https://youtu.be/etlBrw4WKGw?si=NxtN4Gg1iZ02nmgV
Ron Monteiro, Keynote Speaker, Facilitator, Trainer, and Author of Love Mondays, is driven by a mission to help professionals discover their purpose, build fulfilling careers, and burn their boats to fully commit to meaningful work.
We learn about Ron’s journey from a finance executive to an entrepreneur, speaker, and author, and how he embraced the Ikigai framework—a Japanese philosophy for finding meaning in work. He introduces the Path to Entrepreneurship Framework, a four-step approach that helps individuals transition from corporate life to a career they love: Find Your Purpose, Build Your Bridge, Burn Your Boats, and Flex Your Muscle. Ron shares insights on overcoming fear, learning to say no, and balancing financial stability with the pursuit of passion, while also exploring the mindset shifts needed to create a career where every day—not just Mondays—feels meaningful and exciting.
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Burn Your Boats
Good day, dear listeners, Steve Preda here with the Management Blueprint Podcast. And my guest today is Ron Monteiro, keynote speaker, facilitator, trainer, and the author of Love Mondays. Ron, welcome to the show.
Thank you, Steve. I’m very excited to be here.
Well, it’s exciting to have you. You have a very interesting career coming across the world to be here with us. And you also have some interesting frameworks that you’re using. So, let’s start with what drives you. What is your personal “Why?” And what is this Ikigai process that you mentioned on social media and your posts that help people find theirs?
Yeah, I want to rewind. Like I’m a big proponent of purpose and life work and things like that. Many years ago, I would be shaking my head because I wasn’t clear on my purpose. So, I’ve done a lot of work and a lot of personal development work that a lot of it talks about how do you start with what is your “Why,” what is your purpose? Simon Sinek, as you’ve mentioned. And my purpose now is I get a lot of joy from helping others. So, the way I’ve phrased it, how do I help myself and others love Mondays and every other day? And I think it connects to my book, which talks about how do you love Mondays? So today’s a Monday that we’re recording, and every other day. And then
Ikigai is a beautiful Japanese concept that talks about people who don't even have a word for retirement. They love what they're doing so much, and it's connected to their life purpose.
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So, Ikigai is a framework I love.
There’s a whole book on Ikigai, if anybody’s interested, which asks four simple questions. “What do you love to do?” is the first one. And this is something we journal. So let’s say five years from now, what I love to do might be slightly different than today. So it’s not a fixed destination. It’s one of those iterative processes. So, you start with “What do I love to do?” The second is, “What am I good at?” So for me, I love teaching and I think I’m pretty good at it. I’ve done it for a while now. So, what do I love doing? The third is “What does the world need?” Okay, so if I continue with my example, I think the world needs people to teach them things. So, for me, one of my favorite topics to teach is soft skills and story time because I really struggled there. I landed a company that helped me overcome my fear and now I teach it for a living. So that in itself is a “Why” for me. And then the fourth question is, “What can you get paid for?” I know inflation and all these things are coming into play. So, if you can answer those four questions and it’s right in the bullseye, right in the heart of those, and think about four circles, concentric circles. If you find something that’s in the middle there, it’s your Ikigai, it’s your reason for living, it’s your reason for waking up on a Monday and every other day. And that’s, to me, a lifelong journey. And if you hit any of those two questions in isolation, it might be a profession or a vocation or something like that and so there’s a beautiful visual and I can send it to you, I’ve included it in my book, which shows it graphically. And so if you take the time to journal on those four questions, you can find your Ikigai. So I love the concept.
Yeah, that’s awesome. Jim Collins talks about this idea of the economy engine, and what is the economy engine of your business, and it has to be your “Why,” your purpose, and what you are really good at. And the third one is “What can sell?” And then in the middle, but that’s only three circles. So, you have a fourth circle and that’s the Ikigai in the center. Very interesting. So, tell me about how you found your Ikigai. How did you land on what you love doing and what people need and you also pay for? What was your process?
