Hannah's Healthy Habits

07. No One Plans to Fail, You Might be Failing to Plan

Hannah Dill

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0:00 | 25:07

“If you fail to plan, you’re planning to fail.” — Benjamin Franklin

In this episode of Hannah’s Healthy Habits, we’re talking about why failure usually isn’t a lack of discipline — it’s a lack of planning.

Planning doesn’t mean controlling every detail of your life or doing things perfectly. It means deciding with intention instead of reacting on emotion, exhaustion, or convenience. When we don’t plan, we live in survival mode — constantly busy, overwhelmed, and wondering why we still feel behind.

I share personal experiences from building my business, navigating burnout, decision fatigue, perfectionism, and learning how small, intentional planning habits have changed the way I move through my days — from meals and workouts to rest, routines, and long-term goals.

We talk about:

  • Why planning feels so hard (and why that’s normal)
  • The hidden cost of living reactively
  • Planning vs. perfectionism
  • How to plan around your energy, not against it
  • Simple, realistic ways to start planning without overwhelm
  • Reflection questions to help you reset and realign

This episode is a reminder that planning isn’t about becoming more rigid — it’s about creating space for clarity, peace, and momentum.

You don’t need to plan perfectly.
You don’t need to plan far ahead.
You just need to decide — on purpose.

Thank you for being here, for listening, and for choosing to show up for yourself 🤍

