The financial trick that feels weird but works

Choosing a mission for your company is like picking a name for your baby; it sounds easy until you realize all the good ones are already taken.?When we landed on “inspiring better conversations about money ,” I assumed putting it into practice?would be straightforward. Little did I know, every meaningful conversation about money leads back to happiness, so I’ve become an accidental expert on both.?

The biggest issue is that money and happiness are wildly misunderstood. People see them as outcomes when they’re byproducts of other behaviors, and that leads?to poorly worded goals. In fact, a large part of my work is helping people get the wording right because chasing either one directly is like trying to catch smoke with your hands.

Take happiness, for example. There's a theory that we have a happiness set point, or a?natural baseline mostly determined by genetics. So if your parents were Debbie Downers, guess what? You probably are too. ??

It's as discouraging?as?the research that says some zip codes?have a bigger impact on your success? than your?work ethic or intelligence, but all is not lost. We can actually raise?our happiness baseline through intentional practices like gratitude and being kind, and the same is true for wealth. While our circumstances play a role, we can?change our trajectory with the right actions and attitude.

The tricky part is it requires loads of self-discipline.?Discipline sounds great until chaos exposes its limits. The car breaks down, a surprise bill shows up, and suddenly, you realize the?commitments you made have more cracks than you accounted for.?

This is why paying yourself first is critical, even if it feels like showing up to a potluck and packing leftovers before the party starts.?

It only feels?weird because of our typical approach to ‘pay.’ There’s a certain weight and sense of obligation to it. Taxes. Rent. Student loans. Debt. These are non-negotiable things we “have to do or else.”?They join a long list of financial?demands that scream for our attention and drown out our softer-spoken personal interests. It’s become a knee-jerk reaction to pay others before we even have a chance to consider what we give up every time?we shove saving in the ‘maybe later’ pile.?

Being a grown-up means dealing with a ton of financial?trade-offs, but saving can’t just be 'optional' when the money’s good and 'impossible' when things are tight. The goal is for it to be automatic, a non-negotiable payment that we owe to ourselves like any other bill.

When saving?happens automatically, there’s no need to choose between paying yourself and paying down debt. Both work together without constant mental negotiations. This matters because relying on willpower alone makes it difficult to stay consistent.

Our willpower is like Wi-Fi—great when it works, and completely unreliable when you need it most. But automating lets you build discipline without needing motivation. Once transfers happen automatically, saving becomes a quiet habit that strengthens over time until it becomes second nature.

The word “first” also represents a mindset shift. It reminds you that your future self isn’t some distant, disconnected person, they’re a direct extension of who you are right now. Every action you take today has a ripple effect with the potential to influence your life for years to come. So paying yourself first isn’t selfish or irresponsible, it’s an investment in the person you’re becoming.?

The best part is you don’t need to overhaul your entire financial plan. You can start with something manageable, like a round-up app. We recommend them all the time because they?create?the easiest?re-entry point when things fall apart. Every time you spend money, you save some, so you never have to see yourself as a person who struggles with saving.

It’s a virtuous cycle. The automated system builds the habit, which shapes the way you view yourself. That identity shift makes it easier to keep up with the habit on days you don’t feel like it.?Rinse and repeat.

This is the true power of discipline and it?applies to other areas of our lives too. The person who thinks of themselves as a "gym person" is more likely to get back on track than the one who doesn't. And the same principle applies here. When the systems do the heavy lifting, it frees you to focus on the routines and self-talk?that will serve you in the long run.

It turns out self-discipline is another snowball thing , and personally, that gives me the encouragement to get started on lots of changes that seem way too hard (like being disciplined about my writing so this newsletter doesn’t keep hitting your inbox on Friday nights ??)

Just don't overthink it, okay??In this week’s podcast, we share?4 ways to automate, but just pick one and make it happen.

Whether it’s a round-up app or a weekly transfer, the rest will follow and you’ll be happier for it.?

Listen to Episode 184 now or watch it on YouTube below