#169: Reflect on Your Year as an Entrepreneur


Here we are nearly at the end of the year, and it feels like the race is on, the pressure is being applied because if you haven’t figured out what you are doing for the next 365 days, it feels like you’re behind before the year even starts. Do you feel any truth to that? Does that feel like what you’ve been waking up feeling like,

I don’t know about you, but everywhere I turn these days, people are saying, let’s get your planning done. Let’s be ready to go, have the entire year mapped out before we ever get to January 1st. And it feels like a push. It feels heavy as we wrap up the year and enter into an even busier holiday season. Today we’re going to actually slow down.

If you’ve been listening to me for a while, probably not a surprise that I’m going to suggest you slow down and we are going to do a little bit of reflection on what this past year has been like because with that reflection, we can then better plan for the upcoming year.

The Push and Pull

We are at this part of the year where I feel like there’s still time.

There’s so much energy around the year that can happen. I feel like there is a push to wrap everything up, and it just feels like you’re being pushed, pulled, shoved, or tripped in some direction, no matter who you listen to, who you talk to, or where you look. And it creates a lot of stress and overwhelm and frustration and a lot of times a feeling of unrest in our business.

But I’m here to tell you that you do not have to give in to that feeling. You do not have to give in to being pushed, pulled, shoved, or tripped into feeling or doing things at the end of the year in your business that you don’t want to do or that aren’t right for your business. And this comes in a lot of ways.

I hear, and I get emails every single day right now saying that it’s time to get 2024 planned, mapped out and locked in. And all I’m thinking is I still have 17 coffee chats before the end of the year, and I need to see how those flow before I make decisions for this time next year right now. You know what I mean?

It feels a little bit premature to be saying, let’s plan all of 2024 right now so that by the time we hit January 1st, we’re on the ground running. Now, I do agree that we want to start January with a nice running start. We want to be prepared because when we’re prepared, we tend to be more creative. We tend to be able to get more things done, be more effective and efficient, and get into the flow with our business. Whether that is creating a new course, up-leveling a course you already have, maybe it is adding on a backend membership to your course or doing something else entirely, maybe adding a new revenue stream to your business. And none of that can happen if you don’t slow down and reflect.


Today I’d really like to spend some time with you encouraging you to slow down and reflect on the year. And if that feels really big, why don’t you start with the month? Think about how you have felt in the past 30 days in the past quarter. If you want to go a little bit further, maybe in the last six months, even in the last year, how have you felt in your business? How have you felt personally? How have you felt with the two combined? Because business is not just business, it’s this part of who you are. And so the personal and the business do overlap. Even if we can shut our office door magically and not walk into it in our downtime, it does still have an impact.

I would like you to first reflect on how you’ve felt in the past 30 days, personally, professionally, and both. I would encourage you as you do this, to check in with your feelings. Don’t just think about, oh, these are the things I accomplished. No, I want you to use real feelings, words, and if feelings, words do not come easily to you, know that you’re not alone. That many of us have a few feeling words that we use all the time. I’m happy, I’m sad, I’m frustrated, overwhelmed, stressed, anxious, joyful. Yep. That’s pretty much about it, right? We use these words over and over. 

If you find yourself in that boat, or maybe you have a lot of feelings, words, but you’re struggling to find the right one for today, go to Google or your favorite search engine and put in feelings, inventory or emotions, words, and you are going to get lengthy lists, usually a hundred words or more that you can look at and say, ah, that’s what it is.

I’ve been feeling. I didn’t really know how to put it into words before now, but this is it. Okay? Take some time to reflect on how you have felt in the past 30 days. Start there and you can certainly, if you’re feeling up to it right now, go ahead and reflect back further as to the quarter, the half year, even the full year. You can look at that big picture if that is something that you’re ready to do. 

Once you have kind of gotten in touch a little bit with the feelings that you’ve been experiencing, I want you to become really concrete. I want you to list out three wins that you experienced this year. They can be big, medium, small, teeny, teeny, tiny, gargantuan, I don’t care. Three wins that you’ve experienced. Ideally, do this on a personal level and on a professional level. And again, we do this because our businesses often are part of us, but I want you to start separating these things out because sometimes we can forget that we are more than just our business, especially in those early years when you’re grinding, you’re trying to build a course, you’re trying to launch, you’re trying to refine or maybe launch something as an evergreen offer inside your business. 

Our mindset can really get in the way here. I want you to become really concrete. I want three wins that you’ve experienced this year. If that’s too hard to think of, you can do the month. Again, with all of these exercises, you can do it by the month, the quarter, the half year, and the year three wins. You’ve experienced personally and professionally, anywhere from teeny, teeny, tiny to massive wins. Because remember, someone’s small win might be someone else’s massive win. We’re not going to judge these here, and we’re not thinking about size. I just want you to be aware that everything counts, all wins count. 

