How to Conduct an Annual Review

Hey everyone, how's it going? My name is Matt Ragland and welcome to episode 2 of the Connect the Dots Podcast. I'm really excited to share this episode with you because it's one of my favorite topics as we transition from the end of one year into the beginning of a new year. And one of the things that I love to do at the end of of a year is to write my annual review. So we're going to go over annual reviews in this episode today and talk about why you should consider and then actually do an annual review. We'll also talk about some different ways that you can go about conducting an annual review, and it doesn't all have to be writing. I think that writing is probably the most effective medium for doing this, but you can also do it with video, which is of course near and dear to my heart. You can also do it just kind of talking to yourself through like a voice memo. You could record a podcast episode for yourself. And there are a lot of reasons to do this. Let's talk about first, why would you want to do an annual review? Well, for me, it is a way, pun intended, to connect the dots over the past year. So we're getting to the end of 2020, and this has been, we've said it ad nauseam, but this has been one of the most unique years in not just recent memory, but over the past, you know, 100 years, I would say. You had so many things happen in 2020 that are normally like generational things all by themselves. We had, of course, the COVID-19 pandemic, pandemic. Having a worldwide pandemic is not something that happens very often. We haven't had one at this scale since 1918, the Spanish flu. We've had civil unrest, talking through systemic racism and Black Lives Matter and all of these racial unrest and working through a lot of these things that are incredibly important. We haven't talked about race and acted on race at this scale as a country since the civil rights movements of the '60s and the '70s. And so that's the second thing. And the third thing is that we've had a global recession. We haven't had a recession like this. Now, this is a little bit more of the most recent one, but 2008 on with the housing crisis led to a significant recession, and now we're in another recession right now. So these are three things that normally happen to one— it's like a one-time thing that one generation kind of goes through. And we've had all of these things happen within one year. And so 2020, very unique year. And it's important— this is one of the things that I believe is so important about journaling. And the first thing that you can think about when it comes to setting up an annual review is that when you go to do your annual review, one of the most effective ways to do it is to look back through your journals. Now, that doesn't necessarily have to mean that you've been writing a daily journal. It can be just as effective to look back through your Bullet Journal. It can also be effective to look back through your calendar, to look back through just a simple to-do list app that you might have been going through. Anywhere over the past year that you have been writing down or listing tasks, to-dos, events. The first thing that I want you to do when it comes to creating your annual review is to take some time reviewing any of the events, anything that you've written down or listed in the past year. Probably the most effective way to do this is if you've been keeping a journal. Now, if you are not used to journaling, if that's not a practice for you yet, just as a heads up, I do have a course called Building a Journaling Habit that is incredibly impactful for creating that journal habit, hence the name of the course. And it will help you. I guarantee that within a span of a few weeks, if you go through this course, you'll have an effective journaling habit. And what is really important about this and what's really helpful about it is when you have a journaling habit, and this applies for any habit, we're going to talk about habits a lot more in the next couple of weeks, but for any habit that you establish and you have confidence in yourself in, then whenever you kind of take a break from that habit, you still keep that confidence. And I think that's really important. Again, we'll talk about this more as we talk about habits going into the new year.. But one of the things that is really valuable for me when it comes to journaling is even if I've taken a little bit of time off from journaling— this is air quotes for people listening and not watching the podcast— but for me, whenever I take a couple of weeks off from journaling, or even a month, I don't feel bad or doubtful about my ability to get back into the journaling habit because It's something that I've done consistently for so long that I have a confidence within myself to be able to come back to that journaling habit and know that I can get right back into it. So that's the first thing when it comes to conducting an annual review for yourself. If you have a journal, a diary, a logbook, certainly a Bullet Journal, then go back through your entries from the past year and start to put together your own highlight reel. Okay, think about the lessons that you learned, the exciting moments, the sad moments, the highlights that you've had. All of those exist in your journal, in your Bullet Journal. Again, it's one of the most valuable things of keeping a journal or doing Bullet Journaling as a habit for yourself is that you can go back and without having to rely on this top-of-mind, okay, what was, what were the good things that happened this year? Okay, I can think of a few things. You don't just have to rely on that when it comes to conducting your annual review. So now that we've talked about the best way to find relevant information events for your annual review, I'm