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How to End the Year Strong

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Bill Gallagher

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Episode 665

17 December 202521 min

Bill Gallagher argues that the window between Thanksgiving and mid-December is the ideal time to design your best year. Instead of waiting until January to set resolutions, he recommends starting your annual planning when you can still see the current year clearly but have enough distance to reflect. This approach lets you finish strong while building momentum for what comes next, rather than scrambling to recover from holiday chaos.

The process starts with a thorough review of the year using three tools: your calendar, your photo stream, and the hard facts from your dashboards. Bill pushes listeners to feel the wins and the disappointments fully, not just catalog them. Once you've processed the year, you create space for visioning ten years out, imagining specific details about where you live, your relationships, your health, your work, and your purpose. From that long view, you work backward to set reasonable one-year goals and identify the daily habits that will get you there.

Bill shares how preparing his workout gear the night before made the difference between missing his training and completing 45 triathlons over a decade. He closes by recommending a visual collage of your goals placed where you'll see it daily, a tool that keeps your intentions alive all year. The method combines reflection, long-term vision, and tactical habit design to break the cycle of mediocre years driven by busyness instead of direction.

Key takeaways

  1. Review your year by flipping through your calendar and photo stream in addition to checking facts and metrics, because major experiences and turning points often fade from memory.
  2. Vision ten years out before setting annual goals so you plan from where you want to be instead of just fixing last year's problems.
  3. Identify one or two daily habit changes that support your goals, like preparing workout gear the night before, rather than relying on willpower in the moment.
  4. Create a visual collage of your goals and place it where you'll see it regularly to keep your intentions alive throughout the year.
  5. Dedicate focused time and space for visioning in a place that feels abundant and generous, not squeezed between other commitments.

In this episode

  • 00:00The window for planning your best year
  • 01:45Review the year with calendar and photo stream
  • 06:12Create time and space for visioning
  • 10:08Imagine ten years out in specific detail
  • 16:04Set one-year goals and new daily habits
  • 18:24Preparing the night before changed everything
  • 19:24Build a visual to keep intentions alive
Read the full transcript

The window for planning your best year

00:00Bill Gallagher: Have you ever had a week when you're completely slammed, but somehow nothing actually moved? Is this one of those weeks? That's not really a time problem. It's a busyness habit problem. My new book, Busy Is Broken, Do Less, Scale More, is all about growing by doing less, not more. Read or listen to a sample chapter over at busyisbroken.com. That's busyisbroken.com. It's also on Amazon and other booksellers.

00:27Bill Gallagher: Hey, everybody. I want to talk to you about how to have your best year ever. How do we have our best year ever year after year and avoid having an off year or a mid year? So this is really my recipe. Works for me. Works for my clients. I'm going to share it with you in just a minute. Remind you again, my name is Bill Gallagher, host of this super groovy Scaling Up Business Podcast. Our show comes to you every week. We bring you something to help you grow your company and enjoy the journey of growing your business.

00:59Bill Gallagher: So I want to talk to you about our practices around personal strategic planning, how to have your best year ever. So this is totally like, look, you could do it any time of the year, but I think it's particularly important somewhere after the Thanksgiving holiday and before the Christmas break, Christmas, New Year's. And that'll vary by country depending on your country and traditions and calendar year and your fiscal year and things like that. But take that with the background and think about it. For many of us, this is the time to do it. We're dropping the show in that time frame now. This is what we do year after year that I do myself and how it goes and what we do with our clients.

Review the year with calendar and photo stream

01:45Bill Gallagher: So here's the practice. First of all, you want to review the current year. And as you review the current year, especially if you're doing this, starting this right after Thanksgiving, you'll still have time to finish the year. Right? You'll still have some part of December left to do if you're on a calendar and fiscal year. You'll be thinking about your personal goals and things like that, how to finish them up as you do this. But you want to begin to review as if the year is reaching an end. You can kind of see what it looks like. There's a few things that are useful in reviewing the year and some obvious ones. So, obviously, the facts. Right? Maybe you said your business revenues and profit and milestones were going to be a certain thing. We want to review the facts. We want to know if we were going to weigh a certain amount or have certain fitness abilities. I was going to run this much or do that or, like, where am I actually at with all of it?

02:46Bill Gallagher: And so it's useful. Another thing beyond the facts, though, there's a couple other things that are really, really useful. The first one is to flip through your calendar. Most of us, we have rich detailed calendars that highlight trips and experiences and personal things. If you'll flip back through your calendar and just flip through week by week by week, 52 is not very long to flip through, one of the things that you'll likely notice is that a lot more happened in the year than is maybe top of mind for you as you begin this review. So flip through your calendar and notice the trips that you, I don't know, have already faded into distant memory, the special events, the parties, the celebrations, things like that. Scan your calendar. Look for all of it. Notice as you do it, both the facts and now the calendar, start to make notes of the highs and lows. Where are the things that I am good about? And you could really just break it into two columns, highs and lows, wins and misses like that.