Now I want you to flip the script just a little bit and note three challenges that you experienced. Again, teeny, teeny, tiny, up to monstrous challenges. Three personal challenges, three professional challenges. All right, so far you have kind of how you felt personally and professionally. You have three wins that you’ve experienced personally and professionally. Three challenges that you’ve experienced personally and professionally. And now I want you to think about where you felt like you got held back. What kinds of stumbling blocks did you experience?

Again, these can be little tiny pebbles. They can be massive boulders that got in the way personally and professionally from achieving what you wanted to achieve, whatever that is. I know this is kind of vague right now, but I want you to have the latitude, the freedom to really explore where you’ve been, do some good reflection because when you start to identify some of those wins, some of those challenges, some of those stumbling blocks, it’s easier to see that business and life is an ever evolving entity. It’s going to change from month to month. It’s gonna change from quarter to quarter and year to year. You might notice some wins that carry over some challenges that are stubborn companions, and that’s okay. The key here is to become aware of where you stand in your business and personally as well. We want to raise self-awareness so that you can continue to grow and progress in your business and personally. All right, so we’ve thought about some wins. We’ve thought about some challenges, some stumbling blocks. 

I want you to now think about your year in review, and I want you to write down one specific moment that you would love to shout to everyone and celebrate the one that you feel like, you know what? Everyone should be giving me a cake and some balloons for this. Maybe some beautiful flowers. Maybe it’s a day off. Maybe it is a new book to read or a fancy new planner. I want you to identify one specific moment that you’d like to celebrate. Too often we get stuck in these moments of, this isn’t working, I don’t like this, I’m frustrated. I’m too busy. We miss the good stuff. We forget to celebrate the good stuff. Use this moment right now to celebrate something. And as you do that, I want you to dig in a little bit deeper to that thing you want to celebrate. And I want you to think about what strengths you used to make that a reality.

What strengths did you use to make that a reality? And if you have trouble, like 99.9% of the population, in putting words to the strengths that you’ve used, go to Google and put in “strengths list”, and I bet you will find some really good options there. I like, there is one list on positivepsychology.com that has, and I’ll link this in the show notes for you. It has a great list of strengths that you can then start to go through and say, ah, that’s what helped me be successful. That’s what helped me experience that moment that I want to celebrate. That’s what I need to look at more of. Okay? Write down some of those strengths that you’ve relied on in the past year to have these celebratory moments, to have these successes that you’re identifying. And I promise you, this is going somewhere. 

Next, I want you to think about who has been a source of support or what has been a source of support for you in your business? Who or what has helped you to stay on track to be productive? What skills or tools or resources have you relied on?

What are these pieces of support that have helped you get to where you’re at right now? If you’re noticing, you’re probably feeling kind of good about yourself right now, at least that’s my hope. We’ve talked about successes, we’ve talked about things you want to celebrate. We’ve talked about the support that you have engaged in order to make the progress that you desired.

Yes, we’ve talked a little bit about stumbling blocks, we’ve talked a little bit about challenges, and we’re gonna use those now in a minute, but I want you to really focus for a moment on the positives, all of those things that you have accomplished already, because that is going to help us inform where to go next in your business as you move forward with planning for the next year, which is what we’re gonna talk about in next week’s episode. This time, we’re just working on a reflection of this past year and next week as we wrap up the year, I’ll share with you some planning for the coming year. All right? I want you to think back now to the challenges and the stumbling blocks that you identified earlier. Are they still with you? Are they still causing you trouble? Are they still that, that stubborn stain that just won’t come out? If they are, then I want you to think about the biggest thing that you’d like help with for those to be resolved. And if those things have kind of moved off to the side, then now I want you to think about something that you just need help with in general in your business.

And this takes a little bit of time. Sometimes we say, oh, but I could do all of this myself. I could do that myself. No problem. Okay? Just because you can doesn’t mean you have to. What is the biggest thing that if you took it off your plate today would make a difference in your business? Is it scheduling social media? Is it putting all of your beautifully recorded modules for your course into a platform that allows your students to see those beautiful modules? Is it someone who could help make workbooks based on those modules? Is it getting some help with your messaging so that you know what to say in the social posts and the emails and all of the things that you’re creating? The webinar slides, the masterclass invitations, and sometimes when it’s hard to think about, well, what do I really need help with? You can think about what isn’t working well right now. What is giving you trouble? What is keeping you up at night or making you dread getting out of bed in the morning in your business? Chances are that might be something you could use some help with.

I want you to really brainstorm that here. And as part of that exercise, start thinking about how you’ve been using your time. This part of the reflection might be easier to focus on the last 30 days because we tend to remember the most recent stuff first. But if you have notes from the year, you can certainly go back and look at them. I want you to know how you’ve been using your time. And then I want you to think about was it a good use of your time? Yes or no? And if it was a good use, do you want to keep it delegate or stop doing it if it was not a good use of your time? Do you want to keep, delegate, or stop doing it?

