In this personal monologue, Chris Prefontaine reflects on his chaotic, unstructured upbringing with a single, hippie mother and how that lack of planning shaped his early life. He recounts discovering that planning and organization are skills that can be learned rather than innate traits, a realization that emerged as he entered entrepreneurship and people began to rely on him. Chris describes his step‑by‑step development of planning habits: starting with daily task lists, then expanding to weekly "Sunday planning" sessions, monthly reviews, and yearly goal setting. He emphasizes a "brainstorm‑categorize‑prioritize‑calendar" workflow and introduces reverse‑engineering goals—breaking yearly objectives down into six‑month, monthly, weekly, and daily actions. He illustrates the practical impact of these systems by narrating his transition from bartender and personal trainer to full‑time real‑estate investor, highlighting how coordinated communication with his wife, business partners, and coworkers kept his multiple roles aligned. The talk concludes with concrete advice (regular brainstorming, categorization, prioritization, and communication) and an invitation to attend mastermind events in Middletown, Rhode Island, with a promotional link to smartrealestatecoach.com/50off for aspiring real‑estate entrepreneurs.
Chapters
I was told this saying one time, if you fail to plan, you plan to fail. See, I still can't even get my mind wrapped around it because of so many paradigms that I had from a kid. See, I had absolutely no order in my life growing up. I had a single mom who we would consider a hippie. That was late for everything. So there was zero, I mean zero organization or planning that happened in our lives. Like if anything was accomplished, it was made by absolute pure accident. You know, it may sound a bit crazy, but I mean, she's an amazing woman, but she'll even tell you that there was zero order that was happening in our lives. When people started bringing into my world, as I started entering entrepreneurship, this idea of planning Planning and organizing. I thought it was a skill set that you either had or didn't have, meaning like you were either born with it or you weren't born with it. There were organized people and there were unorganized people. But I soon found out that it was a skill set that you can acquire, and after a lot of hard work, it then gets put into play. See, at first, it was like walking with two left feet. I was trying to figure out how to organise a calendar. It's like, how do I set these timeframes where I actually need to be somewhere when I say I'm gonna be there? But not only that, is how do I then create a reminder or a system and process in order to ensure that I am there and not late? See, planning and organising didn't come into my world until people started counting on me. And if people were counting on me, then I had some external forces that would make me grow and evolve in order to learn this new thing called planning, or in trying to figure out a thing called being organised. So it was like walking with 2 left feet when it first started. So if you're anything like me and you feel that way, then it's absolutely normal. But as I started to figure out this, all right, how do I get planned and organised daily? It's like, how do I just look at a day and say, all right, I'm gonna look at what I need to do as far as what tasks do I have, what priorities do I have, what needs to get done today no matter what, and then how do I ensure that goes in my calendar? Well, so I started with this daily activity, and a lot of it just came from some ways in which I set goals, which is I brainstormed, I categorised, and then I prioritised, and I put it in my calendar. And then eventually I figured out that, hey, I might be able to do this thing weekly. And then, hey, I figured out how to do this thing monthly. And we've taught in a lot of these YouTube videos some skill sets, things like Sunday planning, where you take a chunk of your day or a chunk of your morning for about an hour, hour and a half, look at your entire week, look at what priorities you have, look at what goals you have that need to be accomplished this quarter, this year. The next 3 years, and then ensuring that you chunk away at that on a week-to-week basis. Then I figured out how to do this yearly as well, which came down to, all right, how do I actually organize and plan myself from a year standpoint? And then what I found to be best was after I did a brainstorming session to set goals for the year was actually to reverse engineer. And that's when things started clicking for me. Reverse engineering for me then made things really easy, 'cause I said, all right, well, let's look at what I am planning for this year that needs to happen. And then let's see what needs to happen in 6 months, and then what happens, needs to be in a month, and then this week, and then hey, today. Because I was able to have that through line, it then made things that much more simple for me when it came to planning, because there were simple steps for me. So maybe that resonates with you as well when it comes to reverse engineering may be easier for you than foreshadowing or planning into the future. But then eventually there was this opportunity that came into my life which really then tested if I was planning accordingly. See, there was this point in time where I made the leap from being a bartender, to real estate investor. And there was this 6-month gap that, or this 6-month runway that eventually came to fruition where I was bartending, I was personal training, and hey, guess what? Now I was making cold calls to sellers. So trying to organize and plan 3 very distinctive stool or very distinctive legs that, you know, kind of kept my life up in the air is where things started to come into play. With now these 3 components, I had to now ensure that part of my organisation and planning process was really about the communication with each and every individual that I was going to come into contact throughout that week. So I would say to my wife, hey, this is what my plan— this is what I need to accomplish this week. You tell me what needs to now fit into your calendar so that way me and you can connect and still have a life? And then I'd say, Chris, Chris, all right, we have these plans and these goals with real estate investing. What do I need to accomplish? What needs to go in my calendar in order to ensure that me and you are able to work together? And then I'd go to my bartender and I'd do the exact same thing. And by having those external communication, Or those external forces really put me in a position where I needed to be organized. See, if I did not do that, I promise you I would never been able to make that leap and get my first deal, and then eventually make that leap into real estate investing full time. Because prior to that, I had all these hopes and dreams and these goals, and I would say I'm gonna go out and accomplish that. And then I had I'd have no plan in order to do so, and then every year I'd be. Frustrated that I never accomplished that goal. Then once I had that 6-month on-ramp, that completely changed the dynamic of my life, which means that from here on out, I had to be organised and planned. And I'm at such a great— I'm at such— that is such a big piece of my life now that if something is not already planned in the calendar, 8 years later, it becomes very challenging for me to make adjustments. I have ingrained that so much now that planning and organizing, I've gone to the complete opposite and extreme, that now it is very hard and difficult for me to fit that in. So as I bring things to a close here, some key steps that are helpful to help you get more involved in planning and organizing to ensure you accomplish your goals and you don't go through the first 24 years of your life not reaching those consistently is this. First, I would ensure that you brainstorm correctly or brainstorm to a high degree consistently each and every Sunday to say, what in my world would I like to accomplish? Then I would break it down to categorizing very specific things that you would like to accomplish as far as, is it health, is it business, Related. Third, it would be prioritize. And then last but not least, communicate with the people that count on you to ensure that each and every piece of your schedule is covered for. As we bring people together on a biweekly or bi-yearly basis here in Middletown, Rhode Island, these are some skill sets that we focus on. Because we understand that there's a huge gap sometimes going from being a W-2 employee to an entrepreneur. And organisation and planning is an absolute key skill set to understand. I've actually spent many masterminds with our students and our associates on these small groups teaching this skill set. So I encourage you to come and attend one of our events in either March or September. And learn these little skill sets that eventually compile to being a successful real estate entrepreneur. All you gotta do is go to smartrealestatecoach.com/50off. That's smartrealestatecoach.com/50off. And let us lock arms with you and ensure that you have success in real estate.