going to give you 4 sets of questions that you can use to make sure that you're getting the most out of your annual review. Even if you haven't been keeping a journal throughout this year, that's totally okay. There have been lots of years where I have been a very average to non-existent journaler myself, but still have taken the time to do an annual review. It's still very valuable. And so let me give you what those sets of questions are. The first way to do it, or the first set of questions to ask yourself, is what were my goals this past year? And we'll talk about goal setting, we'll talk about like establishing your goals in a future episode of Connect the Dots, a very, very soon future episode of Connect the Dots. But asking yourself, what were my goals when it came to this year? And even if you weren't intentional about your goal setting at the beginning of 2020, and even if your goals, like many were totally, like, totally thrown apart by the events of this year. That's okay. All right, it's okay if you didn't hit all of your goals this year because it's a very different year. We're going to talk more about what do you do when a goal is just not even viable anymore because of the circumstances of work or life or just the world in general. But that's a good first question to ask yourself, a good first set of questions. What were my goals this year? And how did I measure up to those? Now, it's really helpful if your goals have some kind of measurable quality to them. That's something that is really useful because then you really can measure and you can know, okay, I wanted to do this number of videos this year. And just as an example for what I'm talking about, it's okay also if your goals— and again, we'll talk more about goal setting very soon, but It's okay if your goals are more about something that you directly control when it comes to measurement. And so a goal for me that I always have is to create 50 YouTube videos in a year. So that is different than saying I want to have 50,000 new YouTube subscribers in a year. That's something that I don't control as much of the achievement of, but looking at it and saying basically I want to do a weekly YouTube video, so that would be 50 YouTube videos videos in a year, 52 of course, then that is something that I can control outside of how many people join the channel as a subscriber. Does that make sense? And so that is a good example of a goal that I knew I fell short of this year. I didn't create 50 new YouTube videos. I'm still kind of tallying all of those up, but I just know it wasn't 50. So the first set of questions is to ask yourself What did I do about my goals this year? How did I measure up? Now the second set of questions to ask yourself when it comes to an annual review is still kind of related to your goals, to your habits, to the things that you wanted to achieve and do this year. And it's asking yourself, where did I hit my goals? Where did I miss? And where did I need to pivot? Now I really want to focus on this pivot word for how we are going to understand our goals. Because 2020 was the year of the pivot. I think it probably is one of the key words of 2020. Because I know like we went into this year thinking that a lot of things are going to be specific ways. I did a lot of videos at the end of 2019 going into 2020 that were all about how to ace 2020, how to make 2020 the best year ever. And that's very common. Like, here I am, I, I want to be motivational, and here is how you can do these things. It can be frustrating when maybe you get to April or May or June and you're like, okay, maybe this isn't going to be the best year ever for me, and maybe I'm not going to ace 2020. And you can look at that in a couple of different ways. You can just think, well, this isn't the year that I thought it was going to be. And so whatever, who cares for the rest of the year. Or you can think about how you're going to pivot the goals that you have, the things that you want to be doing, and making those adjustments can be incredibly key to not just how your year goes but how your life goes. When you can be a person that can pivot effectively, not just your work, not just your habits, not just your goals, But pivot your mindset on what you believe is valuable and what you believe is effective and worthwhile and successful. I promise you are going to have a better life if you are a person who can pivot when things don't go the way that you want them to. The third set of questions is asking yourself, what am I proud of? What am I proud of for this year? What do I regret? Kind of those two sides of the same coin. What do I have pride in terms of what I did? What was— what I was able to resist doing? What I was able to say no to doing? What do I regret? Maybe things that I did that I shouldn't have, the things that I gave my time to that I shouldn't have. I, for one, probably regret listening to as many sports podcasts as I do. You can kind of— I kind of look at that maybe a little too much and think that's just something that's just a guilty little pleasure that I have. But I listen to a lot of sports podcasts about sports that really I don't have any like true interest in. Like I could tell you a lot about the NBA bubble like machinations that you probably don't— not probably don't have any real impact on anything else in my life. But it's just kind of a busy— it's just kind of a busy noise in my ear. And that's probably something that I do regret from 2020 is how much I just wanted to keep the noise going in my head rather than kind of sitting with some of the things that made me— either made me uncomfortable or that I just didn't want to give any like real mind space and any real thought to. And so that's probably something that I regret. There are a lot of things that I'm proud