Yeah, I love Steve Jobs’ quote, which talks about, it’s really messy going forward, but when you connect the dots backwards, it makes a lot of sense. So, one of my favorite examples ever in business is he took this course on typography when he had dropped out of college because he was interested and then he brought it to the Macbook. So, my story is obviously not comparable to Steve Jobs, but it’s very messy going forward. I didn’t have this plan. I was just trying to do things that I love to do, like teaching and training. And I was doing a lot of speaking for free, whenever I could get some experience to do what I wanted to do, invest the time and energy. I did a free webinar, for example, where I was speaking around the world during COVID. I wasn’t getting paid, and that’s where I met my business partner.
So many things that I’ve tried to do within that Ikigai concept. What do I love to do? What am I going to do? Even if I do it for free, it’s in the spirit of building confidence and competence because I went through a 20-year corporate career. I was doing finance and now I’m a speaker and author and trainer. It’s a very different profession. So I had to find a way to bridge between the two. And I actually hired a coach. And one of the big things was how do I spend more and more time doing the things I want to do, while at the same time, I’m still working full time because I had to pay my bills. So it’s a clean process if you look backwards, but at the time it was very messy. And entrepreneurship for me has been a fun road, but there’s times where it’s been very stressful, there’s times it’s been messy, and even now with all the stuff going on in the political world, many companies might put a hold on training, I still have to say, okay, I’m going to work that much harder to get my business going. So yeah, it’s been a fun road, but but challenging and exciting at the same time.
Yeah, I like to think about this, what you’re talking about, what you’re describing is that during the eight to four, whatever, nine to five, you really are selling your hours to someone. And then the rest of the time, you can work on building your own business. And when you do that on your own time, it’s really hard. It goes very slowly. You’re trying to figure things out. And when you get to this tipping point, then you can leave that job and make your entrepreneur venture the full time. That’s fantastic. But then you have the challenges of entrepreneurship. So, yeah, it definitely is messy. I can relate to this. Let’s talk about your framework. So this is a podcast of frameworks and I’m always looking for something unique. We are over 250 episodes in and what is a framework that you or your colleagues have developed or stumbled upon that really helped you achieve something?
Yeah, so one of the frameworks I use in the book is, how did I get from working full-time to now running my own business? And the four steps, and I go through them in detail, I share my own experiences, I share other stories. Number one is what we talked about already, find your purpose. And so you could use your Ikigai, you could use the Jim Collins framework you mentioned, but let’s be clear on, what is our “Why,” what’s our purpose, what’s our reason for being? So that’s step one. And we’ve got some exercises in there to say how do people actually work through it? That was very important to me. Step two is what I call build your bridge.
So this is me, picture me as a finance person who now wants to go speak on stages and do training sessions. It was foreign to many people. So what I did was I actually hired a coach and he had this brilliant metaphor for me, which is build your bridge. And he always used to say, Ron, one line at a time. We’re gonna do this, we’re gonna do it one line at a time. And, honestly, if I didn’t have that coach, his name’s Wayne, he’s a dear friend of mine now, I probably would not be talking to you today. Because another big lesson I learned is surround yourself with the people who are gonna uplift you and are gonna help you get to where you want to go. So I slowly built my bridge one line at a time. And that step is all about building enough confidence and competence. You talked about, what’s that time to take the leap? Okay, so that’s step two. Step three is pretty provocative. It’s burn your boats. If this is the time, go all in. For me, it was resigning from my job because I now felt like I could do this on my own. And what it also does is it just says, look, you’re going all in.
