
Loading summary
Nick Loper
How to have your best year yet. The New Year's upon us, and with it comes a certain level of optimism and maybe a certain level of obligation to make some changes, to set some meaningful goals, and to aim for some big wins. But it's no secret that most New Year's resolutions fall short. A lot of goals fail and lose steam after even just a couple weeks, the research shows. So we want to make sure that doesn't happen to you. And to help out with that, I have recruited my good friend and master goal planner to help us out today. He is a serial entrepreneur, a real estate investor. He's the author of the book Lifestyle Builders and the head business coach at 2x co Tom Sylvester. Welcome to the side Hustle show.
Tom Sylvester
Oh, thanks, Nick. Thanks for having me.
Nick Loper
Can I start off with a goal setting confession? Because I am not great at this and for the last several years really haven't done the New Year's resolution thing, the year long goal setting thing. And on the one hand, it's like if you don't punch in your destination, how do you ever hope to navigate there? So I, like, I could see that part of it, but at the other time, I just have a hard time with picking that kind of North Star and kind of coming up with an arbitrary number to hit or a goal. So I'm curious to dive into your kind of planning process or your goal setting process here today.
Tom Sylvester
Yeah, well, you know, first off, I appreciate you sharing that because you're not alone. Right. So many people struggle with goal planning and I think one of the things that's most important is we want to use some of the principles, but we want to cater it to what works for you. So for some people, we just need to directionally be right, get started and we'll go from there. For other people, they really want to go in and detail it out more so that they know exactly where they're going to go. So I think the key thing is, as we go through this process, make sure that you're directionally going right and then go to the level of detail that's gonna support.
Nick Loper
All right, so if you're coaching me or you're coaching somebody, where do you even start?
Tom Sylvester
Yeah, first thing I like to do, I like to frame how we think about this. And I don't know about you, Nick, but I never was good with maps and my wife was great with maps. Like, you know, back before, like the GPS days, she always had one in the car. She knew exactly where we're going and how to Use it. For me, that didn't work. But when GPS came around, I loved it because I could look at, like, here's the destination, where I want to go, here's the starting point and where I'm at, and then I can kind of loosely map out a plan to get there. So the place that I always like to start is where we're at. And really that comes down to, like, where we've been. And so one of the things that I really like to do with people is, like, especially when we're talking about goals, I like to look at it from a personal perspective and then like a business or a career perspective. And so if we're looking at it from a personal perspective, I like to use this concept called the wheel of life. And it sounds super fancy. Really, what it comes down to is identify areas that are important for you in your life. Maybe it's your marriage, maybe it's your health, maybe it's your finances, maybe it's your faith. But have a list of those. And then I like to ask two questions for each of those. One, on a scale of 1 to 10, where would you rate that today? And then two, what would need to be true to get it to a 10? And I think if we can start there, it gets us grounded into where we're actually at today, and then we can have an understanding of where some of those gaps are to get it to a 10. And that's going to be the starting point for any goal setting that we're going to do.
Nick Loper
Okay, so identifying it sounds like four or five core pillars or core segments of the pie on this wheel of life, and then taking stock of where I'm at today. On a scale from 1 to 10, how am I doing fitness wise, how am I doing relationships wise, how am I doing financially? And kind of filling in the current state of affairs on the pie.
Tom Sylvester
Exactly. Because here's the thing. If we don't know where we're at now, it's going to be so hard to figure out where we want to go, and we don't know how close or far away we are. So I find that if we can just check in on where we're at today, that's going to give us some clues and some starting point of, like, what should we likely focus on as we go forward?
Nick Loper
Got it, Got it. Okay. It's similar to the GPS on your phone.
Sponsor/Ad Voice
Right.
Nick Loper
It's like it needs a starting point before it could tell you how to get there, what turns to take.
Tom Sylvester
Exactly. And now you can Go as deep into this as you want. So for example, with my wife and I over the years, I think we have like 10 categories and we actually spend a decent amount of time going into this individually. And then we come together and we share ours, we understand each other's, and then collectively we can then plan together. So it's like this could be a quick like 15 minute activity for you.
Nick Loper
Okay.
Tom Sylvester
Or this could be a multi hour activity.
Nick Loper
Got it, got it. Okay. So coming up first with these core areas, the areas of your life that are really important to you, and we named off a few of them. It could be health, it could be relationships, it could be faith, it could be finances, it could, you know, any number of things. It could be community service, whatever it is. And then I kind of like the idea of comparing notes. I'm going to do it on my end. And then you see, it's like, oh, we're not on the same page here. So it could be a good conversation.
Sponsor/Ad Voice
And then do you do the same.
Nick Loper
Thing business wise or, you know, kind of having different categories is, it's like one, it's one piece of the pie to you as an individual. But like, and then on the side hustle or on the business side of things, it's like, well, that's its own entity.
Tom Sylvester
Yep. So I do them separate, but I follow a similar process. So on the business side, we'll do the same thing. We'll look at what are the categories that are important to the business. So for most businesses, it's like, you know, how much revenue did we make this year ultimately? How much were we able to take home and pay ourselves from that? How was my time going? How did my projects go? Like, the major projects and goals I set out, how did I do on them? And then, you know, what are some of the biggest challenges that I'm facing today? So we kind of want to level set on where we're at with the business as well. So if we can level set on both the personal and the business side, now we've got a starting point to plan.
Nick Loper
Got it. Where do you go from there?
