Does the 'how' really matter?

I dunno much about gambling, but the one time I went to Vegas it was with a plan: fifty bucks, low-stakes games to make it last, and to focus on enjoying the experience.

And I did, even though I didn't win.

But imagine if I had.

Imagine you're sitting down at the slots after a few hand of Blackjack and Caribbean Stud Poker. You've had some losses, but also some wins so you're actually ahead by 20 bucks or so.

Then with your first pull of the lever lights start flashing and bells start going off.

You just hit the jackpot!

How do you think you'd feel?

A friend of mine recently had a similar experience and while the smaller wins felt simple and satisfying, the big payout stirred up something entirely different.

Sure, she was excited and grateful, but there was also a sense of guilt, almost shame, and then as the reality sank in, imposter syndrome came knocking. All because she hadn’t “earned” it.

It's interesting that the bigger the windfall, the more complicated the emotions became.

Which got me thinking: Why do we feel so conflicted about receiving money outside of our work?

I could see a bit of the dilemma if it came at someone else's expense. But I think with most windfalls, that's not actually the case. Yet we still end up feeling all these emotions.

Why?

I mean, your bank account doesn’t care if a deposit comes from a paycheck, a bonus, an inheritance, or a lucky bet.

So why do we?

As long as your financial goals are being met and nobody else gets hurt along the way, the “how” shouldn’t really matter.

And yet, it seems to matter deeply—especially when you start considering how others might view that “unearned” money.

I think a lot of us have been conditioned to equate value with hard work and effort, to believe that success should come through struggle and sacrifice.

Society celebrates the “self-made” and their blood, sweat, and tear-filled stories.

Success is something hard-won, hard-fought, and earned through hard work. (Sensing the theme here?)

There’s a certain pride in the struggle—a message that says if it didn’t require effort, it doesn't count.

But what happens when life hands us a gift instead of a grind?

Why does ease make us feel so uneasy?

The truth is, money itself is neutral.

It doesn’t care where it flows; our financial goals don’t discriminate between income sources.

The pressure we feel is almost entirely socially driven—rooted in expectations, comparisons, and fear of judgment—the idea that only effort-based wins are worthy.

But what if we let go of that story?

What if we allowed ourselves to receive with joy, whether it’s from a paycheck or a windfall, and focused on what that money allows us to do rather than how it arrived?

Imagine celebrating all your financial wins, big or small, without feeling the need to “earn” them through struggle.

What if you could fully embrace every opportunity to reach your goals, without guilt? Consider the freedom that would bring.

If you’ve ever felt conflicted about an unexpected windfall, know you’re not alone. It's actually so common there’s even a name for it (Sudden Wealth Syndrome).

But here’s the thing—money doesn’t care how it arrives, and neither should you.

Your goals are being met. Your life is moving forward. The story about “earning it” is just noise in the background.

So what if we chose to let go of the guilt and instead leaned fully into gratitude?

What if every win, big or small, became proof of the abundance all around us—and our worthiness to receive it?

When we release the need to justify the “how,” we’re not just practicing self-compassion—we’re sending a subtle, powerful message to the world that it doesn't have to be hard.

And maybe, just maybe, that’s how we open the door for more ease in all our lives.

So the next time abundance comes your way, what story will you choose to tell yourself?