A Man's Guide to Taking Risk | FRIDAY FIELD NOTES
Episode Stats
Summary
In this episode, I talk about the importance of taking risks in order to achieve your goals, dreams, and desires. I talk with so many men who have big goals and big dreams and desires for their life, whether it's building a family, starting a business, or exploring the world. Every man I've ever talked to has some sort of vision for what his future holds, to varying degrees. But that said, most of the men that I talk to are not willing to take the risks necessary to achieve their goals and dreams.
Transcript
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you leave, if you just quit today, you just march and storm into your boss's office and say, I quit
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and you burn all the bridges on the way out. That's a huge unnecessary risk. And again, I'm not telling
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you not to pursue the new venture, but what you could do, and this is what I did when I started
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Order of Man, I was still doing financial planning while I was doing Order of Man. So I was doing
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both and I had to bust my tail every single morning and every single evening so that I could
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make sure I got the hours in needed to grow this movement, to grow this business. I talk with so
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many men who have big goals and big dreams and desires and wishes for their life, whether it's
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building a relationship with a woman and a family, to starting a business, to getting in shape, to
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exploring the world and having adventures. Every man I've ever talked with has some sort of vision
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for what his future holds to varying degrees. But that said, most of the men that I talk with
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are not willing to take the risks necessary to achieve their goals, dreams, and desires. So
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today I want to share with you some tools that you can use, some mindsets, and some insight that I've
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personally used in my own life to build a family, to starting multiple businesses, and really building
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the type of life that I desire. And ultimately, gentlemen, that's what I want for you. I want
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you to have the kind of life and purpose and meaning and fulfillment so that you can serve
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people, you can create memories, and you can have the experience out of this thing we call
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life for yourself. So let's talk about taking risks. Now, I think it's well known at this point
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and well documented that men have a greater propensity for taking risks. And it should be that
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way. We are the leaders. We are the ones who are casting vision. We are the ones who are putting
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ourselves forward. We are the ones taking on the responsibility of leading and protecting and
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providing for ourselves and for loved ones. And when things go wrong, people look to us and they want
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us to build. Our spouses want us to create a good life. And our children look to us for leadership.
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And part of that is our requirement to take not unnecessary risks, but calculated ones. So the
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first step that you need to really consider when it comes to taking risk in your life, especially if
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you're somebody who has a hard time doing it, is really get clear on the what you want out of life
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and why you want it. Because I'm telling you, whatever you go after, if it's in business, if it's in
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your, uh, in, in finances and money, if it's in relationships, if it's in experiences, it's going
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to be difficult. It's going to get hard. People aren't going to like you. You're going to put
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yourself out there. They're going to say things about you. You're going to face lawsuits and you're
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going to run up against hurdles and obstacles. If you're growing a business and there's going to be
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interpersonal conflict with other people as you're building relationships and it will get hard.
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So you, you can implement everything that I'm going to tell you today and it will help, but it's still
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going to get difficult. And in those moments of difficulty where most men will buckle and they'll
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cower and they'll slink away into obscurity, I don't want that for you. And so you're going to have to
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rely on something pretty powerful in order to propel you forward. Because why take a risk if there's
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nothing on the other side of that risk or the potential for something great is not there. So what is
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your why? And I recommend a great book by Simon Sinek. It's called Start With Why.
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And it will really help you to articulate why you're doing the things that you're doing,
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why you want to take the risk that you want to take, why you want to pursue the ventures that are
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important and significant and meaningful to you. Because when push comes to shove and life gets hard
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and you're not making the kind of money that you want to make in that new business, or the thing isn't
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going well with the relationship with the woman that you, you love, you're going to have to find a way
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to buckle down, remember why you started doing this in the first place, remember why it was important
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to you, and then get on with whatever needs to be done in order to achieve your objectives.
