The Most Dangerous Phrase in Life
"I Should Be Further Ahead By Now"
A few years ago, I paddled 470 kilometres down the Hunter River.
The journey began in the Barrington Tops and finished at Newcastle Harbour, where the river eventually meets the ocean.
At least, that was the plan.
Like most plans, reality had other ideas.
Some days the river flowed beautifully. I could paddle for hours, make good distance and feel like everything was falling into place.
Other days I battled headwinds that seemed determined to push me backwards.
Some days I made excellent progress.
And some days I stood in ankle-deep water staring at a paddleboard I couldn't paddle.
The river had disappeared.
The board remained.
The journey continued.
So I carried it.
I remember looking at my map one afternoon and doing the maths.
At the current rate, I wasn't where I thought I should be.
Not even close.
I felt frustrated.
Not because I wasn't moving, but because I wasn't moving according to the timeline I had created in my head.
That's when a familiar phrase appeared:
"I should be further ahead by now."
At the time, I assumed the problem was the river.
Looking back, I think the problem was the story I was telling myself.
I've noticed that phrase appearing everywhere in life.
Business owners say it.
Parents say it.
Athletes say it.
Students say it.
I've said it while building businesses.
I've said it while writing books.
I've said it while studying psychology.
I've said it while raising a young daughter.
The circumstances change.
The story stays the same.
"I should be further ahead by now."
When my daughter was born, I remember thinking that after a few months I'd probably know what I was doing.
Parents reading this are probably laughing already.
Two years later, I'm still making mistakes daily.
I'm still learning.
Still adapting.
Still discovering that children don't operate according to project plans, productivity systems or carefully designed timelines.
Yet some of the most important progress has happened during moments that felt completely ordinary.
Reading the same book for the twentieth time.
Answering another endless "why?"
Sitting on the floor building towers only to watch them get knocked over seconds later.
Packing lunches.
Cleaning spills.
Reading bedtime stories when I'd rather collapse on the couch.
None of it feels particularly remarkable in the moment.
Yet somehow those small moments become the foundation of a relationship.
Trust is built.
Confidence grows.
Character forms.
Progress is happening.
You just can't always see it.
I've experienced something similar while building SwiftReporter.
When people look at startups, they often see launches, customers, milestones and announcements.
What they don't see are the hundreds of conversations.
The lessons.
The dead ends.
The product improvements.
The customer feedback.
The moments where you're wondering whether anything is actually working.
The truth is that some months feel a lot like carrying a paddleboard through a dry riverbed.
There's no applause.
No finish line.
No dramatic breakthrough.
Just the quiet work of continuing to move forward.
Looking back, many of the things that mattered most weren't visible at the time.
Trust was being built.
Skills were developing.
Relationships were deepening.
Momentum was quietly accumulating beneath the surface.
I think many of us suffer because we compare reality to an imaginary timeline.
By a certain age we think we should have more money.
A bigger business.
A clearer career path.
Better health.
More certainty.
More answers.
We imagine where we thought we'd be and then judge ourselves for not being there.
The problem isn't having goals.
Goals give us direction.
The problem is becoming attached to a schedule that reality never agreed to.
The river certainly didn't.
It didn't care what was written on my map.
It didn't care how many kilometres I wanted to cover.
It simply presented the conditions and asked me to respond.
Adapt.
Learn.
Continue.
Life seems to operate much the same way.
The irony is that when I look back on my life, many of the periods that felt slow at the time turned out to be incredibly important.
Living in a monastery.
Building social enterprises.
Leading soft sand walking meditations.
Writing books.
Recording podcasts.
Paddling rivers.
Studying psychology.
Starting businesses.
Becoming a father.
None of them happened according to plan.
None of them followed a neat timeline.
And all of them shaped who I am today.
If you'd asked me ten years ago how my life would unfold, I would have been wrong about almost everything.
Thankfully.
Because some of the best opportunities, friendships, adventures and lessons arrived by routes I never would have predicted.
These days, whenever I catch myself thinking:
"I should be further ahead by now,"
I try to ask a different question.
Ahead of what?
Ahead of whom?
According to whose timeline?
Because when I look around, most people aren't struggling because they're failing.
They're struggling because they're measuring themselves against an imaginary version of how life was supposed to unfold.
Perhaps the most dangerous phrase in business isn't:
"What if I fail?"
Perhaps it's:
"I should be further ahead by now."
Because hidden inside that sentence is the assumption that we know exactly how the journey should unfold.
The river had other ideas.
Life usually does too.
So here's the question I've been sitting with lately.
Where in your life have you convinced yourself that you're behind?
And what if you're not?
What if you're learning exactly what this chapter is trying to teach you?
What if you're building foundations that aren't visible yet?
What if you're closer than you think?
And what if this part of the journey is simply asking you to keep moving toward the ocean?