The Day I Forgot It Was Monday

In mid June I turned 50.

Rather than celebrating with one big party or a long holiday, AnneMarie and I decided to do something different. We factored in having family and friends in a number of locations and used the celebrations as an excuse to spread visits and hosting.   I had a long weekend in Lisbon with my son and friends we have known since we were first dating.  Last week we had family staying for 5 nights. 

Meals out. Time together. It felt less rushed and gave us something to look forward to throughout June.

And somewhere along the way I realised I was running an experiment I hadn’t actually planned.

Every time I left for two or three days, I found myself asking the same question.

What happens while I’m not there?

Not because I expected disaster. Quite the opposite.

I was genuinely curious to see whether everything I’d spent the last two years transitioning Nuvem9 into would allow the day to day to continue without me.

It wasn’t always like this

Ten years ago, I know exactly what would have happened.

I’d have checked my emails over breakfast.

I’d have answered Slack messages while waiting for dinner.

I’d have jumped into client conversations because “it’ll only take a minute”, much to everyone’s frustration.

I’d have replied to questions that someone else could probably have answered themselves.

At the time I would have convinced myself I was simply being responsive and keeping things moving.

Looking back, I don’t think that was true.

I was reassuring myself that I was still needed.

Like many founders, I had become accustomed to being involved in almost everything. Every decision felt safer if it passed across my desk. Every client conversation seemed better if I was copied in. Every unusual situation somehow found its way back to me.

It wasn’t because I didn’t trust the people around me.

It was because I had never consciously designed the business to operate differently.

I realised something uncomfortable.  If I couldn’t step away for a couple of days without worrying about what I’d come back to, then I hadn’t really built a resilient business.

I’d simply built a business that relied on me being permanently available.

That isn’t freedom. It’s dependency wearing the disguise of dedication.

Leadership changes when the business grows

One of the biggest lessons I’ve learnt over the years is that the skills required to build a business are not always the skills required to grow one.

In the early days, being involved in everything is, in itself, the advantage.

• You know every client
• You make every decision
• You solve every problem

The reason is that, when growing, speed matters more than structure.

However, eventually something changes.

• The business grows
• The team grows
• Clients become more varied
• Opportunities become larger
• The volume of decisions increases

Without realising it, the Founder becomes the operating system that holds everything together. For more on this, our March Operational Debt series covered how these hidden dependencies build up inside growing businesses.

Not because anyone intended it that way.  Simply because that’s how the success inside the business manifested as it evolved.

In Nuvem9 I’ve spent the last few years deliberately trying to change that.  Not solely because I wanted to work less.

It was because I wanted to build a business that wasn’t dependent on one person.

Since then I have been making some deliberate changes. 

• Documenting exactly how we work through a growing library of Loom walkthroughs
• Supporting my team to give people genuine ownership rather simply a list of delegated tasks
• Encouraging decisions to be made within clear frameworks instead of seeking permission

And accepting that other people won’t always do things exactly as I would.

Sometimes they’ll do them differently.

Occasionally they’ll do them better.

Most importantly, creating an environment where the first instinct is to solve a problem rather than escalate it.

None of this happened overnight.  And, I am not finished.  In truth, we’re still learning.

The biggest surprise wasn’t what happened

When I came back after each short break, I expected to find a backlog.

Perhaps a list of decisions waiting for me or a collection of problems that had accumulated while I was away.

Instead, to my delight: 

• Clients had been looked after
• Work had continued
• Questions had been answered
• Projects had moved forward

The biggest surprise wasn’t what had happened inside the business.

It was what had happened inside my own head.

The dolphin example

The moment I realised the experiment had worked wasn’t while I was away.  It was 10pm on Monday this week.

We’d spent the day at a water park with AnneMarie and my granddaughter, Ciarraí. Dolphins, slides, lots of sun and an Uber ride home, exhausted.  I cooked dinner while watching the World Cup and suddenly said, “I forgot it was Monday.”

Then I looked at my phone.

• No emergencies
• No frantic messages
• No client problems

AnneMarie simply smiled and said, “Good.”

Are you still available?

Somehow that single word said everything.

I have realised how conditioned founders become to being available.

• How instinctively we reach for our phones
• How easily we assume our opinion is required
• How slightly uncomfortable it can feel when nobody needs us

Somewhere along the journey we begin to confuse being involved with being valuable.

The two are not the same.

The scarcest resource in a scaling business

Over the past few months I’ve had conversations with many business owners experiencing exactly the same challenge.

• Their businesses are growing
• Their teams are capable
• Their clients are happy
• Yet they finish every day mentally exhausted

Not because they’re working harder than ever.

Because they’re carrying the weight of hundreds of small decisions.

• The constant interruptions
• The quick questions
• The grey areas
• The exceptions
• The client who “just wants a quick chat.”

Individually, none of these things feel particularly significant. Collectively, they consume the one resource that every founder has in limited supply.

Attention.

When your attention is fragmented all day, there is very little left for strategic thinking.

The irony is that most business owners don’t become trapped by a lack of capability within their teams.

They become trapped by their own willingness to remain available.

A different way of measuring your business

Turning 50 inevitably prompts a little reflection.  

I’ve found myself thinking less about revenue targets or growth plans and more about what kind of business I want to build over the next decade.

Not a business that depends on me.

A business that benefits from me.

There’s a subtle but important difference.

One relies on my presence.

The other values my contribution.

That distinction creates freedom.

Not the freedom to disappear.

The freedom to choose where I can add the greatest value.

A question worth asking

So here’s the questions I’ve been reflecting on since my birthday.

If you deliberately stepped away from your business for three days…

• What would continue exactly as normal?
• What would pause?
• What decisions would immediately come back to you?
• Which clients would still pick up the phone and call your mobile?
• Where would your team hesitate because they’re unsure whether they’re allowed to decide?

The answers to those questions will probably tell you more about the health of your business than any management report ever could.

Over the next few weeks I’m going to explore this idea further.

Not from the perspective of working fewer hours.

Instead looking at it from the perspective of building businesses that create confidence, resilience and genuine freedom.

Perhaps the greatest measure of leadership isn’t how much the business needs you.  It’s how confidently it performs when you’re not there.