Tom Sylvester
My favorite question is, I like to like, and this might sound a little weird, but we close our eyes and we imagine that we're at December 31, 2026. So we're basically a year out. And I like to ask myself the question, what would make this year just a 10 out of 10? And then I just let that flow. So it's like, well, what would make it great? And I identify, well, you know, Maybe I'm losing ten pounds. Maybe I've been able to increase my take home income by 5k a month. I just list out all the things that would make it great.
Nick Loper
Okay.
Tom Sylvester
And then I do the flip side and I say, what would not make it great? Like what would make me disappointed in this year? And I list all of those things out. And once again, if you can do that on the personal side and on the business side now, you've got a pretty good plan of where you want to be a year from now.
Nick Loper
What's interesting is you're not the first person to mention this kind of future projecting vision. We talked with Brian Scudamore from 1-800-got junk and he called it his painted picture vision. And I think for him it was like kind of a five year roadmap where he's, you know, he kind of describes early on in the business projecting out five years. Okay, we're at a million dollars in revenue. We have, you know, we're on the Oprah Winfrey show and just these things that would make it a 10 out of 10 for him. And then kind of peeling back, well, what has to happen today to start creeping toward those goals? Because doing the same things that we've been doing might not get us there unless you're already on that trajectory. But something is going to have to change sometimes.
Tom Sylvester
Exactly. And to that point, one of my favorite quotes that I tell every business owner we work with is your results are perfectly designed for who you have been and the actions that you've taken. So when we can understand the results that we have, we can look back and say, all right, well, what did I do and who have I been? And I can see how it created those results. So if I want different results in the future, I get to look at who do I get to be or how do I get to grow so that I can do things differently that are going to create those results versus the ones that I have now. Yeah. So that's a very powerful concept because it really comes back to us being able to start with us and grow first to then be able to do the things, to have what we want.
Nick Loper
Yeah. There was a line, this was Dan Maxwell years ago, he said, do you have or are you getting the results you want? And if not, then something has to change or there's some room for some mindset growth or something has to be fundamentally different to get you there. It's kind of along the same lines of if you really wanted it, almost by definition you would have done it.
Tom Sylvester
Already.
Nick Loper
And it's kind of like this weird shift of like, oh, you're probably right, I probably didn't take the action that was required. I probably didn't make the decisions that I needed to make. And it's like, oh yeah, that's because the results, like you said that I have today are perfectly designed to the person that I've been. And we had Nathan Barry on the show. He's like, you know, at that point convertkit or kit is at like $30 million. ARR. He's like, to get it to 100 million, I'm going to have to become a different leader. I'm going to have to become a different CEO. And he was like really bought into that personal growth challenge of becoming that higher level leader.
Tom Sylvester
Yeah. And I love that you brought up multiple people because at the end of the day these principles apply across the board. Now different people may have different processes for it, but it really does come down to this concept of this called be, do have. And so we want to look out and whether it's a five year painted picture, a three year vivid vision, a one year goal, we're looking out and saying what do I want to have in the future at some time point? And then we bring it back to who do I have to be and how do I have to show up to then do the actions to get there.
Nick Loper
Yeah.
Tom Sylvester
And so it always does start with where do we want to be and then who do we get to be. And from there it's then just about doing the actions and adjusting based on results.
Nick Loper
Yeah. This is very reminiscent of a Tim Ferriss dreamlining exercise.
Tom Sylvester
Yep, exactly. And actually so for my wife and I, what we actually do is we have a five year plan and because we have two kids, we actually on there, we lay out what our ages are each year and then we basically say what do we want our life to look like at that period of time? Like what trips are we going on? Do we want a new house? Like we just detail that all out and what that allows us to do is to know where we're going. But then we can focus back in and say, okay, what are we doing in the next 90 days to move us in that direction? So that's why I tell everyone, I'm like, the process can look slightly different, but at the end of the day it's the same core components. Where do you want to be, what do you have to do? And then ultimately who do you have to be to do that?
Nick Loper
What do you do to take those you Know, you're projecting out 12 months or three to five years even, and then saying, well, what do I do tomorrow about that? If the goal is to double revenue, if the goal is to lose 20 pounds, it's like, okay, but now I got to turn it into something actionable.
Tom Sylvester
Yep. Coming back to the GPS analogy, I think about, you know, if you're on like a highway, there's mile markers along the way. So what I like to do, if we've got a goal that's a year out, I say, what are the mile markers or the milestones that I have to achieve in order to get there? So let's say we want to increase our income by 5,000. Well, we could break that up into four mile markers, one of which is increase it by 1250. Then the next one is increase it by 2,500 and so on.
Nick Loper
Got it.
Tom Sylvester
So it's basically breaking down the bigger end goal into smaller goals so that we can focus on achieving the first one.
Nick Loper
Yeah, it looks, on paper, it looks like a step function, but hey, look, you got 365 days to do it. You can chip away at it a little bit at a time.
Tom Sylvester
Yep. And then to your point, what's really nice is that you can continue to break this down. I mean, this can be ultimately broken down into how much additional do I need to make today to be able to achieve that goal. And that's really where we want to get things down to, because having a 5k goal by the end of the year is, is good. But if we don't understand day by day or week by week or month by month, how we're progressing towards it, we're not going to be able to adjust.
Nick Loper
Yeah. Or all of a sudden you get to Thanksgiving and you're like, I got one month to make it all up.
Sponsor/Ad Voice
Yeah.
Tom Sylvester
And that's one of the biggest issues most people have with goal planning. Right. Is like they set a goal once at the beginning of the year, they maybe give up three weeks in, or they think they're doing the right things, and then they get to the end of the year and they realize they're not even close.
