"Do you want to take a leap of faith, or become an old man, filled with regret, waiting to die alone?" - Inception (2010)

Sitting here and writing this, I'm struck by just how unlikely it is that I'm doing this in the first place.

If you were to run 100 simulations of my life, I'd be willing to bet approximately 99 of them would have involved a safe, stable path through life. I'm naturally risk averse, my wife and parents are the same, and I started my career on a track in finance with an increasingly strong gravitational field known for holding people forever once they've hit a few years of experience.

And yet, here I am, living in that extreme scenario, writing, building, and creating for a living. When people ask me what I do, I often say that I get paid for the number and strength of positive ripples I can create in the world.

How did that change happen?

A leap of faith.

Because of the gigantic shift in my life over the last three years, I'm often asked about how to take that leap of faith.

To answer that question for anyone who has asked, and anyone who might be thinking about it, here's my definitive player's guide to the leap of faith...

The 100 Foot Gap

Let's begin with a simple fact:

The leap of faith you want to take in life is so scary because of the size of the change.

Little pivots aren't scary. No one asks questions about making a tiny pivot in their career or life. You make those tiny pivots all the time, from one track to a slightly different one, from one company to a slightly different one, from one person to a slightly different one. If you're unfulfilled, you can convince yourself they'll solve the problem, but they're just shades of the same color.

The leap of faith is a 100 foot gap—from where you are today on one side, to where you want to be on the other side.

In between, there's a vast expanse of untold nothingness.

You're standing on one side. You look out and see the other side in the distance. It's far, but not too far. Not so far that you can't imagine what it would be like to be standing over there.

But then you look down and stop in your tracks. The fear takes over.

And that fear expands with time, meaning it's more pronounced at 35 than it was at 25, and more pronounced at 45 than it was at 35. Why? Expectations and responsibilities expand with time—you accumulate bills, mortgages, partners, and kids—meaning your cost of a failed leap has grown, and your fear along with it.

The 100 foot gap is the problem to be solved:

If you can shorten it to a 10 foot gap, the terrifying giant leap becomes a manageable jump.

3 Steps to Shorten the Gap

There are three concrete, actionable steps you should use to shorten the gap and make your leap of faith feel significantly less leap-y:

Step 1: Gather Information

The primary reason the gap feels so large is an information asymmetry. You know exactly what this side looks like, but very little about what the other side looks like.

You don't know what you don't know.

That lack of information manifests as fear—which makes the gap feel larger and more intimidating than it really is.

But fortunately, a lack of information is an abundantly solvable problem.

The questions you should be asking (and answering):

• What does the new path look like? Visualize it in detail.
• How reversible is a decision to take this new path? Note: Most people underestimate the reversibility of a big decision. You assume that if you leave your consulting firm, you'll never be able to get another job in consulting. That is usually patently false. Most of these career decisions are reversible.
• What case studies exist on successful (or unsuccessful) execution?
• What perspectives can you learn from people with real, earned experience on the new path?
• Are there any examples of people who have made a similar shift to what you are considering? What can you learn from them?

If you use a thoughtful process to gather information, you'll balance the information asymmetry and shorten the gap considerably.

Step 2: Create Evidence

The secondary reason the gap feels so large is an evidence asymmetry. You have perfect evidence of your ability to build a life on this side, but very little evidence of your ability to build a life on the other side.

Yet again, that lack of evidence manifests as fear.

This lack of evidence is also a solvable problem:

While still on your current path, you need to create tangible proof that you can build a life on the other side.

What proof points can you generate of your ability to execute?

• Find one customer for your prospective new venture.
• Make $100 selling something on the internet.
• Generate a few client leads to your new coaching practice.

The tiny wins build momentum and balance the evidence asymmetry.

If time is your concern, use my 30-for-30 approach. Carve out 30 minutes per day for 30 straight days to focus on creating evidence for your new path. 900 minutes of focused effort should give you a great body of work to start from.

Step 3: Address the Fear

If you've completed Step 1 and Step 2, you're almost there...

Gathering information and creating evidence have narrowed the gap and you're starting to feel better about the leap.

But the fear still exists.

Here's how to address it:

• Reframe the fear as a good thing: It means you care, it means this is something that matters.
• Deconstruct the downside of action: What is the worst that could happen? How bad is it, really?
• Deconstruct the upside of action: What is the best that could happen? How great is it?
• Deconstruct the regret: How much would you regret inaction when you're 90-years-old? Could you live with that regret?

As Seneca famously wrote, "We suffer more in imagination than in reality." These steps get the fear out of your imagination and force it into reality.

If you follow those three steps, you'll shorten the terrifying 100 foot leap into something much more manageable.

That doesn't mean you'll definitively decide to jump, but it does mean you'll be able to make that decision with a clear, rational head.

Close Your Eyes & Jump

You're standing at the edge, looking out at the other side, a mere 10 feet in front of you...

There's only one thing left to do:

You dig your feet in to feel the ground.

You close your eyes, sit back into your legs, fire your arms...

...and jump.