There’s no paycheck coming in every two weeks. I didn’t have a paycheck coming in every two weeks after that. And that’s when it’s like, okay, it’s time to sink or swim. And I had to fight for it. And so that’s an interesting time. And I never tell people to do that too early because you have to do a lot of work ahead of time to get there. That’s the burn your boats. And step four is flex your muscle, which, look, we’re in a constantly changing world. I always want to say it’s a constant journey. There’s never a destination. Like, I listen to a lot of podcasts. I listened to one on the weekend where it was this billionaire and he was talking about there’s no door where you hit the door and okay, success is here. It’s the constantly evolving journey. So that’s my four step framework. And again, it’s like, it’s iterative, like you may do it and then come back to it because your purpose is slightly evolved and change it. So it’s a fun framework that I work through that I reflected on after. Again, when I went through the process, it’s not like I had this four part framework I was working on, but what I tried to do is say, for future entrepreneurs, for people trying to find their Ikigai, here might be a little bit more of a methodical process than what I used.
Yeah, I like this to build the bridge and then burn your boats. It’s when you’re back against the wall and you really have to deliver. It’s amazing the energy it can release, but it’s a scary thing. And I kind of have this thought that the most successful entrepreneurs are the ones that are willing to put themselves in the biggest jeopardy because they know that they have the internal resources that they can mobilize, but they will only be mobilized if you really have to, because it’s very hard, you have to dig really deep. And the ones that are willing to put themselves there, I mean, Elon Musk is not a perfect example these days, but he did sleep under his desk in Tesla when he was trying to get it to 5,000 a week production. He did appoint himself as head of engineering of SpaceX when he was in over his head with how to even do that. So this kind of mentality really helps, but it’s also super scary. You have to have the confidence that you will be able to prevail. What’s been the hardest decision you’ve ever had to make in your business?
In my business, I think what’s hard is also saying no. So for me, it was a great lesson to learn, but it was hard. When I first started, again, as a finance executive, I’m trying to make a living now, I was struggling. There was zero revenue coming through. So what I decided to do is anything that had a dollar sign to it, I’m doing it. So whether it’s write an article, train on subjects which I have no business training on. I did a lot of things in the beginning to say, okay, I just need to start generating revenue. I got to the point where now a lot of opportunities were coming my way and I had to learn how to say no. So it was hard to do, but it’s a wonderful thing when you learn it because before it’s almost like, FOMO, fear of missing out. Am I missing out on an opportunity that I could have some revenue and grow my business and things like that?
And I found, again, it connecting back to the Ikigai concept. I think I learned that a good framework for making a decision of yes or no is not money, it’s “Am I going to add value?” Am I going to love that? So, for example, now if I still, look, it’s a business, so there’s certain things I do where in an ideal world I might not do it, so I don’t want to paint a picture where it’s all rosy. But there’s certain things where I’m just very clear, is it a hell yes or a no? And if it’s not a hell yes, then maybe it’s not worth doing. So that was a hard lesson for me to learn. And then I think the hardest decision was the decision to quit my job. To say, look, I’m going to go in and I’m going to basically tell them I’m leaving. And two weeks from now, there’s no paycheck coming in. Zero. So that is a very hard decision. But that was the burn the boats, as we talked about before.
Yeah, because
at some point, your time becomes the most valuable commodity and your attention. And if you have to split it between your job and between your venture, you're never going to give what your venture needs to really take off.
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And at some point, you have to say, okay, I’m going to lean into this and try to make it happen.Yeah. Amazing. And we’re all different. Like if some people want to run their business as a side hustle and they still love their day job, that’s perfect. Everybody’s journey is a little bit different.
Yeah. So actually what happened to me about 25 years ago now, it’s crazy to think, 23, is that I got fired from a bank and I was 35 years old and since the age of 20 I’ve always wanted to be an entrepreneur but I had these great opportunities that, it’s like I was in a golden cage situation and suddenly I got fired and I just said, okay, this is my time and I’ve walked across the street and I got fired on Friday. Monday, I was in business and it was a wonderful thing in one way to have the freedom that nobody’s looking over my shoulder but then obviously the reality set in as well that there’s no help now. I’m on my own, I have to do everything myself. My company name is completely unknown and people will not necessarily take my call because they just took it because I was part of this big bank and they had this big balance sheet behind me. So that was super scary.
