We had more to lose by standing still

What Changing Direction Taught Me About Leadership

This is a story about:

• Changing direction before feeling fully ready

• Leadership under pressure

• Uncertainty, risk and growth

• Why relationships matter more than ego

• How experience and education quietly prepare us for difficult moments

• And the strange path that somehow involved lawyers, bricklaying, an otter and a former FBI sniper

In my late thirties, I was living in Sydney and working as Deputy Managing Director of a retail advertising agency.

On paper, life looked successful.

I had a senior role, worked with a great team of people and had a career path with plenty of future opportunity ahead of me.

But underneath it all something felt wrong.

• The hours were long

• The client pressure was constant

• There was often a tension between the culture and values we tried to build internally and some of the behaviours we dealt with externally

I loved the people I worked with, but my partner and I had started feeling the same thing:

“We realised we had more to lose by continuing down a path that no longer felt completely right than we did by trying something different.”

So naturally, with no hospitality experience, no construction background and absolutely no real idea what we were doing, we took on a 30 year lease on a piece of land in Indonesia and decided to build a boutique hotel.

Looking back now, confidence had very little to do with it.

It was more a willingness to have a go.

Most Big Decisions Start Before You Feel Ready

At the time, the decision felt enormous.

There were plenty of people warning us about the risks.

Some thought we were making a terrible mistake.

To be fair, there were moments later where we thought exactly the same thing ourselves.

“What I realise now is that major career and life decisions rarely arrive wrapped in certainty.”

Most of the time they arrive disguised as discomfort.

A quiet feeling that something needs to change.

Not because life is necessarily bad, but because part of you knows you are capable of more, curious about more, or simply ready for something different.

The interesting thing is that people often assume confidence comes first.

That you somehow become fearless and then take action.

My experience has been the opposite.

Most of the growth in my life has started with uncertainty.

The confidence usually arrived later.

The Reality Was Much Harder Than the Plan

Like many ambitious ideas, the vision in our heads was significantly more enjoyable than the reality that followed.

What came next involved legal disputes, construction challenges, cultural misunderstandings, stress, setbacks and months of navigating situations we were completely unprepared for.

At one point, a neighbouring landowner challenged part of the lease boundaries.

Meetings followed involving lawyers, agents and multiple parties trying to untangle a situation we barely understood ourselves.

Our lawyer initially assured us our contract protected us and that we were in the right.

Then during one meeting, after reviewing new information, he quietly stood up and walked out of his own office, leaving us sitting there unrepresented with everyone else.

That was not an especially comforting moment.

We eventually discovered we had effectively lost access to around 30% of the land we believed we had secured.

For a period of time, it genuinely looked like we could lose everything.

All the people who had warned us not to do it suddenly felt very loud in our minds.

We were facing the possibility of becoming another couple who tried something ambitious, failed publicly and crawled home with our tails between our legs.

It was terrifying.

But strangely, that became one of the most important turning points of the entire experience.

Leadership Is Often About Letting Go of Ego

Initially, we were determined to prove we were right.

But eventually something more important became clear.

“The goal was no longer proving a point. The goal was finding the truth so we could work with reality instead of fighting it.”

That changed everything.

Once we accepted the situation honestly and calmly, the conversations shifted.

We apologised for the broader conflict, accepted responsibility for what we could control and focused on one simple question:

How do we work through this together?

Luckily, throughout the entire process we had been respectful, honest, fair and calm under pressure.

There was already goodwill toward us because people had formed an opinion about our character long before the conflict escalated.

That goodwill helped create a pathway forward.

• We made concessions

• Accepted compromises

• Paid additional costs we probably should not have had to pay

And slowly, after months of negotiations and difficult conversations, solutions started emerging.

Somewhere along the way, we discovered one of the key players we ultimately needed to negotiate with was a former FBI sniper, which led to a series of surreal WhatsApp conversations!

Eventually we agreed to meet with the neighbour onsite and finalise the boundaries.

And he arrived with an otter.

Not metaphorically.

An actual otter, walking with the casual energy most people reserve for walking a dog off leash.

Which, after the previous months of stress, somehow felt surprisingly normal by that stage.

He agreed to the revised boundaries, walked away, and his lawyer turned to me and simply said:

“Build your wall tomorrow.”

And that was that.

Sometimes the Best Leadership Lessons Come Through Humility

Construction itself became another enormous learning experience.

At one point during the build, I decided the pace of work onsite seemed slower than what I was used to in the corporate world.

Naturally, instead of quietly respecting the fact that these people had spent years mastering their trade, I decided the best course of action was to roll up my sleeves and demonstrate how fast it could be done.

After around nine hours of work, I had only completed two and a half rows of bricks.

The team watched me the whole day. There was a lot of laughing, all at my expense.

Looking back now, it was one of the more important leadership lessons of the entire experience. I think they appreciated that I was willing to try.

But I also learned something very valuable:

“Leadership is less about proving yourself and more about trusting and empowering the skills, experience and processes of the people around you.”