This might be ideas like, I created slides for all of my modules. Was that a good use of your time? You can think about, well, did you get nitty gritty in the design details and Canva? And it took 18 times longer than it should have? And you know you still have five sets of slides to create. Maybe it was a good use of your time because now you know that about yourself, but it’s possibly something that you could delegate to someone else who has an understanding of what it is you want to have on those slides. Maybe you put in the bullet points for the slide and they design them so that you retain all of that creative content in there, but they design the actual visual appeal of your slides. These are the kinds of things to think about.

Think about what you’ve been doing with your time and if it’s a good use of your time or not, and then do you want to keep it delegated or stop it? And I will tell you, most people have a lot of resistance to delegating, myself included. In fact, I have been doing this podcast for three years now, and I have maintained all of the production for it. And I will be honest, I’ve always said, oh, but I like it. I like it. It’s easy, it’s simple. And I recently hired some fantastic people to help me out with my podcast, to help do the post-production, to help me create social media clips and do all of the things that we have to do as podcasters.

And I cannot tell you how much lighter it feels. Even when you say, oh, it doesn’t take me that long, is it the best use of your time? Is it the best use of your zone of genius? I’ll be honest, audio editing, although I can do it and it’s fine, it is not my zone of genius. I want you to really think about, is this a good use of my time? Is it my zone of genius? If the answer is no, it’s not a great use of my time, and no, it’s not my zone of genius, delegation probably moves up.

And I do understand the scariness that comes with that, because we’ve all heard horror stories of delegating something and they drop the ball or something important gets deleted, or they just don’t represent you how you want to be represented in the world. And yes, those moments are going to happen, but what can you gain from a potentially amazing experience? Is it worth a little bit of risk?

You can pay attention, pay close attention, and you can say, this is not working. Is it worth the little bit of risk for the excellent rewards you’re going to reap as a result of delegating? Again, things to start reflecting on. I know that a lot of times we get stuck in this mode of planning for the next three months. We’ve got to plan for the next six months, next 12 months, and so we just scoot forward and hope for the best. 

But this year, I don’t want you to just hope for the best. I want you to take what you have learned, be a scientist, look at the data from this year, from the past month, from the past quarter, six months, 12 months, and notice what worked, what didn’t work, what you accomplished so that you can do more of it. 

In fact, I was in a mastermind today and the person in charge of the mastermind says, do more of what’s working. Don’t spend tons and tons of time trying to figure out why something didn’t work. When you have something that is working, do more of it and move forward. Yes, as a scientist, I want to know why that thing I did didn’t work, but if I have other avenues that are working beautifully, lean into those. 

My point here is that a lot of times we get into this swirl at the end of the year that we’re in right now, and the mantra becomes, plan your next year before January 1st. And while we are certainly going to talk about that, it’s important to take a step back first and review your year because otherwise you don’t know what to keep, what to pitch, and how to move forward. It’s all about looking at the data as a course creator. You know this as an entrepreneur, you know this. You’ve got to look at the data to make decisions. And the same goes with our plan for the upcoming year. Look at the data that we already have in place.

Action Item

Your action item for this week is to do some reflection. Go back to this podcast, start it again. If you have been playing it in real time, start it again in a quiet place with something to write on, take notes on, and reflect. 

Hit pause as many times as you need to and reflect because that’s the data we’re going to use to inform our plan for the next year. It is critical to slow down, look back, examine what has worked, acknowledge what hasn’t, so that we can make a meaningful plan to take meaningful action to move us toward our vision in 2024.


As we wrap up, remember to do your action item, do your reflection. As we prepare for next week, you’ll find that when we come back, we’re going to take this reflection and move into planning for 2024. But my guess is you’ll find that my approach to planning is just a little bit different than everyone else’s, and that has come from years and years of planning and having planning flops.

I’m going to share with you some of the secrets that I’ve learned to make that annual planning more successful, more doable, and more carry outable over the course of the year.

I’ll see you back here next week for another episode of the Entrepreneur Mindset Podcast, where we focus on mentoring, community and implementation. It’s all about taking action so that we can remove the overwhelm of building a successful and profitable business and add in a little dose of momentum.

Until next time, have a healthy, safe, and happy week.

Show Resources

Feelings Words: https://www.nycnvc.org/feelings

Strengths List: https://positivepsychology.com/what-are-your-strengths/#list

Apply to Work with Dr. Moira: https://www.digitalcoursecreatorguide.com/apply/

Check out all podcast episodes at: https://www.digitalcoursecreatorguide.com/digital-course-creator-podcast/ 

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