Windmill Startup Coaching

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Windmill Startup Coaching

I Help Mid-Career Tech Professionals Build A Consulting Business Alongside Their Day Job Using The 3 Pillars of Success Blueprint
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20/08/2026

Changing careers in your 40s doesn't mean starting from zero.

You bring these to the table:
✅ judgment
✅ relationships
✅ experience and ...
✅ lessons from everything you've already done

The direction can change without throwing away the years behind you.

If you've been thinking about a different path, what’s holding you back?

18/08/2026

For thirty years, automation climbed up from the floor
and stopped below you.
This decade, it kept climbing.

Twenty years of experience used to be a wall.
Now the machines treat it like a door.

The part of your job hardest to hand to a machine
is the part your CV describes worst.

The routine office work went years ago.
The expert's desk is next in line.

Follow for more career insights. 💡

11/08/2026

I've always been a fan of time boxing. Deciding in advance which task gets which slot. But I'd only ever thought of it as a way of planning what to do.

The thing that landed on the drive was the other half of it. A time box doesn't just tell you what to work on. It tells you what to stop.

So for the next three months I'm testing something. Work from five until one. Eight honest hours, then done. Not because the work is finished, it never is, but because one o'clock is where I've decided it ends.

And the hours I get back go to the things I've been quietly avoiding. The garage that's become a dumping ground. The garden I keep meaning to sort. Small and often, the way anything that compounds gets done.

The holiday takeaway wasn't work less. It was be honest about when not to work at all.

Do you feel this too lately? Where does yours spill over?

06/08/2026

Who am I without this job?

I've spoken to a lot of people who've reached the point of thinking about doing something different, may it be consulting or other things for retirement and this question always seems to appear.

It's rarely about experience anymore. By that stage, they've spent decades building careers, leading teams, solving difficult problems, and earning the trust of the people around them.

The part that feels uncertain isn't the work.

It's leaving behind the title that quietly became part of their identity.

I've started wondering whether that's why so many capable people wait. They're trying to answer a question that only becomes clear once they take the first step.

One thing kept coming back while I was reading stories from people who'd already made that transition.

Almost nobody said, *"I wish I'd waited longer."*

Quite a few said, *"I wish I'd started sooner."*

I keep coming back to that thought.

And the hardest part of moving on isn't leaving the job at all. It's believing that everything you've spent years building still belongs to you, even after the title is gone.

👇 Comment "IDENTITY"and I'll send you the 10-Conversation Script; the exact, low-pressure way to test what you're worth without quitting a thing.

04/08/2026

I recorded this just after my morning run in Greece, while the thought was still fresh in my mind.

For a long time, I believed that doing great work would speak for itself. In many ways it did, but only up to a point. Eventually I realised that being good at what you do and helping other people understand why it matters are two very different skills, and learning the second changed more for me than I expected.

If you’d like to follow the journey, stick around and hit that follow. I’ll keep sharing the lessons, mistakes, and observations that have shaped how I think about work, business, and life.

30/07/2026

Yet. One word can completely change the conversation you're having with yourself.

There's a big difference between saying, "I failed," and "I haven't figured it out yet."

The first sounds like a conclusion.
It tells your brain the story is over.

The second leaves the door open.
It reminds you that you're still learning, still improving, and still moving toward an answer.

I've noticed that the people who make the most progress in life are the ones who stop treating every setback as a verdict on who they are.

Instead of asking, "What does this failure say about me?" they ask, "What is this trying to teach me?"

That one small shift changes everything.

It doesn't make failure disappear.
It makes failure temporary.

So the next time something doesn't go the way you hoped, try adding one word. Yet.

It might be the difference between giving up and giving yourself another chance to figure it out.

28/07/2026

I spent some time reading through hundreds of comments from people in their 50s about the things that made life better.

Honestly, I expected to see more answers about money, promotions, or career success. Instead, the themes were surprisingly simple.

💡People talked about caring less about what others think.
💡Trying new things without worrying about looking inexperienced.
💡 Protecting their peace.
💡 Looking after their health.
💡Learning to say "no" without feeling the need to explain themselves.

The more I read, the more I realised something. None of those lessons actually belong to your 50s. Most of them are things we could start today if we chose to. Maybe that's what wisdom really is; not getting older but just letting go of the things that were never helping us in the first place.

I'm curious...

Which one do you wish you'd started ten years ago?

23/07/2026

One thing I've noticed about experienced professionals moving into consulting is that they often worry about the wrong thing.

They think pricing is going to be the hardest part.

In my experience, it rarely is.

Most people don't push back because the price is too high. They push back because they haven't fully understood the value yet.

If you've spent twenty or thirty years building your career, you've almost certainly solved problems that saved time, reduced risk, or helped businesses move forward. Your experience has value. The challenge is learning how to communicate that value in a way that's clear to someone who's hearing it for the first time.

Once people understand the outcome you're helping them achieve, the conversation changes. It stops being, *"Why is this so expensive?"* and becomes, *"How soon can we get started?"*

I'd love to hear your perspective.

If you're already consulting, what's been your biggest lesson when it comes to pricing?

And if you're still thinking about making the move, what's the biggest thing holding you back from charging for your expertise?

21/07/2026

Half the year is already behind us, and it's a good time to pause before rushing into the next six months. Looking back honestly is often more valuable than setting another ambitious goal. In this video, I share the five questions I use to review what worked, what didn't, and where my focus needs to be next. One of my biggest goals didn't go as planned, and that ended up being the most valuable lesson of all. If you're due for a reset, I hope these questions help. What's the one thing you'll focus on over the next 90 days?

The link to the paperback version of my book “Action Before Clarity” and the Webinar is in my bio. Go check it out!

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