Midlife Revolution Unleashed

Fortune Favors the Bold: Embracing Courage at Midlife

• Stacy M. Lewis & Wayne Dawson • Season 3 • Episode 61

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Season 3 of Midlife Revolution Unleashed launches with a powerful exploration of boldness, risk, and possibility in midlife. Coaches Wayne and Stacy discuss how to cultivate courage without ignoring wisdom and why taking bold steps is essential for creating a fulfilling next chapter.

• Fear of failure and fear of success can both prevent us from taking bold action in midlife
• The "fortune" that favors the bold includes opportunities, relationships, and purpose, not just financial gain
• Internal obstacles often present bigger barriers than external circumstances when taking risks
• Assessing readiness before taking bold steps includes asking challenging questions about resources and capacity
• Creating a clear plan with specific intentions allows for evolution while maintaining direction
• Having a cushion (financial, time, or support) is responsible preparation, not lack of faith
• Leveraging a trusted network provides honest feedback that helps refine bold moves
• Continuing to learn and grow keeps us adaptable as we take new risks
• Breaking bold moves into micro-steps makes progress more achievable
• Celebrating small victories maintains momentum toward larger goals
• Asking what we gain or lose by taking action versus not taking action helps clarify decisions
• Your bold step should align with your values and purpose, not someone else's definition of boldness

What bold step will you take in the next 30 days, and how will you hold yourself accountable? 

Grab Coach Wayne's Free Self-Alignment Assessment: https://viptl.fillout.com/purpose-self-assessment

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Share your thoughts in the comments or send us a text. We love to hear from our listeners

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Coach Stacy:

What's one bold step you've been putting off and what might happen if you actually took it this year. Season 3 is about boldness, risk and possibility in midlife. Today, we'll explore what boldness looks like, why it's often hardest in midlife and how you can cultivate courage without ignoring wisdom.

Coach Wayne:

You found a midlife revolution, unleashed the space to embrace your wisdom, reignite your passions and move boldly into what's next. I am Coach Wayne, the VIP coach.

Coach Stacy:

And I'm Coach Stacey M Lewis. We're here with insights, stories and strategies to fuel your midlife journey. So take a breath, Lean in. Your revolution starts now.

Coach Wayne:

Hey, welcome back everybody. We are live on direct. We have had a break a little step away from the microphone, but here we are bigger, bolder and better. Good evening, stacey. How are you?

Coach Stacy:

Coach Wayne, I am well and welcome to Midlife. Revolution Unleashed Season 3. We are so excited to be back and, Wayne, it is always good to share space with you. Same here, Stacey.

Coach Wayne:

I was suffering a little bit from withdrawal throughout the course of not having us together, sharing with our audience, and so I'm happy and delighted to get back. In fact, you know, I'm going back to the bottle, I'm going to have a drink to us you should include me in.

Coach Stacy:

You know cheers.

Coach Wayne:

Cheers. Absolutely so Stacey. What has been happening with you and in regards to what we're going to talk about tonight, which is stepping out and fortune favors the bold, what sort of bold steps have you either not made or intend to make?

Coach Stacy:

Well, I'll talk about a bold step I made today, which I don't know if it was my wisest, but I was bold and so I was invited to speak on a panel, and while I had prepared, I did not necessarily refresh the way I normally would. So usually the night before I'm refreshing, I'm reviewing, and I decided that fortune favors the bold, so I'm gonna move forward. I have everything I need to be successful, and so I stepped on that stage and I gave it my best, and I will say I felt bold in the process and I was elated to hear that, indeed, what I had to say was resonant with others and that others appreciated my contribution to the event event, I love it.

Coach Wayne:

And you speak to something that later on we want to touch on, which is when we are deciding to get bold. We have to just overcome that voice that's saying to us you're not ready, You're not prepared, Maybe you're not even good enough right, and we have to step out on faith, overcoming fear. That's part of the idea of being bold where fortune favors the bold.

Coach Stacy:

Right, and I think we're talking not fortune wealth, financial wealth but really fortune, the opportunities fortune, the new relationships, fortune really moving forward in your purpose and your passion and your possibility. So that's the fortune that favors the bold, and for some, yes, it also becomes a lucrative type of fortune, but we want to make sure that we're really focused on you, and I spend a lot of time talking about values and things of that nature, and while, yes, wealth financial wealth is a value, it is not paramount, and so we're talking about fortune that favors the bold, in midlife in particular, to help us live the next seasons as our best seasons. Yes, Stacey the Alchemist.

