Why your old playbook is holding you back

Hey there — here’s your weekly dose: what I’m testing in content, learning in business, shifting in mindset, and passing on to my kids.

Tiny (Content) Experiments

We are hosting a workshop in less than 2 weeks.

This will be for anyone running a business who wants to:

• Establish themselves as an authority through organic content
• Not be just another “thought leader”
• Post content that converts

I will cover content experiments like the one I am running on LinkedIn right now that has helped me increase my impressions by 718% (see image below).

This is a 5-day masterclass from someone who has done content for 4 years and used it to build a multi seven-figure business.

Founder’s Lens

The most dangerous moment for a founder isn’t when you’re broke and scrappy — it’s when things start working. That’s when hunger fades and you start protecting what you have instead of chasing what’s next.

The founders who keep compounding don’t get stuck in comfort. They keep a beginner’s fire alive even as their companies scale. They try things that might look “foolish” from the outside, because they know every new level of growth requires fresh experiments.

The paradox of leadership is this: the bigger your business grows, the more foolish curiosity matters.

Reframe of the Week

Thought: Scaling means doing more of what worked.
Reframe: Scaling means creating space to try what might not work.

What got you here won’t get you there. The levers that fueled your first $1M stall out on the path to $10M. If all you do is double down on the old playbook, you’ll plateau.

When I reframe scaling as exploration — building systems that allow room for bets, not just repetition — I start seeing compounding again. Growth isn’t a straight line; it’s a series of controlled risks.

Notes to my kids

Don’t be afraid of looking foolish. The people who laugh today are often the ones asking for advice tomorrow. Stay hungry, stay curious, and never let comfort kill your fire.

Keep building,
Clifton