of from 2020. The biggest one being is that I'm proud that I was finally able to get to a point both financially, relationally, and mentally where I was ready to say— where I was ready to put in my notice at my job at Podia and say, I'm going to be a full-time creator. I'm going to be a full-time YouTuber and coach and course creator. Those are, those are the decisions that I'm really proud of. There are a lot of other things. I'm proud of how my little family came together during the pandemic and how we all took care of each other. And so there are a lot of things to be proud of, but asking yourself a question: what am I proud of? What do I regret? And one really important piece of this question because it's a dangerous question in the sense that it can be loaded and be a thing that makes us feel bad. And I'm not here to make your annual review something that makes you feel bad, makes you feel bad about things you regret or missed opportunities. Like, missed opportunity for me, I wish I would have put so much more money into Penn National Gambling because wow, it did great. I'm not here to make you feel bad about things that you did or didn't do. And so when you ask yourself this question, what was I proud of this year and what do I regret? When you ask that question or any question that is like it, remember that you need to go into it as from the perspective of someone who is observing and reporting on you as like an objective third party. Okay, so an observer, a reporter, just like, what was Matt really proud of? What did Matt kind of regret? Okay, you don't want to go into it, and too often this is what we end up doing when we ask ourselves questions like this, is don't go into a question like this asking yourself or saying to yourself, acting as a judge and jury, someone who is here to be like, well, shame on you, you didn't do the thing that you were supposed to, you did a lot of things that you weren't supposed to, you're full of regret, and you have a head full of— you're full of regret and nothing to be proud of. That is not the case. I can assure you that's not the case. So don't get yourself in the mindset of acting like a judge when all you really need to do throughout this process is be an observational reporter, that, that objective third party that's just kind of looking at your year saying, okay, what was I proud of and what do I regret? The fourth and final set of questions that you can ask yourself when it comes to an annual review is just a really simple question of, am I trending up or am I trending down, or am I just kind of staying the course? With the things that really matter to me, these areas of my life that are most important to me. And again, ask yourself this as an observer, as an objective third party, not as a judge and jury, but asking myself, am I trending up? Am I trending down? Or am I holding steady when it comes to my family, when it comes to my relationships with friends, when it comes to my work, to my hobbies, to my personal health, to my fitness, to the way that I eat? You could even ask yourself really simply, am I trending happier or sadder or just kind of at the same state? When you ask yourself these questions, then you— and you ask yourself this question over the course of several years, you want to kind of get a gauge with yourself of, you know, even if you're asking yourself in the moment, because there's a lot of recency bias often when it comes to asking yourself these questions, but just knowing where is my life trending? Where are my relationships, my family, where are all of these, where are all these aspects of my life trending? Are they trending up? Are they trending down? Or are they just kind of holding steady? Because then you can identify, and I know for me I want to be able to identify, okay, without really trying, My personal health and fitness tends to steadily like trend up. Okay, that's great. Now maybe there's something else within my family or with my friendships that has, you know, maybe been trending down a little bit, or the very least held holding steady. Well, then I can make it kind of a theme and something that's an objective for the year to spend more time on relationships than I do on fitness, making sure that is a priority for me, maybe a little bit more than it has been in years past. So to give you those 4 sets of questions that you can ask yourself about— so just to give you a— so here are those 4 sets of questions again that you can ask to give yourself a starting point for a way to ask yourself through So here are those 4 questions to ask yourself again when it comes to how to conduct an annual review, ways to give yourself a starting point in terms of just a really simple question and answer format that you can have with yourself. And question number 1 is, what were my goals last year? What were my goals? Question number 2 is diving into that a little bit more, which is, where did I hit my goals? Where did I miss my goals? And where did I need to pivot? Okay, how did that happen? Why did it happen? What can I learn about this going forward? What were the lessons that I can learn based on the goals and objectives that I set up at the beginning of the year? Number 3: What am I proud of? Is there anything that I regret? And as a quick little addendum to this, just as a reminder, is when you ask yourself these questions, you want to ask them as a third-party observer like a reporter. You do not want to ask yourself these questions as like a judge and a jury. That it's just going to hate on yourself and say these are all the things that you didn't do well enough this year. And then number 4, you can ask yourself a really simple like trendline question. In the most important areas of my life— family, work, friendships, relationships, personal happiness, personal