Debra Chantry-Taylor: Use Your Holidays to Set Yourself Up for Success
In this holiday episode of Better Business, Better Life, Debra Chantry-Taylor tackles a familiar but rarely confronted reality for entrepreneurs: most don’t truly rest over the Christmas break, they simply pause while staying mentally tethered to work.
In this holiday episode of Better Business, Better Life, Debra Chantry-Taylor tackles a familiar but rarely confronted reality for entrepreneurs: most don’t truly rest over the Christmas break, they simply pause while staying mentally tethered to work.
Debra unpacks the subtle behaviours that sabotage real downtime, from “just checking emails” to quietly solving work problems in your head and explains why these habits prevent genuine recovery. She shares why true rest isn’t indulgent or irresponsible, but essential for clear thinking, strong leadership, and sustainable businesses.
Through her signature lens of fierce clarity and loving truth, Debra outlines five practical steps for a healthy Christmas break, choosing presence, resting without guilt, reflecting lightly, reconnecting with who you are beyond the business, and letting go of martyr behaviour. She also explores why family businesses often struggle at Christmas, and how blurred boundaries can quietly undermine both rest and relationships.
The episode closes with Debra sharing her own plans for switching off properly, offering a grounded reminder that a business strong enough to survive your absence is a sign of leadership done well.
So if you’re heading into the festive season exhausted, distracted, or secretly planning to “just check in,” this episode is your permission slip, and your plan, to truly rest.
CONNECT WITH DEBRA:
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►Debra Chantry-Taylor is a Certified EOS Implementer | Entrepreneurial Leadership & Business Coach | Business Owner
►Connect with Debra: debra@businessaction.com.au
►See how she can help you: https://businessaction.co.nz/
►Claim Your Free E-Book: https://www.businessaction.co.nz/free-e-book/
Episode 252 Chapters:
00:00 – Introduction
00:38 – Christmas Break Realities for Entrepreneurs
02:32 – The Truth About Entrepreneurs’ Christmas Breaks
04:23 – The Importance of Rest for Entrepreneurs
05:20 – Family Businesses and Christmas
08:50 – Preparing Your Business for a Proper Break
11:26 – Debra’s Personal Christmas Plans
Debra Chantry-Taylor is a Certified EOS Implementer & Licence holder for EOS worldwide.
She is based in New Zealand but works with companies around the world.
Her passion is helping Entrepreneurs live their ideal lives & she works with entrepreneurial business owners & their leadership teams to implement EOS (The Entrepreneurial Operating System), helping them strengthen their businesses so that they can live the EOS Life:
- Doing what you love
- With people you love
- Making a huge difference in the world
- Bing compensated appropriately
- With time for other passions
She works with businesses that have 20-250 staff that are privately owned, are looking for growth & may feel that they have hit the ceiling.
Her speciality is uncovering issues & dealing with the elephants in the room in family businesses & professional services (Lawyers, Advertising Agencies, Wealth Managers, Architects, Accountants, Consultants, engineers, Logistics, IT, MSPs etc) - any business that has multiple shareholders & interests & therefore a potentially higher level of complexity.
Let’s work together to solve root problems, lead more effectively & gain Traction® in your business through a simple, proven operating system.
Find out more here - https://www.eosworldwide.com/debra-chantry-taylor
Debra Chantry-Taylor 00:00
Let's have a talk about the Christmas break, because it is that magical time of the year. It's usually when entrepreneurs announce they're going to switch off rest, spend quality time with family and come back refreshed, which in real life translates to checking emails in the loo, whispering Just quickly before sneaking a phone call, refreshing the bank balance like it's an advent calendar, and pretending you're relaxed while your eye twitches from suppressed stress. And I'm not here to stroke your ego. I'm here to stop you sabotaging your break, because if you're going to rest, then please rest.
