Bold Decisions vs Reckless Decisions | How Top Leaders Actually Tell the Difference

31 Jul 2026 · 19 min · 7 chapters

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In short

How to distinguish bold, high-stakes business decisions from reckless ones, using a decision-making framework (information, reversibility, risk ownership, fear vs calm, conviction vs stubbornness, and learning from outcomes).

Guests

No guests. The episode is hosted solo by Jeannette Livingfoot (entrepreneur, business leader, corporate CEO turned portfolio business owner).

Key claims

Boldness is a learnable leadership skill (not personality/extroversion). Bold decisions use the best available information without “moving blind.” Recklessness skips homework, ignores reversibility, and is driven by ego/validation or fear suppression/bravado. Bold leaders treat failures as feedback/data.

Notable examples

Jeannette’s TUI role recommending expansion targets—China joint venture vs buying Brazil’s market leader (including acquisitions around £600M). She also references life-or-death emergency decision-making in travel.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Understanding Bold vs. Reckless Decisions

0:45 to 2:19

Exploring the difference between bold and reckless decision-making in leadership.

“You know, and after 30 plus years in business, I've had to make some really high stake decisions over the years.”

The Skill of Boldness

2:19 to 4:48

Discussing boldness as a skill that can be developed rather than a personality trait.

“And that can often be also linked to, you know, extroverts versus introverts.”

Information and Reversibility in Decisions

4:48 to 6:52

Emphasizing the importance of information and reversibility in decision-making.

“So bold decisions are made with as much information as is reasonably available.”

Assessing Risk and Motivation

6:52 to 10:21

Evaluating whose risk is at stake and the motivation behind decisions.

“Are you operating from a position of fear or are you operating from a position of calmness or as calm as it can be?”

Conviction vs. Stubbornness in Decision-Making

10:35 to 12:06

Exploring the balance between conviction and flexibility in decision-making.

Frameworks for Bold Decision-Making

12:06 to 14:00

Providing frameworks and questions to guide bold decision-making processes.

Navigating Bold vs. Reckless Decisions

14:00 to 16:49

Learn how to differentiate bold decisions from reckless ones and the importance of resilience in decision-making.

“We want to be making them with confidence and clarity and as much information as possible.”
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Transcript

Automatic transcript. May contain errors.

0:10Welcome back to Brave Bold Brilliant. I'm Jeannette Livingfoot, your host, entrepreneur, business leader, corporate CEO, turned portfolio business owner. But what I want to talk to you today about is what's the difference between bold decisions and reckless decisions? Because as business leaders, we have to make decisions all of the time. But actually, how do we know if we're going too far and being reckless versus being bold and kind of brave with our decisions? Now, bold is a word that I absolutely love, as you all know. You know, and after 30 plus years in business, I've had to make some really high stake decisions over the years.

0:56And it isn't easy. It really isn't easy. But what I want to do today is to kind of break it down, in all honesty, into more manageable chunks so that we can actually really have a proper conversation around what does it take to be bold in our decisions? What does it take to actually have that right mindset for how you approach decisions and take risk, etc? So if you are not already subscribed to Brave Bold Brilliant, the YouTube channel, hit subscribe. It always really helps. And of course, you might prefer audio. You may be listening to this while you're in the gym, walking the dog, dropping the kids off at school, whatever it may be.

1:40So if audio is your thing and you're not subscribed to Brave Bold Brilliant, just hit the subscribe button again. You know, it could be on Apple Podcasts or on Spotify, wherever you listen to your podcasts, because it's great. And what we're doing at Brave Bold Brilliant is we are building a community of like minded leaders that don't want to play safe. They don't want to play small. They want to live their best life, have the maximum impact possible. but we've got to do it in the right way and that's what i want to talk to you today about is what's the difference between bold decisions and reckless decisions all right so the first thing i want to say and you might want to make some notes actually it really helps if you take notes when we do these um these sort of short episodes of you know quick fire content to get you thinking but it's always helpful i think to write things down i'm a big believer in that so that you know the first point I wanted to make is that, you know, boldness is, it's a skill, not a personality trait, you know, and very often you might actually hear a myth, you know, that, oh, you know, some people are just born naturally bold or naturally brave and others aren't.