fitness— hobbies, side hustles, whatever it might be. Am I trending up? Am I trending down? Or am I just holding steady? Because then you can look at that and start to identify, okay, well, I've been trending up in personal health and fitness for a number of years, whereas maybe some of the relationships that I've been building have just been holding steady and maybe deteriorating a little bit. And so I need to make a priority of the new year focusing on those relationships a little bit more. And there are a couple other ways that you can— maybe things that you wouldn't normally think about when it comes to places and ways to review the year and start to surface those highlights and important memories for you. So we've already talked about how to do it with your journal or with your bullet journal. Even just a task manager or looking back through your calendar can be good ways to look back and be like, oh yeah, well, I forgot, I forgot that I did that. I forgot that this was something that I did way back in June because that feels like years ago at this point. Another way that you can do this though is just through photo albums. Take out your phone. Yes, actually, I'm telling you to take out your phone. Take out your phone and go to your photos app, whichever one that you use, and just start scrolling through. I know that, I know that the Photos app on an iPhone will actually show you some. Yeah, if you go to For You here, then it'll show you like important, it'll show you important memories. It'll just show you, you know, things. Night out in Nashville, March 22nd, 2019. So maybe not that far back, but it'll kind of, it'll flip you through different pictures that you've taken over the past year. And that can start to spark memories and highlights and events and things that you did. And so I really actually like the Photos app. You could also do it like on Instagram. I mean, if anything isn't a highlight reel the way that Instagram is, then that's a really good way to kind of start to look back. If you write blog posts, right, look back through your blog posts, What was I thinking at that time? If you record podcasts or make YouTube videos like I do, that will give you more and more information, more and more reference points for thinking about, okay, what happened this year? What were some of my goals? What were some of the memories, the highlights, the lessons learned? And the reason that we want to do this is it's tough to always rely on what is top of mind for whatever you're doing in the moment. Now this is one of the most valuable things about note-taking, about journaling, about making a point of making a reference to things in the moment, so that when you get to, say, an example like this, when you get to the end of the year and you're like, okay, you know, what happened this year? What most people do, and it's better to do this than do nothing at all, but what most people do is you take like a handful of minutes or maybe an hour and you just spend time kind of thinking about what we're the highlights? What were the lessons? What were the things that I enjoyed? What were some of the, the big moments? Now the reason that I give you all of these different touch points and all these different reference points and ideas for how you can go back through the year and find your highlights, find your lessons, find the things that get you thinking about what happened this year is because it's so much more valuable and important and meaningful to have those reference points, to have things that you actually did and said and took pictures of and wrote down in the moment, rather than relying on whatever is top of mind for your biggest takeaways for the year. Now, this is what most people do, and I'm not judging it because it's better than not doing anything, but this is where the small practice of discipline, that daily application of basics comes in so handy and so important because what most people do when it comes to writing an annual review or just kind of doing any kind of review at all is we just kind of take 30 minutes, take an hour, what can I think of in this moment that mattered to me in the past year? And it's very much like what is top of mind there, it's very like strongly bent towards recency bias of, okay, well, this thing that happened to me last week, because I can remember it now, becomes one of the most important events of 2020, like, for me personally. And so that's why if you are a person that records things, whether it is in a journal, a bullet journal, whether it is creating content online, even just, you know, very simply in taking pictures and like having some kind of reference point to them, adding a sentence of context, being someone who takes a lot of notes and takes those permanent durable notes that I've been talking a lot about on my YouTube channel recently. That is where instead of relying on what is top of mind, then you can actually sift through the information library that you've built for yourself over the past year and beyond to look at it and say, "Ah, this was so important to me, and I would have forgotten about it if I hadn't been mindful and disciplined and intentional in the moment to make sure I was capturing how important this was to me." So make sure that if this is something that you haven't done much of in the past, then I would really encourage you to make it more of a habit and a practice in the new year, and that is to be intentional and consistent about recording the information in your life, recording the experiences of your life. I'm going to talk a lot more about this in future episodes, so make sure that you are subscribed, rate, and review and all that stuff that, you know, podcasters say. But this is something that I'm making more and more of a point of in my life going forward