I have this nasty habit of being extremely stingy. There’s those stories of Warren Buffett who calculates in his mind the expected return of every dollar spent on “frivolous” things out into the future. That habit can stop you from spending on anything. Every dollar saved is a dollar invested, which means a brighter and more secure financial future. That thinking has served me in many ways. I have a large amount of savings. I have college savings for my kids. All good things. But as with most things in life, there is a need for balance. Spending can be extremely productive. Even more productive than saving. Hard for me to really wrap my head around that sometimes.

As I mentioned yesterday, I’m on a trip. One that makes me uncomfortable in how much we’re spending (granted, I always feel that to some degree). My wife likes nice things. And in all honesty—now that I’m here—I realize I do too. Liking nice things, wanting them, even enjoying them, shouldn’t be a source of guilt. At least not when it’s done in balance.

I come from a lineage of over-savers. My parents and grandparents didn’t just avoid debt—they saved above their means. A kind of asceticism that’s about control as much as security. This trip, stressful as it was to plan and pay for, is something they simply wouldn’t take. “Too expensive,” even though they make three to four times what I do. Meanwhile, I pay my rent, max out my 401(k), carry no debt. It’s not reckless. It’s just… uncomfortable.

And it’s not new. I still remember interning in New York City and walking 40 minutes to the office not just to enjoy the city, but to save the subway fare. I go way out of my way to get to Costco, and obsessively optimize travel spend like it’s my job. These are habits formed over years. They’re efficient. But sometimes, I wonder: are they still serving me?

Can I do a trip like this all the time? No. But once a year? Maybe. Once every two? Probably. With two little kids and full lives, the opportunity doesn’t come often. And when it does, I’m starting to believe it’s worth seizing.

Because sometimes spending is an investment.

This trip isn’t just a vacation—it’s a re-centering. Four days together, away from kids, community, and routine, gives our relationship breathing room. A chance to be not just co-parents and co-managers of life, but a married couple again. And if compound interest is real for money, it’s real for connection too.

But maybe there’s another kind of wealth: having some wants, and allowing yourself to meet them.

I’m trying to rewire how I think about value. Support at home. Activities for the kids. Even clothes that make me feel confident. Not all spending is wasteful. Some spending elevates. Some creates space, energy, alignment. That kind of spending, I’m realizing, can have a higher return than another hundred bucks in the index fund.

And then there’s the bigger shift I’ve been circling around: mindset.

My wife talks about abundance. So do people in my Jewish community. It’s an unfamiliar framework for me. I’m the analytics guy who sees every dollar in terms of future net worth. I run the 8% compound return math like a reflex. It’s safe. Predictable. Reassuring.

Let’s say I play it safe and retire with multiple millions. That’s success, right?

But what if I don’t love the life I built to get there?

Deep down, I know that constantly optimizing for security is killing something else—something more essential?

What if I actually believed I could make $5 million in a year? Or sell a business for $100 million? These aren’t just financial fantasies—they’re questions of belief. Do I have the grit, the vision, the faith to bet on myself?

Because if I did believe, I think I’d stop worrying so much about a hundred dollars here, a thousand there. I’d trust that I can create value. That my effort, my connection to something larger, and the timing I don’t control will all align—eventually.

The real risk for me isn’t spending too much – it’s building a life that’s financially safe but spiritually bankrupt.

Believing I’m worth investing in may be the most productive thing I could do right now.