Nick Loper
Yeah. And this is maybe another question. Like, is a year long goal even realistic? Because you almost have to break it down into the quarterly or monthly plan as the next step. Otherwise it's like, well, it's, it's too far off in the distance. I don't have to worry about that just yet.
Tom Sylvester
Yeah, my, my general thoughts on this are I always want to have the longer term goals, but the way I look at it is the further out it is, the more blurry and less detailed it is. Right. Like is a great example for me. I ended up retiring young, you know, similar to you. And so when I set that goal, I was 21 and I set a goal to retire by 35. Yeah, I had no idea how I was going to make it, but I knew that was like, the direction. And then when I broke it down along the way, I focused first on, let me get clear on how much money I need and let me try things to make that additional money. Now, several of those things didn't work out, but then a couple of them did. That ultimately got me there. So I do think it's important to have the direction and the longer term goal, but the further out it is, the more likely it's going to shift and the better off you are focusing on what's in front of you and getting more detailed.
Nick Loper
Got it. What's your take on this line? So we had Paul Jarvis on the show years ago. He wrote a book called Company of One, and in that episode he drops this line and he said, most goals are fake. And I was like, what do you mean most goals are fake? And he's like, so I set this goal to make a million dollars, have a million dollar business, and three weeks in or two months in, I'm making myself miserable. And he's like, I don't need a million dollars. It was a fake goal. Like, it was just an arbitrary number. And that line kind of stuck with me. And it's like, well, how do I make sure that my goal isn't fake? Tom's response, plus how he uses AI to help with goal planning coming up right after this.
Sponsor/Ad Voice
January is the season for leveling up, not just personally, but in your business too. Make it a resolution this year to simplify and automate the parts of your business that you don't love or aren't core to driving revenue like running payroll or guessing at tax forms. Our partner, Gusto, is the online payroll and benefits software built for small businesses like yours. It's all in one. It's remote, friendly and super easy to use, so you can pay, hire onboard and support your team, whether they're 1099 or W2 from anywhere. I'm talking about automatic payroll tax filing, simple direct deposits, health benefits, commuter benefits, workers comp 401, you name it. Gusto makes it simple and has options for nearly every budget. You can do unlimited Payroll runs for one monthly price. Gusto was rated the number one payroll software according to G2 for fall of 2025 and is trusted by over 400,000 small businesses, including many a side hustle show guest. Try gusto today@gusto.com Sidehustle and get three months free when you run your first payroll. That's three months of free payroll@gusto.com SideHustle G U S T O one more time, it's gusto.com Sidehustle New Year New systems. Right? It's the time when we all look at some of the messier parts of our business and think, well, what would it look like if it were easy?
Nick Loper
There's got to be a better way.
Sponsor/Ad Voice
Streamlining your communications is one of the quickest and easiest upgrades you can make. That's why today's episode is brought to you by Quo, spelled Q U O. This is the smarter way to run your business communications. Quo, formerly OpenPhone, is the number one business phone system on G2 with over 3,000 reviews. It's built for how modern teams work. That's why more than 90,000 businesses ranging from side hustlers and solo operators to growing teams, all rely on Quo to stay connected, professional and consistently reachable. Quo works right from an app on your phone or your computer, and it lets you keep your existing phone number. What's really cool is Quo's AI automatically logs your calls. It generates summaries, it highlights the next steps so nothing gets lost. And, and it can even qualify leads and respond on your behalf if you can't take the call. So let's make this the year where no opportunity and no customer slips away. Try quo for free. Plus get 20% off your first six months when you go to quo.comsidehustle that's q u o.comsidehustle quo no missed calls, no missed customers.
Tom Sylvester
Yeah, it's a great question because I think most people get into, especially the million dollar one. Like, because we work with business owners, this comes up all the time for some. Everyone wants to hit a million dollars.
Nick Loper
Yeah, it's like almost like a badge of honor. And it's like a validation in some way. Like I, I did it, you know, I built this seven figure operation.
Tom Sylvester
Exactly. And so whenever we hear that, and this goes for any goal that we set, we should be asking ourselves, why do I want that? Because it's not really the thing that we set that we want. It's the meaning or the feeling that we associate with that. Right. When I make a million dollars, then I will be worthy. When I make a billion Dollars, then I can buy.
Nick Loper
Yeah.
Tom Sylvester
When I make a million dollars, then this will happen. So what I think is important is to ask, why do I want that goal? Get clear on that.
Nick Loper
And maybe I would take it even another why or two deeper than that. You've probably heard, like, the five whys exercise.
Tom Sylvester
The five whys is phenomenal. So keep going until you get to it. And then I like to come back and say, is that goal necessary or even the best way to achieve that? Because in most cases, we don't need nearly as much as we think we do. Yeah, we just have a story in our head that that thing will get us what want, but we can usually get what we actually want or that feeling way easier and simpler.
Nick Loper
Yeah, there's definitely some truth to that. What's the part from the Wall street movie with Charlie Sheen? Right. He's like, oh, I'm going to make all this money. I'm going to go ride my motorcycle across China. He's like, you could probably do that today.
Tom Sylvester
Well, there's that old tale of the fisherman. I'm going to butcher it. But it was like this fisherman was fishing. This business guy came, told him he could increase his fishing and get more fish. And ultimately it came down to, why would he do all of that? So that he can spend his day fishing. He's like, I'm already doing that.
Nick Loper
I'm already living the dream.
Tom Sylvester
Yeah. So I think a lot of times people look at other people's lives or other people's businesses and think that's what they need, but they don't actually get clear on what they actually want. And that's why we started this whole conversation with check in on where you're at and then what would make it a 10? Because that should be the filter and the guide for everything else that we do from a planning perspective.
