How to Improve Your Time Wealth (feat. Justin Donald)
16 Dec 2025 · 29 min
Justin Donald moved from grinding as an entrepreneur to buying back his time through cash-flowing assets and delegation. He breaks wealth into seven categories, with time ownership as the key to living purposefully. His Freedom Vision ritual: ten goals taped to a mirror, reviewed quarterly with his wife.
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Hi, I'm Susan Drumm and welcome to another episode of the Enlightened Executive, where your personal evolution sparks your leadership evolution. Each episode we feature groundbreaking techniques and strategies to help you get the edge in personal and leadership effectiveness. Today we're focusing on building true wealth in your life beyond just money. And I'm excited to introduce my guest, Justin Donald. Justin is leading people to realize their investment dreams and gain financial freedom. Entrepreneur magazine calls Justin Donald the Warren Buffett of lifestyle investing. His ethos is to create wealth without creating a job. And in the span of 21 months and before his 40th birthday, Justin's investments drove enough passive income for both him and his wife Jennifer to leave their jobs more multiply his net worth to over eight figures and maintain a family focused lifestyle in less than two years. Justin is author of the Lifestyle Investor and he now consults and advises entrepreneurs and executives on lifestyle investing. So welcome Justin.
Thanks, Susan. It's great to be here. I'm excited to hang out with you and every time we hang out, I feel I'm a better person. So I'm glad to be here.
Oh, that's so nice. I feel the same. We have such a good exchange and I was recently on your podcast and enjoyed talking about the Enneagram and how it influences people to invest and so excited to have you on mine.
Well, people loved you from my audience and I mean, no surprise they should. But it was such a cool look into how to apply the Enneagram principles and just ways to kind of understand behaviors and personalities in a context that was consumable for investors or even the psyche of an investor. So very, very cool.
Oh, thank you. It was a great conversation and I encourage our listeners to go check it out on Justin's podcast, the Lifestyle Investor. So with you here, I wanted to bring you on to talk about how you're leading because you've had quite a shift in career and how you got to where you are. And I think some of the mindsets you bring around generating wealth and what that really means could be extremely valuable for our audience. So do you want to kick us off by sharing a little bit about your journey and what you believe now and where you see you could help people.
You bet. In fact, this is what I love the most, is to really speak on and teach the concepts that were pivotal and instrumental for me as I evolved as a leader, an entrepreneur and an investor. So I know that your audience is highly comprised of entrepreneurs and executives, and I love that because that's my former Life. I started in the business world as an entrepreneur and I've had to operate in many roles as an executive, though I'm pretty sure in most roles we could have found someone better than me. But I wore a lot of hats in a lot of different businesses and so that was really fun to learn what I did know, what I didn't know and when to basically bring in an executive team for a business that I'm in because it's outgrown me, it's outgrown my skillset was or it's outgrown the time that I can dedicate to multiple roles. So I love your audience and who you're spending time with, educating and sharing things with because it's the backbone of, you know, my professional life and my professional journey. And so early on, you know, I did the startup route and that's a lot of work. And I mean, I had a huge takeaway early on where I was working some crazy hours. And when I say that, I mean I was sleeping five hours a night and I was working the rest in the early days. So I mean truly, truly putting in 18 hour days, 19 hour days. And I did this for a stretch and I feel like it was so great to have that experience of being able to flex my work ethic muscles. But a huge mindset shift I had around that was how much smarter it was to build a team that could do a lot of the things that I was doing. My hang up, my belief issue was that they weren't going to do it as well as me, and so I needed to do it. But what I found and what I rationalized before I found it was that someone that could do 70% of what I did or 70% of the job that I did in five different departments is exponentially better than what I can do myself. So in theory that made sense and then in practice it really does. And so I really shifted from this attitude of work ethic and working as hard as you can to really working as smart as you can and being as resourceful as you can. And so like in that process, there are a lot of takeaways of that. I didn't want to work in my business as much as on my business. And eventually I wanted to just be a capital partner and a consultant or advisor or board member to the businesses that I invest in or just businesses in general that I really like, appreciate and want to have influence with.
Got it. So what made you leave that entrepreneurial side and want to be more into the investing side?
