"What would I do if money wasn't a factor?"

This question changed everything for me.

Not because it gave me a plan. But because it revealed what I actually care about.

Why This Question Is Hard to Ask

Most of us don't let ourselves ask this question seriously.

It feels impractical. I have bills to pay. I can't just ignore money.

It feels privileged. Not everyone has the luxury of asking this.

It feels naive. Money is ALWAYS a factor. That's just reality.

So we dismiss the question before we really sit with it.

But here's what I've learned: the question isn't asking you to ignore money. It's asking you to see past it- just for a moment - to find out what's underneath.

The Distinction That Matters

When I first heard this question, I thought it meant: "What would you do if you won the lottery?"

That's the wrong framing. Lottery fantasies are escapism. They're not useful for actual discernment.

The better framing is: "What would I do if I had enough?"

Not rich. Not unlimited resources. Just... enough.

Enough that you're not making decisions from fear or scarcity.

Enough that money isn't the PRIMARY factor in what you choose.

What would you do then?

My Answer (And Why It Surprised Me)

When I first sat with this question seriously, I expected my answer to be something like:

Travel more. Retire early. Work less. Relax.

That's not what came up.

What came up was: I'd be doing exactly what I'm already building on nights and weekends.

  • Helping people go deeper in their faith

  • Creating community for people on the journey

  • Coaching leaders through transitions

I'm already doing these things - without getting paid for them.

Which tells me everything I need to know about where my heart actually is.

The money question didn't reveal some hidden dream I'd been suppressing. It revealed that I already know what matters to me. I'm already doing it. I just hadn't fully acknowledged it.

What This Question Reveals

The money question is a filter.

It strips away the external motivators - compensation, status, security - and shows you what's left.

For some people, the answer is: "I'd keep doing exactly what I'm doing." That's great. It means you're aligned. Your work and your calling are the same thing.

For others, the answer is: "I'd do something completely different." That's important information. It means there's a gap between what pays you and what calls you.

Neither answer is right or wrong. But both are useful.

Because once you know the answer, you can start making decisions with that knowledge.

The Money Question Exercise

Here's how I'd encourage you to sit with this question:

Step 1: Define "enough."

Not rich. Not extravagant. What's the number where you'd feel secure? Where money would stop being the primary driver of decisions?

For me, it's: mortgage covered, kids' education funded, reasonable cushion for emergencies. That's enough.

Step 2: Ask the question honestly.

If I had "enough," what would I wake up excited to do?

Don't censor yourself. Don't be practical yet. Just notice what comes up.

Step 3: Notice what emerges.

Is it something completely different from what you do now?

Is it a version of what you do now, but with different constraints?

Is it something you're already doing in the margins?

Step 4: Look for the overlap.

Are you already doing any of this - even in small ways, even unpaid?

If so, that's a signal. Your heart is already moving toward it.

Step 5: Ask what this means.

You don't have to quit your job tomorrow. But what would it look like to make more room for this? To take it more seriously? To build toward it intentionally?

What I Did With My Answer

When I realized I'd keep doing what I'm already building in the margins, it clarified things.

It meant Deacon Life, Emmaus Disciples, runDis Dad, and Lead and Keep aren't just hobbies. They're not distractions from my "real" work. They might BE the real work - or at least, the work that matters most.

It meant I should take them more seriously. Invest more intentionally. Build toward a future where they're not just margin work - they're the main thing.

It didn't mean I should quit my job tomorrow. I have four teenagers, a mortgage, and responsibilities I take seriously.

But it meant I should start building the bridge. Honoring where I am while preparing for where I'm going.

That's what I'm doing now.

The Permission to Ask

Here's what I want to give you: permission to ask this question.

Not as escapism. Not as fantasy. But as discernment.

You're allowed to ask what you'd do if money wasn't the primary factor.

You're allowed to notice that your answer might be different from what you're currently doing.

You're allowed to take that seriously - without blowing up your life.

The question isn't asking you to be irresponsible. It's asking you to be honest.

What would you do?

And what does that tell you about what the second half might be for?

-Michael

The 5 Questions for the Second Half launches February 26.