Coach Wayne:

The book the Alchemist. Did you read it?

Coach Stacy:

I did not.

Coach Wayne:

Okay, it's a good read. And the author, paulo Coelho. He says he's a Brazilian novelist and he says that there is only one thing that makes a dream impossible to achieve, and that is the fear of failure. And I agree with him. I know, stacey, that oftentimes I am double guessing myself, I self-flagellate, but I was speaking with someone the other day and he said that, wayne, it's not always the fear of failure, but sometimes we fear success, taking a step. And so what might we have to become to be able to step out boldly and take the risk of either success or failure, just by stepping out boldly?

Coach Stacy:

It's a great question, and what comes to mind for me is, you know, as you, both you and I do coaching is that what we really have to overcome? Is that mindset? So, whether it's fear, whether it's not going to be successful, for some negative narrative that we have going on in our have going on in our heads that those are really the barriers to press through, it's usually not the external obstacles, but the internal obstacles. At least, when I've been challenged with doing something bold, it's been the internal obstacles, and many that I interact with feel the same.

Coach Wayne:

I agree. So, if I may follow your direction, stacey, what you're saying is that oftentimes it's not the external stuff that gets in the way, it's the internal game, the inner game, that gets in the way in terms of stepping out. And that would mean that, as we adults greater than the average person, because we're talking about midlifers that we have oftentimes gone through lots of failures, and so we inform ourselves based on failures, saying, oh, I don't want to fail again. And we have that dialogue, that conversation, that inner conversation. To your point, what you're saying is we have to shut that down and have that mindset and mind shift where we have a growth mindset if we want to achieve that fortune.

Coach Stacy:

Absolutely, because in midlife the risks or what we might have to lose feel larger. Right, we've acquired things, we own things, we are responsible for things, whether they be people, finances, homes, our reputation, that we, those risks, risking those things, feels much more heavier than it did, at least for me, when I was 25. You know, it felt like that was the time to take a risk, but realistically, this is a good time to take risks, yeah.

Coach Wayne:

Stacey, you know I fired Corporate America four years ago now, at the end of or the start of COVID, and that was tough. I was in a position where great benefits, fair income and I struggled with the idea that what if? What if I failed at this, you know, would people?

Coach Wayne:

mock me Would people say, hey, you're too old at this point to be making that kind of risky decision. You got to protect your family, serve your family. But it's one of the best decisions I've made because of the freedom and the exercise that I've gotten to live my purpose right and live my dreams, and so I wanted to go through with you some of the steps that I have adapted and perhaps you could help to walk us through that so that our audience, if you're listening, that that may be something that is calling on you.

Coach Wayne:

And the first thing that I had to do Stacy was to assess my readiness. I had to be pretty clear that I had some savings. I had to be pretty clear what direction I wanted to go and I had to be pretty clear you know who I was going to be serving and what I was going to be dishing out. My readiness assessment.

Coach Stacy:

Yes, assessing your readiness is critical and, to your point, really asking yourself the challenging questions right, or the thought provoking questions that may not be answered in one sitting, those that you might have to journal about or those that you might have to really come back to come to one response, one answer, one conclusion, and then give yourself some time to come back to that, to really thoroughly assess your readiness. It's critical Whenever we're making real decisions, we have to assess our readiness.

Coach Wayne:

Thank you, and Stacey, I also had to you there, so I had to have a very clear plan as I was stepping out of corporates to go into entrepreneurism. Would you say that that makes sense to you, stacey?

Coach Stacy:

I would say a plan is critical, even if you create a plan that you know will evolve. But that level of preparation should come with very direct intention, right that you are building a plan with the intention of taking this bold step, making this new action. And so planning is critical. Planning is critical and I would just add, planning with very clear, direct, specific intention is what we would encourage tonight.

Coach Wayne:

Yeah, this one may be controversial, I don't know what you think about it. And so some people. I tell people oftentimes that, like Cortez, when I entered the realm of entrepreneurism, I burnt the ships in the harbor so that there was no retreat. But some people often think that you should have a cushion. So when you're taking a bold step, especially in midlife, it is oftentimes advised to have a cushion. And I would say this though I burnt the ships, I had savings put aside, so I did have a cushion. And I would say this though I burnt the ships, I had Sabins put aside, so I did have a cushion of sorts. What say you, stacey?