Well, it is really hard, Susan, to fully remove yourself from a business that, that either you started or you came on as it's ramping up. And though I feel I did a good job of putting people in place and being able to work through them, there's just a certain degree of time that's going to go towards that, that it's hard to completely carve out. And so I really wanted to get to a point where my time was not dependent upon earning an income, that I could earn money whether I was working or not, whether I was sleeping or hanging out or doing something that I value or there's purpose in, or I have passion around. I just wanted to divorce time equaling income because I believe it gives me more options. I believe that it really kind of clears maybe even just mental baggage that you can have around the word work when you shift from having to work to simply just getting to work or having the privilege to work. And so that was a big aha moment for me and it paid dividends, literally and figuratively.
Yes, yes. Well, after you had the experience of working 18 hour days, you certainly were in the other end of the spectrum. Right. And so now you want to shift into a whole different way of working. Tell us when I started this. We're talking about building wealth beyond just money.
So.
So maybe you can share a little bit about your philosophy around that. Because I think it's particularly important for executive and entrepreneurs who are focused obviously on building wealth generating wealth. Where do they get caught and what is the mindset shift that they need to make around this concept?
Yeah, I write about this a bit in my book because I think this is important and I think most people misunderstand what the word wealth is and what it means. I think people have this idea that wealth is just about money. Oh, that person's really wealthy, meaning they've got a lot of money. And I think that that's, you know, it's a portion, it's a component of wealth. I think wealth breaks down to many different categories and there are several categories that we need to be working on and have strong to really be wealthy. Because I meet people all the time, and I know you do too, because we've talked about this, we even talked about this, you know, offline here before we hit the record button. But there are so many people in the world, and I would imagine most listeners here in your audience know people that have done very well financially, but are miserable and, or are just rude or are unpleasant to be around. And I would in a heartbeat take Not a lot of financial wealth to have an abundance of, you know, connection, relationship wealth. You know, to me, that's a much greater component of that equation, if you will. So when I think of wealth, it breaks down into several categories. So we can talk financially. That is a component of it. I just don't like when that's abused to just represent money. But I think the physical wealth component is imperative because you can have all the money in the world, but if you don't have the health to be active and go do things, what's the point of having that wealth? I'd rather have my physical health than I would, you know, just a tremendous amount of money.
Health is your wealth in that case?
Yeah, without a doubt. And when I think about, you know, other components, so, I mean, we've got physical wealth or physical health as a component of wealth. You've got the emotional component of it. You've got intellectual. Like, how stimulated are you in the things that you do? You've got the spiritual component of it. Where are you with your faith and what you believe in? You have a component, to me, that's like purpose and passion. So if you've got a lot of money or if you've got certain things, but you aren't doing what you're passionate about or you don't feel there's purpose in your life, this is where a lot of depression comes from. And anxiety is just this mismatch of where you thought you would be with these things, but what the reality equals, you know, expectations not meeting reality. And then one of the biggest components of wealth to me is time. How much time do you own? Is your time really a slave or connected to someone or something else? I feel like most owners, entrepreneurs, executives, are a slave to the business that they work for or the business that they've created. And their time is not managed as much by them as it is by the demands externally on their time. I mean, you want to talk about someone who's really wealthy, they own their time, and they invest that time into relationships, which are the thing that matter most. If you don't believe that, check with anyone who's on their deathbed, and that's exactly what they'll tell you. When Steve Jobs was dying and he only had a couple days to live, he said he worked so hard for all these things, all these toys, all this wealth, all this notoriety, and that it was all worthless like, that he'd been focused on the wrong thing. And for, you know, his last couple of days, like, he just really wanted to focus on his family and the relationships that mattered most. So if you don't own your time, that's really hard to be able to live the purpose that your life is and represents with the passion that you want. And I really think that when you are in a place where you love your life, you love the people in your life, you own your time, wealth from a financial standpoint is just going to show up.
That is so fascinating. So when you think about wealth in terms of your time, I'm sure a lot of listeners are saying, but how do I get there? Right? If I'm working with a company or I'm in the midst of leading a startup and I'm working the 18 hours that you did, how would you coach them to reevaluate what matters in their life?
