The Pure Bookkeeping Blog

Jumping Off the Cliff — and Why Entrepreneurs Need Systems to Fly

Written by Katrina Aarsman | Jan 7, 2026 4:20:40 AM

Starting a business rarely feels safe.

There’s no instruction manual. No guarantee of success. No moment where everything feels “ready.” And yet, entrepreneurs leap anyway.

Reid Hoffman’s quote — “An entrepreneur is someone who jumps off a cliff and builds a plane on the way down” — captures this perfectly. It’s not reckless optimism; it’s courageous action paired with continuous problem-solving.

Most entrepreneurs don’t start with:

  • Perfect financial clarity
  • Documented processes
  • Strong cashflow systems
  • Predictable workloads

They start with an idea, a vision, and the willingness to learn fast.

That leap is necessary — but it comes with pressure. As the business grows, so does complexity. More clients. More staff. More transactions. More decisions.

That’s when “building the plane” becomes critical.

Without systems:

  • Cashflow becomes reactive
  • Financial data is late or unreliable
  • Business owners make decisions based on instinct, not insight
  • Stress increases as growth accelerates

Many entrepreneurs don’t fail because their idea is bad.
They struggle because the business outgrows the way it’s being managed.

This Is Where Bookkeeping Changes Everything

Good bookkeeping doesn’t just record the past — it stabilises the future.

With the right systems:

  • Business owners gain confidence in their numbers
  • Decisions are backed by real data
  • Cashflow becomes predictable
  • Growth becomes sustainable

This is why structured systems, like the Pure Bookkeeping System, are so powerful. They turn chaos into clarity — and help entrepreneurs finish building the plane before they hit the ground.

Entrepreneurship will always involve risk, but flying blind is optional.

If you’re an entrepreneur, don’t wait for things to “settle down” before getting your numbers under control.

If you’re a bookkeeper, you’re not just keeping records — you’re helping businesses stay airborne.

Jumping off the cliff takes courage. Building the plane takes systems.