Coach Stacy:

That is a good one and I can see why you prefaced it by saying it sometime controversial. Some of the arguments we say that I've heard about, you know, having a plan B or you know having that cushion is in competition with faith, right that? Like? Well, either you believe you're supposed to do this or take this bold action or you don't. And at the same time, going back to the point you just made about preparation or planning, right that it is planning for the rainy day or for the?

Coach Stacy:

If this goes a little bit to the left, the, if this goes a little bit to the left, how would that impact? Or what would I want? How would I want to respond to whatever takes place and sometime? That cushion is critical. And in this season, going back to not having a lot to risk, I think that the cushion becomes even more critical in this season because we have so much more on the line. So, while it might not be the most fluffy cushion you ever had in the whole wide world, I do agree that having a cushion, whatever that looks like, a cushion, whatever that looks like when it comes to taking bold action, is warranted.

Coach Wayne:

Yeah, and the reason it's controversial to your point is that, as people of faith, oftentimes folks are saying just make a move, god will provide and take care of you. But there's a thin line between responsibility as well, in terms of, you know, rational thinking and being responsible, doing your part. So that's that having a cushion piece.

Coach Stacy:

Yeah, you want to make sure that, as you are relying on God, that you are also hearing and heeding instruction. So if the instruction is, make sure you have this cushion. Whatever it is, whether it's financial, whether it's time Right, sometime a bold action requires time. Whatever that cushion is, make sure that you are in alignment with what God is saying. And if God is saying like you want to make sure you have this cushion, go in faith that you need a cushion.

Coach Wayne:

Yeah, and, stacey, I think it's so important that we leverage the network. And so, again, though you may be looking and saying, oh wait, stacey, I'm not trying to be a business person Taking a bold move doesn't necessarily mean opening up a business. It could be a bold move asking someone to marry you. It could be a bold move in terms of moving to a new address, a new part of town, a new country, but these things are important and we think that. I think, and we're going to flesh it out today, stacey and I are talking through it today. Think, and we're going to flesh it out today.

Coach Wayne:

Stacey and I are talking through it today that these are applicable principles that you could use throughout your decision making. And this other one, stacey, is leverage your network. So when I was leaving corporate, the first persons that I checked in with about my idea were family and close friends and did my quiet survey in terms of how does this name sound, how does and even practice my coaching with close friends. So leveraging your network you know, getting information if you're going to move to another part of the country that sort of thing.

Coach Stacy:

Absolutely, you must leverage the network, because a trusted network will give you not only feedback, but they will give you real, accurate feedback. Right, we don't want, as we are taking bold steps and making bold moves, we don't want Pollyanna, yes, people. We want people that are going to give us the authentic truth about what we're doing, how we're moving, and so, you know, scripture talks about there being wisdom in counsel, right, in godly counsel, and so really making sure that, yes, we leverage that network is critical, yeah, and Stacey I also had.

Coach Wayne:

I recognize that you're never too old to start learning or to improve upon what you already know and to grow from past experience, but also to add new opportunities to keep learning. In other words, it's important when you're going to make a move, a bold move, that you stay open to receive information, to grow, to learn, to adapt, especially right now, stacey, that we're dealing with technological jumps, with AI and the whole idea of robotics, augmented intelligence, all of that stuff. Yeah, we really have to.

Coach Stacy:

Yeah, we really have to. While we want to be mindful, prepared, we want to be intentional. We want to do so really asking ourselves the thoughtful questions. We don't want to allow all of that data to hinder our forward movement, and so it is really important that we look at what we're saying is taking bold steps is important in this season. It really is, because each of us have so much more to give, whatever that looks like that we don't want to miss our opportunities to make the most meaningful, the deepest impact, whatever that looks like for you. So we want to make sure that we are not giving you work or things to think about, things to do, in a way that serves as a stumbling block or holding you back. This is us saying let's prepare for some bold moves. We're not being reckless, right, but we want to really be intentional about making, taking, leveraging, bold moves.