Well, I think that there are seasons in life. I'm glad that I put in the hard work that I did, because now, if anything happened, I know that I've got the grit to do whatever I need to accomplish the mission. So I'm glad I had that season. Even in it, when I was working a lot, I wasn't upset about it. I just knew that that's not how I wanted the rest of my life to be. I didn't want to be married with kids, having a schedule that is, you know, similar to that, or demanding like that. And so that was a big kind of, kind of shift for me. But I think for people that feel like they are time poor right now, it could be.
And most people do. They do, right?
You know, you could just start flexing the muscles of what it is to buy your time back. So it's not like you just have to leave your corporate gig or close your business down and get your time back. Sometimes it's that, you know, and you need to figure out what, you know, your situation is. Everyone's kind of in a different place. But it could be as simple as hiring someone else to take a role on that you don't want to do anymore or that you probably shouldn't do. It could be instead of cooking dinner that you hire it out. It could be instead of driving places, you have someone you know drive you places. It could be any errand that you need run, someone else does it. There's always a market to pay people for virtually anything. So that's one way to buy time back. But another way to buy time back is to buy assets or start investing in assets that produce income. And in time, that income can be strong enough. The cash flow can be strong Enough that you don't need to work if you don't want to. What I found with most people is most of them really need to be doing something other than what they're doing because they've done it so long, they don't appreciate it. But there are some people that love what they do. They just don't love the timeframe that they do it. There are tons of people that I work with that are working 60 hours as a lawyer, as a doctor, as a whatever. And then once they achieve financial freedom, it's not that they quit and do something else. They just work at 20 hours and they love it. And they think it's the greatest thing. And they're like, why would I ever stop doing this? It's so much on their time. So I just think each person's different. But to take the time to get clarity instead of just constantly reacting to what's going on in the world, putting out fires. If you can carve out time to be proactive and intentional and figure out what it is that you want out of life. In my book, I call it the Freedom Vision, where you articulate what that looks like, that really is where the magic begins. Because there's something that happens when there's alignment and kind of a goal or a focal point that you're pursuing.
Yes. Let's talk more about this freedom Vision. And you have an exercise that you do every year to really clarify the what you want to be experiencing through the year. So take us through that exercise and maybe also how that's impacted you and how you got started with it.
That's a great question, Susan, and I'm glad you brought this up, because this, to me, is one of the most important things that I ever did. So back when I was single, I wasn't dating anyone at this time. I just heard this incredible message that really inspired me from Matthew Kelly about creating a dreams list and living the life of your dreams and kind of crossing some dreams off every year. And that this list can just be this ongoing masterpiece. And so I created this list, and then I started making my top 10 goals for the year. And I would write these goals down, and I taped them on my bathroom mirror, and I looked at them every single day because I knew if I taped them on my bathroom mirror, I couldn't not look at them. It was obnoxious. Luckily, I had another bathroom for guests, but in my own personal master bathroom, I looked at that darn thing every single day. And it was such a great reminder to be on purpose and every year, I tracked this. And for years and years and years and years, I did this where I had my top 10. And then I would just kind of check them off as they happened. And by the end of the year, I would have close to all of them, if not all of them accomplished, and then I would have a bunch of subcategories. But I always focused on my top 10.
Can you give an example of, like, what type of goal you were looking?
Yeah. So, you know, at one point in time, it was, you know, to meet the love of my life. Right. So that was a goal back in 2008 that I was really intentional with. I wanted to become certified in scuba diving and dive at a few places that I had listed. At one point, it was to go hang gliding or skydiving. I mean, so each of these are things that I've done. I wanted to become knowledgeable and whine because I just thought it was such a fascinating world. So, you know, I hired some people and did some reading and training and figured out really how to be knowledgeable in that world. One time, it was to become a good cook. You know, I almost said chef, but I would do a disservice to anyone else that really is a chef. So to just be good at cooking some food and, you know, so just tons of stuff like that.
Were there financial goals, too?