into the next year, going into 2021 and beyond. Because when you are consistent and intentional and disciplined about writing down notes and about journaling, even just making lists in your bullet journal, you will start to realize how much more you are capable of. Because often we do things in the moment without really paying attention to to them without recording them. And so when we get to the end of the year and all of a sudden you're like, what did I really do this year? It is tough. It is very tough to actually feel fulfilled because you don't have a record of what you've been doing. Now that doesn't mean that you aren't enough and that you aren't a fulfilled, wonderful person. I believe all of that is true, but it is so much easier to look back and be like, ah, yes, Here's 2 full bullet journals. Here's a full, like, personal journal, personal diary of things that I did, emotions that I had, experiences that I had over the past year. And that fulfillment is so much easier because it's just, ah, yeah, this is what happened in 2020. It's all written down right here. It's all recorded in voice memos for myself. It's all in these hundreds of durable notes that I've taken. It's all in Roam, it's all in Notion, Day One Journal. No matter where you put all this in, if you have an intentional, disciplined practice of capturing information that you have about your life, the more that you will feel as if you have a full life, because you have actual evidence that you can look to every single day every single week, every single month, and then at the end of the year to be like, ah, that's what the year was about. Okay, here's one of the last things about writing an annual review, and one of the things that I find people have the toughest time in getting over mentally when it comes to writing a review, when it comes to doing a monthly, weekly, or even a daily review, a daily recap, a daily journal entry. Because that's really all I'm talking about when it comes to an annual review is I'm looking at instead of the day at a glance, I'm looking at saying what happened this year instead of what happened today. Now again, the easiest way to do this is to have steadily and consistently written down things like a highlight of the day, a lesson of the day, a lesson of the week, So instead of trying to think about what is top of mind, whatever's recent, you can instead look at tens or hundreds of different reference points throughout the year and actually find, you know, the things that made the biggest impact on you in the year in review. But one of the other things that is, you know, really tough for a lot of people is not wanting on a daily, weekly, monthly, or annual basis to confront some of the things that they maybe don't like about themselves very much. And especially if you get yourself stuck regularly thinking about, "What am I struggling with? What are the lessons here?" You'll come to find that there are things about yourself that you probably don't like all that much. And there is a fear, and I can totally understand this, there is a fear that if people knew this about me, then they wouldn't like me as much. If I knew this about myself, if I really confronted it, then I wouldn't like myself as much. And that is really tough to kind of get over. A related part of this is not thinking that whatever you've done this past year is worth reviewing, is worth remembering, is worth like kind of annualizing. But again, that's not true. Because think about even if you feel like you're at your lowest point and you're making a decision that you want things to change in 2021, that's the first decision you have to make, a decision that you want to change. Then you can look at it and think, I mean, think about all the stories that we hear. We love to hear started from the bottom, now I'm at the top kind of stories. If you feel like you're at your bottom right now, Just think about what a great story that it's going to be when you reach the pinnacle, when you reach the next summit of what you want to be doing. Because this becomes really powerful working material. The things that you're going through in your life, the struggles, the difficulties, the doubts, the questions that you pose to yourself on a daily basis, the existential dread that you may feel regularly, this becomes excellent working material for transformation in your life. And not only is it transformation in your own life, but when you start to share this with other people— and I'm not talking about you have to start your own podcast or YouTube channel or blog or start tweeting things about the difficulties that you're facing in your life. If you want to, more power to you. But I'm just talking about Transformation within yourself, transformation within your family, within your relationships, within your community, within your city, wherever it is, whatever you are going through, there is a great chance that there are people in this world, and not just in this world, there are people in your city, there are people in your social circles who are going through the same difficulties that are in need of the same transformation that you are seeking in your own life. Life. So instead of looking at your pain, instead of looking at your problems, instead of looking at your difficulties and challenges as something to be dismissed, something to be ignored, look at them instead as powerful working material for transformation, not just in your own life, but in the lives of others as they start to see you transformed through action, through faith, and through consistency of purpose. Preach! I felt pretty good. I felt pretty good. So as we wrap up this episode of Connect the Dots, I just want to tell you that in the next episode we're going to talk about goal setting. And so make sure you pay attention