Coach Wayne:

Well said Stacey, you know to encapsulate all that we've said and really to make this, to stress this the biggest part of making and I think we said it before, but making a bold move in terms of seeking your fortune, what we call your fulfillment is that shift in the mind, in the thinking, the mindset to recognize that you are usually your loudest critic and your worst enemy when it comes to decision making and and when it comes to risk-taking and when it comes to believing in yourself and your vision that bold step, that bold vision?

Coach Stacy:

right, we don't usually take big leaps. We usually, at least, when you're watching the high jump or the hurdles, right, there's some steps in there before we leave. And so a reminder to maybe identify some micro bold steps. Right, what are some small, strategic, thoughtful to your point, bold steps that we can begin to take toward that large bold move you?

Coach Wayne:

know tiny steps and it's important, I think, to stacy that we celebrate each progress, each step, each advancement. An inch is a cinch or something of the sort, but sometimes we don't recognize that if we're trying to lose 30 pounds and the bold step is to start exercising every day and we miss every day, but we're exercising three times a week we can celebrate.

Coach Stacy:

Mm-hmm, I couldn't agree with you more. And as I was thinking about this episode, I actually went back to what I would consider some of my earlier bold steps, and one bold step that I took it's 20 years ago now, um was to decide to leave my job, buy a home, move to a new state with no job, and I believe that there was some courage in there. There was a scripture that was very resonant with me at that time and it said that God would go before me and that God would be my rear guard. And when I read that, I took that as a very clear directive to step right. And so, yes, there was some micro steps in there, but, to your point of celebration, there are still moments that I celebrate that bold action, although it was 20 years ago, because it changed the trajectory of my life and of my son's life, and so we often have more to celebrate.

Coach Stacy:

We've often made or accomplished more, we've often experienced and engaged our own wisdom in ways that have helped us move forward, and we don't often celebrate that, we don't often acknowledge that. Even it feels like, yes, that was 20 years ago. Yes, 20 years is a long time, but it was a critical, a critical bold step in my life, and so I encourage you, our listener, to really think about some of the previous bold steps that you've taken and while all of them may not have worked out, I can't imagine that there weren't some that did and so to really take that as fuel to begin to take those micro bold moves, or to really do that deep thinking that you talked about earlier, wayne. We've got to get moving, people Got to get moving. Since you came back in the heavyweight division.

Coach Wayne:

I see Throwing some heavy punches here. I hear you, you know. I tell folks, as a coach, the question when folk are deliberating about making major decisions or taking bold steps, I ask them to challenge themselves by asking these questions what is the greatest gain that they can conceive if they took action? And then I asked what would be the loss, the gravest loss, if they took action? But behind that comes two other questions and if you didn't take action, what would be the gain? And if you didn't take action, then what might be the loss? Right, right, because every decision is going to have a cost. Yeah, and if you didn't take action, then what might be the loss?

Coach Stacy:

Right? Right, because every decision is going to have a cost.

Coach Wayne:

Yeah.

Coach Stacy:

Right, there's going to be a gain or a loss, or there's going to be some cost, a gain or a lesson. Whatever it is, there's a cost, and so I love that and I hope that you our listener take that nugget and think about that as you're really planning Right. Here we are. We're in the in the last third of 2025. There are moves to make. There is life to live. There are moves to make, there is life to live, there are lives to impact and there is a deep sense of purpose and possibility, I believe, for each of us to connect to in that inner purpose and possibility. And so this is the revolution, right Taking midlife and not looking at it, as you said, really focusing on the aging, but focusing on the saging, on the gifts, all of that, all of those gifts that we've amassed over time, and looking at how we can use that to propel us into this next season.

Coach Wayne:

Yeah, absolutely. You know, stace, we to share. I think I shared it with you before I'll share with the listener. Audrey and I we're closing on a house in a week or so, right, in a week or so, right. And was it a bold step? Yes, because the way the market is right now, with prices being elevated, there is a lot of caution about diving in.

Coach Wayne:

So we had to weigh a lot of things and, to be sure, some of the principles, in fact all of the principles that I just shared, around starting a business, we had to get through in terms of making the decision right to purchase at this time in an economy that's tithering on inflation, right. So we had to see how ready we were. We had to certainly had to have a cushion. We had to have a solid plan. We were. We had to certainly had to have a cushion, we had to have a solid plan. We leveraged network, we.

