5 Signs You Must Postpone Retirement (Especially if You Hate Your Job)

By Zach Lundak | October 10, 2025

Why "Rage Retirement" is the Most Expensive Financial Mistake You Can Make

If a return-to-office mandate or a truly miserable boss has you staring at your calendar, ready to retire in 2025 or early 2026 right after bonus season, stop. Before you send that letter, you need to verify that your decision is based on a sound plan, not just emotion.

The difference between retiring well and retiring poorly is stark: one leads to immense satisfaction, and the other can lead to regret, anxiety, and a mood tied entirely to financial headlines. You can watch my video on this topic here as well. Let’s break down five signs you should reconsider, or hold off, sending that resignation letter.

Sign 1: The Only Reason is Rage (The Emotional Trap)

This may be the hardest truth to hear, but retiring because you are micromanaged, exhausted, or burned out is called Rage Retirement, and you must avoid it.

  • The Problem: The decision is purely emotional, often made right after a particularly challenging week or when you feel disrespected (60% of people report leaving a job due to feeling disrespected—Pew Research Center).

  • The Danger: This leads to a rushed timeline, and you often retire thinking, "I'll be okay," without having actually put pen to paper to calculate your precise expenses.

  • The Solution (Find Your Impact): As the CEO of Spotify stated, happiness trails impact. If you're not finding impact at your current job, don't retire until you identify what your next source of impact will be. Retirement without purpose feels like falling into a void.

Sign 2: You Haven't Calculated Health Insurance Costs

For almost all of us, health insurance has been covered by our company. In retirement, health insurance often becomes the biggest source of anxiety and expense.

  • The Cost Trap: You are retiring before Medicare kicks in (age 65). Options like COBRA are the most expensive (you pay the full two-thirds your employer used to cover). ACA marketplace plans offer subsidies, but you must calculate your projected income accurately.

  • The Inflation Risk: Medical costs have risen faster than general inflation over the last 30 years (3.3% vs. 2.5%). The money you spend on healthcare will continue to rise faster than the cost of everything else.

  • Action: Before you hit send on your resignation letter, do a precise calculation of how much insurance is going to cost you before Medicare kicks on.

Sign 3: You Haven't Explored Other Job Opportunities

Don't let one bad job force you to exit the workforce permanently.

  • Internal Mobility: Try an internal mobility strategy first. Your company has invested in you and is incentivized to help you find a different role (rotational program, different team, advisory role, or a sabbatical).

  • The Tom Brady Principle: Tom Brady noted that the tension between him and Coach Belichick required a split, but he went on to win another Super Bowl elsewhere. Sometimes, changing the setting is the answer.

  • The Hard Reality: If you exit the workforce after age 55, it is incredibly difficult to re-enter. The Urban Institute found that only 10% of workers 55+ were able to regain the level of income they had before exiting the workforce if they were forced out. Trying a new role first is the preferred option.

Sign 4: You Are Chasing Market Returns

This is most common among those who have undersaved. Chasing returns means buying an asset or fund after it has performed well, hoping to capture those gains—essentially buying high just because something is "hot."

  • The Investor Gap: Studies by Morningstar and Dalbar consistently document a 2% to 4% gap between the returns generated by the total market and the returns individual investors actually capture. This gap is largely driven by emotional buying and selling (chasing what's hot).

  • The Analogy: Compare investing to fishing. You're not going to catch any fish by swimming around the lake after them. You have to put your line in the water and wait. Be patient and disciplined.

Sign 5: You and Your Spouse Are Not Aligned

Retirement introduces an insanely large increase in the amount of time you will spend with your spouse (you gain 40+ hours per week of interaction).

  • The Conflict: If you and your spouse are not aligned on how you will spend your time and financial resources, it will inevitably lead to conflict. Divorce rates for people aged 50 and older have doubled in the U.S. since 1990.

  • The Solution (The Venn Diagram): Think about your time and financial resources in a Venn Diagram. Discuss what you both want individually, what you want together, and what activities you are mutually opposed to. Alignment is key to a harmonious retirement.

Actionable Health Insurance Savings Tip

Finally, before you send that resignation letter, you need to be prepared for the major ACA premium tax credit change. If you are retiring before 2027, knowing how to manage your income during the subsidy period could save you $22,000 in health insurance premiums.

At Barrett FP LLC, we offer expert financial planning on an hourly basis, focused entirely on helping you achieve your goals.

Learn more about how we can help you build a resilient and fulfilling retirement plan and see if we’re a good fit.

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