Retirement Gets Harder the Longer You Wait

Retirement gets harder with time because their are more decisions to make, and the decisions are more complicated.

Made-up-Marcus always had a plan. From the moment he landed his first job and straight through his executive career, he has been thinking ahead. Not just to his next job, but to his future — his retirement. He did everything by the book: contributing to his retirement accounts, diversifying his investments, and following the advice of financial planners. Yet, despite his careful planning, Marcus found that the decision to retire was getting harder as time passed. At every stage of his life and career, new variables entered the equation, making the decision to finally step away from work more complicated.

Let’s take a look at Marcus's journey. We’ll explore the different paths Marcus could have taken and how waiting too long to retire could have impacted his financial and personal well-being. If you’ve been delaying your retirement, you’ll relate to how much more complicated the decision can become over time.

Early Career: A Steady Climb with Big Savings

In his late 20s, Marcus landed his first major promotion, setting him on a fast track to success in the corporate world. At the same time, he began contributing to his company’s 401(k) plan, taking advantage of employer-matching contributions and maxing out his contributions annually. With decades ahead of him before retirement, Marcus had time on his side — and time is the key when it comes to retirement planning.

During this phase, Marcus’s biggest retirement decision was simple: keep saving. He figured that if he just kept doing what he was doing, he’d retire comfortably. But here’s where it started to get tricky: What if Marcus could retire early? What if, by the time he hit his 50s, he had enough saved that he didn’t need to work anymore?

At this stage, retirement seemed like a distant dream. Marcus focused on climbing the corporate ladder, taking on bigger roles with bigger paychecks. Life was straightforward — save as much as possible and invest wisely.

Decisions at this point:

• How much should Marcus contribute to his retirement accounts?

Mid-Career: Career Growth and Increasing Complexity

Fast forward 15 years. Marcus is now in his early 40s, establishing his executive career. His income has increased dramatically, allowing him to build significant wealth. He’s maxing out his retirement contributions, investing in real estate, and even dabbling in rental properties for additional income.

But this is also where things start to get more complicated.

With kids entering college, Marcus now has to consider how tuition costs will impact his savings. Should he continue working to cover these expenses, or should he pull from his retirement savings early? On top of that, Marcus’s parents are aging and may need financial support in the future. These new financial obligations add complexity to his retirement decision. He’s still on track for a comfortable retirement, but the number of variables is increasing.

Here’s where Marcus’s decisions start to look more like a tree with many branches. Each choice affects another, and each new responsibility — like his kids' education or potential elder care — puts added pressure on his timeline.

Decisions at this point:

• Should Marcus set aside funds for his children’s education, or let them take on student loans?
• How does Marcus balance saving for retirement while supporting aging parents?
• How should Marcus manage the new rental property income? Should it go directly into retirement savings, or be used to fund day-to-day living costs?
• Should Marcus adjust his investment strategy now that his portfolio is larger and more complex?

The Executive Pressure: Should Marcus Keep Working?

In his 50s, Marcus faces a dilemma. On one hand, he has more than enough saved to retire early. On the other hand, he’s at the peak of his career, earning his highest salary yet. Does he leave the workforce now and enjoy early retirement, or does he keep working to ensure an even more secure future?

Retiring now means tapping into his savings early and potentially facing higher tax burdens. On the other hand, continuing to work means more time for his investments to grow. But here’s the catch: The longer Marcus works, the more complicated his retirement becomes. His expenses are increasing, his investments are becoming more diverse, and health-related costs are starting to come into focus.

Retiring now could mean missing out on future income, but continuing to work introduces new risks. What if Marcus’s health deteriorates and he’s forced to retire sooner than planned? According to the U.S. Social Security Administration, around 35% of retirees stop working earlier than expected due to health issues, leaving them unprepared financially. Marcus knows this, and it’s one more thing to factor into his already complex decision-making process.

At this point, Marcus starts to explore the different retirement phases and how they’ll impact his lifestyle. He uses the Retirementize calculator to run scenarios, looking at different timelines and income strategies. He knows that the earlier he retires, the more he’ll need to account for healthcare costs in the long term.

Decisions at this point:

• Should Marcus retire now and tap into his savings, or continue working to build a larger nest egg?
• How can Marcus protect himself financially in case of unexpected health issues?
• Should Marcus sell the rental properties now, or continue managing them as income streams in retirement?
• How should Marcus adjust his retirement strategy to account for his increasing health care costs?
• What income strategy should he follow — the 4% rule or a more conservative withdrawal rate?

Late-Career: The Decision Looms Larger

Now in his 60s, Marcus finds himself closer than ever to retirement — but it’s not any easier. In fact, retirement feels more complicated than ever. He’s got a significant portfolio of investments, including rental properties that generate income, a substantial 401(k) (or RRSP), and a well-funded Roth IRA (or TFSA). However, with more money comes more decisions.

At this point, Marcus has to consider:

• How to maximize his retirement withdrawals. Should he use the 4% rule and withdraw a consistent percentage of his savings each year, or should he take a more conservative approach to account for market volatility?
• How to manage taxes. He realizes that if he’s not careful, a significant portion of his withdrawals could go toward taxes. He starts to look into strategies like the 401k/RRSP Meltdown to manage his withdrawals more effectively.
• Should he keep working part-time in retirement? Like many retirees, Marcus considers staying active in the workforce to continue earning an income. But working in retirement brings its own set of challenges, from managing income taxes to balancing personal time.

By this stage, Marcus is not just thinking about his personal finances. He’s also considering his legacy — how he’ll pass on wealth to his children, and whether he should help them financially while he’s still around. According to recent data, kids are staying home longer, and many young adults rely on their parents for financial support well into their 20s and 30s. Marcus is weighing whether to provide more help to his children now or focus on his retirement nest egg.

The decision tree grows more complex every day, and Marcus is feeling the weight of his financial choices. The more assets he’s accumulated, the more he has to manage in retirement.

Decisions at this point:

• How much should Marcus withdraw from his retirement accounts each year to balance his spending needs and tax obligations?
• Should Marcus continue working part-time to supplement his retirement income, or should he fully retire?
• How should Marcus plan for his healthcare expenses in retirement?
• Should Marcus begin transferring wealth to his children now, or preserve his nest egg for future generations?
• How should Marcus manage his rental properties in retirement?
• What strategies should Marcus use to minimize the taxes on his withdrawals?

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