Why Retiring Early Is Hard Even When You Can Afford It

When you have spent your entire life working hard and saving for a secure retirement, it can be surprisingly difficult to flip the switch and actually walk away. Many people find it emotionally challenging to stop earning and start spending down the nest egg they spent decades building. This is exactly the struggle one Reddit user recently described.

The original poster shared that he had always planned to retire at 55 and had invested carefully to make that dream possible. By the time he reached that milestone, he had saved twice the amount he believed he needed. But his lifestyle had expanded, his spending had grown, and his colleagues urged him to stay a little longer. Tempted by the offer of an additional 6 million dollars, he pushed retirement back another year, even though he felt the after tax amount would not truly change his quality of life.

Now he is looking at retiring at 57, which hardly feels early at all, and he does not understand why it is so difficult to walk away from work when this was his goal for decades. His experience is not unusual. Psychological research shows that people often attach a deep sense of purpose and identity to their careers. Studies on wellbeing in later life, as well as research on affluenza and the tendency to overvalue future earnings, support the idea that quitting can feel far more daunting than expected. This post was updated on November 9, 2025 to reflect these insights.

Giving up good earnings can be harder than you’d think

While the OP’s dilemma is one many people might envy, it is still a real issue and one that affects plenty of high earners who have spent years building the kind of wealth that can buy financial freedom. After working so hard to accumulate millions, the idea of stepping away from a huge paycheck can feel far more complicated than it seems.

When you are earning large sums of money, it becomes difficult to walk away knowing that just a few more months of work could add millions to your net worth. Watching that number climb can feel addictive, especially if you did not grow up wealthy and you take pride in how far you have come. It is completely human to want to keep pushing that success even higher.

This behavior lines up with research on affluenza, lifestyle creep, and loss aversion. As income grows, spending often rises along with it, and people become emotionally attached to the status and identity their career gives them. Studies from Harvard Business Review and the Journal of Economic Behavior and Organization have found that people tend to overvalue future earnings and undervalue present life satisfaction, making it even harder to walk away while the money is still good.

Even with millions in the bank, the urge to pad the score with a few more million can feel rewarding. Meanwhile, the idea of leaving the familiar world of high earnings for the uncertainty of retirement can feel both scary and anticlimactic. For some, the fear of losing that identity as a high achiever is just as powerful as the financial incentives that kept them working in the first place.

What should you do if it’s hard to give up work?

If you are financially able to retire but find yourself reluctant to leave work, it is worth stepping back and asking what will genuinely make you happiest. Some people truly love what they do. If your job is fulfilling, you enjoy the people you work with, and you are earning millions doing something that brings you energy, there is no rule that says you must retire early. Plenty of wealthy individuals choose to keep working well into their 80s and 90s because their careers provide purpose, structure, and joy. Research on psychological wellbeing and longevity, including a 2019 study in the Journal of Epidemiology, shows that meaningful work and strong social ties can support life satisfaction in later years.

On the other hand, if you are only staying because you want to earn more money and you would rather use your time for travel, hobbies, or being with family, then trading the limited hours you have left for additional income may not be worth it. Many high net worth retirees discover they already have more than enough to last a lifetime, with several future generations financially secure as well. Once you reach that point, working purely to watch your account balance grow becomes unnecessary, especially when your time could be spent on things you care about far more.

The OP needs to determine which of these two situations describes his own mindset. If he truly enjoys his work and wants to stay, he should feel free to continue. But if he is staying out of habit, fear, or the lure of extra income he will never need, then it is time to call it quits, accept that he is financially set for life, and let his coworkers know he will not be sticking around for one more year.