Yeah, I can see that. But that’s a lot of courage you took.
Well, that’s the point that I did have to take the courage because I was pushed. I was by default courageous. But anyhow, tell me a little bit about your book and why did you pick this title, Love Mondays, and how to love Mondays? How should we love? How do we get to the point where we can love Mondays?
Yeah, so I’ve been in business for 20 something years, working for businesses and I always used to hear people, oh, it’s Monday, like the energy is very low. And then you get to the middle of the week, oh, it’s pump day, a little bit of excitement. A hint of a smile. Well, before that, I even hear Happy Junior Friday, which is Thursday, and I’m just like, I get it, like I love the weekends as well, but imagine a world where everybody was excited on Monday, where people were like, happy Monday, and they really meant it. And when people do not have as much anxiety on Sundays, because many people feel anxiety on Sundays, because the work week is starting. And I know people in my book who jump out of bed at 4:30 in the morning on a Monday because they’re so excited about the week. I’m not quite there yet. I love what I’m doing, but imagine if we can help more and more people find what they truly love to do. So that’s the reason behind the book. And I’ve been fortunate to have a lot of people around me who have helped me build my business to the point where I love Mondays. I do love it, so I want to share. How do other people who maybe don’t believe it’s possible, go step by step and find that journey and that path.
I used to love Mondays a lot. I still actually like them, but I absolutely loved them when my children were small, and sometimes the weekends felt like a heavier lift than the week. It was a combination of, I love my business, I knew I was gonna do my stuff on my business. I couldn’t wait to get going. Sunday afternoon, I already started. And it was also my comfort zone because I no longer had to chase these three or four year olds down the playground and I could actually work at my desk in a comfortable situation with my mind. And I hated Fridays because I was always guilty that I still haven’t finished my stuff and it’s already the weekend and I have to go home and I have unfinished stuff. So I kind of cringed about this Happy Friday for years because I thought it was very lame.
But that’s a wonderful example. If you loved your Mondays and every other day to the point where you weren’t super excited about the weekend. My kids are teenagers now, so I know what stage you’re talking about. And for me, it’s like, how do I find, I don’t wanna use the word work-life balance, how do I find harmony between the two where I love both? I love the weekends and I love the week. I love everyday. And that’s what I’m chasing. Like, how do I find that sweet spot? And it takes a lot of work. It’s like the flex your muscle. You gotta keep flexing your muscles.
Yeah, that’s right. I love the flex. So, the flex your muscle, so what is the process exactly? How do you flex it? So you burned your boat, you’re kind of gaining traction with your business. How do you go from kind of surviving or getting by to flexing your muscles?
Yeah, so I think the way I was using flex your muscles is really adapting to the environment as well as adapting to changes in yourself. And I’ll give you two examples. So, for example, during COVID, I had to switch from in-person session to Zoom or Teams, like most of us did. But you could look at that as a glass half empty, which is, oh man, I’m gonna have to learn Zoom and it’s gonna be so hard. Or you could say, instead of now, I live in Toronto, Canada, instead of my market being Toronto, Canada, it’s the world. Taking that opportunity to say, wow, now instead of just being limited to Toronto, I can keep around the world. I got this chance to teach in Vietnam, in Hawaii, in India. Whereas before the pandemic, I was doing it in Toronto, which I loved.
But now, so that’s number one, being flexible to say, okay, maybe there’s an opportunity even when something seems hard. And now the second part of adapting to yourself. So, when I first started, I wanted to be a coach, personal coach 101. I realized where do you get paid and it hits your other questions was corporate training, so I started switching more into corporate training. I still do coaching as well and now my latest evolution is because I wrote the book there’s more speaking opportunities I want to adjust to. So it’s being able to really be flexible and say, okay, there’s coaching, there’s training, there’s speaking and if I just said, oh, I want to be a coach and I’m not leaving that zone, that would have really limited me. So I’m saying, okay, how do I be flexible but still try to hit those Ikigai questions and adapt to the environment and myself because I’m changing. I’m a different person than four years ago when I first started my business.