2:50And that can often be also linked to, you know, extroverts versus introverts. And none of that is true. You know, boldness is a skill and it's a skill that can be learned. And it's a skill that actually, once you master that can really transform your leadership journey can allow you to be equipped with the right attitude the right approach so that you know you don't crumble whenever there's a really big decision to make but you do it in the right way so it can be learned which is the great news so boldness can be built practiced and developed just like any other leadership capability. So that is the good news.

3:32And, you know, here's the thing. I look back through my career and I think about, gosh, you know, some of the big decisions that I've had to make, you know, and I think around when I was the managing director of the emerging markets at TUI, you know, we had to make, I had to make a recommendation to the investment committee, which of these huge markets were we actually going to go for? You know, were we going to expand our joint venture partnership in China? Or were we going to go buy the market leader in Brazil? Now, these were huge, huge numbers at stake. Big risk. Big, big, big risk. And, you know, some of these were acquisitions of 600 million pounds.

4:12And it was on my shoulders to make those decisions, to make those decisions and those recommendations. So I've had my fair share of having to make those tough calls you know and today as a business owner and an investor you know I make decisions on where we're going to invest and obviously that's coming from a different perspective because it's actually investing your own money as opposed for a big corporate like a you know footsie 100 which two he was so bold boldness it's a skill it really is a skill not a personality trait and it does get easier the more you practice therefore so you know the other thing I would say is the information test.

4:50So bold decisions are made with as much information as is reasonably available. Now you are never going to have perfect information, let me tell you, you are not. But those decisions that skip the homework, if you like, that because maybe there's a sense of urgency, they can feel uncomfortable. And that might be where recklessness comes in, where you're making these really big decisions but you know without actually being fully informed that can be reckless rather than bold so there is a difference between the two and i'm trying to sort of show that through this conversation you know and you know moving fast does not mean moving blind you know there are some decisions that we have to make in the moment and it can be really debilitating to not make a decision to procrastinate but at the same time you have to be able to assess you know how fast do i need to move here how much time have i actually got to make this decision are there information gaps that would be really helpful to have more data or more insight and some cases you don't have any more time right you just don't if it's an emergency situation maybe it's a life or death scenario which you know i've had to face many times in my career in the travel industry um you know so you don't always have time on your side but you need to actually get as much information as possible as much insight as possible and i think the other the other thing to consider when you're making these really big decisions is the reversibility question you know is this a reversible decision if it doesn't work out can i pivot again can we change again can we make another decision you know and often reckless decisions will ignore that distinction and not even think about it at all so you know ask yourself is this decision reversible and that will help you when you're actually trying to make those those big those big moves now bold decision making normally involves risk all right so when you are looking at risk in your business risk in your department risk in the area that you're responsible for ask yourself whose risk is it really you know because because bold decisions account for not just the impact on the business but the team customers stakeholders it's not just about your ego here so actually whose risk is it that you're putting at stake here um you know and reckless decisions often are more about personal validation than the actual business outcome and let's be honest we all have an ego but when it comes to making bold decisions when taking risks actually it's really helpful to ask who am i really doing this for who am i doing this for and why super super simple questions but very very powerful and you know the other thing that is worth considering is are you operating from a place of fear or calmness now bold decisions still can feel scary don't get me wrong fear doesn't necessarily disappear it's just you learn to manage it but reckless decisions can often come from you know suppressing the fear entirely or from bravado and it's important to be able to distinguish the two so what's the role of fear in the decision that you're making.

8:26Are you operating from a position of fear or are you operating from a position of calmness or as calm as it can be?

