The Illusion of Readiness: Simon Squibb on Why Starting Now is Key to Entrepreneurship

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Simon Squibb

LinkedIn Author

Co-Founder at Dream

In a recent LinkedIn post, entrepreneur Simon Squibb tackles the pervasive feeling of not being “ready” to start a business, arguing that this hesitation is a universal barrier that must be overcome through action rather than waiting for ideal conditions. Squibb, who has founded 20 businesses, shares his personal experience of never feeling fully prepared, even for his latest venture, DreamBrew.

Squibb highlights the commonality of this sentiment, stating:

“Every single time, I felt like I didn’t know enough yet.”

He emphasizes that this feeling of inadequacy is natural and persists even among successful individuals. “The people you look up to still have it,” Squibb writes, challenging the notion that readiness is a prerequisite for entrepreneurial success.

The Myth of Future Readiness

A core theme in Squibb’s post is the fallacy of waiting for the perfect moment. He contends that the future rarely brings less responsibility or fewer demands. Instead, as time progresses, individuals typically face increased obligations, greater financial commitments, and more people relying on them. Squibb directly addresses this common procrastination tactic:

“This is the emptiest your diary is ever going to be, and you’re already telling yourself you’ll start when things calm down.”

According to Squibb, this mindset is a significant impediment to progress. He suggests that the perceived “calm down” period is largely a myth, and the present moment, however busy it may feel, offers the most opportune time to initiate action.

Taking Action Over Waiting

Squibb’s overarching message is a call to action, urging aspiring entrepreneurs to bypass the paralysis of overthinking and self-doubt. He posits that the drive to start is more crucial than possessing complete knowledge or resources.

The World’s Biggest Business Competition

To facilitate this, Squibb announces the World’s Biggest Business Competition. This initiative is designed to provide a structured, low-commitment pathway for individuals to launch a business. He explains the program’s parameters:

“Four weeks, a few hours a week, completely free… and by the end you’ll have a real business, plus a shot at the $1,000,000 I’m giving away.”

This competition, as described by Squibb, aims to remove the perceived barriers to entry, such as lack of experience or capital, by offering a supportive environment and a significant incentive. The underlying principle, as Squibb articulates it, is simple: “You don’t need to be ready. You just need to start.”

Squibb encourages interested individuals to find the entry link on his profile, reinforcing his belief that the initial step is the most critical component of any entrepreneurial journey. His insights serve as a powerful reminder that readiness is often a byproduct of action, not a precursor to it.

📝 About This Content

This article is based on insights shared by Simon Squibb on LinkedIn.

📅 Originally posted on September 13, 2026 | View original post on LinkedIn →