There were always financial goals. Yeah, every year I had financial goals, and I broke it down into different categories. It was actually the categories that when I look at wealth, it was just those categories. It's physically, emotionally, spiritually, intellectually, purpose and passion Time. You know, I just broke it all down there. And, of course, course, the financial one was a big driver for me as a young guy trying to make his mark in the world, maybe prove to himself and his parents that he's got what it takes. I mean, I actually put the amount that I wanted to earn early on in my career and literally to a T like, almost every year. My number was so close to that. And then at one point, I was like, man, maybe I'm focused on the wrong thing. Maybe I shouldn't be focused on income. Maybe I should be focused on net worth. And then I was like, you know what? It's probably not net worth. Maybe I should be focused on cash flow. Maybe that's really what it should be, because you don't have to have a lot of net worth if you have cash flow. And so my numbers started shifting around, and there was, like, you know, assets that I wanted to buy and my first real estate, first home, first rental. And so it just kind of evolved from there. Over time. I saw the pattern that when I did this, I hit all my goals or most of my goals. And when I didn't, in the years prior, I was really far away because it wasn't like I didn't set goals. Well, at one point in my life, I didn't, but there was a period of time where I set goals, but I just didn't look at them a lot. So they weren't top of mind when I had them taped on my bathroom mirror. I mean, they were top of mind. And I got some stuff done. And then when I started dating my wife, Jennifer, she thought I was crazy. I mean, she had to have thought I was crazy for, you know, having these taped on my mirror. But additionally, she was not from this world. So when I talked about doing, like, an annual planning meeting, because I always planned everything out, I did a year in advance. And at that point in time, it was a ritual that I did on New Year's Day. Just whenever I got up that day, I just always took that day off before I, you know, watched sports or whatever. And I just got intentional with about, you know, four to five hours. That eventually kind of evolved into something more. And then I started doing it earlier because I wanted to be planned out before January 1st. Like, I needed a little bit of a Runway, but my wife just kind of fell in. You know, she. She trusted me in doing this stuff, even though she thought it was weird, but she trusted me. And we started doing this together, and we created this incredible plan where we talk about everything. We talk about marriage, where we are, and we're real, you know, where we are, how we're doing, where we're falling short. We talk about education for our daughter, we talk about our role in it, and, you know, the things that we can influence. We talk about parenting, we talk about.
Our faith, we talk all those different categories. This stuff works. I do something similar. It's. It's slightly different, but it's creating experiences. So what experiences do I want to have this year? And Every year since 2012, I've been doing that. And I describe it rather than things I want to accumulate. It's what do I want to be experiencing? And I break it down similarly into different categories. And I found the same thing, that usually at least 70 to 80%, sometimes 90% of the things I have on there come true in the weirdest of ways that I could have never planned it out. So I love what you're saying, because if you haven't been intentional and create some vision, you know, you think about the track star. They visualize crossing the finish line every day, every day, every day, every day without you sort of visualizing that experience and I think also connecting the emotion that you'll feel behind it. You connect those two things and you've got magic in your hands.
Yeah, there's no doubt. And I think that a lot of this comes from the space of, you know, if you don't do it, the default is just whatever happens, the default is whatever someone else is trying to accomplish in their life and the role that you play in that. But if you take the time to do it yourself. And now, you know, my wife and I have a much more drawn out plan. We actually have a template that we follow and we make fun of it. I mean, we make it fun. So what we do is we'll go out for, you know, a fun little breakfast or brunch and then dig into some planning, and then we'll have a nice lunch, and then we'll have a dinner to celebrate, and we just have a good time with it. We have our daughter that, you know, has someone else that's watching her for the day so that we're just totally present with each other and in the zone. And then quarterly, we do an overnight, just the two of us, and we check in on it. And so it's. We can assess the progress. But I just think it's important to discipline the habit of intentionality and of planning a life by design. Because most people, they're very clear on what they don't want. I ask this all the time, what do you want out of life? What are your goals? What do you. And nine times out of 10, it's, well, I can tell you I don't want this, or I hate it when this happens, or this. I dislike this. It's always what they don't want and what they don't like versus, you know, writing down and having clarity and vivid technicolor of what it is that you do want. Exactly.
Focus on what you want, what you don't want. It's funny, I say this to my mother all the time, even in simple things like watching a football game. She'll literally say, don't fumble. Don't intercept the ball. And I'm like, mom, stop putting that energy out there. Talk about what you want to have happen, not what you don't want to have happen. Because when you talk about what you don't want to have happen, you're giving energy to that and most likely you're going to create it.
