In short
How to decide whether to quit a job and become your own boss, using “warts and all” lessons from the host’s real transition, structured into timing, readiness vs frustration, and financial planning.
Guest backgrounds
No guests; it’s a solo episode.
Key claims
There’s rarely a perfect time; distinguish misery from readiness. Ambition without clarity and motivation without structure fades. Staying employed is valid if it serves you. Financial reality is central: plan for an income gap and aim for at least six months of living expenses in savings; many businesses take ~3 years to reach profitability.
Notable examples
Host was managing director of emerging markets for TUI and CEO of Saga’s travel division; traveled ~70% of the month. After quitting (~age 47–48), COVID erased revenue/pipeline overnight, forcing reliance on non-liquid property assets and pivoting via mentoring and podcasting.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VODeciding to Quit: A Personal Journey
0:09 to 1:18
The host shares her personal experience of contemplating quitting her job.
“So welcome back to Brave Bold Brilliant.”
Understanding the Leap to Self-Employment
1:18 to 6:17
Discussion on the emotional and practical considerations when deciding to become your own boss.
“But for other people, it's more of an evolution of who you are becoming as you progress through your career.”
Financial Realities of Leaving Your Job
6:25 to 9:54
Examining the financial aspects and preparations necessary before transitioning to entrepreneurship.
“So how to tell if you're chasing an exit because you're miserable versus because you're genuinely prepared.”
Navigating Challenges and Opportunities
9:54 to 14:00
Insights on handling unexpected challenges in business and the importance of networking.
“You know, you need to know what your weekly, monthly outgoings are from a point of view of paying the mortgage, paying your gas bill, how much you need for food, etc.”
Transcript
Automatic transcript. May contain errors.0:09So welcome back to Brave Bold Brilliant. So it's just me today and I want to talk about the decision that quietly sits behind almost every message I get from this audience. Should I quit my job? Now I remember the day that I handed in my notice like it was yesterday and that mix of kind of terror and relief you know the voice in your head telling me I was either about to ruin my life or finally start living it. You know and 30 plus years on I can tell you it was neither as dramatic or as simple as it felt in that moment. You know it was a decision made of a hundred smaller decisions most of which I got wrong before I actually got right but here's the thing you see I was never one of those people that hated their job.
0:51So, you know, I was actually really, really loving my career. So you might be in that position. You might not actually dislike your job or what you're doing career-wise, but you might have that little feeling in your stomach that actually there's something else that you want to be doing. So it doesn't have to be dramatic. In some cases, it can be quit your job, become your own boss. Absolutely. But for other people, it's more of an evolution of who you are becoming as you progress through your career. So what I want to do today, because this is very much a lived experience, I want to walk you through what actually goes into making that leap.
1:34And I'm not talking about the highlight reel version, you know, I'm talking about the real one. So again, we like to break things down into manageable chunks. I'm a big believer in keep it It's simple. We overcomplicate things in business and life. And certainly in our careers, we can go overcomplicate things. So I'm going to take you through these five different chapters. And this is the stuff that nobody tells you before you actually, you know, become your own boss. So you might be standing at the edge of this right now, wondering if it's time. So if you are in that place, stay with me. But if you're also thinking, this might be something that I'm not quite ready for yet, but it could be in the future, maybe an X number of years ahead of from where we are today, then also it's worth you listening in on this.
2:26And if you've already made the move, but maybe you're doubting whether it is the right thing for you to be your own boss, there's going to be also some points in here that could be helpful for you. All right, so remember, there is no judgment. Every one of us is different. There is nothing wrong with staying in a job as long as it is serving you, as long as you are enjoying it, as long as you can add value, and as long as it actually fulfills you in the ways that you need. Equally, if you want to go out into the big wide world and become your own boss, then you want to be able to do it with some knowledge and you know thinking ahead of time so this is why I'm really passionate about this because I think a lot of people glamorize the move and it isn't all easy it never is right whatever change you make in life so let's help you understand the different steps and let me share with you some of the warts and all in terms of how I made that move and actually, you know, what's worked and what maybe I would do differently next time.
3:40All right. So grab a pen and paper if you haven't already. You know, I always say that I'm a big believer in writing things down because then it actually lodges in our brains a little bit more. And equally, you might actually be wanting to listen back to this a few times. And that is the beauty of having a podcast. It's the beauty of having a YouTube channel. If you like video, then YouTube head to the YouTube channel you're probably watching it right now and hit that subscribe button but if you prefer audio you should know our podcast we have over 650 episodes so let's get into it the first chapter I want to take you through is knowing when it's actually the right time to leave is there ever a perfect time not sure there is however there is a difference between and frustration and readiness.
4:32But 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 is not theory. It isn't fluffy motivation, although you will be motivated. And it certainly isn't another online course that you never finish. It's actually a fully structured growth environment for ambitious entrepreneurs, leaders and founders who absolutely are ready to do all of these things.
5:28Sharpen 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. So 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.
6:17So 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. So how to tell if you're chasing an exit because you're miserable versus because you're genuinely prepared. So, you know, I think the important thing here is to actually understand why, you know, why, why have you got this feeling that you want to leave your job and become your own boss? And I think, you know, for, for me, if I just share with you the catalyst really, that really made a difference when I was making that decision, remember, I came from a place of having loved my career, so proud of the businesses that I'd been fortunate enough to lead, incredibly, you know, fulfilled with the experiences that I'd had in the corporate world.
