This year I did something I have never done before.

I joined a small group mastermind for business owners at a similar level to me.

Now, I realise that some people might find that odd, given that small group masterminds are the bread and butter of my business, but a year or so ago I reached a point in my business journey where I felt stuck.

I probably do not need to tell you what a rollercoaster ride being in business can be, and the last thirteen years of entrepreneurship have had their fair share of ups and downs. But what I experienced over the past couple of years felt new to me. Gone were the highs and lows, and in their place was something else.

After a few dramatic increases in income from 2020 onwards, my annual income eventually levelled out. I had settled into a business model that felt easeful to operate and a marketing system that I could rely on, even when I could not rely on my fluctuating energy levels.

In short, things got really stable. Which felt great… until it did not.

Something I have a hard time admitting is that I had started to feel a bit bored.

Offering the same things year after year and doing marketing the same way began to lose its appeal. I started to miss the creativity of trying new things and seeing what happens. But as I mentioned in a previous letter, making any big changes felt scary. I did not want to break something that was working.

That was when I realised that I needed a shift in perspective. I needed to work with someone further along in business than me, who could show me what I could not see for myself.

As is often the case when we reach the point of being ready for change, the universe put in front of me exactly the kind of support I felt I needed: a small, yearlong group mastermind called Quiet Ambition for established business owners. And even though I was tempted, I had my doubts.

What almost stopped me

What if I disappeared in the group? As a raging introvert and HSP, even though I have no problem leading a group, being a participant has always been more challenging for me, so I have tended to favour one-to-one support.

How much progress would I actually make with only two calls a month? Given that my own yearlong programs have always had weekly calls, I worried about paying more than three times what I charged for half the time I gave.

What if the advice given, or my fellow participants, did not believe in ethical marketing the way I do? The last thing I wanted was to be given advice that I could not implement because it felt out of integrity.

And possibly the biggest concern of all: what if the coach running the group or my fellow participants told me that the only way to get to the next level in business was to put my prices up? I have always prided myself on accessible pricing, and yet the only advice I ever seem to find online about growing our income is to raise our prices.

Despite my doubts, I got on a sales call and, after a good conversation with the coach, decided to go for it.

The experience of being a participant rather than the guide

When the first call came around, back in January, I will admit that I was a little nervous before joining. I had to laugh at myself for finding it edgier to be a participant than to lead a group. I am still not exactly sure why.

My initial fears soon gave way to a deep feeling of relief. The kind of release that comes when you let go of control and surrender to the support available to you. It felt wonderful to know that it was not my job to hold space or provide support; my only job was to be open to receiving it.

It was also fascinating to watch how someone else held space and structured the calls inside an offer somewhat similar to mine. It felt different, and that was exciting. There were moments where I wished things were done the way I do them, and others where I thought, perhaps I could try that in my groups. I felt inspired.

But it was not all plain sailing.

I think it was on the second call that my heart sank when one participant shared her struggle with sign-ups for a launch and another said, “Just spam them!” You can imagine my horror. Thank goodness I was muted because I think I gasped out loud.

The mirror I needed

Something that being part of a small group mastermind gave me was the wisdom of a group of fellow business owners and their honest reflections about my work.

It was so interesting to see how they responded to my business. There were several moments when people had noticeable reactions.

There was the time I shared my annual income alongside the number of subscribers on my list. People were shocked that I could make the income I was making with such a small list and asked how I was doing it. Some of the other women had lists five or ten times the size of mine but were struggling to convert them into clients. I remember thinking, perhaps it is because I do not spam them.

Then there were the gasps when I shared the pricing for my yearlong group program, the Conscious Business Mastermind, and the number of calls I offered.

And despite my initial fear that I would be told to raise my prices, simply saying them out loud became a huge turning point for me. (I will share more on that in a future letter.)

What changed for me

So much has changed in my business as a result of being in the mastermind. I have re-thought my entire business model, decided to close a program I have been running for six years and, yes, in the end, I have raised some of my prices and put tighter boundaries around my time.

What I learned is that the biggest shifts and breakthroughs come not through information and advice but through taking action and reflecting on it. A big part of my previous programs focused on teaching and sharing the strategies and tools that helped me reach the level of success that I have.

Being in a group where teaching was not the priority, but reflection and action were, has changed my whole approach to facilitation. It is the reason I have decided to remove live classes from my programs next year. The strategies and tools will still be there, but what I will facilitate more is the reflecting and doing.

The permission and courage this group has given me to let go of what no longer serves me and to lean into my creativity and intuition has been such a gift. The changes you’re seeing unfold in my business are a direct result.

What this experience reminded me

Even after more than a decade in business, there is always more to learn, not just about strategy but about ourselves. Being in a space where I was not the one leading helped me reconnect with the curiosity and humility that got me started in the first place. It reminded me that growth doesn’t always come from knowing more; it comes from having the space to explore, reflect, and uncover what works for us.

More than anything, this year showed me that I do not have to do it all alone. Letting myself be supported does not make me less capable. It makes me more resourced, more creative, and more alive in my work.

I am so grateful I said yes, even with all my doubts. It has changed how I see my work, how I hold space, and how I define success.

DO YOU WANT TO ROOT & RISE IN 2026?

If you’re interested, I’d love you to check out Root & Rise. My two, year long programs in 2026 designed to help you grow your business with clarity, ease, and integrity.

Head to www.carolineleon.com/mastermind for all the details.