How Much is Enough?

By John Curry

If you’ve read Alice’s Adventures in Wonderland by Lewis Carroll, you may already know the famous first encounter between Alice and the Cheshire Cat. Alice comes to a fork in the road and asks the cat which path she should take. “That depends a good deal on where you want to get to,” he says. Alice admits she doesn’t much care. “Then it doesn’t matter which way you go.” 

The cat is right. Without a destination, direction is meaningless. Clear goals provide the framework for making complex decisions. 

Road to Nowhere 

Consider almost any meaningful endeavor. We structure our lives around specific time horizons. We tell ourselves we’ll focus on our health, relationships, or passions once this current project is finished or as soon as we reach the next milestone. 

This pattern is everywhere. The professional who reaches a long-sought title then sets her sights on the next promotion. The parent who looks forward to the freedom of an empty nest, then fills the space with new obligations. 

There’s nothing wrong with raising the bar. Ambition often drives a purposeful life. But at what point does preparation become a permanent state of being? When does the habit of striving make it harder to appreciate what you already have?  

Once in a Lifetime 

When it comes to money, many people spend decades saving and investing without ever defining where they’re trying to go. Most know exactly how much they have. Far fewer know how much is enough. 

That gap is common, even among the financially successful. According to Northwestern Mutual’s “2025 Planning and Progress Study,” two-thirds of American millionaires don’t consider themselves wealthy. Half say their financial planning still needs improvement. 

If a million dollars isn’t enough to feel wealthy, then what is?  

For many investors, financial success is a moving goalpost. Bryan Fitzpatrick, a principal and financial advisor in CAPTRUST’s New Orleans office, says, “The question of how much is enough sits beneath almost every financial planning conversation, whether clients articulate it or not.” 

Financial planning professionals help clients find their own unique answer. Some focus on withdrawal rates, others on net worth or income replacement. The specifics matter less than the process. The point is to define your destination. Without one, you cannot answer the most important financial planning questions: Is it time to retire? Should you adjust your risk? Can you afford to be more generous with your family, your causes, and yourself?  

We often assume more information will solve the problem. Better projections. Better planning. More analysis. But investors who have now accumulated more than they ever thought was possible still struggle to name what they’re aiming for. 

An established financial horizon transforms financial freedom from a vague aspiration into something that can be planned for, measured, and enjoyed. It won’t answer every question, but it does provide a reference point. 

Seen and Unseen 

If goals are so useful, why doesn’t everyone use them? Partly, the answer lies in how our minds process success, risk, and uncertainty. Several well-documented behavioral tendencies make it difficult to recognize when we have enough. 

The first is hedonic adaptation, our tendency to adjust to improved circumstances. Fitzpatrick sees this pattern often. “For a highly motivated person, there is no such thing as success with finality,” he says. New goals emerge, benchmarks rise, and what once felt sufficient can quickly become a new starting point. 

A second challenge is loss aversion, our tendency to feel the pain of losses more than the pleasure of the same gains. As wealth accumulates, the focus often shifts from building assets to protecting them. This makes every potential risk, from market volatility to healthcare costs, a reason to delay and continue accumulating, just in case. 

Finally, there is social comparison: measuring success against the achievements of others rather than against our own goals. A person who is fully financially prepared for retirement may still feel behind if they compare their wealth to friends’ and colleagues’ or the curated images of wealth that surround us. 

Individually, these tendencies are manageable. Together, they create a powerful force that keeps us in the habit of moving our goalposts. And as they move, the feeling of readiness remains continually out of reach. 

The consequences show up in opportunities we postpone: another year of work, another trip deferred, another gift delayed, or another chapter of life waiting for a level of certainty that never arrives. 

The Reverse Bucket List 

One way to make those trade-offs more tangible is to create a reverse bucket list. Instead of asking, What do I still want to accomplish?, ask, What opportunities become impossible if I wait another five years? 

This shifts the focus from someday to soon, and from abstract goals to the specific moments that may not stay available forever. 

The answers are often deeply personal: traveling with aging parents while they are still able, taking an active adventure while your health allows it, or spending unhurried time with grandchildren before their calendars fill and childhood gives way to adolescence.  

These are not extravagant luxuries. They’re finite opportunities. Money can help make them possible, but it cannot always restore the timing. 

A reverse bucket list reframes wealth not as an infinite accumulation challenge but as a tool for protecting the experiences that have an expiration date. It asks whether continuing to wait is truly prudent, or whether the greater risk is allowing meaningful chapters of life to pass while you collect more money. 

Fitzpatrick says he’s seen many people spend decades mastering the accumulation phase but struggle to transition into what he calls “the use-it phase.” The downside can often be measured not in dollars but in time—time we could have spent with family, pursuing interests, or enjoying the freedom that financial security was meant to provide. 

This Must Be the Place 

The solution isn’t complicated, but it can be challenging. Name your destination, and don’t let yourself keep moving the goalpost. While no amount of planning can fully eliminate uncertainty, a clear definition of success can counter many of the psychological forces working against you. 

Four principles can help anchor your plan: 

1. Define success in advance. A retirement number is most powerful when it’s established before market returns, lifestyle changes, and shifting circumstances have a chance to reshape the objective. The goal doesn’t have to be perfect; it only needs to exist.  
2. Get specific about what the money needs to do. When the objective is clear, the number becomes a tool, not the goal itself. Ask yourself what your wealth needs to accomplish. Do you want to fund a specific lifestyle, support family, build a philanthropic legacy, or structure a multigenerational transfer of wealth?  
3. Separate your needs from the extras. Not all financial goals are equal. Some assets support essentials like housing, healthcare, or a sustainable lifestyle. Others fund meaningful but discretionary goals, like a larger inheritance, charitable giving, or a financial cushion. There is nothing wrong with pursuing the extras, but many people who already have enough wealth to meet their true needs continue accumulating because they have never drawn that line. 
4. Measure against your own plan. There will always be someone with a larger portfolio, more possessions, or a longer list of achievements. Social comparison has a way of making almost any level of success feel inadequate. The antidote is to measure progress against your own goals, not someone else’s circumstances.  

More important, a clear definition of enough creates permission. Permission to retire. Permission to spend. Permission to give. Permission to enjoy the wealth you’ve spent decades building. Without permission, wealth can become an end rather than a means. It becomes a scorecard instead of an instrument.  

Yes, knowing how to accumulate wealth is a useful skill. But defining enough is much more valuable, because the years after enough are often the years when your money can do its most meaningful work.