Nick Loper
Yeah, I think that's really important to start there and also to maybe take some level of reflection on where you been or where you started. There's this book, the Gap and the Gain. It's like so many people live in the gap of like, well, here's what's missing. Here's how far there's still left to go without kind of appreciating the gain, how far you've already come. And so starting there and saying, yeah, of course you got to have something to strive for. I'm all about that. Like, this is an entrepreneurial show. We're not going to be all, woo, woo, Yeah, I just appreciate what you have. But, like, there is some level of saying, yeah, we've already made some progress, and, yeah, there's still a ways to go, but we can. We're not. We're not starting at the very bottom.
Sponsor/Ad Voice
Of the mountain here.
Tom Sylvester
I had kind of always looked at it that way, and then when I read that book, it solidified it for me. It's like, yeah, because, like, what do most of us do when we look at, like a goal? We say, did I hit it or not? And let's say the goal is to make 5,000 and we only made 4,500.
Nick Loper
Yeah.
Tom Sylvester
Well, we would look at that and say, we didn't hit the goal, we failed. And we're looking at the 500 that we missed and not the 4,500 that we made. And so I do think that's really important. And that's why the reflection is key, because we do want to appreciate what we've had as well as learn and adjust to then decide what we're going to do going forward.
Nick Loper
Got it. There was a question that you mentioned early on, and it was this what would need to be true question to make this area of my life a 10. Do you have any other questions or kind of guiding frameworks to kind of itemize out different action items under those different pillars? Yeah.
Tom Sylvester
You know what would need to be true is probably my go to one of the other ones, actually, the author of the Gap and the Gain, he wrote another book called Scaling Simplified. And basically what he talks about, and a question that I love and I steal from him is if I had to do this goal in a fraction of the time, like, what would I do or what would I change? Because he wrote another book called 10x is easier than 2x. And the point of that book was if we give ourselves a long time frame, we have a lot of options for how to achieve it.
Nick Loper
Yeah.
Tom Sylvester
And most times we'll stick in other things that aren't really required. But if we simplify or condense that time frame, we cut out so many options and there's only a couple left, and those are usually the best. So whatever the timeframe is, like, if we have a goal to hit 5,000 in a year, we might just ask, as a thought exercise, well, what would it take to hit 5,000 this month?
Nick Loper
Right.
Tom Sylvester
And that's going to completely change how we think about solving that problem.
Nick Loper
Yeah. You'll find that constraint breeds creativity in that way. Because I find the same thing I ask people, well, what kind of side hustles are you interested in? And it's like, you know, very much choose your own adventure. There's 700 something episodes to choose from. But if you say, look, gun to your head, you got to make a thousand bucks by next week, all of a sudden it's laser focused in. I'm like, okay, here's what I would do. It's like, oh, well, maybe just do that.
Tom Sylvester
So, yeah, that's the biggest thing with all of this. We tend to overcomplicate it. And the reality is a couple of these questions can really give us the clarity we need. And then it's not so much about overly planning this. It's getting enough planning to then be able to take action. So one more thing I'll actually share with that. Sometimes people can't make a decision. They're like, I'm not sure if I should do this or I should do this.
Nick Loper
Could I raise my hand as being decisively indecisive?
Tom Sylvester
Yeah, I think all of us do this.
Nick Loper
Right.
Tom Sylvester
And so what I like to ask people is if we think about this decision being hard, ask yourself, what would you need to know to make that decision easy? Because sometimes it's not about making the decision. Our next action is about getting more information or trying something so that the decision's easier. So that's another thing I like to think about or look at is like, if you're really struggling to make a decision, don't think about making the decision. Think about what you need in order to make that decision easier and then go and do that.
Nick Loper
I like that question. Or those combination of questions. What, you know, what's it going to take to condense the timeline? How, how could be, how can we make this reality in four weeks instead of four months? And what would it look like if it were easy? What would it look like if it were fun? I think that's another Tim Ferriss question. You know, how can I get excited about this and bring a sense of speed and play to it versus, you know, just an automaton that says, well, this was the, this was the goal. This is how it broke down to the daily action plan. And now I just do do my thing and, and keep at it.
Tom Sylvester
Yeah, and I'll give another tip too. Like as we're executing on this because it can get stressful or, you know, we can get frustrated if things. And it doesn't work. What I always tell people is be committed but not attached. And this is one of the biggest, I think, mindset shifts because when we try something and it doesn't work, what we end up doing is we tell ourselves a story about that. It didn't work. I'm a failure. This is never going to work. All the people that told me I shouldn't start a side hustle were right. But if we realize that that was just one way it didn't work. But I'm committed to getting the result, then I'm going to show up the next day and just try something different. So I think it's really important to know the results we're going after. But if we don't achieve them right away, realize that's part of the journey and just keep showing up and taking what you learn and try something different.
Nick Loper
Be committed, but not attached. Do you have a rule of thumb for like when to throw in the towel of a side project you mentioned? Hey, my goal was to retire at 35. A lot of the projects I tried didn't work out. Like, at what point were you like, this one? It's not going to be the one. I'm going to call it quits on this one.
Tom Sylvester
Yeah, I think it changes based on the type of goal and stuff you have. But here's the guideline I like to think about. So if you remember back in high school science class and we would design an experiment. So I'm a huge proponent of designing experiments with all of these goals. And so my experiment starts with a hypothesis. I believe if I do this, I'm going to achieve that. And then so I give myself a timeframe for that. And then at the end of the experiment, I then say, okay, is this like showing me some proof or some progress where I should continue on, or is it not showing me where I should pivot or ultimately let go of this and do something else? So I don't think it's an easy answer, but I think the biggest thing is like, give yourself a timeline, run some experiments, and then usually in your gut you'll figure out, okay, I've tried enough of these things. It doesn't feel like it's gaining momentum. Let me go back and try something else to get there.