03:47Bill Gallagher: Two columns, two rows, two pages, whatever works. Separate the good and the bad for you. Right? And, and, look, some things will be kind of on the line, but you could just put it clearly into one. If it's just kind of, you're not sure, then maybe ignore it, because we're really looking for the highs and lows in these things. What are the things we feel really good about? And then here's one, new one that has only emerged last I don't know. Well, since maybe 2007. Flick through your photo stream. Look at whatever your collection of photos is on your mobile device or your desktop that backs it up or whatever, and you'll notice another angle or an aspect of it. You'll see all the kinds of things that happened in the year, and mostly, you're going to see good things.

04:33Bill Gallagher: But you'll see a range of other kinds of things. So first, the facts and the stats and things like that, your dashboards, whatever you take, your plans, review all that stuff, both personal and business. And then look at your calendar, and then look at your photo stream, and get a full picture and make some notes, good and bad, of whatever's there. The things you feel great about, the things you don't feel so good about. Now go share it. Share it with at least one other person, maybe a couple other people. Feel it. Notice how it is. I notice almost every year, there are things to be grateful for that I've forgotten about. And then there are things that I'm feeling sad, disappointed, regretful, just, like, icky, like bad. I wish it had gone a different way, and it didn't go that way. And I'm disappointed, and I feel bad in lots of different ways.

05:25Bill Gallagher: Feel it. Lean into it. Right? But as you take it all in, you probably will notice that it's better than you maybe thought at first. In general, I think most of us will notice that it's all a little bit better than we started off thinking. So get all into it. Take it all in till you really can own all of it, the good and the bad, till you can accept it, till you can feel into it, till you've had a chance to process it. I always start this right after Thanksgiving. It's a natural time. We start to see the year ending. Family's gathered. Family's gone away. And then I start to lean into, okay. There are things to finish, but there's all, it's time to begin. And I give myself a lot of time to go through this process.

Create time and space for visioning

06:12Bill Gallagher: Then sometime, usually after the Christmas and Hanukkah break, depending on how those fall and both of those kind of affect us and travel and family and things like that. And you could have others depending on your background tradition and like that. So, but right after that, I set aside a time. I maybe even begin it sooner, speculating on the future, the year ahead. I want to set aside a time and space for visioning between the end of December and the beginning of in January 2. Right? January 1, January 2. And depending on, I don't do a whole lot for the New Year's evening and day. That's just a time to just turn the page for me. It's not a super drunk, get out and hoot and holler anymore at this age of my life.

07:11Bill Gallagher: But I want to set aside time and space. So place like a mountaintop, a beautiful view, a warm place, by the sea, on the beach. I don't know. Some place that feels really great, abundant, generous, blessed that I'm grateful for, and I want to dedicate a little time to doing a little visioning for myself. So time and space in the best place possible, at the best time of day, free from distraction with support permission of it, not, like, peeling away to do this and cramming it in between other things, but really designed well to give me a place to invent my life, continually reinvent my life. Alright.

07:52Bill Gallagher: So what are we going to do there? We're going to first settle in, breathe. Right? Feel my body. Settle my body. I'm going to do something called a body scan. I don't know if you've done this kind of a thing before, but it's a kind of a meditation practice

08:06Bill Gallagher: We start maybe at our toes and we move up and through our body, noticing and relaxing our body, slowly taking inventory of things, settling it, connecting to all of the feelings that we have in our body through the toes, up the legs, through the torso, out to the fingertips, up to the shoulders, into the head and scalp and all that. And then more breathing through the whole thing. I'm pretty slow with that. You could look it up if you're not familiar with it, or if you have a different practice, that's fine too. But something that really gives you plenty of time, not rushed, to really settle into something. Settle in and center.

08:48Bill Gallagher: And if you're curious about that when you're not familiar with it, I don't know, maybe type in body scan to your favorite AI tool or to Google or to YouTube, and you could find some instructional walkthrough specifically on that. I could take ten minutes or more on a body scan and really be in a groovy place.

09:11Bill Gallagher: I could also have sometimes you may have a practice where you have like a safe space or your own personal creative lab or studio in your mind, and you could go to that place after a relaxation and then begin to design and imagine.