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If you fail to plan, you're planning to fail. Benjamin Franklin. You don't need a perfect moment to start living a healthier, happier life. Welcome to Hannah's Healthy Habits, a podcast about learning, growing, and building a healthier life from the inside out. And now we're doing it together. Hello everyone. Welcome back to the podcast. I am so grateful for each and every one of you listening this week. Thank you for all of the kind words from last week and. All of your continued support. I am so, so grateful, so thankful, and honestly, so blessed to be able to sit here and to talk for 30 minutes or so and get into the things of life that might seem obvious, but aren't always easy. If you fail to plan, you're planning to fail. Benjamin Franklin. Failure usually isn't a lack of discipline. It's typically a lack of planning. Planning doesn't have to mean that you have to be in control of everything. it's almost like that safety net, so you can make decisions from a balanced, centered place instead of acting on emotion, sometimes hearing the phrase fail to plan, plan to fail can sound a little bit harsh. Like if you don't have everything all figured out perfectly, you're already behind. But that's not what this quote is actually saying. It's all about intention, not perfection. The fail to plan doesn't mean that you're lazy or unmotivated it means you're reacting instead of deciding, letting your emotions, your circumstances, your energy, choosing something on default, whatever's easiest, familiar, or feels good in the moment where the failure really comes in isn't because you're not capable, but because there was no structure to support you with your goals. Planning and simple is the act of deciding ahead of time. Who do you want to be? What matters most right now? And what are you willing to say yes and no to? A plan doesn't control you, but protects you from burnout, from distraction, and constantly starting over. If you don't choose your direction in advanced life will choose it for you. And most of us don't fail because we aim too high. We fail because we never gave ourself a clear path to move forward. If planning ahead is so helpful, why do so many of us avoid it? Most people don't skip planning because they don't care. They skip it because. Brings stuff to the surface that we'd rather just not look at. One big reason is fear of commitment, because once something's written down and real, it can be failed at. So instead of risking disappointment, we stay vague and resist planning ahead of time. Planning can be very overwhelming. It can feel like standing at the bottom of a mountain, staring up and thinking, where do I even start? So you don't. You wait for motivation and clarity or the right time. But the thing is with life is we have so many things coming at us in different directions that we need that structure. We need that clear path on what's going to make us feel better in the moment. And. The choices that we choose ahead of time, that really determine the way that our day's going to go. Some of us have an unhealthy relationship with perfectionism. We think if we can't do it perfectly, then why do it at all. So we don't plan unless we know that we can plan everything and do it all perfectly. And that usually means getting nothing planned. Some people avoid planning because they identify as going with the flow, and flexibility is great, but there's a difference between being flexible and lacking direction. When you lack direction, The days continue to pass by and before you know it, you're halfway through the first month of the year and are wondering where all the time went. Why haven't your goals started? Why do you feel this way? This is all normal, but there's a way out of it. A big reason people refuse to plan is because sometimes your past plans, they didn't work. You tried, you planned, and you fell off. So now planning feels like you're setting yourself up for failure again. But the truth is, avoiding planning doesn't protect you from failing. It guarantees insistency. It's not giving you the future that you're looking for, the direction the support. Planning isn't about boxing yourself in, but giving you that freedom and the clarity day to day, knowing that you have a plan, that you're taking the steps towards your goals that you are moving with momentum instead of a hope and a prayer, which is great, but you need to take action. You need a plan, and not because you're incapable of doing it without it, but it's so much easier when you have something figured out instead of reacting on impulse. The cost of not planning doesn't always show up right away. It's that constant feeling of being behind the decision, fatigue on things that should be easy. And burnout that doesn't make sense because you were busy all week. So let's talk about what really happens when you don't plan, and why it's so important that we start and why the cost is more important than you would realize. It shows up as days that feel full, but inevitably are unproductive weeks that end up blurring together. And a constant sense of being behind. Even when you're trying your hardest. When you don't plan, you live in a reactive state. You respond with what's loud and urgent and demanding the emails, the texts, the other people that need things around you rather than what's actually important. And over time, that creates a life that feels misaligned. Whenever I first opened Rainforest, my business partner and I would joke about how we were living in autopilot and fight or flight, and it's sad, but it's true. We were doing so much and a lot of the things happened to be responding to emails. Just the day to day little things that needed checked off, but a lot of the stuff that we weren't dealing with were the things that we're dealing with now, the internal problems and the exhaustion. That doesn't come from taking a day off or resting or getting a massage, but going to therapy or exercising, fueling your body with really good foods, doing things that pay off in the long run that seem small in the moment. I am really bad with decision fatigue. Every day becomes a series of small, exhausting choices. What should I work on? What should I eat? What should I wear? What should I work out today? When will I rest without a plan? You're making these decisions in the moment, often when your energy's low and you're tired, and we don't choose what's best. We choose what's easiest. This is one area that I have really been trying to master in the last year, especially meals, breakfast being the most important one. To have planned out ahead of time because if I don't, I'll either skip breakfast, I will eat a couple small things, and I won't be fueled properly for the rest of my day. Breakfast is one of those things that I can eat the same thing over and over, but if you can't, you can always prep something ahead of time or making that decision at the beginning of the week so you don't have to think about it in the morning. Another thing I like to do is set my clothes out the night before. It makes it way easier to get up in the morning, get ready, because I don't have to make any choices about what I'm