or rest time and you have to do that.

K now, how much is up to you. What season is this for you? Is this your version of medical school where it’s year one of your business? Is this your version of law school, right? Or are you at a stage where you are able to have that balance, that full balance where you’re not working any nights and weekends like I am right now. Right. My goal is to get down to working only three days a week, but right now I work five days a week. Fridays will certainly be the first day to go once I get there, but I have so much downtime and family time and rest time scheduled. Okay. Time with friends. I’m very active in my life. I go to the gym a lot, almost probably every day, maybe six days a week for sure. So make sure that you schedule that because what happens if you’re just back to back to back and you don’t have the downtime in there, you’re not going to have time to rest your mind.

You are not going to have time to recuperate. You’re not going to have time to think, right if you are on like a bicycle, I love this analogy I got from Brooke Castillo and you’re on a bicycle and you’re going so fast trying to get somewhere, you don’t realize that you could just stop and take a minute and hop in a car and get there a lot faster.

So the analogy there is that when you are doing something and overacting without taking a break and kind of looking at working on it, is this the best strategy for whatever result I’d want to get? And then you were keep doing the same action without getting different results. So make sure you have that downtime in that thinking time. Listen to the episode on Thinking Time. It will be really, really useful for you here.

The next mistake, I don’t know why, but it’s a personal pet peeve of mine, is it’s not evaluating what’s not working. So someone will come and they’ll get coaching from me and they’ll say, I’ve been doing this and this amount of time forever and I keep getting this result that I don’t want to get. And like they think that I for sure have the answer and right. Every good coach knows that I help your client get the answer themselves.

So you have to ask yourself, why isn’t it working? Do you need more time? Do you need fewer distractions? Do you need to increase your focus? You have to evaluate what’s not working. I would see this so much when I was a blogger. There would be, um, you know, O G bloggers, like the original gangsters, like all of the OGs, and they would be doing this same thing for years, like seven to 10 years, getting the same result, thinking that by putting in more time, you will get different results.

You have to take action. Yes. But then you have to evaluate if you’re not losing the weight. If your revenue isn’t going up, if you are not improving your relationships, then something isn’t working and you need to create space and evaluate that. So in your calendar and in your planning, if you are constantly going over time, you need to make the judgment call, do I need to give myself more time? Right? And if you do that, then you know, do that for a month and evaluate that. And then if that doesn’t solve the problem, if you’re still running out of time, then you know it’s not the amount of time it’s actually you and your thoughts.

The last kind of mistake that I see in this category is beating yourself up. I have this thing where I’m all obsessed with growing and I know that you are too, or else you wouldn’t be listening to this, right? I think that really to lead and live a fulfilling life, you need to grow. Because if you’re staying the same, you will not only get bored, but you will really be unfulfilled, right? That growth in yourself is what leads to an amazing life.

But part of that means doing new and different things and getting outside your comfort zone. And that means failing. Okay? And that includes planning. And what I see happening, this mistake is to beat yourself up over it. So it’s like you schedule an hour to do your workout and it keeps taking you an hour and a half. And during your workout you’re not getting the results that you want. And instead of just looking at that as math as a way for you to take in new information and make changes. What I see most of my clients doing is that they’re beating themselves up. So I want you to notice this and I just want you to know that it’s totally not useful at all.

It’s just not useful, okay? It doesn’t get you a better result. So you can skip the beating yourself up and you can just evaluate without judgment and just seek to understand yourself with curiosity and then make changes from there. Okay.

The next category is my favorite. So that was all the planning category, which is like the action of the planning. The next category is the forgotten category and that is not following through. So when you do the plan and you have your G calendar and you have it in front of you and you’ve taken the time to plan ahead of time and give yourself specific, you know, results that you’re going to produce, you know you’re doing all of the actions. Then what I see happening, the first mistake is in the follow through category is not following through, okay? And this has to do with a lot of things, but I want you to know that it’s a really big problem and it is separate from your planning.

So if you’ve done the actual planning, right, that’s the action of planning. That is one part of it. Now the next part is you actually doing it and following through. If you’re not following through, you need to take a look at that and it just means you need to take a look at your mind. And what I first want to encourage you to do is to notice when you’re not following through. Notice if it’s all of the things on your calendar, notice at which times of day for what categories. Just become the watcher and become really aware of it without judgment. K, because from that awareness you can kind of seek to understand what’s going on and that really brings me to the second mistake in this category, which is misunderstanding why planning is important. Planning is important because it allows you to intentionally live your life.

It reduces the need for willpower and it reduces decision fatigue. So when you decide something 24 hours in advance at least or more, you’re clear minded. You’re using your prefrontal cortex, you know you are future-focused and there’s no drama about it, right? If you ask me what I want to eat next Friday, I can tell you exactly, you know, the salads that I want to eat, how I want to hydrate, if I want to have a snack, whatever. There’s really, there’s no like feelings involved. It’s very much from my prefrontal cortex.

