Hosting My First Visionary CEO Planning Day Event: Reflections and Insights

On Wednesday 27th November 2025 I hosted my first in-person event – the 2025 Visionary CEO Planning Day LIVE. As someone who loves going to in-person events, but runs an online business, I’ve known for a while I wanted to expand and offer in-person services too. First I started offering Strategy Days in person, then I started delivering talks and trainigns in-person for other businesses, and then in November I took the next step by running my own events. There are lessons I learnt from running my own event that I know some business owners will benefit from. And there are lessons based on the focus of the day (annual planning) that I know other business owners will benefit from. So in this blog post I’m sharing my reflections on hosting my first Visionary CEO Planning Day event.

 

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HOSTING MY FIRST VISIONARY CEO PLANNING DAY EVENT: REFLECTIONS AND INSIGHTS 

 

The Power of Saying Your Goal Out Loud

 

One of the biggest things I was reminded of was the power of saying your goal out loud. At the end of the day one of the attendees, for their biggest takeaway, wrote “Saying things out loud makes me really want to do it!”  Having the opportunity to say your goal out loud, and to others, is a rare opportunity if you are a solopreneur or solo business owner. But everyone had that opportunity during the visionary CEO Planning Day and it was an opportunity people took – and that made a difference.

 

As someone who has  numerous people to share my goals with I had forgotten how other business owners don’t and how powerful having that opportunity can be. But I quickly thought back to year ago where I had first-hand experience the power of being able to share your goals out loud, when usually they just be in your own head.

 

I first learnt that lesson in 2015. I was in a Lean In circle (of the back of reading Sheryl Sandberg’s Lean In) and it was in that group that I first shared with other people that I wanted to start my own book club. Saying it out loud to others made me realise just how much I wanted it and in January 2016 PropelHer’s Book Club was born.

 

Then in 2021 I was working with a business coach called Kerry Lyons and I shared how I wanted to run in-person events. I went to her event in Birmingham and every part of my body knew I wanted to do the same. And whilst it took me a few years I can finally say I did it.

 

People’s Brains Work In Different Ways – Plan in the Way That is Best For You

A key part of any annual planning is putting together the annual timeline. It’s a key part of my annual planning process. But I don’t say there is one way you have to do it. In fact, on this day I shared 3 different approaches. And it was lovely to see all 3 different methods being used.

 

So often when it comes to planning people will try and force themselves into a particular approach, but it’s pointless. Find a way that works for you and stick to that. That’s why I said everyone could plan on their laptop or on paper. And it’s why I gave 3 different options for the annual timeline.

 

To get your best results you need to understand your preferences and lean into them. And sometimes that can be a subtle shift. For example I gave people an option of planning their 12 months in 2 different configurations.

 

It might not seem a big difference but it was so clear that most people naturally preferred one over another. Historically I hadn’t thought about changing the configuration, but after having a conversation with annual planner creator Anna Rigby, who creates her annual planners in landscape and portrait (You can check out Anna’s wall planners in her shop by clicking here.), After that conversationI thought it would be interested to suggest more configurations and see what people preferred. And I’m so glad I did.

 

Planning Will Increase Your Confidence in Relation to Achieving Your Goals

 

One of the things I asked attendees to do was share a goal and how confident they were in achieving their goal. Then after the planning day was over I asked again how confident they were in achieving their goal.

 

On average people’s confidence increased by 2.2 (on a scale of 1-10).  This reinforced what I already felt anecdotally from planning with mentoring clients or running Strategy Days, but it was the first time I got some data.

 

I know it seems counterintuitive to those who haven’t planned, but the reality is if you just have a goal and you’ve done no planning then it is easy for something to not feel achievable as you don’t even know where to start. Whereas planning helps you to really think about who you need to do, and in most cases once you’ve broken it down it’s less daunting and makes you feel as if you can do it – hence the increase in confidence.

 

 

Ready to start planning for success?  My Strategy Days are perfect for business owners who are short on time, but want to plan for business growth. I’ll guide you through my annual planning process and by the end of the day you’ll clear goals for the next 12 month – and a plan for achieving them. To find out more and book a Strategy Day click here.

 

As a Service Provider it is can be so Tough to Make the Time to be the CEO of Your Business and Plan

There were a few cancellations for the event. Business owners who knew they needed to plan for the year ahead, who had bought a ticket so they could plan, but then were swamped with client work.

 

I know all too well that as a service provider it is so easy to spend all your time on client delivery, and supporting your clients, and keep pushing working on your business further down the to-do list.