wearing, setting your clothes out the night before gives you one less thing to make a decision on in the morning. If you're struggling with going to the gym or working out, maybe setting your clothes for a workout out the night before, getting yourself in the mindset. So when you see those clothes, you can put them on and go do your workout. You don't have to think about, Hmm, what do I wanna wear today? Think smarter, not harder. Another thing I like to do is I try to plan my workouts ahead of time, so I go to a gym that has heated workout classes, so I'll look at the beginning of the week for any classes that work with my schedule or something that I'm interested in. Write those down, figure out when I'm going to the gym and when I'm doing my workouts at home, it makes it a lot easier. I can plan my morning according to that, I wake up and I know what workout I'm doing that day. One area of my life that I could definitely benefit from planning is on trips. I always think ahead of time that I'm going to plan it all out and have an itinerary and do all of the things, and then it gets down to it. I run out of time. The trip is here and we get there. And my biggest struggle, especially when I'm hungry, is to pick out a place to eat. Because everything sounds good. I will eat anything. I love all foods. I am definitely a foodie, but for whatever reason, especially when I'm hungry, I have the hardest time choosing a restaurant. So that's something that I really wanna work on. And not even just eating, but things to do. The last couple trips I went on, my friend, she is really good with the itineraries and the planning, and I felt like those were the trips that I've gotten the most out of. We did so many different things and squeezed so much into such a little amount of time, so that is an area that I really, really want to improve on this year. Not planning can lead to inconsistency. You might have good days, even great days, but without having that rhythm, progress feels up and down. It's not a constant grow, and of course every day is different. You're going to have ups and downs in life, but having those small wins, it builds confidence within yourself. It helps making those goals a little bit easier and more achievable, and you start to really trust yourself and believe that you can do those things. I've started working out daily doing. Even small workouts, but making sure that I'm not missing more than two days in a row and staying consistent with my routine, with my habits, checking each thing off every day. And again, if I miss one day, that's okay, but being really adamant about not missing more than one day at a time, Being busy without direction is exhausting. When your effort feels like it's unclear and not connected to your purpose, it starts to feel pointless, and eventually your motivation will fail. It will run out, and it's not because you're lazy, but you're exhausted, you're depleted. You're running circles where you don't know the finish line. I've done this for years, and this is something that I really feel called to talk about and to share, is finding direction in actionable steps. I always used to make my goal so big and so broad, and then I would feel lost. I would be doing certain things every day, checking the boxes, replying to emails, getting things done, but in reality, I was. Staying busy, I wasn't being productive. And there's a really big difference between those two things. And the biggest cost of all is missed potential. Because you never gave your goals, the structure they needed to grow. It's so crazy how much your life can change when you really stay focused, have a clear path. On the goals that you're wanting to accomplish, the steps you wanna take to get there. It's not rocket science and it's not hard. It doesn't even take that much determination and dedication. It's routine. You build a routine and become confident in that routine and do something that makes you feel good and you are rewarded. Each day you check that box or get closer to your goal. Don't make it something that feels like it's wasting your time or your energy, but something that long term really is going to pay off. So if not planning costs, time and energy and peace, what does planning actually look like in real life? The kind that works when life is busy and unpredictable. For a long time, I thought planning meant I had to become a completely different person. I had to be more disciplined and more structured and more put together. And as much as I love filling out planners weeks in advanced and having perfectly timed routines, it was an unrealistic level of consistency that didn't feel like me. So I avoided it all together. What I've learned is this, planning isn't about turning yourself into someone else. It's about supporting the person you already are. The biggest shift for me was realizing that planning doesn't start with a schedule. It starts with deciding what is most important to you. As much as I love to schedule things out, I can have an unhealthy balance with perfectionism. So. Getting honest and clear about my energy and my capacity for the week and what I can really handle in this season of life. planning for me right now looks like scheduling workouts and deciding on my meals ahead of time. Meal prepping, getting my outfit picked out the night before. It's the little things to where when I wake up, I don't have to make all of these decisions. Instead of filling every hour, I focus on non-negotiables, like exercise, movement, healthy eating, and genuine rest, whether that's a massage, stretching, sitting on the couch reading a good book with a nice warm cup of coffee or tea. When I don't plan rest, I'm very good about not taking it. I almost feel a sense of guilt for resting, even though it's something our body needs and that's something I'm still working on. So when you wake up. Don't worry about asking, what should I do first? Am I doing enough? Should I be doing something else? Those decisions were already made in advance On the days that things don't go as planned, don't spiral. Adjust your plan. Just because you have a plan in place doesn't mean that it's black and white and that if you don't do it, you failed. Adjust and pivot, keep going. Planning isn't to make life perfect. It just makes it a little bit more intentional and a lot easier to. There's different layers of planning. First, there's macro planning, the big picture stuff. What season of life am I in? What am I prioritizing this month? What actually deserves my energy? This macro planning gives direction and without it even the most productive days can still feel empty. And then there's micro planning, the day-to-day decisions. Micro planning can be setting three non-negotiables for the week, choosing a specific workout, or setting a time when you move your body. Choosing times when you rest and times to disconnect and to stop working. You don't need a perfect schedule. You just need a few minutes a week to plan ahead of time. Instead of asking, when can I fit this in? Maybe ask for when is the best time for me to do this thing? High focus tasks need high energy, or low energy moments are perfect for simple, repetitive tasks. Plan with your energy