Now that is the benefits of planning ahead of time. There’s no willpower needed. It’s easy. Okay. In the moment your primitive brain will always want to do what’s most pleasurable and what is least painful. Your primitive brain, your survival brain, the brain that we as the humans have evolved to get to this place, right?

In an efforts to keep the humans alive, right? The brain is always wanting to seek pleasure and avoid pain. But in modern society we are at a point where pleasure is not the blueberry on the tree, it’s blueberry pie and Netflix K and the pain isn’t fear of being attacked or a bear or tiger coming at you. If you leave the cave, the pain is totally different. It’s emotional pain, it’s going the gym and you know, kind of having that negative self talk. It’s the pain of feeling afraid if you quit your job. So the reason that this is a problem with following through is that people think that because they created a plan in the moment, they should want to do it. And that’s just a lie. Your primitive brain is not going to want to do what you plan to do. And if you know this, you can plan for this.

You can actually expect resistance. So I know that when my alarm goes off in the morning to workout, if I don’t want to go to that workout class, I’m not going to feel like it. But I need to like really nurture that relationship with myself and trust myself and follow through with what I’ve already planned. Now if you are not following through and you’re setting really big ambitious goals, you can set the ambitious goal, but you need to start really small with the habit.

So like let’s take the example of working out. If you are not working out when your alarm goes off in the morning, what I want you to do is set your alarm and get up and just put your workout clothes on and get in the car and go to the gym for five minutes. You have to make it really, really small at first and then increase over time with that habit.

Read the book atomic habits that will really help understand this. And what’s happening with the brain. But if you understand really like your prefrontal cortex and how future focused it is and how it will always decide the right thing ahead of time, you can use that to your advantage with planning and expect for it to not feel good in the moment. It not feeling good doesn’t mean you shouldn’t do it. Okay, this is really, really important. I don’t know, like I am all about all the woo woo stuff. I actually really am. I’m spiritual. I feel like, you know, I’m into law of attraction and energy and all that. I don’t really teach it, but I personally believe it. However, you will have to understand that it’s not just about doing what feels good. If you want to get new results, you have to be in your truth about that.

And that means when it feels uncomfortable, you do it anyway because you promised yourself that you would do it. So part of this is the next mistake I see a lot with the follow through, and that is believing your own excuses. So people will kind of get into this like victim mentality where they’re like telling themselves excuses and they’re believing them as if it’s a reason not to do it. So they’ll be like, well, my life is hard, or I just got so busy, or these other things are a priority. You know that if you’re doing this, if you’re blaming it on something outside of you, right?

If you are not taking responsibility for not following through, that is where you need to start because you’re the one, and this is great news, right? You’re the one who will make the change, who will change your life, who will achieve your impossible goals, but you can’t do that if you think that someone else is responsible for why you’re not following through with what you say you’re going to do.

So I really want you to notice if you’re blaming something external, it could be a friend, it could be your spouse that you’re blaming. It could be your kids, it could be your parents, it could be the government, right? Like I would, you know, we’d had wealthy clients and their kids come in once in a while and we’d help them with student loans. And it was like always like with student loans, for whatever reason, people love to blame someone else. It’s not that it’s not true, it’s just not useful.

So even if you believe that for sure the government should not be encouraging people to take out student loans in this way, right? Let’s just say like, you believe that and you don’t want to change that belief, that’s fine. But blaming the government for your student loans is not useful because you have student loans and you have to accept that and take responsibility for it being a great opportunity.

Once I did that, I really relied on myself and my own beliefs in self confidence and I was able to turn it into my career, the love of my life, right? My passion, my purpose for being here. It’s my obsession and I don’t overwork and it’s now created me the opportunity to help so many people, including you. It’s super fun.

But if I would have listened to everyone else and believed that this was a problem and that it was someone else’s fault, I never would have taken the risks and followed through with my business having the student loan debt that I had. Okay.

The last mistake I see in the follow through category, and I kind of touched on this already, but I want to say it separately, is that you think it’s going to feel good when it’s time to do the thing. So right now, if you’re planning for next week, you’re like, Oh, I definitely want to go to this networking event because I want to get my name out there and I’m a new coach and I want people to know me.

I’m going to do it. I’m gonna put it on my calendar. And you feel really great about it now. I promise you, when next Tuesday comes at five o’clock when you’re supposed to go to this event, your brain will tell you every reason why you don’t need to go and why you shouldn’t go and why you’re tired and why. Thinking time would just be better right now. No. When you make a commitment on your calendar, it is more important that you follow through with what you say you’re going to do than it is whatever result you’re going to get from doing the thing.

