Why Taking a Leap of Faith is Often the Best Business Decision

Some of the best decisions we make in business start with a leap, into the unknown, away from the comfortable and often against the advice of the well-meaning people around us.

It’s scary.  It’s uncomfortable.  And yet, it’s often exactly what’s needed.

If you’ve ever found yourself stuck in indecision, weighing up the “what ifs” or talking yourself out of a dream because it doesn’t come with a neatly printed guarantee, this post is for you. 

Because while logic and planning are critical, there comes a point when the biggest growth happens only after you take the leap.

What Does “Taking a Leap of Faith” Really Mean?

Let’s clarify what we’re talking about.  Taking a leap of faith doesn’t mean closing your eyes and hoping for the best.  It’s not about being reckless.  It’s about choosing action in the face of uncertainty, when you don’t have all the answers, when the path ahead isn’t clearly mapped out, but something inside you says, This is worth doing.

It might mean:

• Leaving a secure job to start your own business

• Launching a new product before it's 100% perfect

• Turning down a client who isn’t a good fit (even when your bank balance says otherwise)

• Saying yes to an opportunity you don’t feel quite ready for

In business, these moments come up more often than we think.  And how we respond can shape everything that comes next.

Why It’s So Hard to Take the Leap

Fear of failure is a powerful thing.  Most of us were raised to value stability, predictability and safety.  The problem is, those things don’t always exist in business.  At least, not in the way we’d like them to.

We crave certainty, proof that this idea will work, that this client will pay, that this new direction will lead to success.  But business doesn’t hand out guarantees.  You get progress through action, not assurance.

And yet, many would-be entrepreneurs and seasoned business owners alike spend years stuck in analysis paralysis, tweaking, planning, over-preparing and waiting for the “right time”.  That time never comes.  The longer we wait, the more we convince ourselves that we can’t take the leap.

So what changes?

The Moment Everything Shifts

Often, it’s a moment of frustration.  Redundancy.  Burnout.  Or simply a rising desire for more, more freedom, more fulfillment, more alignment with who you are and what you want from life.

For me, it was redundancy and the recognition that life is too short to keep waiting for the perfect plan.  I’d always loved helping others get organised, tick things off their to-do lists and make sense of the chaos.  Pair that with a love for spreadsheets, a background in business and a growing number of friends saying “you could do this for a living” and the seed of Ask Wendy was born.

I didn’t have all the answers.  I didn’t have a big budget or a slick launch strategy.  I had an idea, a laptop and a decision: to leap.

What You Gain When You Leap

Here’s what they don’t tell you about taking a leap of faith in business: it forces you to rise.  Not in a superhuman, hustle-24/7 kind of way, but in a way that builds confidence, character and momentum.

You Learn Faster

No amount of planning can replace real-world experience.  Once you’re in it, actually doing the thing, you learn what works, what doesn’t and what your clients need.  It’s like switching from theory to practice overnight.  You can read all the how-to guides, but nothing beats the education you get by doing.

You Build Confidence

Every decision you make builds confidence.  Not just when things go well, but especially when they don’t.  You realise you can handle setbacks.  You can figure things out.  You can make decisions without needing someone else’s approval.  That’s gold in business.

You Attract Opportunities

People respond to action.  When you put yourself out there, even if it’s messy, even if it’s new, you start attracting the right kind of people.  Clients, collaborators, mentors and supporters.  It’s as if the universe (or the algorithm) notices your momentum and starts backing you.

You Get Clarity

One of the biggest myths in business is that you need clarity before you start.  The truth is, you get clarity from starting.  By showing up and doing the work, you learn what you enjoy, who you like working with and what you want to build.  That clarity only comes after the leap.

Real-Life Leaps That Paid Off

If you look behind the scenes of most successful businesses, you’ll find a leap of faith somewhere in the origin story.

• The marketing consultant who left a well-paying agency role to freelance full-time and now runs a thriving boutique agency.

• The online coach who pivoted from in-person workshops and now reaches clients worldwide through digital products.

• The VA (hello!) who went from being a behind-the-scenes organiser to a business owner with clients she chooses, not just accepts.

None of these journeys were straight lines.  But they all started with a decision to back themselves.

What If It Doesn’t Work?

Let’s address the elephant in the room: what if you leap and fall flat?

You might.  Sometimes things don’t go to plan.  Sometimes you take a risk and it doesn’t pay off, yet.  But here’s the thing: falling isn’t failing.  Failing to try is.

Even if your leap doesn’t land where you hoped, you’ll still gain:

• Experience you can apply elsewhere

• Skills you didn’t have before

• A stronger sense of who you are and what you want

And often, one “failed” leap opens the door to something even better.  You don’t have to get it perfect.  You just have to start.

How to Take a Smart Leap of Faith

Just because it’s a leap doesn’t mean it has to be blind.  Here are a few ways to leap smartly:

1.  Set a Minimum Viable Plan

Don’t over-plan, but do prepare.  What’s the bare minimum you need to get started? That could be a basic website, a list of services, or a few outreach emails.  Focus on action, not perfection.

2.  Define Your Safety Net

A leap of faith doesn’t mean ignoring reality.  Know your financials.  Set a runway.  Can you freelance part-time while building your business? Do you need a certain amount saved? A little security can give you the freedom to leap without panic.

3.  Surround Yourself With Support

Find your people.  That might be fellow business owners, an accountability buddy, or even a virtual assistant (yes, shameless plug) to help with the things you don’t enjoy.  Having support makes the leap feel less lonely.

4.  Embrace Iteration

Your first version won’t be your final version.  That’s a good thing.  Allow your business to evolve as you grow.  Stay open.  Stay curious.  And remember: progress beats perfection every time.

Leap Anyway

If you’re standing at the edge of a decision in your business, wondering if you should wait a little longer, until you feel more ready, more qualified, more certain, I want to gently challenge you.

What if now is the right time?

What if the readiness comes after the leap, not before?

What if your future clients are waiting, not for the perfect version of you, but for the one who dares to try?

You don’t have to have it all figured out.  You just need to trust yourself enough to take the first step.

Because some of the best business decisions aren’t based on spreadsheets, forecasts, or expert opinions.  They’re based on belief.  In yourself, in your idea and in the possibility that it might just work.

And if it doesn’t?  You’ll pick yourself up, learn from it and leap again.

That’s the kind of business owner who doesn’t just survive.  They thrive.