8:36But before we continue, I want to speak directly to those of you who are listening and thinking, I know I'm capable of more, but I need structure. I need some help. Because here's what I've actually learned after, gosh, more than three decades in business. You know, ambition without clarity creates frustration. And motivation without structure, it really does fade very, very fast. So that's exactly why we created Rise Academy. You know, and Rise Academy, it's not theory. It isn't fluffy motivation, although you will be motivated. And it certainly isn't another online course that you never finish.

9:20It's actually a fully structured growth environment for ambitious entrepreneurs, leaders and founders who absolutely are ready to do all of these things. Sharpen their strategy, elevate their leadership, increase revenue with intention and build businesses that actually support the life that they want. And inside Rise Academy, we focus on the foundations most people skip. Leading yourself, leading your teams and leading the business. It's about clarity, standards, decision making, commercial intelligence and execution. Because scaling, it really isn't about doing more. It's actually about doing the right things and doing the things right consistently.

10:08So if you're serious about stepping up into your next level of your leadership, your business life, and not just consuming content, but actually implementing it, then Rise Academy was absolutely built for you. So you can find all the details on our website, go to www.brave-bold-brilliant.com. And now, let's get back to the show.

10:34You know, sometimes we also can be quite stubborn, right? So I know I've had plenty of times in my career where I can be quite stubborn and I've stuck to my guns on something when actually it would have been a better thing to do to listen and to change the perspective but you know there is a difference between conviction and stubbornness so really passionately believing in the decision you're making and being clear with what why you're making it who it's affecting having as much information as possible allows you to have conviction in your decisions to be able to communicate it in a way that brings other people on the journey with you to get get buy-in from stakeholders if they need to be you know on board with the bold decision that you're making and you know but but actually you also if even if you're really convicted and you're really passionate about your decision you still got to stay open to new information and not be stubborn and stuck in your ways or maybe something shifts maybe a competitor makes a move that you weren't expecting or something has actually you know changed the conditions that you're in so reckless leaders dig in and ignore the evidence sometimes whereas actually a leader that is coming from a place of calmness and conviction but is prepared to re-look at the facts is going to make a better decision than someone that's operating from a position of just being very fixed and very stubborn so you know if this is giving you a new way of thinking about your own decisions then i'm absolutely delighted because that's what we're here to do we're here to challenge each other we're here to help each other grow so you know but if you are enjoying this conversation and you're not yet subscribed hit that subscribe because then you are going to get notified every single time that we drop a new episode and it could be a solo episode like this where i'm just sharing some perspectives from my 30 plus years in business or it may be an interview with amazing entrepreneur an incredible ceo that's doing really great things in the world of business so don't miss out hit that subscribe button and put your notification buttons on as well because that will mean that you never miss out um life's too short to miss golden nuggets of advice and information so you know when you're looking at making bold decisions it can be really helpful to build a framework around that as well you know and you know maybe some key questions to ask before you make any high stake decisions you know having a true sounding board is fantastic as well you know i always say be really careful who you've got in your life have you got the right people around you that allow you to bounce ideas are going to support you with what you're trying to achieve or are you surrounded by people that are actually quite negative and possibly so entrenched in their own uh what they're trying to achieve that they don't really support you in the right way so having a framework having some key critical questions so you might you know as i say is this decision reversible or not is the risk of this decision within our parameters our appetite for risk whatever that might be it could be a financial metric is this decision actually going to have a commercial benefit and a commercial risk what's the range that we're looking at here in terms of this decision and why are we doing it who is it for so just some simple questions like that can just really help you check in on your decision making and whether you're being bold or reckless okay and then of course we don't always get it right do we but procrastination is is not what we want.