 

It’s one of the reasons I repeatedly say “You need to work on your business not in your business” and “You need to give yourself time to be a good CEO”.  I know that so many businesses aren’t reaching their full potential just b because the business owner doesn’t spend enough time in CEO mode and working on the business.

 

It’s one of the reasons I created Strategy Days and why I decided to run the 2025 Visionary CEO Planning Day. And as those cancellations came in I remember just how important it is to keep on pushing those messages.

 

Events are task-engines

This was my first in-person event and if you have been thinking about running in-person events I’ll be honest about sharing events are task-engines. This was a concept I came across in Cal Newport’s Slow Productivity and it’s about projects that involve a lot of administrative work. Putting on an event, even a small masterminding-style day, still took a lot of work. Finding a venue, booking a venue, liaising with the venue, getting tickets on sale, selling tickets, communicating with attendees – the list goes on and on.

 

As it was the first time I was doing lots of things for the first time so I know in the future it will be easier. I was documenting as much as possible so that in the future it will be easier. And documenting would make it easy for me to hand over to someone else.

 

A Lot of Events are Loss Leaders

One thing I was very aware of before I ran my event was that a lot of events are loss leaders. As someone who has a background in ticketing and live entertainment I know all too well about the economics of putting on performances and putting on events isn’t massively different. Also, as someone who speaks at events I’ve lost count of how many times I’ve been told an event doesn’t make a profit and that’s why they don’t pay their speakers.

 

In the last few years more and more businesses have been putting on event, but there are two different approaches. Businesses that are running events where there focus is making a profitable event, and those who are running events that make a loss but they have other aims from the event. Now I could write about this more, and if you want me to let me know, but if you are going to go down the loss leader route you need to understand the bigger picture. For example, many businesses will be selling from the stage and that is where they make the money.

 

For me I knew I wanted to event to breakeven. That was my goal and so I created a budget from the beginning and managed to achieve that goal. And this is something you definitely need to think about if you decide you want to start running your own events.

 

Starting Small is Better Than Not Starting at All

Running an in-person event was one of my main goals for 2024. As an extrovert I love attending events and being in-person with people. You can check out my round up of the events I went to in 2023 here.

 

In 2024 the aim was to not only speak, and deliver trainings, online (which I did more of) but to also deliver speeches/talks in person and run my own events.

 

After a difficult summer personally when I sat down to review my goals as part of my Q4 planning I asked myself is this something I want to make happen and I’m going to go for it OR am I going to just push it back to 2025.

 

I decided to go with the former, but be comfortable with something that was smaller/more pared back than what I’ll be doing in years to come. Do I see myself in years to come hosting events where hundreds of business owners come together for the day to plan for the year ahead – and then who knows maybe have a full-on party afterwards? Absolutely! But it doesn’t have to be that or nothing.

 

Instead I decided to start small, but take actions that were leading up to my ultimate vision. I focused in one of my zones of genius – annual planning. And because I knew it would be a small group I crafted the day to be more interactive than it could ever be on a bigger scale. I asked questions and people shared their responses with the group. People had the space to plan on A3 paper. We had giant post-it notes that we stock on the wall.

 

I designed an experience that was based on my expertise, but delivered it in a way that made sense for that context. There is no doubt as I run more events they’ll evolve and I can’t wait to see that evolution. Different venues, more people, a microphone, goodie bags etc

 

But it would have been easy for me to say it’s all or nothing. I see other business owners do that all the time. And the fact is starting small is better than not starting at all. As you can tell I learnt (or remembered) so much from putting on this event. All of that will help for the next one.

 

So if there is a big goal for your business and right now it feels years away think about what you can do to lead up to that. What are the activities you can do in next 3 months, 6 months or 12 months that will move your business in that direction? Remember direction is more important that speed (even though I love some fast growth). Do the things that are helping you to build a business you truly love and that work for you.

 

That’s it. You now know my reflections on hosting my first Visionary CEO Planning Day event.

 

I had such an amazing time that I decided to run another 2025 Visionary CEO Planning Day (You can find out all the details here) and I have no doubt I’ll be running more Planning Days in the future.

 

And if you are thinking I need to put an annual plan together but I don’t have any upcoming planning days you can always book a one-to-one Strategy Day. These are available all year round and obviously on a one-to-one level we can do much deeper.

 

Plan for success – Get a personalised strategy for the next 12 months.  My Strategy Days are perfect for business owners who are short on time, but want to plan for business growth. I’ll guide you through my annual planning process and look at your business growth strategy, offer suite, pricing and marketing so you can experience more income, impact and freedom over the upcoming 12 months. To find out more and book a Strategy Day click here.