09:28Bill Gallagher: I think the best thing to do is to imagine 10 out. Start way out. Ten years is about the right time. If you're particularly young, if you're fairly young, thinking ten years out might be a little challenging, confronting. Oh, I can't think that far. I can only go five years. Right? You want to go as far, but I suggest no matter whether you're 20 or whatever, go ten years out. So if you're 20, think about being 30. If you're 25, think 35, 30, 40, 40, 50, 60, 70, like that. Go ten years out at whatever age you are and imagine your life. Right? How old will you be?

Imagine ten years out in specific detail

10:08Bill Gallagher: Family members, a spouse, a partner, children, no children, your parents, your extended family. How old will everybody be? Sometimes that creates a picture of things, of dealing with stages of education, of life, of certain life events and things like that, and that's useful and interesting. Right? I think about like taking care of my parents today, but I'm at an age and my parents won't be alive in ten years. But I suppose they could be, but it's unlikely. Right? So I don't imagine myself dealing with them to the same degree. I think about my kids being at a different stage of life and not dealing with the same things that I'm dealing with today. So whatever age, whatever it is, picture yourself in your life. Then think about where do you live? What does that look like? What is your house, apartment? Like, are you in the same one? Have you improved it? What do you really want? Right? Ten years from now, with a lot of circumstances aside, what kind of a place do you want to be living in? What do you want? And what does it look like, feel like that?

11:15Bill Gallagher: Think about your primary, if you have a partner, a wife, husband, whatever, primary romantic relationship. What does that look like? If you don't have one, do you want one? What does that look like? If it's one way and you'd like it to be in a whole new chapter, imagine that. What do you really want it to look like? Who's the person? How does it go? How does it feel like that?

11:43Bill Gallagher: Start to think about then about your family. Right? How's your family changed over time? Who are they? What are you dealing with in your family? What do you really want in terms of family and the quality of family? And then think about not just who's there and how old they are and that kind of thing, but what you do with them. What are your family traditions and practices? How's that evolved over the last ten years?

12:08Bill Gallagher: Then go out maybe to friends and the kinds of people you live with and play with and what you do with the friends in your life. And then you could go naturally into your hobbies. Right? What are your personal hobbies and that kind of thing? And then that leads kind of naturally to your health and fitness. What are your health and fitness goals? What does it look like? What do you really want your life to look like at that age? Right?

12:36Bill Gallagher: I think about each of those steps. And then from my health and fitness, it's pretty natural to go to then my work. How do I spend my time? So I spend a lot of time on myself and where I live and who I love and my family and my friends and what I do for fun. And then I go into my health and my fitness, and then I start to think about my work and my work life and what's my role? And then what does my business look like? Most of you all have businesses here or departments within businesses. What does that look like, and how does it feel, and how's it evolved over ten years? Or maybe you imagine yourself exiting in the next few years and you're looking back on the business that you created. Great. Imagine that and how it looks today after you.

13:25Bill Gallagher: So we imagine our work, and then that naturally leads us to our finances and our security. Right? So what do your finances look like? What is your security? And I think even more than like a number here, it's useful to have a picture of what the number buys you. So I want to be able to live at this level and this way, like be able to afford these things. That's much more useful for most of us to think about that than an arbitrary, I want this much money in my account and that kind of thing. So what would it buy you? And then that will translate to a particular number and help you set a goal.

14:02Bill Gallagher: And then you might think even past your work and then your money and your financial security. Think about then your life purpose and your spirituality. What are your practices around purpose and spirituality? If you have a formal religious practice, then you'll have something there. If you don't have that, there's an expression of your life's purpose or quality that might pull through all those things and alter all of those things. And so go there next and think about that. Now the order of these things, I don't know. With practice, that pretty much works, but you could change it as suits you. It doesn't matter really what order. But inspecting and creating all these kinds of things can be really helpful place to look. So we're creating a ten year picture. We're really envisioning what do we want ten years from now.

14:59Bill Gallagher: When you're settled with all that, when you've exhausted it kind of, and imagined all the little pieces and details, and you really could go think about what does it look like, sound like, feel like, smell like, go to all the senses of your life in all those different areas. Imagine all the details, the trips, the family holidays, the events, the fun, the play, the hobby. Like, get a rich picture of all of it.

15:23Bill Gallagher: When you're settled with that, allow your eyes to open and then just write like crazy. Just empty your mind. Write wildly. Don't edit or correct anything at all. Just write, write, write, write, write. You could also dictate. I think handwriting, even now, is best for most of us. The thing I'd probably least do is type it out. So I'd handwrite it or dictate it and be as messy as you can. Just empty your mind and keep like writing, writing, writing till you've got nothing left. And then you could use AI to edit it. So I can upload pictures of my writing or I can insert my transcription.

