The final stretch before retirement can feel like the longest part of your career. After decades of hard work, the last two or three years sometimes become a mental and emotional challenge — the finish line is in sight, but the daily grind can make it seem out of reach. For many people, staying engaged and motivated during this period is one of the toughest parts of the journey.
Here are four practical strategies to help make those last few working years not just bearable, but meaningful and rewarding.
1. Make the Journey More Enjoyable
One of the biggest challenges as you approach retirement is rediscovering enjoyment in your daily work life. Many professionals in their final years forget that they can still make choices to improve their experience.
Use your vacation days.
It’s surprising how many employees nearing retirement don’t take full advantage of their paid time off. In the U.S. especially, people often skip vacations because they dread the pile of work waiting when they return. But using your vacation is essential for mental health, stress relief, and maintaining energy. Think of these breaks as an investment in your wellbeing — a way to recharge so you can reach the finish line strong.
Let go of unnecessary ambition.
When retirement is only a few years away, it’s time to focus on balance, not the next promotion or bonus. If work feels overwhelming, shift your mindset from competition to conservation. You’ve likely already achieved plenty. These years should be about protecting your energy and mental health, not proving yourself one last time.
Improve your work relationships.
Interpersonal friction — especially with a manager or colleague — can make even short stretches feel endless. If strained relationships are causing stress, take steps to mend them or establish clear boundaries. Two or three years can feel much longer if unresolved tension lingers, but with communication or reframing, your work environment can become much more tolerable.
Explore flexible work options.
If possible, consider hybrid or remote work arrangements. Even working from home a few days a week can reduce stress and make your schedule feel lighter. Combining remote work with strategic use of vacation time can give you more freedom without sacrificing productivity.
Plan meaningful experiences.
While counting down to retirement, start planning what comes next. Use this time to outline travel goals, personal projects, or new skills you want to develop. Author Bill Perkins’ book Die with Zero encourages people to live fully by aligning experiences with their age and energy levels. Some adventures, like hiking Spain’s Camino de Santiago or learning to surf, are best enjoyed sooner rather than later. Begin thinking about what “living fully” means to you — and start making it real.
2. Strengthen Your Financial Foundation
The second key to navigating these years smoothly is having a clear financial plan. Sometimes, people assume they must work a few more years without realizing they might already have enough to retire comfortably.
A detailed retirement plan helps clarify whether the tradeoff of continuing to work is worth it. The most reliable approach is to work with a qualified financial advisor who can project your income, expenses, healthcare needs, and tax obligations. While many advisors charge around 1% of assets annually, that cost can be a worthwhile investment for peace of mind and professional guidance.
If you prefer to manage your plan independently, consider using comprehensive retirement planning software instead of basic spreadsheets. Many people underestimate two major expenses:
- Healthcare costs, which can average more than $165,000 in lifetime expenses after age 65, even with Medicare.
- Taxes, which can remain significant in retirement, especially if withdrawals come from tax-deferred accounts.
The right planning tool can help you forecast these expenses realistically and avoid surprises.
Once you have a clear financial picture, you might discover that you can afford to work fewer hours, spend more on self-care, or even stop saving aggressively. Learning to spend comfortably is often one of the biggest mental shifts in retirement — practicing it now can make the transition easier later.
3. Prepare for Your Next Chapter
Many people retire from something, but the happiest retirees also retire to something. The years leading up to retirement are an ideal time to explore interests that can later grow into fulfilling pursuits.
Ask yourself what you want your first few years of retirement to look like. Do you want to travel, volunteer, learn a new skill, or dive into a hobby you never had time for? Start experimenting now.
Taking classes, pursuing creative hobbies, or exploring new technologies like artificial intelligence can stimulate your mind and add joy to your routine. If your employer offers training programs, use them. This period can also be a bridge to discovering a part-time passion project or consulting role that provides both income and purpose after you retire.
Building these interests ahead of time helps ensure that when work ends, you’ll already have momentum and enthusiasm for what’s next — rather than facing an identity gap or boredom.
4. Test Drive Retirement
Finally, consider experimenting with what retirement will actually feel like. If your plan assumes you’ll live on 80% of your current income, try living on that amount for a few months. This “practice phase” helps you gauge how your budget feels in real life and whether adjustments are needed.
You can also test-drive the lifestyle itself. Take an extended vacation — maybe using most of your remaining paid leave at once — and see how you respond to a slower pace. If you plan to relocate or spend more time in a specific setting (like the mountains or near the beach), spend a few weeks there first.
These trial runs can provide invaluable insights, ensuring that your financial and emotional expectations align before you officially make the leap.
Final Thoughts
The last few years before retirement can either feel like a slow trudge or a meaningful wind-down — it depends largely on how you approach them. By focusing on enjoyment, building a strong financial plan, exploring new interests, and rehearsing your post-work life, you can transform this period from a struggle into a stage of growth and anticipation.
Remember: this isn’t just about making it to retirement. It’s about arriving there ready — financially secure, emotionally balanced, and excited for the next chapter.
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