What on earth is a CEO Day, and who needs one?!

Having just released the CEO Day Workbook, I’ve had a lot of questions about what a CEO Day actually is and who they are for. So instead of answering them all privately, I thought I’d share them with you too.

I’ve been a huge fan of CEO Days since I started scheduling them regularly about 5 years ago. When I had a “proper” job I was well and truly on autopilot, so goal-setting looked like cobbling together some very random “objectives” with school friends at our annual Christmas get together (like getting another ear piercing and hosting a roast dinner). Let’s not even mention the twice yearly cringefest that was the “performance review” at work – gross. Did anyone ever get anything out of those things?! But that was the extent of it. So when I first went freelance, it just all happened kinda accidentally. I took everything I’d learnt in my corporate jobs (namely that setting goals was a pointless timewasting tickbox exercise designed to make you feel rubbish) and carried those values and rules over into my own business.

It was only when I started coaching 5 years ago that I realised I could control what felt like a runaway train at times. I didn’t have to say yes to every potential client. I could run errands in the day without feeling guilty for leaving my desk. In fact I could even meet fellow small business pals for coffee without feeling guilty (or at least if I felt guilty I could carry on drinking coffee regardless). I could finally go to the gym regularly and not have these wellbeing needs squashed around the edges of my life. I could do more peopling during certain times of my monthly cycle, and work from my soft office (… my bed!) on other days.

And all this felt possible because I’d sat in my fave cafe for a couple of hours with tea and cake, asked myself what I actually want and need (simples?!!) and set some intentions. As it’s impossible to separate life and business when you work for yourself, I didn’t just set business intentions – I also spent time editing the life stuff too (adding in more paddleboarding and walks and sea swims and quality time doing crosswords in the garden with my partner) and designated non-negotiable time in the calendar to take care of my wellbeing. I can’t imagine a time when I’ll stop doing CEO Days now – they literally have been a gamechanger in my life and in my business. No to living and working on autopilot – yes please to dedicated time to ask yourself exactly what you want your life and business to feel like, space to consider what your wellbeing needs are right now, and cake – don’t forget the cake.

What is a CEO Day?

This seems like a good question to start with.

The term CEO Day was coined (sorry, no idea who by!) because when you have your own business it’s easy to get stuck working “in” the business all the time (i.e. being the employee), so this is a time to do the work “on” the business (i.e. being the CEO).

A CEO Day is a designated time when you step away from the day to day, and take the opportunity to look at an overview of what’s going on for you at work and in your life… and compare that with what you want your life and business to look or feel like. If there is a gap between what is currently going on and what you want and need, the CEO Day is an opportunity to make plans to close that gap.

How often should I have a CEO Day?

This is totally up to you – I’ve met people who do a monthly CEO Day and others do a quarterly CEO Day. Some stick to rigid schedules, and personally mine are a little more ad hoc. Mine are usually approximately in early February (I do not enjoy the January new year energy in general!), early April (harnessing that Springtime awakening vibe), July (planning the chilled Summers I crave), September (birthday month and hangover from school days!), and often a mini one in late Nov / early Dec (ensuring I navigate the Winter months in my own gentle way).

Basically – as with many things – my answer is to experiment and see what works for you.

Do I have to spend a whole day on this?

Short answer: No.

Long answer: It depends!

Some CEO Days are quicker because you know exactly what you want the next season to look like for you in life and at work. You’ve set some goals earlier in the year and you want to continue working on those. And you’ve got good habits to lean on so your wellbeing is ticking along just nicely. You’ll probably just need the one slice of cake for this type of CEO Day.

Other CEO Days take longer and require more thinking time with no distractions and maybe two slices of cake. When you’re perhaps feeling that burnout is creeping up on you, or you’ve fallen out of love with your business, or you just can’t face another freakin’ Zoom call… that’s a good sign that a change of scenery and a good chunk of time will really benefit you.

My preferred CEO Day schedule is a cafe with cake and tea in the morning, then a decent walk to blow away the cobwebs and allow my subconscious to process all the big thoughts and decisions of the morning, and finally I’ll spend the afternoon at my dining table (not in my home office – the change of scenery from my normal routine feels good) with my laptop and several notebooks to get all those decisions and wishes into my calendar to ensure they actually happen!

Some people prefer to split the thinking up across several days to reduce the intensity and give themselves time to process things in between decisions. That’s ok too.

All of these options are totally ok – again, it’s all about experimenting and finding what works for you… and also about being flexible and listening to the signals your body and brain are giving you.

Who are CEO Days for?

A CEO Day is for anyone who wants an opportunity to review what’s going on in their life at the moment and to compare that with what they want their life to look like (and then make a plan to take steps towards what they want). It’s a way to make sure your wellbeing needs are being met (thus helping to avoid burnout). It’s a way to help you clarify your priorities and tweak any boundaries. It’s a way to make sure you notice when the fun stuff is being squeezed around the edges of your relentless to-do lists (sometimes when you are knee deep in this, you forget to check in with yourself), and it gives you an opportunity to change something if the balance has tipped too far in one direction.

It’s a way of escaping from the hamster wheel of your busy life, from society’s toxic productivity obsession, from the expectations of those around you, from the autopilot that keeps you marching onward towards a life that feels like that weird “not quite right” feeling of borrowing someone else’s trainers. A CEO Day is more than just a planning day – it’s about tuning into your feelings, it’s about trusting yourself, and it’s about ensuring your wants and needs are met.

Do I have to be a business owner to have a CEO Day?

Absolutely not. You may wish to call it something else if “CEO Day” doesn’t feel right to you, but other than that a CEO Day is totally relevant if you have a “normal” 9-5 job or if you don’t work for any reason. Whatever your employment status, a CEO Day can help you review whether the things you are doing each day are helping you move towards the kind of life you want to be living.

I’ve got this far without a CEO Day, why do I need one now?

Fair point. If you are totally fine without having CEO Days, your work is fulfilling, you are feeling the way you want to feel about your life (creative/energetic/calm/joyful etc), and your calendar is full of things that leave you feeling that gorgeous glow of contentment, I’m genuinely delighted for you – please feel free to share the CEO Day with those around you instead.

But if you have a niggling feeling (or it’s glaringly obvious) that life or work could be better for you (and you’re willing/able to do something about it), this could be for you.

If you too are feeling like life’s whizzing by at breakneck speed and you want to press pause, the CEO Day workbook is a great way to structure a calm and gentle day just for you – you’ll spend the day setting intentions for the season ahead, ensuring that life and wellbeing aren’t forgotten when you set your business goals. Click here to check it out.

If you’d like to hear more about editing your life and business so you feel gloriously nourished, sign up to my email “The Rebel Edit”.

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