Coach Wayne:

You know, I can't tell you how many times I drove through the neighborhood in the rain, at midnight, early morning, sunday, saturday, and ask people around, you know, willing to learn, get more information from a mortgage person or finance person, and just to change the mindset about at this stage, do we want to make that move and the packing and all that stuff? And so I would say to folk that if you're right now at a place in your life where you're thinking, oh, I'm too old, oh it's too late, no, oh it's too late, no, this is an opportunity, a season for something fresh, for renewal, for revival, for regeneration, and I would say go in two feet, two arms, head and body head and body and take that bold step.

Coach Stacy:

I could not agree with you more. The boldness with intention, that's values driven, is doable in small steps. And so I pose the question what is the boldest action that you're willing to take in the next 30 days and how will you hold yourself accountable? That's for me, that's for you and that is for you, wayne, and it doesn't have to be I'm going to move to Japan, because that's always been a wild dream. Your bold step could be you know what? I'm actually going to buy that new dishwasher, or I'm going to do this addition on my home, or I'm going to ask for that promotion right, I'm going to put this new offer out there as a business person. And so what is that? Let's identify that step, that bold step we're willing to take in the next 30 days, and then identify how we're going to hold ourselves accountable. I know that that's something that I would engage my coach to hold me accountable on, and I can only encourage you, our listener to do the same.

Coach Wayne:

I love Unleashed and Stacey. I'm feeling like we're warming up, but we got to go and so, Stacey, how do people get in touch with you? And what's next?

Coach Stacy:

Sure. So before I share that, I do say I was a little remiss and want to acknowledge Pat Cadreau and Lisa Johnson. Thank you so much for being a part of the Midlife Revolution Unleashed. I am Coach Stacey M Lewis. I'm a nonprofit executive. I am a midlife women's coach. I'm a lover of God and his people and I am excited to move forward in a new level of boldness. I just came out of a workshop. I was like you know what? Yes, this is it Like. Take that next bold step. And so my next bold step is focused on my business and I'm looking forward to the accountability and the impact I'm going to make. You can reach me at thestaceymlewiscom and here on LinkedIn or on Facebook all the places you know. What about you, wayne?

Coach Wayne:

Folks can reach me at there we go VIPTransformativeLivingcom. All my handles are there and Stace, I actually do have an assessment that I'd like to put up for free assessment. It's a self-alignment assessment, so if you want to know if you're aligned in terms of your purpose, your why and your values, where you are right now, right here, take this assessment.

Coach Wayne:

It's one that will have you really getting inside and thinking, but it will come out on the other end helping to shed some light, and you're going to get a lot out of it. So just make sure that you can fill that out.

Coach Stacy:

So, wayne, we're going to make sure both you and I we're going to hold each other accountable to make sure that you put that link in the comments on LinkedIn and in the comments on Facebook so that people can more easily access that, because we really want people to get that assessment in their hands and learn more about themselves and see what their next bold step can be.

Coach Wayne:

And folks can DM me on any of my channels and just put the word assessment and I'll have it forwarded to you. Oh, there we go, that's nice and easy. Type the word assessment and I'll have it forwarded to you.

Coach Stacy:

Oh, there we go, that's, that's nice and easy. Type the word assessment in the DMs.

Coach Wayne:

States next week, I think. Shall we declare what we're speaking on now, or we should just promote it through the week?

Coach Stacy:

Feel free to declare Wayne. Feel free, Take it away.

Coach Wayne:

We're talking about AI next week and we were going to have a guest and we still may, but at least we're going to talk about what that looks like, what that means to us in midlife. Some folks are afraid that they will be replaced and others think that they will be part of the team that replaces those that think they'll be replaced. So we'll talk about that.

Coach Stacy:

I'm looking forward to the conversation, no matter what we're talking about, because our heart's desire is to really be of service and add value to our midlife community. So, wayne, I think that this has been a great episode three kickoff. It's been my joy to spend this time with you, and I remind our listener that you are the revolution. It's time to celebrate the richness in midlife.

Coach Wayne:

Enjoyed being with you here, stacey, and our listeners. We'll see you next time.

Coach Stacy:

Thanks for tuning in to Midlife Revolution Unleashed. We're grateful you're part of this journey.

Coach Wayne:

If you love this episode, share it, subscribe and hit that notification bell so you don't miss another episode.

Coach Stacy:

I'm Coach Stacey and I'm cheering you on.

Coach Wayne:

And I'm Coach Wayne and I'll see you at the top.

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