Also, bricklaying is significantly harder than it looks.

Connecting the Dots

During some of the more stressful periods, we would escape to our favourite cafe.

It became a calm space in the middle of complete uncertainty.

We would sit there with tea and cinnamon scrolls talking through problems, exploring options and trying to work out what was to come next.

And somewhere during those conversations, I realised something important.

“Our experience and education to that point had been subconsciously guiding us through the entire process.”

• Every difficult client conversation

• Every leadership challenge

• Every negotiation

• Every communication issue

• Every lesson

• Every mistake

• Every role I had held

• Every piece of academic learning

All of it had quietly shaped how we thought, communicated and responded under pressure.

Not consciously.

But because those experiences had gradually become part of who we were.

At that point I realised it was never one single thing that prepares you for uncertainty.

It is the combination of everything.

• The leadership experience

• The difficult moments

• The communication skills

• The academic study

• The business knowledge

• The mistakes

• The personal growth

• The continuous learning

“All of those things had slowly built the capability to navigate uncertainty when it eventually arrived.”

My experience to that point connected the dots.

Why More People Should Have a Go

Over the past 30 years, not everything in my career has gone well.

I have had growth opportunities, setbacks, difficult periods and moments where I have needed to adapt quickly.

I have had to:

• Improve constantly

• Learn constantly

• Communicate better

• Lead better

• Handle pressure better

• And most importantly, learn from mistakes

Over time, the boutique hotel became more successful than we could have imagined.

We achieved occupancy rates above 90%, built a social media audience of more than 30,000 people and received a 5 star TripAdvisor rating.

Eventually, we achieved exactly what we originally set out to do.

We built something valuable.

But looking back now, the success itself is not what stayed with me most.

What stayed with me was who we became while trying to build it.

We could have remained safely in our previous careers.

There would have been nothing wrong with that.

“But we wanted something different and eventually realised that nobody else was going to create that change for us.”

That did not mean the process would be easy.

It definitely was not.

But many of the skills, experiences and values we had developed throughout our lives turned out to be exactly what we needed once we stepped into uncertainty.

The lessons from that experience shaped much of what came next for us.

Including another major move later to Detroit, a city with its own fascinating story and incredible people that taught us entirely new lessons again.

But that is probably a story for another time.

What This Experience Taught Me

• Leadership matters most under pressure

• Relationships often matter more than being technically “right”

• Communication can solve problems ego cannot

• Experience and education quietly prepare you for uncertainty

• Growth often begins before you realise it has started

• Sometimes the biggest career changes begin with a simple decision to have a go

Final Thoughts

Looking back now, building that hotel in Indonesia was one of the most stressful, difficult and uncertain experiences of our lives.

There were moments of genuine fear.

Moments of doubt.

Moments where hiding in the bathroom briefly felt like a reasonable coping strategy.

But it was also one of the most rewarding experiences we have ever had.

Not because everything worked perfectly.

It definitely did not.

“Looking back now, I realise the confidence to have a go did not appear out of nowhere.”

It had been built slowly over years through experience, learning, mistakes, leadership challenges, relationships and education.

Long before we stepped into Indonesia, we had already been developing the capability to navigate uncertainty.

• Every difficult conversation

• Every leadership role

• Every setback

• Every lesson

• Every piece of academic learning and business theory

All of it shaped how we thought, communicated, adapted and responded under pressure.

When the challenges eventually arrived, we did not magically become capable overnight.

We drew on everything we had learned and experienced along the way.

That experience had already started shaping us long before we realised it.

Sometimes having a go is not about blindly jumping into the unknown.

Sometimes having a go is about recognising that your experience, values, learning and personal growth may have prepared you far more than you realise.

“And often, it is only in hindsight that all of those dots finally connect.”

Thinking About Your Own Next Step?

One of the biggest lessons this experience taught me is that meaningful growth rarely happens in perfect conditions.

Often, growth begins with curiosity.

A quiet feeling that something needs to change.

Or simply a desire to challenge yourself and see what might be possible.

At Connect Business Academy, that philosophy sits at the centre of how we think about learning.

We believe leadership, business and entrepreneurship capability are built through a combination of experience, education, reflection and action.

If you are considering your own next step, you might find these pathways helpful:

Leadership & Management

BSB50420 Diploma of Leadership and Management
BSB40520 Certificate IV in Leadership and Management

Business

BSB50120 Diploma of Business
BSB40120 Certificate IV in Business

Entrepreneurship

BSB40320 Certificate IV in Entrepreneurship and New Business

Looking to accelerate your growth?

Double Diploma of Business + Leadership and Management

If you would like to learn more, feel free to book a no-obligation phone or video call with me directly.

I’m always happy to have a conversation about where you are in your career, what you’re aiming for, and whether one of our courses may be the right fit for you.

And if it’s not, I’m very happy to help point you in the right direction.

— Andrew Sisley
CEO & Head Trainer
Connect Business Academy