14:27We want to be making these decisions. We want to be making them with confidence and clarity and as much information as possible. But we don't always get it right. Let's be honest. I've made loads of decisions that haven't gone my way. The key here is that bold leaders that have failed or a decision hasn't gone their way, they actually look at that and they see it as feedback. They see it as data in order to improve. They don't take it personally. They don't take it is you know it's completely entrenched in their identity and that is a big difference as well so the difference between a bold decision that didn't work and it having been the wrong call is is is how you perceive it in your mind you know so actually you know resilience after a hard decision matters as much as the decision itself because you've got to be able to say to yourself okay i didn't get that right i made a mistake or i didn't have all the information but i still made the decision it didn't go our way what have we learned what would we do differently next time how do i need to look at my own process my decision making process what do i need to do as a leader so when we can interrogate that reality of a decision that hasn't gone well that allows us to grow it allows us to be more confident the next time and of course to learn from that so you know if you're facing a really big decision right now and it might be professionally it might be from a business point of view but it might be personally and you're not sure whether it's bold or reckless that's exactly the kind of clarity that a good mentor sounding board you know can really give you fast now one of the things that i love doing i love working with business leaders one-to-one to help them with this because it is lonely it can be daunting you can lose sight of actually am I being bold here or am I being reckless and actually having a mentor in your life can really make a huge huge difference so if you haven't got a mentor and you're operating at a certain level of professionalism at a certain level of decision making I honestly it's the best thing you could do so if you're interested and you want to be even mentored directly by me then reach out don't be shy life is too short but let's make make these bold decisions together in the right way that's why we're here that's why i've created everything that i do with brave bold brilliant and i love working with people one-to-one so get connected drop me a line so as we close out this episode you know just remember being bold you know it's not about being fearless or reckless it's actually about making clear-eyed decisions with real conviction and the courage to own the outcome either way so thank you so much for joining me today i've really enjoyed the conversation i hope it's giving you some food for thought and you know and as i say if we're not connected let's get connected come and join brave bold brilliant community and remember it is by being brave and bold that you will unlock your brilliant i really hope you've enjoyed this episode of brave bold brilliant remember check out our new website www.brave-bold-brilliant.com you're going to find loads of resources on there that's going to help you with your leadership journey and with the businesses that you're trying to scale up and grow so take care everyone and remember there are no limits to your growth but it is by being brave and bold that you're going to unlock your brilliant

From the publisher

Jeannette looks at the critical difference between making bold leadership decisions and falling into reckless ones. She busts the myth that courage is just an innate personality trait, framing true boldness as a learnable skill built on solid data, self-awareness, and emotional calm. 

Whether you are navigating massive strategic pivots or personal career moves, she shares a practical framework to help you move fast without losing control, assess risk responsibly, and lead with unwavering conviction.

You'll Learn Why:

Boldness is not a fixed personality trait, but a dynamic skill that any leader can learn, practice, and master over time.

Moving fast in business doesn't mean moving blind, as true bold decision-making relies on using all available data rather than skipping your homework.

High-stakes risk requires evaluating whether a choice is reversible and asking who is genuinely bearing the brunt of the outcome.

Failure should be treated as neutral feedback rather than a personal identity, allowing you to build resilience and refine your decision-making process.

Whether you're a founder, CEO, small business owner, entrepreneur, startup leader or executive, these lessons will help you make smarter hiring decisions and build a stronger, more successful business.

🚀 Want to accelerate your business growth?

Join Rise Academy today and gain access to expert business coaching, leadership training, proven growth frameworks, live coaching sessions, and practical strategies designed to help you build a thriving business.

About Jeannette Linfoot

ABOUT THE HOST

Jeannette Linfoot is a highly regarded senior executive, property investor, board advisor, and business mentor with over 30 years of global professional business experience across the travel, leisure, hospitality, and property sectors. Having bought, ran, and sold businesses all over the world, Jeannette now has a portfolio of her own businesses and also advises and mentors other business leaders to drive forward their strategies as well as their own personal development. 

Jeannette is a down-to-earth leader, a passionate champion for diversity & inclusion, and a huge advocate of nurturing talent so every person can unleash their full potential and live their dreams.

Podcast Description

Jeannette Linfoot talks to incredible people about their experiences in business and life, gaining first hand insight into how they unleashed their potential to become Brave Bold Brilliant.

From the boardroom tables of big international businesses to the exciting world of entrepreneurs it's all about stepping up to the next level while staying true to yourself.

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