18 months in: Lessons from my solopreneur journey

It’s been 18 months since I left behind the comfort of a full-time leadership role and stepped fully into the world of solopreneurship.

Looking back, it feels like both a blink and a lifetime – a stretch of months filled with freedom, growth, lessons, and plenty of self-check and self-evaluation moments.

And while this is a personal story, many of the lessons from solopreneurship echo the challenges leaders face in organisations – balancing vision with execution, freedom with responsibility, and growth with sustainability.

The seed of this journey was planted back in 2018, when I was in the middle of an intense NLP (Neuro-Linguistic Programming) practitioner programme. Ten days of rewiring, reflecting, and asking myself bigger questions.

At the time, I was still head of HR at the Westin, and I was not planning to leave. But that training opened up a space in me, a new sense of curiosity about what else I could do, and a quiet whisper that maybe there was a different path ahead.

That whisper grew louder over the years as I started to experiment on the side: delivering training programmes, coaching, and slowly shaping what would eventually become my brand, Speak to Move.

Communication was the edge I wanted to sharpen – it has always been my passion, and it is what people consistently recognised in me.

Eventually, in late 2023, I made the leap. I said goodbye to the safety of a career that had been home for over 20 years and chose freedom, creativity and the unknown.

The first weeks: Liberation and flexibility

If I had to describe the first weeks of being “fully in,” one word comes to mind: liberating. For the first time, I was setting the terms. I could choose the projects, decide who I wanted to work with, and give myself permission to be creative in ways that were harder to do in corporate structures.

That freedom extended beyond the nature of work itself. It was also about family. Suddenly, I had flexibility to be present with my kids in a way that mattered deeply, like being around more during my daughter’s O-level exams. That balance, that sense of living and working on my own terms, made me realise I had chosen the right path.

Moments that remind me why

There have been plenty of times along the way where feedback from clients has lifted me in ways I cannot fully describe. One moment that stands out happened recently: I had trained a group in a financial services organisation, and soon after, their COO turned to their head and said, “These two are different. They have changed. Their presence during presentations feels transformed.” The head wrote to me afterwards, sharing the story and even recommended me to the COO. That kind of feedback provides the fulfilment of validating the work and fuels me immensely.

Another moment was more personal: receiving a testimonial on a day I felt a little flat. She wrote, “The moment Michelle walks into the room, the place lifts. She breathes confidence and passes it on to others.” I remember reading it with a huge smile on my face, thinking, this is why I do what I do.

And then there are the surprises, like the client whose development I was not sure had taken root yet, who later came back asking for more coaching because she had seen real progress. Those are the moments that remind me my purpose is in the right place.

The challenges (yes, there are many)

But let me be honest: this is not all freedom and glowing testimonials. One of the biggest surprises was how quickly I filled my time. At first, I thought solopreneurship would mean more space, but as work picked up, I found myself working evenings and weekends again, sometimes longer than I did before.

I also underestimated how long things take – especially with my perfectionist streak. What I thought would take me a few hours often stretched into double that. The result? More late nights, less rest, and a creeping feeling that I was falling into the very trap I left my corporate role to escape.

I am still in the process of learning how to balance this. These days I try to be more mindful of how many projects I take on, because if I do not protect my own energy and family time, what is the point of this whole adventure?

What I would tell ‘Month 1 Michelle’

If I could go back, I would tell myself this: not every task is worth your time. In the beginning, I tried to do everything myself, from content creation to marketing to admin, and a lot of it kept me busy without truly moving the needle.

This year, I finally realised I needed to let go. I brought on two students to support me: one in digital marketing, another in video production. And already, I can see the difference it makes when I can focus on the work that really matters – developing programmes, serving clients, and growing the business.

A friend of mine, financial coach Patrick Debattista, shared something recently during a community event that stuck: if you are doing tasks that someone else could do for a quarter of the value you could generate in that time, then you are better off delegating them.

I wish I had heard that in Month 1.

This lesson applies far beyond solopreneurship. Leaders in organisations also grapple with holding on too tightly versus trusting others to step in. In both cases, real growth happens when we learn to focus our energy on what only we can do, and empower others to take ownership of the rest.

Finding my circles

Another revelation has been the power of community. Family support has been essential: my husband, kids, and parents have been there for me in ways both practical and emotional, cheering me on even when my ideas sounded a bit wild.

And the professional networks have been just as transformative. I joined SHE, a community for female founders, and FPEI, a network for entrepreneurs. These spaces have shown me that while solopreneurship can feel lonely, you are never truly alone if you find the right circles. We share struggles, swap skills, and lift each other up. It is like having a safety net, but one made of people who understand exactly what you are going through.

For leaders, the parallel is clear: building strong networks, both inside and outside the organisation, is not optional. It is often the difference between carrying the weight alone and creating a culture of shared strength.

The inner shift

Perhaps the most surprising change has been internal. I have always believed in my abilities, but solopreneurship has strengthened my self-belief in a different way. I have invested more time in my own learning than ever before – reading, studying, exploring new ideas daily.

And alongside that confidence, I have also found more calm. A friend recently told me over dinner, “Michelle, you are different – more confident, yet also calmer.” And she was right. I feel it too.

Looking ahead

So where next? The next 18 months excite me even more than the last. For one, I am no longer entirely solo – I have decided to keep one of my student assistants, Iman, on long-term, and Zack on a part-time basis. Building a small team feels like the next natural step, and I can already sense the joy of having others to share ideas and energy with.

The other big focus is my Digital Learning Academy. Right now, it is still in its infancy, but I see it as the key to scaling Speak to Move globally. I want to share knowledge not just with clients in Malta, but with professionals around the world who need to communicate with confidence. That vision gives me energy every day.

Eighteen months in, I would not trade this journey for anything. It has been liberating, inspiring, exhaustingly self-reflective, and deeply fulfilling – sometimes all in the same week. If there is one thing I have learned, it is this: solopreneurship is not about having all the answers. It is about trusting yourself enough to step into the unknown, learn as you go, and allow the journey to shape you.

And perhaps this is the essence of leadership too – in business, as in life.