rather than against it. A plan isn't meant to control your entire life. It's meant to remove unnecessary decisions because when something's already decided, you don't have to negotiate with yourself in the moment. If it's not scheduled, it's optional. And when everything is optional, that's when consistency starts to disappear. Planning gives you a framework, so even on the hard days, you still know what's important and what matters. Planning versus perfection. For a long time, I treated plans almost like a contract. If I didn't follow them perfectly, I felt like I'd failed. And once that feeling set in, I usually quit altogether. And maybe you've done that too. You miss a workout. You fall behind on a task, one day doesn't go as planned, and suddenly the mindset becomes, what's the point? Or you don't even think about it because the thought of knowing that you failed is too much. That's perfectionism. Talking, not planning a plan isn't a promise to perform perfectly. It's just a starting point. Life is so unpredictable. You can have days where you don't have as much energy or things come up and a good plan isn't one that never changes, but one that you can pivot from without breaking it completely. Some weeks success looks like doing everything you'd planned. Other weeks success looks like doing one thing and choosing not to spiral about the rest, A plan gives you something to return to when things start to go off track, because without a plan, there's nothing to recalibrate. It's easy to feel guilty and to be confused, and to start spiraling. Honestly, I used to be so bad about this, and I can't even say that I'm not anymore. I still tend to spiral at times, but I've learned to ask myself different questions like, what still matters today? What can I realistically do? How can I support myself instead of punishing myself? Some days I get to the end of the day, I haven't journaled, I haven't read, I didn't even work out, sometimes I have to choose one, But remembering that tomorrow is a new day, and to maybe prioritize those things first instead of beating yourself up in the moment. It's showing up again and again. Even if it's imperfect. The goal of planning isn't controlled. It's about being consistent and being compassionate with yourself. How to start without overwhelming yourself if planning feels intimidating or stressful. You don't need a completely new system. You don't need a fresh notebook, and you don't need to overhaul your entire life. Step one, choose one area to focus on. You just need to start with small, clear goals. What helped me most was letting go of the idea that I had to plan everything and choosing to plan one or two things really well. Instead of planning your whole life, pick one area of focus. What feels the most chaotic right now, and what would benefit from a little bit of structure? Step two, define success. This week, this part changed so much for me. Instead of asking, what should I do ask, what would success actually look like this week? Not next week, not next month. Not in an ideal perfect world. But this week, success might be two workouts instead of five, making your breakfast ahead of time, or planning out all of your meals for the week, when success is realistic, it starts to become more achievable. Step three, decide ahead of time. Once you know what matters, decide it then and there before the week even starts. Write it down. Put it on the calendar. Treat it like an appointment that you have with your future self because when you don't decide ahead of time, you'll decide in the moment. And that moment usually chooses comfort over growth. We are lazy creatures and I feel like over the years we have become more and more inclined to easy and in the moment choices. So set those things ahead of time and enjoy the benefits. Step four, review without judgment at the end of the week. Don't ask, did I do it all? Ask what worked and what felt hard? What do I need to adjust for next week? Planning isn't about proving anything. It's about learning yourself and learning what works best for you. Every week gives you more data, some weeks will feel easy, some weeks will feel messy, but both count and starting small builds trust within yourself, and once that trust is there, planning stops feeling restrictive and starts feeling really supportive. Now that we've talked about how to start, I want to slow things down for a moment, because planning isn't just about action, it's also about taking the time to reflect. When you look inward, it gives you a clear idea of a way to pivot and to keep going, to reset that motivation and to realign your goals. Sometimes throughout the process, we realize what we're heading toward isn't even what we really want. So before you rush into the next week, I want to invite you to slow down for just a minute. Planning isn't about doing more, it's about becoming more aware. Awareness comes from reflection. You can write these down if you'd like, or you can answer them in your head, but give yourself the time and let these sit with you. Ask yourself, where my life am I choosing chaos over clarity? What area of my life would feel easier if it was a little more structured? What decision am I making over and over again that I could decide once ahead of time? What's something that drained me this week? What's something that gave me energy? Where did I feel most aligned and where did I feel most scattered? And what is one small thing I can decide ahead of time today that would support my future? Self planning doesn't have to start with a full reset sometimes. It starts with a single intentional choice. As we wrap up today, I want to leave you with one final thought because planning isn't about becoming more rigid. It's about creating space for what matters most. If there's one thing you take away from this episode, I hope that it's this. Planning isn't about controlling your life, it's about choosing it. When you don't plan, life decides for you based on urgency, emotion. Whatever's the loudest, easiest choice in the moment. But when you begin to plan even a few small things, You create space for intention, clarity, and peace. You don't need to plan perfectly, and you don't need to plan far ahead. You just need to decide and have purpose. So my invitation to you is choose three priorities, Write them down, put them somewhere you'll see. And then when the week feels messy or unpredictable, come back to those three things and give yourself the direction that you deserve. If you made it to the end of this episode, I just wanna say thank you so much. I appreciate each and every one of you If you feel like this episode was helpful, please send this to a friend or a family member that you feel like could benefit from it as well. Someone who might feel overwhelmed or stuck or constantly restarting, life is messy and imperfect, but the least we can do for ourselves is give a little bit of a plan and make life easier. As always, thank you so much for being here. I have linked a Google form with a q and a, so if you have any questions, feel free to leave those there. Thank you for listening, and thank you for choosing to show up for yourself I hope you have a great start to your week. Bye.