Nick Loper
Have you played around with using AI as kind of a brainstorming or goal setting tool to plug in maybe some information about your lifestyle and your business and seeing what comes back, what kind of recommendations come back?
Tom Sylvester
Absolutely. And I'm so glad you asked because AI has been a game changer for this entire process. Now what I'm about to say is probably going to be controversial to some, but I recommend you give AI all of this information that we're talking about now. Some People are worried. They're like, I don't want to give all that information. I believe that all of our information is already out there between Facebook, Google, Instagram, all these platforms. So here's what we do. I have a personal AI that I had to interview me on all those areas on the Wheel of Life. So I said, hey, here's the areas that are important. I want you to interview me and ask me how I feel about these and what a 10 would look like. So then I just spoke my responses into it, and I had it summarize all of that for me.
Nick Loper
This is ChatGPT, or a different tool.
Tom Sylvester
Yep, this is ChatGPT.
Nick Loper
Okay.
Tom Sylvester
And so what I did was it then summarized all of the things that I gave it. And so I then created a project, and each of those categories became a different list or a folder. So I have one for my health, I have one for my marriage. I have one for my business. And then I said, based on this, here's where I want to be a year from now. Help me define a roadmap or a plan to get there. And the first version it came up with was probably 80% of what I would have done.
Nick Loper
Yeah.
Tom Sylvester
And so I gave it some feedback, it tweaked it, and then now it gave me the plan. So just like gps, it gave me the roadmap.
Nick Loper
Okay.
Tom Sylvester
But here's what's super cool. Every day, I give it two additional things. When I wake up in the morning, I tell it 10 things I'm grateful for.
Nick Loper
Okay.
Tom Sylvester
And it connects back the things I'm grateful for to those categories. And then at the end of the day, I give it my daily rating, and I just summarize what went well and then what my challenges were, and it then connects those back to the goals I'm working on. So it's kind of giving me this ongoing feedback and then recommendations for where I can adjust.
Nick Loper
Okay. This is chat GPT. Just like the 20, like, custom plan.
Tom Sylvester
Chat GPT, $20 plan. I bas made a project, I had it interview me, and then I just give it updates every day and then ask it for any feedback or if I'm running into a problem. Like, for example, I'm working on improving some areas of my health. So I gave it, like, my blood test results.
Nick Loper
Yeah.
Tom Sylvester
And then I said, based on my goals and what you're seeing, help me come up with, like, a meal and a workout plan that will help me achieve this.
Nick Loper
Yeah, I've done the same. It's a really cool use case for that. Because like, when you go to the, go to the doctor, in some cases they're just kind of like, yeah, you're, you're, you're fine, don't stress, you know, and it's like, whoa, whoa, whoa. I know you got to get onto the next appointment, but I was hoping for a little more analysis than just that.
Tom Sylvester
Yeah. And what's really cool with this Nick, too, is a lot of people talk about, like journaling or writing things down, and that's really good. But what AI and ChatGPT will do, which is next level, is it can take a ton of data and understand patterns and make connections that we don't. So, for example, when I did one of my end of the week, kind of like check inside, it actually called out that there was a correlation between my energy being low and some things that I wasn't doing. So it reminded me that when I do these things, my energy is higher. And it recommended that next week I focus on incorporating those back in. So just like GPS will tell you like, hey, you missed a turn, go back this way. ChatGPT is kind of doing that for me with my plan.
Nick Loper
You're using it almost like as a accountability partner where it's like it came up with the roadmap for you and then you're checking in and how you're doing and it's like, hey, yeah, you missed a turn back there. No wonder you're not feeling so great.
Tom Sylvester
Exactly. And the biggest thing I'd say with this is use it as a thought partner. The more context you give it, the better the responses are going to be. And then just like any AI, it can hallucinate or not be correct. So we always want to double check it. But I find, like, for example, a lot of people will type if you do the voice note and you talk. Like a lot of times I'll go and do like a 15 minute walk and I'll talk to it the whole time. I'll give it a summary of how I'm feeling, what's going on. The more information we give it, the more accurate the responses are going to be for us.
Nick Loper
And this is true of a text prompt as well. But the more detail you can feed in, the more context it has to give you what you need on the other end.
Tom Sylvester
Exactly. And the reason that I talk about voice so much is we can usually type 40 to 50 words a minute, but we can talk 150. And when we type, sometimes we'll like, try to filter it when we talk. We don't filter and we might say ums or pauses or whatnot. And all of that gives context too.
Nick Loper
Oh, okay. Okay. And you know, have used the voice just for quick questions out and about, but not, not having this whole back and forth conversation.
Tom Sylvester
Yeah. Usually what I'll do, like when I go on a walk, it's not a back and forth conversation. It's like, hey, I'm going on a 15 minute walk. I'm gonna just brain dump what I'm thinking and what's going on. And I want you to basically save this to help. Help as I'm asking you questions later on.
Nick Loper
Okay. Got it.
Sponsor/Ad Voice
Yeah.
Nick Loper
It's like a robot therapist.
Tom Sylvester
Robot therapist.
Nick Loper
While we're on this, you know, AI and kind of the different tools, are there any other tools that you recommend here or apps or tech that might be helpful in the goal planning and execution process?