Set one-year goals and new daily habits

16:04Bill Gallagher: My dictated thing into another tool, and I can have AI transcribe it, whether it be handwriting or dictation, and clean it up for me. So I can go ahead and clean up the thing considerably. You could also have it write it in a future past-based language, like it's 2035 and I'm 71 years old. I'm speaking for myself now. And I'm looking back on my life, and what I really love about the last period is that it's gone like this, and I've done that, and my marriage is like this and my family. I could speak about the spaces we went through like that. The AI can translate that and write that in a format. You could say, write in a Vivid Vision style from the future looking back. That would be a useful way to prompt AI. After the basic transcription to clean it up and format it, it can create something really beautiful with what you've said, with what you've imagined, not giving you things.

17:00Bill Gallagher: All right. From that then, and you could use AI for this, what are some likely and reasonable goals that I might set for my life in each of these areas just for one year from now? How would I get started? What should I take on? So now, rather than just fixing the problems and frustrations of the last year, I look forward at where I want to be in 10 years, and that changes the lens significantly. Now we are, as Stephen Covey says, planning from the starting with the end in mind, planning from the future looking back. So we stand in the space, the mindset of the creation of what we want 10 years out. We look back and we say, what's reasonable to take on then for the next year? What am I going to do in the year ahead? So we set some one-year goals. And then from that, and again, AI can be very useful for this, is say, what are some new daily habits, daily and weekly habits that I would want to undertake now to accomplish those things if my life looked like that? And you might need to tell AI, so I want to do this, but today I only do this thing, and I'm in this situation. So you can problem-solve and create and brainstorm some new habits and steps.

18:11Bill Gallagher: Years ago, I wanted to transform my fitness. I was going to take on triathlons, and I went on to run about 45 triathlons and endurance events over about a 10-year period. In the beginning, it was really hard. I would forget them. I would miss them. I would escape them because I would wake up in the morning and then I'd dawdle around getting ready to do the workout, and then I'd shorten it or miss it entirely with distractions in my ADD self. So a key thing that made all the difference in the world was a new habit to prepare everything the night before. If I was taking a bike ride in the morning and pump up the tires, I'd set it out. I'd put my bike clothes out, and I'd fill the water bottles, and I'd stick those in the refrigerator. Now in the morning, just pull on the clothes that's laid there, grab the water bottles, get on the bike, and go. Same thing with running, swimming, a gym workout, whatever it was I was going to do. Setting it up the night before set me up for success. It was a simple habit change that I did.

Preparing the night before changed everything

Build a visual to keep intentions alive

19:24Bill Gallagher: So I go through this visioning. I've done my review. Now I envision 10 years out. I set some one-year goals. I start to then change my habits in the here and now that'll do it. There's one more thing. Many of you will create a plan from this and a detailed thing. In this area, that's been less effective for me because of my wiring. Some of you are really great at this. People like my friend Jack Daly or Andy Bailey or that kind of thing will create a more detailed plan for this kind of thing. I usually have a detailed plan, but the thing that drives me the most is now creating a visual. So once I've got my annual, I start to create, and I've got some new habits that I envision and imagine, I'll create a visual collage. And it's just done on a page, and I slap images. You can use a slide tool or a Word app and just move images around and resize them and crop them for the major areas that I want. What does my relationship look like, my family look like, my travel, my hobbies, all kinds of things? I create or find images. You can find images on Google. You can make images on things like Midjourney. You can do all kinds of things like that. I put all that stuff together. I create a visual that I print out, and I stick in bold color in my closet, here next to my desk, inside the door of the medicine cabinet in my bathroom, like a few places where I'm going to see it regularly. And then all year long, that's there as a visual reminder to make me feel into my goals and intentions for the year ahead.

20:40Bill Gallagher: That's it. That's how to have your best year ever. How to accomplish more of what you actually set out to accomplish is to first get in a clean space. Clean the space out, review the year, be eyes wide open, and be able to set the past aside. Leave yourself with something fresh for the future. Imagine 10 years out, create some reasonable goals for one year, and then some habit changes, and then find a way to keep it alive with a plan and or a visual like that. I think that works for me year after year. It's likely to work for you. Works for so many of the people that we work with. I hope that's helpful. I hope it helps you set up the best year ever. Go kick some butt. Have a great year. Have a great planning and imagining of your future. Talk to you again next time. Keep scaling.

21:28Bill Gallagher: Thanks for listening today. One last thing. If anything in this episode hit home, my book digs into it further. Busy Is Broken. Do Less. Scale More. It's all about how to stop drowning in work and build a business and a team that scales without you. Available right now with content samples at busyisbroken.com. Go grab it. Be less busy.

Bill Gallagher coaches CEOs and leadership teams on the Scaling Up framework. If something in this episode landed close to home, the free 20-question diagnostic is a good place to start.

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