That's right. Yeah. There is absolutely no doubt, just so much to be said about focusing on what it is that you really want out of life. You know, we break it down so far as to say, you know, who are the couples that we want to be intentional about spending time with? Who are the top five to 10 people that we want to get one on one time with? So maybe it's not a couple's activity, it's just us individually with our friend group, you know, who are the mentors that are imperative that we have in our life this year and who are people that aren't in our network that we really want to be in our network. You know, being intentional about finding people that we resonate with that maybe play the game of business or marriage or health at a higher level than we do.
That is so great. These are great questions. And to that level of detail now, I can imagine some skeptics might say, God, it feels like your life is too planned out. What about serendipity? What about, you know, letting some even say, the universe just bring things to you? How would you respond to that?
I'd say that it's going to happen one way or the other, so you might as well be intentional. If you're unintentional, then the same thing happens, but you don't get intentional results. So I think that serendipity happens all the time. It's all around us. It's an everyday type of occurrence. Like there are just things that are out of our control, but there's enough in our control. I mean, it's the same thing where it's like, okay, well then, you know, don't pay your bills and see what happens. You know, there's this cause and this effect. I think that when you know what you want, that cause creates this, you know, brilliant effect that helps you support this life. And if you are living a life that you want, then you have that much more passion and the ability to impact and reach people.
Yeah. And I think your categories of wealth as you've broken them down beyond just financial, you know, as I think about that I term it, as opposed to wealth abundance or an abundance mindset versus a scarcity mindset. Where do you see people getting tripped up between this distinction of an abundance mindset or scarcity mindset?
Well, most people look at resources in the world as finite. And I think the answer is that most things are pretty infinite. You know, I mean, you can Even look at natural resources and say, well, there's only so much gold or there's only so much silver or oil or whatever it is. But the reality is, if and when we run out of these, there are new compounds, new things that we find to replace what now doesn't exist. So you could look at it from a scarcity mindset, or you could look at it abundantly where the whole idea is that everything's unlimited, that there's nothing scarce with the exception of a handful of things. I mean, time is one of them. And that's one of the big things why I want to teach people that the time scarcity is a horrible trade off from the abundance of time. But the reality is your mindset is going to dictate and control all that. So until you can train your mind to be more of an abundant thinker, your default is often going to be more of a scarcity mindset. And the shift can happen real easy. It's just meeting a certain person, reading a certain book, having a certain concept explained or experienced, and it just is a moment in time where that flip can switch.
Yeah, well, I hope that's the case with this podcast. And I'm hoping that some light bulbs might be going off for people around. How am I really quantifying my life and what I want it to be and designing with much more intention after this conversation. So I'd love for people to know where they can learn more about your work, how you help people create the cash flow coming in and think differently about their time.
Sure. Well, there are a few places that people can go. Of course they can, you know, find my book on Amazon. But for anyone in your audience, they want to get a free copy of the book, they can go to lifestyleinvestorbook.com and all they got to do is pay for the shipping. We'll send it out with some other goodies and anything else that anyone wants to find is available on my website@justindonald.com I've got a handful of programs from an online course to my podcast to masterclass, Mastermind and private coaching that currently is wait list only. But there's a lot of free and unique resources. My blog is of an interesting, fascinating thing and we're revamping it right now so it will be up again here shortly. But the proceeds of my book, I want to make sure that everyone knows that as they are purchasing this. However they do, all the proceeds go to an organization called Love Justice International and it's a group that has 17 locations around the world where they're helping stop child sex trafficking and sex slaving. And so I'm just so impressed with this organization and my goal with this book is that the education can help free people and give them financial freedom, but that the proceeds of the book can actually help people gain their real God given rights and freedoms back to them.
What a higher level intention that is. So thank you for letting us know and I think that that all the more reason for our listeners to get a copy of so that's wonderful. Well, thank you for being with us today, Justin. I know you've given me a lot to think about and I know you've given our listeners some additional things to think about, particularly around how they're thinking about their time. If you like this episode, you're not going to want to miss my interview with John Rulin, founder of Giftology, who Justin also knows on maximizing customer and employee loyalty through radical generosity. Let's lead the way. Hope you enjoyed today's episode and I'd like to point you to the next important step. Hit the subscribe button to get notified when we release new content. I'll see you on the next episode of the Enlightened Executive.
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