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Now again, I'm not telling you to take unnecessary risks. I'm not telling you to put yourself in harm's
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way or to potentially create unnecessary weaknesses and chinks in your armor for your family. That's not
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what I'm saying. I'm saying take risks so that you can propel yourself and move forward, but you have
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to know why you're doing it. And by the way, I would also suggest that you share that with the
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people who are vested in the process. You don't need to share your why with everybody. The world
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doesn't need to be privy to the why you're doing the things that you're doing, and most people just
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aren't going to understand anyways. But if you want to share it with your wife or your kids or the people
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who will be impacted by the decisions that you're making, then absolutely. The best way to create
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your why is to start thinking about the things that you enjoy. What would you do if money were
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not an option? What are you doing when time moves the fastest? What are people coming to you for advice
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on? And you're going to start answering these questions and notice some common themes between
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the answers, and that's going to really help you uncover some things that maybe you have a propensity
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towards addressing. Another great why type exercise is to really consider what injustices you've
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experienced in life or that really resonate and speak with you. You know, I grew up as a young man
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without a permanent father figure in my life, and I think that was a great injustice. It's not fair,
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and we all know life is not fair, so I'm not here to complain about that, but I believe that every man
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or boy, I should say young man, ought to have an engaged and present father in his life.
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So much so, because I went through what that's like, that it's now become my life's work. So what
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is my why? To serve men so they can serve their sons and daughters and create a better opportunity
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for them than they may have had for themselves. Now, I'm uniquely qualified, not exclusively qualified,
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but uniquely qualified to have those conversations because it speaks to my heart. It speaks to my soul.
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I have firsthand experience with it, and because I have that firsthand experience, I'm willing to
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double down. I'm willing to invest. I'm willing to pour in where other people might falter and fall
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behind. What is your why? Why are you doing the things that you're doing? Why is that important
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to you? And the more emotionally charged it can be, where you get that little shimmer in your eye or
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shed a tear of excitement or whatever it might be over that opportunity or that new venture you're
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going to take, the better it's going to be. Make sure you're using emotion to your advantage.
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All right. Number two is you need to measure the risk versus reward. And I've talked with a lot of
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guys who will take a lot of unnecessary risk without any anticipation of anything in return.
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Obviously, at least I hope it's obvious that you're not going to do that, that you're not going to just
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wing it, that you're not going to fly by the seat of your pants, that you're not just going to do big
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things because somebody once told you that's what you ought to be doing. But it doesn't align with
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your vision. It doesn't align with your why. And there's no potential gain on the other side of
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it. But what I would also say is measure the amount of work that you do. And we're going to talk a
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little bit more about some of these things. Measure the amount of work you do based on the potential
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reward. So if I'm going to invest a thousand dollars and I might make ten dollars in exchange for
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that thousand or a rate of return of ten dollars, so less than one percent, then I'm not going to
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invest a lot of time in that. I'm not going to spend a lot of time thinking about whether I should
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or should not do this or spending my nights thinking about it and not being able to sleep.
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But I see people do that. They just pour over all of this unnecessarily. You should match your
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investment of time and energy to the potential return. If it's minimal, just do it. There's
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nothing to think about. Just do it if it seems like it's something that is in alignment with what
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you want. If it's something a little bit more potentially dangerous or puts you at a greater
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risk for loss, then you want to match your energy proportionate to the risk that you're going to be
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taking. So measure what I could potentially gain out of this versus what I might potentially lose
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and ask yourself, am I willing to lose in exchange for the potential return? And this leads us into,
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and I think this might be the most important thing here, is that you have to hedge your bets.
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And I'm not saying that you hedge by not going all in on the thing that you're excited about. That is
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not what I'm saying. I'm talking about shoring up other areas of your life so that the risks that
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you take aren't as risky as they might be to somebody else. So let me give you a prime example.
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Let's say you've been working for a consulting firm for the past 20 years, and the work is decent.
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The people you work with are fine, but you feel something calling to you, and you want to start a
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business. Maybe you want to start your own consulting company, or maybe you want to consult
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on something different, or maybe you want to pick up some new work in the tech field, or name it.
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It doesn't matter, but you want to start this other business. The way that you hedge your bets against
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things like that, because if you leave, if you just quit today, you just march and storm into your
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boss's office and say, I quit, and you burn all the bridges on the way out, that's a huge unnecessary
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risk. And again, I'm not telling you not to pursue the new venture, but what you could do,
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and this is what I did when I started Order of Man, I was still doing financial planning while I was
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doing Order of Man. So I was doing both, and I had to bust my tail every single morning and every
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single evening so that I could make sure I got the hours in needed to grow this movement, to grow this
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business. But I was doing both. When I started my own registered investment advisory firm
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in, gosh, this would have been 2011-ish, somewhere in there, I knew that I was going to be leaving
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another, a previous employer. And so I continued to work with that employer, and I served that
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employer. I fulfilled and met my obligations and responsibilities. But I was also doing the
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back-end work and research behind what does it take to start a registered investment advisory firm?