Tom Sylvester
Here's what I say. Like I come from a tech background, but I actually tell most people, like, don't get too caught up in tech. So I like to keep it simple. ChatGPT is probably the main one and if you use a different AI, like that's fine. Just pick one and stick with it. There's a tool that's called Whisper Flow. It's essentially going to allow you to talk and then it will translate it into text. So a lot of times as like we're actually doing goal planning with a lot of our business owners next week. And so what we'll do is we'll take them through the process and we'll have them talk out their responses to all the questions that we have as part of the process and then they'll feed that into ChatGPT to then give them their initial plan. So those are the two main tools that I use. There are definitely other ones that are out there, but I tell most people, keep it simple and don't get too complicated.
Nick Loper
Yeah, I think another key component to any goal planning plan or goal setting session is, you know, after you've broken it down into the. Well, what are the, you know, monthly, weekly, daily actions to move forward and make progress is some kind of measurement system, some kind of tracking system so you know you're making progress and kind of like having that daily, weekly accountability where like I gotta go fill in the spreadsheet or I gotta, you know, check the, like there was a streaks app on your phone like people use for a long time. Like, oh, I, whatever it was, I did my meditation or I did my 10 push ups or whatever it was. I'm gonna keep the streak Alive.
Tom Sylvester
I think the biggest thing with that is twofold. When we think about tracking, there's the ultimate result. So in our case of like adding an additional 5k in income, that's the end result. But what we want to think about is like, what are the leading indicators or the things that we can track on like a daily or weekly basis.
Nick Loper
Yeah.
Tom Sylvester
So if we're breaking this down, the goal might be add an additional $500 this month. So we may break that down and say, okay, well we're going to add an additional $100 this week. So whatever that goal is for the week or the day, we want to be able to know what that is. And then every morning look at where we're at and then adjust our actions based on that.
Nick Loper
Well, then breaking down the value chain of where's the hundred dollars gonna come from, it's like, okay, well I gotta call five clients or five prospects or I gotta make this type of social content post. Because when I do that, you know, every so often it hits and I get 100 new email sign, kind of figuring out, well, what are the inputs? And I'm glad you brought that up because it's like a lot of the goals that we set are going to be outcome goals. The $5,000 a month, the dropping 20 pounds versus the process goals, the input goals of, well, what do I actually have to do to make it happen?
Tom Sylvester
Yeah, and the process goals are actually really important because like the example I always go back to is like weight loss, right. Like if we want to lose 30 pounds and we break it down to a pound a week, well, when we step on the scale at the end of the week, the scale is going to tell us if we hit it or not, but we can't really change it. But if we know every day that we're going to have a 500 calorie deficit, part of which is by working out, part of which is by the food we eat. That is the thing every day that we do that creates the result at the end of the week or the end of the goal. So it's really important to know correlation because a lot of people will, for example, they'll be like, I need to go make more money, let me go make all these soap social media post or let me go do this thing. But if we don't understand how that thing is going to lead to the result, we may do a ton of actions that don't get us there. So it's really important to your point with the value chain to say, I Know that this leads to this leads to this. So I'm going to start with that first thing.
Nick Loper
Yeah. And sometimes, especially if you're early on in your business, you're not going to know. Well, you know, this many social followers leads to this many email subscribers leads to this many clients. You may not really have all that data just yet. And so there's a certain element of throwing spaghetti at the wall, but trying to come up with some kind of process or input goal. I mean, early on, for side Hustle Nation, the goal was just write 500 words a day because that turned into blog content, that turned into book content, it turned into social media content, and that was the goal. It didn't matter if it got published or not, but it was like, could I do this consistently to try and build up this body of work? And ultimately, like the authority in the side Hustle space, there's a process goal versus an outcome goal. Oh, I want 10,000 more followers.
Tom Sylvester
And kind of like what we talked about earlier, even if you didn't explicitly say this, you basically had a hypothesis in your head. Your hypothesis was, if I wrote 500 words a day for long enough, it would turn into assets that would then be monetized. So what I like to do is to have us identify what is that hypothesis? And then we say, how can we test it? We might test it on a week, we might test it on a month, but if we can then check in, that's going to help us to say, hey, the process things that we're doing are leading to the result, so let's do more of them. Or the process things aren't leading to the result, so maybe let's change that or try something different.
Sponsor/Ad Voice
More with Tom in just a moment.
Nick Loper
Including getting goal buy in from other stakeholders in your life, like your spouse.
Sponsor/Ad Voice
And your team, and carving out time to do the goal planning when it just feels like you're too busy to.
Nick Loper
Come up for air.
Sponsor/Ad Voice
Coming up right after this. 2026 is going to be your year. I can feel it. With Our partner, Shopify, 2026 is when you finally make it happen. Time to go from ideas and inspiration to action and results. Shopify gives you everything you need to sell online and in person. In fact, millions of entrepreneurs have already made the leap from household names to dozens of side Hustle show guests. You've heard their stories. Now it's time to write your own. Shopify gives you all the tools you need to easily build your dream store. Choose from hundreds of beautiful, customizable, and proven to Convert templates so you can launch fast. Plus, you can use Shopify's built in AI tools to help you write product descriptions and headlines and even edit your product photos. Marketing is built in too. You can easily create email and social campaigns that reach your customers wherever they're scrolling. In 2026, stop waiting and start selling with Shopify. Sign up for your $1 per month trial and start today at shopify.comsidehustle go to shopify.comsidehustlE that's shopify.comsidehustLLE and hear your first this new year with Shopify by your side.
