When Money Starts to Feel Like a Game

Compound Emotion

Weekly essays on money, time, energy, and the decisions that shape our lives.

After publishing The 7 Pillars of Wealth, two readers sent me comments that stayed with me. One had finished the book and discussed some of its ideas with his sons. He told me he was worried about what he described as a growing “gambling mentality” among young people—from sports betting and betting on event outcomes to same-day-expiration options and collectible cards.

Another reader raised a seemingly different concern: buy now, pay later. His point was that products designed to make purchases feel easier can also make it easier to consume beyond what we otherwise would.

At first, these seemed like two different problems. The more I thought about them, the more I saw the same thing underneath both.

More and more financial decisions are becoming frictionless.

For most of my life, financial decisions came with at least some friction. Investing required opening an account, moving money, paying commissions, and often waiting. Borrowing usually involved applications and paperwork.

Much of that friction has disappeared, and that is progress. Lower costs and better technology have made financial markets more accessible and given ordinary investors choices that once weren’t available to them.

But removing friction can also change behavior. The SEC has specifically examined behavioral prompts, game-like features, and other digital practices designed to increase retail investor engagement.¹

We can also see a shift in what people trade. In 2025, options expiring the same day accounted for 59% of SPX options volume, according to Cboe. Cboe has separately estimated that retail investors account for roughly 50–60% of SPX 0DTE trading, while noting that most of those trades have defined maximum losses.²

Something similar is happening with spending. Buy now, pay later can turn one purchase into several smaller payments. CFPB research found that about 63% of BNPL borrowers in its data had multiple simultaneous BNPL loans at some point during 2022.³

None of this means these products are inherently bad. It does make me wonder what happens when spending, borrowing, trading, and betting all become easier to do than to think about.

The examples are everywhere. Crypto can trade around the clock. You can place sports bets from a phone. Prediction markets let people put money behind views about future events. Options can provide exposure to outcomes measured in hours rather than years.

These aren’t the same, and I don’t think we should treat them as such. Options can hedge risk. Prediction markets can aggregate information. New financial technology can lower costs and expand access.

What interests me is less the instrument than the behavior around it.

There is a difference between making financial markets easier to access and making financial risk feel effortless. When the distance between an impulse and a transaction becomes a few taps on a phone, we lose some of the time that once existed between wanting to do something and actually doing it.

Sometimes that friction was inconvenient. Sometimes it was useful.

A little friction gives us time to ask: Do I understand this? How much can I lose? Am I doing this because it advances a longer-term goal, or because I want to see what happens next?

That last question matters because much of wealth building is surprisingly boring. Earn something. Keep part of it. Build margin. Invest. Wait.

Many modern financial experiences pull us in the opposite direction: check again, make another decision, take another position, see what happened.

Compounding asks us to wait. Gamification asks us to act.

I think that tension matters, especially for young people. Activity feels productive because it gives us immediate feedback. Long-term compounding often gives us almost none.

A diversified portfolio quietly compounding for twenty years isn’t particularly entertaining on a Tuesday afternoon. That’s part of what makes staying with it difficult.

Writing The 7 Pillars of Wealth made me think about wealth through three resources: money, time, and energy. I’ve realized that gamification can affect all three at once.

A speculative loss consumes money. Constant checking consumes time. The emotional cycle of winning, losing, checking again, and wanting another chance consumes attention and energy.

The most expensive part of a trade may not always be the money.

That thought matters to me personally because I’m a father. By the time my daughter is old enough to make her own financial decisions, I suspect access will be even easier than it is today. But this isn’t only a question for parents. We’re all learning how to make decisions in an environment increasingly designed to make acting easier.

I want to teach my daughter how compound interest works, along with saving, investing, budgeting, and understanding debt. But I’m increasingly convinced that financial literacy—for her and for the rest of us—also requires something harder to quantify: recognizing when someone is competing for our attention.

Why does an app want me to come back? Why is this purchase being divided into four smaller numbers? Why does another opportunity appear immediately after the last one ends?

I don’t want to teach her that risk is bad. Risk is part of investing, entrepreneurship, career decisions, and life itself. Learning to take intelligent risks matters.

Nor do I think someone trading crypto, buying an option, collecting cards, or participating in a prediction market is necessarily gambling. The instrument alone doesn’t tell us the purpose, process, or risk being taken.

The distinction I hope she eventually understands is subtler:

Are you choosing the risk, or are you being continually invited to take one?

Technology will keep making financial decisions faster and easier. In many ways, that’s a good thing. But the easier money becomes to move, borrow, spend, trade, and bet, the more valuable a little deliberate friction may become.

As access becomes easier, I suspect restraint will become more valuable, not less. That’s something I want my daughter to understand someday, but it’s also something I’m still learning myself.

The financial skill we may increasingly need isn’t knowing how to find the next opportunity.

It may be knowing when not to act.

P.S. What concerns you most about the way our relationship with money is changing? If you’re a parent, what do you hope your children understand about it? Just hit reply. I’d be interested to hear your perspective.

1. U.S. Securities and Exchange Commission, “SEC Requests Information and Comment on Broker-Dealer and Investment Adviser Digital Engagement Practices, Related Tools and Methods, and Regulatory Considerations and Potential Approaches,” August 27, 2021. The SEC’s request addresses behavioral prompts, differential marketing, game-like features, and other digital engagement practices used with retail investors. SEC source

2. Cboe Global Markets, “The State of the Options Industry: 2025,” January 22, 2026, and “0DTEs Decoded: Positioning, Trends, and Market Impact,” May 2, 2025. Cboe reported that SPX 0DTE options averaged 2.3 million contracts per day in 2025, representing 59% of total SPX volume; its 0DTE analysis estimated retail participation at roughly 50–60% and reported that more than 95% of the examined 0DTE trades used limited-risk structures. Cboe 2025 options review · Cboe 0DTE analysis

3. Consumer Financial Protection Bureau, “Consumer Use of Buy Now, Pay Later and Other Unsecured Debt,” January 2025. The CFPB found that approximately 63% of BNPL borrowers in its matched data had simultaneous loans at some point during 2022; 33% borrowed from multiple BNPL providers. CFPB research

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See you next Tuesday.

Bill