It doesn’t matter if nothing happens from that networking event, what matters is that you made a promise to yourself and that you followed through. I cannot stress this enough because here’s what’s going to happen. If you do this work and you plan and you make decisions ahead of time and you follow through, you will increase your self love and you will love yourself so much and you will increase your competence that when things are happening in the world and it’s chaotic and you’re going through something, you can rely on you and you’re stronger for it.

Calendaring is such a problem and it’s so much drama because it requires you to look in the mirror and look at the relationship you have with yourself and when I realized that it made so much more sense why it’s such a problem with everyone who I coach and help, right? Because it’s like getting on a meal plan. It’s not really hard to figure out what to eat and how to exercise. Right. Just figure that out. Write it down. That’s it. The hard part is the follow through. It’s showing up when you don’t feel like it. It’s looking in the mirror and saying, this doesn’t feel good and it’s really hard, but I’m gonna do it anyway and I’m going to do it from love. Right? I’m going to do it because I love myself, not because I hate myself. When you do it from love and you honor yourself, you are unstoppable because where you start from is where you end up from.

So it will compound that love for yourself. The commitment for yourself will compound and that’s what you will attract in your life. It is life changing, I promise you. Okay.

The last category that I want to leave you with is the beliefs category. So we talked about the specific mistakes that I see with planning and you know, the action of planning and then the specific mistakes I see with not following through and now there are mistakes that I see with respect to your beliefs around planning that are really, really important. And the first one is that people who don’t plan at all think that planning is really limited and rigid. Okay? There’ll be like, Oh, I would never want to be that like rigid. I want more flexibility, I want to be spontaneous. I’m like, okay, well let’s look at your life. How’s that going?

Right. Often they are repeating the past. Okay, why is that? Because planning is actually where you get freedom. I don’t want you to plan for the rest of your life and never have downtime. Quite the opposite. I want you to think big and plan for the downtime and plan and set big goals, right? So you have the money freedom and the time freedom to live the life that you want.

Planning is my parent, it’s my boss. It’s what moves me forward in the direction of my intentions. Instead of me relying on how I feel on the moment, which is using that willpower and it not working because of my primitive brain. It’s so important that you understanding that planning is going to give you the freedom that you want the most.

Another mistake that I see people thinking is that they think that they’re always going to be behind. So maybe you haven’t been a master at planning right now and so you just feel like very overwhelmed by the thought of like, I’m just not good at planning or I’m just not good at time management and how you feel is what you’re going to create more of and it’s caused by your thinking. So what I want you to do is just think of this as an opportunity to start fresh, to plan for the first time doing it right and doing it really, really small baby steps. You’re like, you know what? I haven’t been showing up for myself and I have these big business goals. So what I’m going to do is every night for 15 minutes, I’m going to sit down in front of my laptop and work on my business from 7:00 PM to 7:15 Monday through Friday. That’s it. Just 15 minutes.

That is more important than you sitting down on a Saturday and cranking out 12 hours of work. Why? Because you’re getting in the habit of training yourself to show up for yourself because if you say you’re going to do something and then you do it, you’re like, Oh, all right, I see you. I’m going to do that again. And then you show up again and then you show up again and then you show up when you don’t feel like it and it doesn’t always feel good, but you do it because you love yourself. Okay?

So if you think that you’re always going to be behind, that’s just a thought and it’s totally optional and you can let go of it right now and you can just think of this as the opportunity to start fresh.

The last kind of belief that I see people really cling to that is a struggle and an obstacle for them is that they believe that they don’t have enough time for what they want. So there’s this constant, you know, sense of time scarcity. Make sure you’ve listened to that podcast, but it’s all about I don’t have enough time, I’m busy, there’s not enough time and I just want to offer it to you that you have enough time and that time is your most precious resource and that we all have the same amount of time and that there is absolutely no rush to get to the goal that you want.

Now, don’t confuse that with thinking that you can just randomly and haphazardly work on it. What I mean is that you don’t need to make $1 million from your business that you haven’t started by the end of this year. Kay. Don’t add that type of pressure. What I mean is let’s put $1 million business as the five year goal. Okay? Or as the seven year goal and this year you want to break even, and next year you want to make six figures or $50K starting there with a very reasonable goal that leads to your impossible goal will allow you to plan and give yourself time. And then you show up for that one hour every day and then you build that muscle. Okay?

Imagine where you would be a year from now if you believed that you had enough time. It’s amazing to think about. So these are the biggest planning mistakes that I see. It’s been super fun to coach everyone on planning and time management and productivity. So a little shout out to everyone in Grow You. I love you and appreciate you and for everyone else. I will talk with you next week. Have an amazing weekend. Bye bye.

Thank you for listening to the Design Your Dream Life podcast. Subscribe to the podcast to get the latest episodes sent directly to you. To learn more about designing your dream life visit