Nick Loper
So earlier you mentioned having kind of going through the process with your wife and kind of doing it separately and then coming back together and comparing notes and kind of doing a joint version of that. And I imagine that probably comes up up quite a bit for listeners who have big business goals or side hustle goals and their spouse maybe or partner may be a little more lukewarm on that. Like, why are you hanging out over here? Or if you have a team in place and they're like, well, who are you to just set these big arbitrary goals? And now it's on us to go hit them. We don't have any buy in in that. So do you have any suggestions or advice there?
Tom Sylvester
Yeah, well, it's funny because people will take like me and my wife, people hear us do this process now and they're like, like, oh, it's so good that you guys are like on board and aligned. And I'm like, it wasn't always that way. So whether it's your partner or your team, usually we have an idea of where we want to go, but we don't stop and ask the others around us where they want to go and what's important. So I find the key part of this planning process, like, let's start with your spouse. Like first off, ask them the same questions that you're asking yourself, like, where are you at today? Like, how are you feeling in these areas that are important to you? And then like, where would you want to be a year from now? And like when my wife and I did this originally, what we found was that we were similar on the things that we wanted, but our time frames were very different.
Nick Loper
Okay.
Tom Sylvester
So a great example was we both wanted a new house, but her time frame was like two years. My time frame was like five.
Sponsor/Ad Voice
Okay.
Tom Sylvester
And so just through having these discussions and really asking what she wanted and uncovering them, that we could see where we were aligned and where we were different. And then Talk about how do we bring this plan together that works for both of us.
Nick Loper
So you compromised and got the house in two years.
Tom Sylvester
We actually ended up pushing it off. But the reason that that worked was because we, we planned out, like, where we wanted our life to be. And in my case, I was like, well, if I can spend a little bit of time getting this business working to where we're making more money, then we're going to be able to afford the house you want. If I can't get this working, then it's going to be a bigger stretch. So which one do we want? And we mutually agreed we would rather wait a little bit longer and have exactly what we wanted.
Nick Loper
Yeah. So you're working with a lot of business owners who are neck deep in the weeds of their business and putting out fires day to day. It's really hard. And I'm kind of guilty of this sometimes too, where it's like very much maintenance mode versus growth mode. Like, how do you get people to come up for air when it feels like I'm too busy chopping down trees to sharpen the saw here. Like, you're talking about, you know, 12 month goals. It's like, I'm worried about tomorrow or making payroll at the end of the week or, you know, stuff like that. It's really challenging.
Tom Sylvester
I start with results. So I check in, I'm like, hey, Nick, how are you feeling with the business? Like, is it where you want to be or do you want it to be different? And if you're like, well, I really want to make more money or I'd rather have more time, it's like, okay, sweet talk to me a little bit more. What does that look like? How much more money? How much more time? So it starts out with understanding that they don't have what they want. And then we define what do they want? And then we go back to that question of like, well, why do you want this? Okay, because if we can start there, we're exposing the gap and then we can start talking about, okay, now is this really what you want? And then we can define how do we go about getting it and making that happen.
Nick Loper
Yeah, sometimes it's tough to carve out even a half a day of on paper, like, do nothing time, like thought time, reflection time, planning forward, planning time. But it's really some of the most important work that you can do if it dictates the future direction of your business.
Tom Sylvester
Absolutely. And here's a thought practice that I do with a lot of people and I call it Future pacing. So it's like, hey, Nick, we're going to kind of walk through two scenarios. Scenario one is you're too busy to do this planet and you just keep doing what you're doing today. Then what happens? And you tell me something and I say, okay, so if you then are heads down and doing this thing, then what happens? And we play it out until we get to a point of where you're going to end up in the future.
Nick Loper
Yeah.
Tom Sylvester
And I'm like, sweet, Nick, now let's come back and play a different scenario. Let's imagine you were able to carve out this time, get super clear on what you wanted and then a good plan to get there. Then what would happen? And you'd tell me that and I'd say, then what would happen? And by the time we get to the end of both, I say, great, great, Nick, you get to decide, do you want pain now, which is the planning to make it easier later, or do you want it easier now by not doing the planning and the pain later? And usually that will help people realize, yeah, it makes sense to do the harder thing now because I want that result later.
Nick Loper
Yes. Set the GPS versus continuing to just drive around in circles doing your thing.
Tom Sylvester
Yeah.
Nick Loper
Well, Tom, this has been a blast. I've got a ton of notes from this and some homework to do as well as I'm sure listeners do as well. What's going on with you? What's next? What are you excited about this year?
Tom Sylvester
What we're looking at is for business owners that are looking to build their business, to create that freedom, how can they properly leverage AI to do what AI does best so they as business owners and their team can do what they do best? So we've got some projects that we're working on now and we'll be announcing soon to really support that. But I just think in this time where there is like so much innovation and so much going on, there's such an opportunity for all of us to be able to really be in our zone of geniuses. So that's my focus, is how do we identify what all of our zone of geniuses are and then how do we focus on spending more of our time in there?
Nick Loper
Yeah. Is this on the lifestyle builders side? The 2x side?
Tom Sylvester
Yeah. I think just in general, like, if I, if I look at, you know, where my focus is, it's all of us want to be happy and live our ideal life and the group that we work with is business owners. So we basically say, how do we do that across all the things that we do. So in every business I touch or every effort I'm in, it's coming back to that question of what's the zone of genius for this person and how do we help them get more into that?