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Um, what skills do I need that I don't currently have? Taxes, for example, and bookkeeping, accounting,
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et cetera. And I would learn about those things while I was working over here, and that's how I
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hedged that time so that when I left, it wasn't that great of a risk. Another thing to consider is,
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are your, is your financial house in order? If you're up to your eyeballs in debt, and you don't know how to
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budget, and you don't know what your cash flow is on a monthly basis, you're not in the position to
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take that risk. You can't take advantage of an opportunity that's there because you're not in the
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position to do it. So for, another thing I've seen is, employers might come to you and ask you to do
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something that goes against your, your morals, and your principles, and your why, and your purpose,
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like we talked about earlier. Well, if you're strapped for cash, and up to your eyeballs in debt,
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and you're living paycheck to paycheck, yet the likelihood that you will do something that goes
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against what you believe is significantly greater than if you had $20,000, $50,000, $100,000 in the
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bank. I've heard people call it an FU fund or a walkaway fund. If you've got that kind of money,
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then you're not going to need to jeopardize your morals and principles to the degree that another
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man might need to in order to put food on his table and a roof over his kids' heads. So guys,
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get all of your things in order right now. As the proverb goes, the best time to plant a tree is
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before you need the shade. But what most men do is when they are presented with an opportunity,
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then they start fixing themselves, right? So a guy who's going through a divorce will not take care
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of himself all throughout the marriage. But then when he's going through a divorce, now it's like,
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oh, okay, now I'll get in shape and be strong and try to make myself more attractive. Or the guy who
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wants to start a business, instead of learning about how to grow a business, how to start a
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business, all the ins and outs of business, while he's not in that position, he waits until some
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friend of his comes and says, hey, I'd like to do a business together. And he's not ready for it.
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So you've got to put in the work now, get your mind right, get your finances right, get your physical
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fitness right. And not only is it going to help when you're ready to make these decisions in your
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life, but it's also going to help you live a more fulfilled life now where you currently are. So there's
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no downside to improving yourself. There's only upside down the road when opportunities inevitably
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present themselves, whether it's asking that attractive woman on a date, starting that business,
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going on that adventure, or whatever else it might be. Now, the next thing, guys, and this is point
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number four, is when we look at these risks that we're going to take, we're going to look at what's
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called a SWOT analysis. A SWOT analysis. It's an acronym. It's spelled S-W-O-T. So you're going to look
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at strengths, weaknesses, opportunities, and targets. These are the things that might end up hurting you.
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These are the things that might end up helping you. These are the, oh, I'm excuse me. I said targets,
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threats is what I meant. Strengths, weaknesses, opportunities, and threats. So when you go through
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this SWOT analysis, you're going to ask yourself, well, what are my strengths? If I'm going to go out
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and start this business, but I'm extremely, extremely disciplined, I've got the time and energy to put into
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it. I'm driven by my why. Great. Those are my strengths. We're going to lean on those strengths.
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My weaknesses, however, might be that I am not very organized or that maybe I have a lack of
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knowledge in that arena that needs to be shored up. Well, okay. Recognize what your weaknesses are
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because you can either shore them up now or you can bring people in to help you address those
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weaknesses. Opportunities are, again, to go back to what we're saying earlier, the risk versus reward.
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So opportunity is the potential reward. And the more specific you can get, the better.