I mean, what’s wonderful about writing books and being a speaker is that you grow from coaching one-on-one to coaching one-to-many and then to speaking one too many, like keynotes. And then with the book, you can reach people who are in different time zones and they are following you through your books and you’re expanding your audience, you’re expanding your impact. So if your Ikigai is to help people, then this is a really great opportunity to do that. So just a question related to this, the switching, the flexing the muscle and kind of shifting the priorities and saying no to things that are not, hell yes. One way for me to do that is to look at, okay, where do I deliver more value? What are the ways I can deliver more value? And if I prioritize those ways where there’s more value and say no to the lesser value, then I’m freeing up time to be available for those opportunities with the higher way. Of course, there’s the in-between when I’m not doing it, but how do you make the difference? Do you just use your emotional resonance to it?
Yeah, I was thinking about that question even this morning. I go for a morning walk with our dog, and I have these thoughts going on in my head, and I actually still think I’m doing too many things. I was listening to a podcast by Seth Godin, and he has this concept which I’ve heard before. He’s like, how do you be the best in the world at one thing? And so, it’s something I’m starting to think about to say, okay, I’ve taken on a lot. I still have a lot of things I’m doing. Do I need to refine that search? Do I need to bring it in a little? But again, it takes a little bit of courage to, but it’s a little bit of another burn the boats moment, which says, okay, I’m getting revenue from a few different things here. If I stop A, B and C and focus on D, there’s probably gonna be a short-term dip again. And it’s gonna take that same courage, that same persistence, that same resilience. So I think it’s a continuous journey. But I think, again, when you think about people who are very successful, many of them have chosen to be best in the world at one thing, which is very hard to do. Even for me, it would be very hard to let go of these things I’m pretty good at, to say, okay, I’m just going to do the one thing I’m great at. So maybe that’s like a future discussion between me and you.
Yeah, and then obviously there’s a risk that you pick the wrong lane and suddenly that market dries up and then you have completely bet on the wrong horse. I love this quote from Andrew Carnegie when they ask him that, Mr. Carnegie, why do you put all your eggs in one basket? And isn’t that too risky to just double down on the steel industry? And he said, I put all my eggs in one basket and then I watched that basket.
Yeah, a wonderful story. I mean, I think he commissioned Napoleon Hill to write Think and Grow Rich. So, he knew what he was talking about. And so like, for example, where I started my business was soft skills for accountants. If I doubled down and said, I’m gonna message every single accountant I know, and I just focused on it, I think I could be very successful. So, I think it’s like, it’s another level of courage to say, I’m going to just go all in on one thing.
Especially in a globalized world where people want to seek out the number one expert in something because our time is so valuable. We don’t want to squander it on second rate people. You want to find the one person and let them teach you so that you become the best in that regard. Well, I also started life as an accountant, so I can totally relate to this.
All right. So as we are wrapping up this interview, what do you think is the most important question an entrepreneur should be asking themselves?
I think it is what we are just talking about is like, what is the value that you’re providing to your customer? What’s the value you’re providing to the world? And being very authentic, like, what is Steve uniquely positioned to provide value to his clients and serve them in a way that’s, like there’s a book somewhere on my shelf, I think I see it’s a yellow book, it’s called Unreasonable Hospitality. I don’t know if you’ve ever seen that book. But it was a restaurant that basically became the number one in the world because they were unreasonable in the way they served their clients. So, I think with entrepreneurship, and it’s very hard to find a company that just says I’m going to be the best in the world at this. So, I think the big question, to me, is like what is something that you, or your listeners, or me say I can do this better than anyone in the world because I have passion, energy, skill, all these things that when business gets hard, you’re still gonna be motivated.