7:15You know, I was the managing director of the emerging markets for TUI. I was a CEO of the travel division for Saga. I'd had an amazing career. So why did I leave? Why did I jump out given that that was a scenario? Well, let me tell you how it played out for me was I was at a certain stage of life, I would say. All right. So I would have been around about 47, 48 at the time. I'm 54 now. So we're talking about six years ago. And at the time, you know, my husband, now husband, Chris, is 10 years older than me. Not a problem at all. We have an absolutely brilliant life together. We love each other dearly and we're both thankfully in good health.
7:55But nonetheless, unless when you are in a certain stage of life, it really, what it happened for us was that we said, well, what do we want the next phase of our life to look like? I'm hugely passionate about business. I'm hugely passionate about people. I will never retire, right? I will never retire because I love what I do. But the point was, I also recognized the toll that the corporate life was taking on me. You know, the absolute extreme stress, the hours, the travel. I could be away 70 % of every single month traveling. My weekly commute was to Delhi or to Beijing or to Moscow. Sounds very glamorous, but it takes its toll on you.
8:36So for me making that decision, it was very much around the next phase of life and creating a life by design. So there was the time was right. okay and we did we sat down and we said right what does this look like you know and what do we want it to look like the next phase and I am so glad that I did because I sit here today with a portfolio of amazing businesses with a wonderful team being able to work with clients and help them step up I am still in that world of you know great business but I'm doing it on my own terms. And that's the difference. So, you know, the move, the time was right for me, but I spent a lot of time thinking about it before actually making the final move.
9:23So have a think about what you actually want and why. The second part of this is really about the financials. You know, and this is the reality that no one talks about because, you know, it sounds great, doesn't it? Just leave your job and go and set your own business up. But we all have commitments. You You know, most people have financial commitments that they need to make. So, you know, you can't be naive to that. And what's important is to have a good look at what money you have got before you make the leap. Right. So it could be savings. You know, you need to know what your weekly, monthly outgoings are from a point of view of paying the mortgage, paying your gas bill, how much you need for food, etc.
10:09I know it sounds boring, but you need to know what your monthly financial commitments are for living a pretty modest, but a normal life. And then, of course, it's really important to actually see what have you got in the bank that's going to allow you to make the move without totally stressing out and being worried for every second about every single penny that you're spending. So I would, I mean, everyone is different. And this comes down to your appetite for risk, right? So I would say in order to make the move, you really want to have at least six months of money in the bank that allows you to survive and move forward into that next phase.
10:51A minimum, I would say. If you've got more, then great. But as I say, everyone is different. So I'm not giving you a definitive here, just a bit of a guide. You know, and the income gap that a lot of people underestimate, you know, can often be about how long it's going to take before the new venture actually starts, you know, paying you in real money. so you know money mistakes in year one it can actually cost you a lot because what can happen is if you are struggling in year one and you haven't got enough cash and capital behind you it can mean that you have to give up on your dream even if you don't want to and the reality is when you're starting a business any business most businesses actually really take three years to get to a profitable position.
11:41So you need to be able to understand where you are financially before you make the move. Because then when you make the move, you can concentrate on building the business, not worrying about, can I pay the gas bill this month? All right. So I think that's a really important thing to do. And certainly, you know, when we made the move, when I made the move out of corporate, we had a really big ambitious plan to invest in our property business. And I also was building my advisory practice at the time. And I had three deals, three mergers and acquisitions deals. I've done a lot of M &A work in my corporate life.
12:20And I had three businesses that I was buying, two businesses for a big corporate and one for private equity. So we were flying. And then all of a sudden, COVID struck. And we went from having a good pipeline and a good visibility of revenue coming into the business to zero. Zero. All right. And it was a shock. Now, we had assets in properties, but that's not liquid. That does not pay the bills. so it was a really difficult time and this is what people don't realize when you actually set up your own business it is not easy you carry that burden this is not like getting a regular paycheck regardless all right so what did we do we regrouped we looked at the resources that we had around us and a lot of that was around my network my capability I started my mentoring business at that time and I started the podcast because I had a little bit more time those deals disappeared overnight.
13:25How do you value a travel business in the middle of a global pandemic? Well, the answer is you don't. Okay, so it isn't always easy, but this is why you have to be aware of your financial position. And I'm not saying this to put you off, I'm just giving you the truth. 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 brilliance.
From the publisher
This time, we unpack the real, unvarnished truth behind leaving corporate life to work for yourself—moving beyond the glamourised highlight reels to what making the leap actually requires.
Jeannette breaks down the crucial difference between simple workplace frustration and genuine readiness, how to design the next phase of your life with intention, and the exact financial safety nets and realistic timelines you need in place before handing in your notice.
You'll Learn Why:
Hating your current job is not a requirement for deciding it is time to build a business of your own.
Having at least six months of living expenses in liquid cash is critical before making the leap into self-employment.
Most new businesses take up to three years to become profitable, making early financial buffers non-negotiable.
Designing the next phase of your life by intention matters more than chasing an impulsive exit from daily stress.
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.