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So if you're going to start a business, don't just say, oh, this is a growing space and I could make
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a lot of money, although it might be. Why specifically is it in this space? What about this space? What
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about you creates these opportunities and makes it a worthwhile investment for you? Because you might
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find out, and I've done this with a couple of businesses, ideas anyways, just recently where it just
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doesn't make sense. I'm all hopped up and excited about it. And I started doing the research and it's
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like, it's not a good time to do what I would want to do all because I did this SWOT analysis, which
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leads to the next point of SWOT, the threats. All right. If, if, if you're trying to get into a space
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that is heavily automated, that AI is currently replacing by the second, then maybe that's a threat you
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ought to be aware of and consider that it's not the best time to take that, that risk. Um, if you're
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doing something wild, like, uh, going, you know, skydiving, the threats are the, the parachute
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doesn't open up or the, the parachute malfunctions or your instructor teaches you something wrong,
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or you get scared in the moment and do something wrong. And so anticipate those things. Here's what
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could go wrong. That's why you always have a backup parachute just in case the first one
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malfunctions or doesn't deploy. You have the backup. And that's why it's important to know
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what those threats are because you're hedging to go back to point number three, you're hedging your
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bets against the loss you could inevitably face if you went into it ignorant and blind. So use that
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SWOT analysis. Now, if it comes to taking a risk by asking a woman on a date, again, to go back to
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what I said earlier, you don't need to spend a lot of time thinking about the SWOT analysis, whether
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or not, um, she's going to reject you or, or be open to your solicitation. Like it's just not
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something you should do, but if it's something bigger and greater and grander with a potential
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of risk and loss, then the SWOT analysis is, is crucial. And then the last thing here, guys,
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that I want to share with you is getting coaching. All right. I, I cannot tell you how many men
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that I've talked with and told them to coat, to get coaching, to get advice, to get insight,
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to listen to podcasts, to, um, sign up for email newsletters, to go to events that these
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individuals put on, to invest in books and courses and programs and events that are available.
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And then ultimately hire for group coaching or individual coaching. If you're in that position,
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because those individuals have already done what you're going to do, which means they've already
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stepped in all the cracks along the road. They know where it's dangerous. They know what happens
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when you mess up. They know where the threats are that you can't even possibly acknowledge right
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now. So get yourself a coach, hire a mentor, hire a coach, go to courses, go to events, get programs,
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listen to, um, podcasts, read their emails and their books and everything else, because they're
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going to help you understand what you're actually signing up for, because you don't know right now.
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You have an idea. You've done some research as we talked about, you're hedging your bets like we
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talked about, but ultimately you're still going into it somewhat blind and you don't need it.
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You don't need to reinvent the wheel. I get it. It's sexy. It feels like you're actually doing
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something good. But if somebody has already invented the wheel, just take the wheel and then focus on a
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different problem because that one's already solved. And that's the power of coaching guys. I really
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want you to take more calculated risks. And I should say righteous risk. I hope that, I hope
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that's inherent in what I'm saying, that we have a righteous mandate to protect, provide, and preside
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for ourselves, for our loved ones, and also for people who can't do it for themselves. That's our
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job. That's our responsibility and duty. And it's going to require that we're bold and courageous and
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that we take risk and that we put ourselves out there and we potentially expose ourselves to
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financial hardship, to emotional frustration, to maybe even cultural pushback. It's part of the
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deal, but we have to take the risk to do something big in our lives. And every single one of you,
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I know because you're listening to this podcast, have a goal for what your future holds. It's going to
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require you doing the work. And I hope that these steps help. Again, know what you want and why.
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Start with why by Simon Sinek. Measure the risk versus reward and then act accordingly. Invest your
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time and energy and resources accordingly. Number three, hedge your bets, not by not going all in,
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but by shoring up every aspect of your life right now. So you lessen the risk that you're going to
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expose yourself to. Number four, the SWOT analysis. And then number five, get yourself some coaching.
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And on that note, if you are interested in whether it's coaching, one-to-one coaching with me,
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I am going to be taking on a few, a handful of men that I'm going to work directly with
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in Q4, rolling into Q1. If you want to, and I've never done this before, this is brand new.
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So if you want to improve your finances, you want to start a business, you want to figure out how better
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to connect with important people in your life, you want to get fit and strong. Again, I'm going
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to be doing individual coaching for a handful of men throughout the rest of the year. And as we go
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into 2026. So if you're interested in that, you can email me, Ryan at order of man type in coaching,
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and I'll talk with you about what that would entail and what that looks like. And outside of that,
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make sure you check out our group. It's called the iron council. We've been going for 10 years now.
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It's open. I think as of yesterday, we had 59, I think 59 new members. These are all men who are
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motivated, ambitious, driven, and they're working with a one-to-one coach for 30 days to get them
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up to speed so they can start implementing the systems that we have in place. A couple of resources
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for you. Guys, it's important that we as men take those risks and we do what needs to be done in order
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to serve ourselves, our families, our communities, and the world. I hope that helps. We will be back next
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week. Until then, go out there, take action, and become the man you are meant to be.
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Thank you for listening to the Order of Man podcast. If you're ready to take charge of your
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life and be more of the man you were meant to be, we invite you to join the order at orderofman.com.