Debra Chantry-Taylor 00:38
Hello and welcome to another episode of Better Business, Better Life. I'm your host, Debra Chantry-Taylor, and I'm passionate about helping entrepreneurs lead their ideal life through creating a better business. And as you know, we're approaching that magical time of the year, Christmas. It's one of my favourite times. Unfortunately, for last seven years, I was with a partner who wasn't very fond of Christmas, and so I'm on my own this year, and I've been able to put up a Christmas tree. I have got Christmas stuff everywhere. I am super excited about the season and just the fun. I'm not necessarily religious, and I'm not there celebrating the religious side of it, but I just enjoy the fact we can get together with friends and family. We can take some time out. We can have some good food, some good wine, good conversations, and probably just take a bit of time out to rest and relax. But let's have a talk about the Christmas break, because it is that magical time of the year. It's usually when entrepreneurs announce they're going to switch off rest, spend quality time with family and come back refreshed, which in real life translates to checking emails in the loo, whispering Just quickly before sneaking a phone call, refreshing the bank balance like it's an advent calendar and pretending you're relaxed while your eye twitches from suppressed stress. And I'm not here to stroke your ego. I'm here to stop you sabotaging your break, because if you're going to rest, then please rest. If you're going to think, then please think. If you're going to burn mince pies as a bonding experiment, then commit to it and do it properly. This is the devil's advocate Christmas special using my own personal three uniques, which are fierce clarity, cutting through your festive nonsense, loving truths, the things you need to hear, not want to hear, and tenacious teams, because your break impacts their January and their new year. So grab a drink, settle in, and let's make Christmas actually useful, not just decorative. So why your Christmas break is usually a lie? Let's get straight to the point most entrepreneurs don't take a Christmas break. They take a Christmas pause, dressed up as leisure. You tell everyone, I'm totally switching off this year. Your behaviour says if one more person sends me a message, I swear I'll check it. Reply, escalate it. Solve the issue, delegate something, redesign the process and write a three year strategy, but only after lunch. So that's the very first problem. It's denial. You tell yourself a story about how you behave in December, but the data says otherwise. And here's the truth, if you're like me, you're probably exhausted, you're over responsible, you're worried the business will fall apart if you're not looking directly at it, and you will carry guilt in every direction, guilt for working, guilt for resting, guilt for breathing too loudly in front of your partner. You name it, you will carry guilt. So here's my fierce clarity moment. If you don't acknowledge the reality of how you shop at Christmas, then nothing changes. Your family senses it, your team senses it, your dog sense it, possibly even Santa Claus senses it. You're really not fooling anyone. So this is where the loving Truth comes in. You need rest, not sit on the sofa, but still mentally running the numbers. Rest, actual rest, the kind that recalibrates your brain, your body, your leadership and your presence. And entrepreneurs usually avoid rest for three reasons. Number one is that rest feels unproductive. If you're not generating something, fixing something, or controlling something, you feel a little bit useless. You've built your identity around forward motion, and so stillness feels like failure. Loving truth here for you, your business is tired of being led by someone running on fumes. Do you know you do mediocre thinking when you're tired? You also make avoidant decisions when you're tired, and you become a reactive leader when you're tired. So the real best version of you is not the tired version. And number two is that rest reveals the truth. When you stop moving uncomfortable things rise to the surface that idea that you've ignored, the conversation, you've avoided, the family dynamic you've tiptoed around, the decision that you should have made back in September. Rest gives you real space to feel which entrepreneurs treat. Like an optional extra. Number three is that rest exposes the team gaps. If you take time off and the whole business trembles like a jelly, the message is simple, you don't have a tenacious team. You have a dependency. That's not a leadership badge of honour. That's a systems failure. So the loving truth moment here is, if you're afraid to step away, your business truly isn't healthy. You're a single point of failure wrapped in tinsel with a nice shiny bow on top. Going to look now at how family businesses mess up Christmas. So let's add in the family business layer, because Christmas is the annual reunion of the personal circle, the family circle and the business circle that we see in the Harvard three circle family business model, and they're all colliding together like an emotional Venn diagram after too much pudding at Christmas time. So you take the business into Christmas like it's part of the Nativity scene. Your family feels it. They feel the tension. They feel the mental absence. They feel the constant hum of responsibility that follows you around like an anxious elf. Family businesses generally make three mistakes at Christmas time. Mistake number one is pretending that family time will magically make everything harmonious. Nope, no, it won't. Those unresolved issues from last quarter have not disappeared. You've just put tinsel on them. Mistake number two, avoiding the conversations you actually need to have. You say no, not at Christmas, fine, but then January you'll be angry that you procrastinated. Mistake number three, blurring boundaries completely. You know what it's like. The kids are opening the gift, someone mentions the account. Someone else says we need to talk about day's performance, and suddenly it's an AGM with crackers. So the first clarity moment here for me is that your family deserve the version of you that isn't secretly running next year's strategy in your head. So what can a healthy Christmas break actually look like? Let's be honest about what a good break really looks like. Number one is that you choose presence deliberately, not perfectly, not constantly, just deliberately. This means that you choose to be in the moment. You choose