And I have like 20 people in the back of my book who, for example, Nancy MacKay, the CEO of MacKay CEO Forums, I’m a part of that organization. She tells me she wakes up at 4:30 in the morning and she’s excited to run her business. And then she can connect it back to her childhood where she wanted to be a teacher and she’s, in a way, a teacher now. And so it’s like, think about those people, like so excited, like you were talking about how you were excited on those Mondays and not excited on Fridays. You’re naturally going to do it even when the going gets tough. Because in business and life, we’re going to hit these tough periods. And to me,
the people who are willing to just fight through those tough days are the ones who ultimately are happy, fulfilled, have more joy.
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And that’s the provocation of my book, where it’s so easy to just settle. Like for me, I was an accountant, a finance executive, senior director title, every outside in looking in, people are like, this is a successful guy, he has a family, a house. I wasn’t happy on the inside, because I wasn’t doing my work. And especially the first couple of years, I wasn’t making anywhere near the same money, but I was much happier. Like people tell me, oh, you have so much energy. It’s because I’m doing the things I love.
Was your wife happier as well?
My wife’s very happy. She actually was such a big support, because look, we have two kids at the time. They were less than 10 years old or just around 10 years old. Big mortgage, big bill. So, it wasn’t an easy decision. She was very supportive. And what’s been amazing is now she’s on her own journey. Like she’s a teacher, but she’s learning how to be a yoga instructor and she went on this retreat a few weeks ago and stuff. So she’s kind of seen what I’m doing and now she’s on her version of that journey and she’s inspiring a whole bunch of people to do that. So, it has this nice ripple effect when you, as you talked about risk earlier, and I don’t want people to take an uncalculated risk, a risk where you’ve done the preparation ahead of time, you’re ready to burn your boats is such a rewarding risk. Because I honestly, even if my business didn’t succeed and I went back to corporate, I would be a much happier person because I tried. And so it’s a good lesson in life is to, a lot of us have these ideas and many times I never acted on them. I now talk about, okay, what’s the one action I’m going to take?
Actually, I know people who have tried entrepreneurship and failed and went back to corporate life and they were actually much more contended in their corporate life.
They knew that entrepreneurship was not for them, they didn’t leave anything on the table, they did try and now they know that they were in the right place, they were doing what was the right thing for them and they didn’t worry about missing out, they didn’t have the FOMO anymore.
Yeah, one of my favorite quotes is by a guy named Wayne Dyer, a spiritual guy, I don’t know if you’ve ever read his work.
Amazing, and he says,
Don't die with your music still in you.
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And so for me, writing my book and starting my own business, I feel so much joy because I’ve gone for it. Whether it’s successful or not, I mean, that’s all subjective anyway, it’s more the fact that I’m now willing to put myself out there.
And what’s the worst thing that can happen anyway?
There you go. And I’m naturally an introverted person. Like I’m very quiet naturally, but now like, because I’ve done all these things, I have so much to talk about and share with people. And similar to you, like I see your book beside you and I see all those books there and I see how much you’re sharing. Here’s what I’ve done in my entrepreneurship journey.
That’s awesome. Well, Ron Monteiro, keynote speaker, facilitator, trainer, and the author of Love Mondays. So if people would like to connect with you or learn more about it or buy your book, where should they go?
Yeah, so my book, Love Mondays, bright yellow book, it’s on Amazon. So go to your local Amazon. And LinkedIn’s where I spend most of my time. So I’ve chosen to spend time on LinkedIn and pretty much nothing else on social media. So LinkedIn is my place to be.
That’s right. So you’re inch wide and mile deep on LinkedIn. You’re doing the right thing. You’re burning your boats on Twitter and the other social media. Very good. So Ron, thanks for coming on the show and sharing your wisdom. And those of you that enjoyed this interview, please make sure to comment and follow us on YouTube and give us a review on Apple Podcasts or wherever you’re listening to your podcast. Thanks for coming, Ron, and thanks for listening.
Important Links:
Ron’s LinkedInLove Mondays! By Ron MonteiroRelevant Summit OS® tools: Summit Vision™, Rock-Step Planner™, Vision & Strategy Map™, and Your Company Why™