to this— to that one. It'll be a really good— so as we wrap up this episode of Connect the Dots, I want to let you know that the next episode I'm going to shoot and record is going to be all about planning for the new year and planning for the year ahead. So it offers a really good bookend to this episode. But as we go ahead and wrap up, I want to give you again those 4 sets of questions and different reference points and sources that you can use to create your own annual review of 2020. So here are the 4 questions that you want to ask yourself. Number 1, what were my goals this past year? Number 2, where did I hit, miss, or need to pivot on the goals that I set? Why did that happen? How did it happen? When did some of these changes occur? What were some of the things that I could do different? The 3rd question is asking myself, what am I proud of? Is there anything that I regret? The fourth question is asking yourself honestly, asking yourself, am I trending up? Am I trending down? Or am I just kind of holding steady in the areas of life that matter the most to me? Family, friends, work, side hustles, personal health, hobbies, whatever those core areas of life are. Asking yourself, am I trending up? Am I trending down? Or am I holding steady? Because then you can use that to think, to think towards the year ahead, be like, is there something that maybe I do really well without trying too much? And if so, maybe I can kind of put that on autopilot and prioritize something that is just kind of holding steady or even maybe deteriorating or trending down a little bit. And for any of these questions, especially questions like What am I proud of? Is there anything that I regret? What were the lessons? What were the highlights? You want to look at it as an objective kind of like third-party observer or reporter and not ask yourself these questions as like a judge and jury. Okay, that's really important. I want to reiterate that. We talked about that a lot during the episode, but I really want to reiterate that it's too often and too common when we ask ourselves reflective questions like this that we tend to be too judgmental on ourselves. And the other part of, okay, where do I find the actual material to do an annual review? Well, the best place to have done this is in the daily application of basics and like small moments of discipline and in intention every single day as you're creating a journal entry, as you are going through your bullet journal for the day. But those are the best places to do it because they're actual records, archives of what you were doing, what you were thinking in the moment, instead of trying to rely on whatever is top of mind, instead of trying to rely on recency bias a little too much. That's often how we do these annual reviews. A lot of times just kind of think and be like, well, this happened last week, and because I can remember it in more detail because it was last week, it all of a sudden becomes one of the most important events of my life in 2020. Whereas if you can consistently journal and make entries in your bullet journal even, or anywhere that you want to like record information, that becomes the place where you can look back and be like, okay, These are the things that happened in the moments that they happened, and that was really important. I just wasn't thinking about it right now. So those are the two best places to do it. A couple other unconventional places to look for memories, to look for events, to look for records is one of my favorite places is to look back through the photo album on my phone. If you go to the photos album and just on your iPhone iPhone, then you can go to the For Me section and they kind of naturally put together some highlights for you. Now they're not always from this year, so make sure you kind of check the timestamp on some of the highlights and memories that, you know, Apple Photos will generate for you. But that's a really good place. Instagram is a good place. If you create any content online, make sure you check your blog, your podcast, your YouTube channel. What were you talking about over the summer? What were you talking about over the spring? What were your videos about? Any record like that is good, and even something really simple like maybe you just keep a really, a really simple task manager app, or maybe you, you know, just, you know, list events in your calendar. Those can be really good ways to go back through and make sure that you're going to different reference points instead of just thinking about whatever's top of mind, whatever happened recently. Because what we're going to be talking about more in the next couple of weeks is that we want to take this time that we're in right now, this time of Advent, this time of kind of waiting and shifting into the new year, and think about like, how am I creating momentum going into the new year? That's something that's going to be a big topic over the next few episodes of Connect the Connect the Dots. So make sure you check those out. Please go ahead and subscribe, rate, and review wherever you listen to podcasts. If you're watching this on the Connect the Dots podcast channel, please subscribe and give this a thumbs up. Let me know your biggest lesson from this episode. I would love to hear in the comments. You can also tweet or Instagram at me @MattRagland. That's where you can best find on any social channel. I tend to be on Instagram and Twitter the most, definitely Twitter the most, maybe Twitter a little too much of the most, but that's where you can often find me. So thank you so much for listening to and watching this episode of Connect the Dots. The next episode is going to be all about annual planning, previewing instead of reviewing, planning your year going ahead in 2021. I'll see you then. Bye.