to just be there. Number two, you rest without guilt. This might be the first year that you genuinely allow your shoulders to drop. You need to rest without guilt. It's not doing you any favours. It's time to just relax and take that rest. Step number three, you reflect lightly, not obsessively. This is not the time to reinvent your operating model. It's a time to ask simple questions like, what's working, what's draining me personally, what needs to change? What am I avoiding? These little questions just start to get you thinking about what's working and what's not working in the business, in your personal life, in your family, and it just helps you to have a little bit of quiet time to review those questions. Step number four, reconnect with your identity outside of the business. I know it's shocking, but allegedly we are humans, and so allegedly you're a human too, and as a human, we need to actually think about what makes us happy outside of business. I get it. I love business. I could do business every waking moment and not get fed up with it. But the reality is that you have a family, you have friends, you have people who love you and they want to spend time with you. You've probably also got other outside interests that maybe you're not spending time doing. So please take the time reconnect with that identity, your identity and the family, your identity as yourself outside of the business, and please, my desperate plea number five is stop playing the martyr. The business will not collapse if you're not glued to your inbox, and if it does, let's be honest, you've got bigger issues than Christmas. So how can you prepare your business that you can actually switch off? I'm going to be honest, your Christmas break is only possible if your team can function without you. So here's my devil's advocate. Punch in the guts. If you can't take a proper break, then you haven't built a tenacious team. Because tenacious teams, they know their roles. They've got clear priorities. They can make decisions without panicking. They don't rely on daily approval. They don't escalate everything through to you, and they certainly don't interrupt your Christmas dinner with a quick question. So if your team crumble when you disappear for five minutes and your leadership system is fragile, your job is not to be Santa. Your job is to build competent elves who don't need to wake you up every time the sleigh squeaks. You deserve a life. They deserve empowerment. Everyone wins.
Debra Chantry-Taylor 09:48
So let's end with a festive slap of reality. If you say you want rest this Christmas, then please stop lying to yourself about just checking in. Stop pretending you're indispensable. Stop calling overworking dedication and stop using guilt as a productivity tool. Stop letting your brain sprint while your body sits on the sofa pretending to watch love. Actually, you are allowed to rest. You are allowed to switch off. You are allowed to be human, and if you don't, you'll enter January exactly the same way you leave December, tired, distracted, overwhelmed and annoyed past you for not taking the break you said you would. My fierce clarity is you need this break. My loving truth is You deserve this break, and tenacious teams will make it possible for you to actually take the break. So now go and have a Christmas that restores you rather than drains you. Your business will thank you. Your team will thank you. Your family will thank you, and frankly, future, you will build a shrine to you. I myself, I am stopping on the 19th of December. I've got friends flying over from Wellington to join me in Melbourne, and they're here till the 29th of December, and during that time, there will be absolutely no work for me. I'm coming back to work on the second of January. So I've got lots of stuff lined up for the future, but I'm going to make sure that before I break completely on the 20th, on the 19th, I'm going to take some time out to do a clarity break. I'm going to sit I'm going to really decide what I want to achieve personally over the Christmas break, and I'm going to make sure that I've got some fun activities planned. Because I am an active relaxer. Like most entrepreneurs, we don't sit still. We're not good at just sitting there doing nothing, but there's certain things that I know I really want to do. So I'm going to make sure that I'm going to go into a hot air balloon ride over Melbourne. We're going to visit a few of the Melbourne comedy clubs. We're going to have some time just chilling by the poolside and reading some good books. And most importantly, I'm going to spend time with my best friends and my dogs and my cat and just really enjoy the festive spirit, having some good food, some good wine, and all the great things that come with the Christmas season. So I hope that you have a fantastic Christmas break. I look forward to seeing you in the New Year. Merry Christmas, everybody. You.
EOS Implementer | Entrepreneurial Leadership Coach | Workshop Facilitator | Keynote Speaker | Author | Business Coach
Debra Chantry-Taylor is a Professional EOS Implementer & licence holder for EOS Worldwide.
As a speaker Debra brings a room to life with her unique energy and experience from a management & leadership career spanning over 25 years. As a podcast guest she brings an infectious energy and desire to share her knowledge and experience.
Someone that has both lived the high life, finding huge success with large privately owned companies, and the low life – having lost it all, not once but twice, in what she describes as some spectacular business train wrecks. And having had to put one of her businesses into receivership, she knows what it is like to constantly be awake at 2am, worrying about finances & staff.
Debra now uses these experiences, along with her formal qualifications in leadership, business administration & EOS, to help Entrepreneurial Business Owners lead their best lives. She’s been there and done that and now it’s time to help people do what they love, with people they love, while making a huge difference, being compensated appropriately & with time to pursue other passions.
Debra can truly transform an organisation, and that’s what gets leaders excited about when they’re in the same room as her. Her engaging keynotes and workshops help entrepreneurial business owners, and their leadership teams focus on solving the issues that keep them down, hold them back and tick them off.
As an EOS implementer, Debra is committed to helping leaders to get what they want and live a better life through creating a bet… Read More