Nick Loper
Yeah, I'm glad you framed it that way as just building the lifestyle that you want. And you probably saw this Harvard study from probably a few years old at this point point. But they asked all these millionaires, you know what. What level of wealth would you feel happy or would you feel comfortable? And inevitably, whether you were worth 1 million or whether you were worth 10 million, it was double. So the 5 million people said they wanted 10 million. The 10 million people said they wanted 20 million. It was like the goalpost keeps moving. Right. If you're only measuring in terms of monetary success. So you have to have these other measures. That's one. In this wheel that you're describing, wheel of life that you're describing as one pillar killer. It's fine. But it doesn't. It can't be the only thing, because you see plenty of really wealthy, unhappy people. So make sure you're designing your goals for this year with. With the holistic view in mind.
Tom Sylvester
Absolutely. And I'll share one more thing, Nick, that I do that has helped a lot. I've always had this, like, challenge between being grateful for everything that I've created and achieved in the life I have, while also feeling, like, driven to do more. So, actually, in my office here, I've got one wall, and there's a sign on it that says, create your future. And it has my vision, my goals, and I look at that every day to remind myself of what I'm creating. But then on my other wall, there's a banner that says, love your life. And I've got pictures of key moments in my life, people, places, experiences. And every morning, one of the practices I do to reset is I remind myself of where I'm going and what I'm creating. But I bring it back to gratitude and just a reminder of letting go. Like this experience I had or this impact that I had on somebody. And I find that that helps me stay grounded and grateful while I'm also building. Because otherwise it can be so easy to just see the goal post moving and not really appreciate everything that you've created. Like we talked about with the gap and the gain.
Nick Loper
Yeah, yeah, yeah. This. Create your future, love your life. This combination of growth plus gratitude and the best way to predict the future is to create it. So, yeah, it's on you to go out and make it happen this year. 2x co is for six and seven figure business owners looking to scale up and grow their operations while reducing the businesses reliance on themselves as a business owner. Stop you in the bottleneck and we are lifestylebuilders.com check out the Lifestyle Builders book by Tom and Ariana, his wife. Really fun read there. Let's wrap this thing up with your number one tip for side Hustle Nation.
Tom Sylvester
Yeah, I'd say take time to really think about what you want and then be intentional with everything you do to get there. There's a quote, Tony Robbins says it. I don't know if he created it, but we often overestimate what we can do in a year, but we underestimate what we can do in a decade. And if you're not where you want to be now, just realize you're on the path and you get to go through this process to get there and you can probably do so much more than you think is possible.
Nick Loper
Yeah, totally. You're in the driver's seat so it can be really, really powerful there. Tom, again, this has been awesome. I put together a goal tracking, goal planning template based on our conversation, based on everything that we've been talking about today. You can download that for free as your free listener bonus@sidehustlenation.com goals again side hustlenation.com goals or just follow the link in the episode description. It'll get you right over there there. Big thanks to Tom for sharing his insight. Thanks to our sponsors for helping make this content free for everyone. Side hustlenation.comdeals is where to go to find all the latest offers from our sponsors in one place. That is it for me. Thank you so much for tuning in. If you're finding value in the show, the greatest compliment is to share with a friend. Fire off that text message, let them know you're thinking about them and you want to help them have their best year yet. Until next time, let's go out there and make something happen and I'll catch you in the next edition of the side Hustle Show. Hustle on the.
Host: Nick Loper
Guest: Tom Sylvester, serial entrepreneur, real estate investor, author of “Lifestyle Builders,” head business coach at 2x.co
Release Date: January 1, 2026
In this actionable New Year’s episode, Nick Loper is joined by Tom Sylvester to break down the most effective ways to set, plan, and actually achieve meaningful business and personal goals in 2026. Tom, a master planner and entrepreneur, shares practical frameworks, mindset shifts, and innovative tech (especially AI-powered tools) to help you move from vague resolutions to intentional progress. He also covers making goal-setting collaborative (with your spouse or team), staying motivated, and how to know when to quit a path that isn’t working.
Nick’s confession: He hasn’t done New Year’s resolutions or long-term goal planning for years, often struggling with picking a “North Star” (00:48).
Tom’s approach:
Quote:
“If we don’t know where we’re at now, it’s going to be so hard to figure out where we want to go.” – Tom (03:56)
Quote:
“Your results are perfectly designed for who you have been and the actions that you’ve taken.” – Tom (07:42)
Quote:
“Having a 5k goal by the end of the year is good. But if we don’t understand day by day or week by week how we’re progressing, we’re not going to be able to adjust.” – Tom (11:53)
Quote:
“We should be asking ourselves, why do I want that? Because it’s not really the thing that we set that we want. It’s the meaning or the feeling that we associate with that.” – Tom (17:43)
Quote:
“The more context you give it, the better the responses are going to be.” – Tom (29:36)
Quote:
“We often overestimate what we can do in a year, but we underestimate what we can do in a decade.” – Tony Robbins (as quoted by Tom, 46:07)
On tailored planning:
“For some people, we just need to directionally be right, get started and we’ll go from there. For other people, they really want to go in and detail it out more…” – Tom (01:25)
On consistency:
“Just realize you’re on the path and you get to go through this process to get there and you can probably do so much more than you think is possible.” – Tom (46:07)
On AI as a personal GPS:
“Just like GPS will tell you, ‘Hey, you missed a turn, go back this way.’ ChatGPT is kind of doing that for me with my plan.” – Tom (29:23)
Tom’s #1 Tip:
“Take time to really think about what you want and be intentional with everything you do to get there. You’re on the path, and you can probably do so much more than you think is possible.” (46:07)
Nick’s closing reminder:
“The best way to predict the future is to create it. So, it’s on you to make it happen this year.” (45:32)
For more templates, resources, and actionable tips, download Nick’s goal planning toolkit at sidehustlenation.com/goals