4 Mistakes Rich But Unhappy People Make

I run a boutique financial planning firm, meaning we work with a very specific type of client.

We specialize in serving tech and biotech employees who, between their regular salaries, bonuses, commissions and grants of equity compensation, earn between $500,000 and $1 million per year.

In theory, these households shouldn’t want for much. If money buys happiness, wouldn’t you think this group is downright ecstatic?

What we’ve found is that things aren’t quite that simple and straightforward.

Money can be an extremely effective tool to building an incredible life — or it can just exacerbate the worst qualities about yourself, and biggest challenges you faced before you became wealthy.

More money makes life easier, but whether it makes you happier depends on many factors

More money does make life easier. It provides more conveniences and luxuries. But what I’ve observed is that “more money” does not create a direct path to happiness or fulfillment.⁠

I see that clients tend to fall on either end of a spectrum: there are folks who are truly content and happy, living their best lives, and sharing that joy with others…

And there are those who struggle. Something is always going wrong. They experience very high levels of stress and anxiety. They can’t figure out why they find themselves chasing “more,” never feeling settled or secure.⁠

⁠Each group has a household income most other people envy, yet their experiences couldn’t be more different.

These are the patterns I’ve noticed that create the differences between clients who thrive and those who, no matter how much money they make, experience dissatisfaction.

What the unhappily rich have in common

Those who can’t seem to find happiness, regardless of how much they earn, tend to go astray in four key areas:⁠

1. They feel controlled by their jobs, which they might have chosen due to very high-value comp packages⁠.

They feel like tied to their current positions because of their spending habits and lack of savings power; they usually have very high run rates and rely on things like generous employer contributions to retirement plans or other high-value benefits to make up the difference.

2. They use “spending money” as a way to escape difficult emotions, instead of dealing with the underlying problem (like relationship issues with friends or family; lack of self-awareness; or simply bad habits that are unproductive and lead to emotional pain)⁠.

This also contributes to their spending more than advisable, which can actually lead to financial problems — even though they make enough to put them in the top 5% of income earners in the U.S.

3. They avoid defining what “enough” looks like, and constantly move the goalposts of their own goals or definitions of what they want for their lives⁠. This is a huge mistake that will always keep happiness and fulfillment at arm’s length, no matter how much you make.

4. They blame others for bad outcomes rather than taking accountability or responsibility⁠. There’s always a reason something they wanted (financially or otherwise) didn’t work out, and that reason is never “myself” or “my impulses” or “my bad habits.”

Things happen to them and they are quick to give up agency in their own lives, preferring to believe that either the deck is stacked against them or they’re simply the victims of bad luck.

The tendencies of those who are both wealthy AND happy

The people I work with who are both wealthy and genuinely happy tend to be reflective, thoughtful, and self-aware.

They’re interested in understanding their emotions and accepting them⁠. They cultivate growth mindsets, want self-improvement, and enjoy learning.

Those who are happiest also have a lot of flexibility within their careers. They exercise at least some control over when and how they work⁠.

They may have very demanding jobs requiring huge commitments of time and energy. But they have enough power over their time that they can take an afternoon to attend a kid’s recital. They’re able to unplug at night and will leave their inbox alone on Saturday and Sunday.

They also feel in command of their careers in general. They don’t completely rely on particular benefits or the generosity of an employer’s outsized retirement account match to make their financial plan work.

Instead, they prioritize their own savings first. They may still spend a lot, but it’s after they’ve ensured they set savings targets for the year⁠.

They tend to save more than they “have to” on paper, which leaves them less dependent on any single source of external support.

My clients who I see experience the most joy and satisfaction in their day-to-day lives are those who did a lot of work to identify their priorities and core values.

Once they shared these north stars, we could create a financial plan that aligned specific strategies, tactics, and actions to take with what they say is most important to them⁠.

More money helps (a lot!) …but it isn’t everything

There’s no doubt that having more money solves many problems that you might run into in life.

But earning more without also making an active, deliberate effort to understand yourself, your emotions, your motivations, and your core values is a good way to get locked into a hedonic treadmill.

You can easily find yourself using your wealth to constantly seek “more” and “better” without actually feeling satisfied or content.

If you do the deep work required to accurately identify your priorities and what feels true and authentic to you, you’re much more likely to actually enjoy what the money you make allows you to afford.

Eric Roberge, CFP®, is the founder of Beyond Your Hammock, a Boston, Mass., financial planning firm that provides wealth management strategies to couples and young families. To jumpstart your financial planning journey, get a free copy of Eric’s ebook 5 Strategies to Optimize Your Finances.