Picture this:
Now, your reward for decades of hard work is finally here – sleeping in, traveling the world, and doing whatever you want. The world is your oyster! You’ve got 7 Saturdays a week and total freedom.
But here’s what nobody talks about: retirement can be a complete disaster.
I’ve seen it firsthand. Professionals who built incredible careers, accumulated millions in assets, and checked every box on the traditional retirement planning checklist. Then they actually retire and find themselves depressed, aimless, and wondering, “Is this it?”
A recent Schroders retirement study reveals the uncomfortable truth: Only 4% of retirees say they’re truly living their dream , while 15% report they’re actively struggling. The rest? They’re somewhere in between – not miserable, but not thriving either.
Here are five key strategies that can help you avoid the landmines and secure the happy, fulfilling next chapter that you deserve:
1. Be Intentional with Your Time Psychologist Barry Schwartz says something counterintuitive when it comes to choice: too much of it makes us miserable. When researchers gave shoppers 24 varieties of jam to sample, fewer people made purchases than when they offered just six options. More choice, less satisfaction.
Retirement is the ultimate choice overload.
Every day is a blank slate, and that’s precisely the problem. Humans thrive on structure. Research shows that routines improve mood and reduce stress. Removing 40+ hours of scheduled activity from your life creates a massive void that won’t fill itself.
What exactly are you going to fill that time with?
Before you answer “whatever I want,” reflect on how you feel during longer vacations. Do you find yourself getting antsy after a few days? Are you actually good at being idle, or do you start daydreaming about productive activities and creating your own projects and deadlines? I know I do.
Most high-achievers discover they’re terrible at unstructured time. The irony is that weekends and vacations feel so good precisely because they serve as a contrast to our structured weekdays. But large blocks of free time can have drawbacks – without that contrast, freedom can feel stifling. And spending that free time surfing the internet or obsessing over politics is hardly the fulfilling retirement most people dream of.
→ The solution: Retire “to” something, don’t just retire “from” your job.
Start building intentional routines before you hand in your resignation. I’m not talking about rigid schedules, but purposeful structure that gives your days meaning.
Think about what sounds appealing to you. Is it teaching courses, writing about your area of expertise, or mentoring young professionals in your field? Many retirees find that part-time teaching or consulting keeps their skills sharp while providing mental stimulation. You’ve got decades of valuable experience that others can learn from!
Another option is using your skills for causes you care about. This might mean serving on nonprofit boards, volunteering for organizations that align with your values, or starting passion projects that provide value for others. The most satisfied retirees often describe feeling “useful” – like their experience and knowledge still matter in making a positive impact.
For some, phased retirement might be the answer, gradually reducing work hours or responsibilities rather than stopping cold turkey. This can ease the transition while maintaining some structure and income.
What does purposeful structure actually look like? Maybe it’s Tuesdays and Thursdays for consulting work, Monday mornings for writing, and Friday afternoons with grandkids. Or perhaps it’s volunteering at the local food bank on Wednesdays, taking a Spanish class on Thursday evenings, and dedicating Saturday mornings to that novel you’ve always wanted to write.
Test some of these ideas during long weekends or vacations before you retire. What new (or old) hobbies do you want to cultivate? What activities energize you? What makes you feel productive and satisfied? Build those into a sustainable weekly rhythm that you can implement from day one of retirement.
2. Master the Art of Spending This is where even the most financially savvy people stumble. You’ve spent decades accumulating wealth, but nobody taught you how to spend it. Many people have no idea how much they can afford to spend in retirement, so they wing it. Some retirees overspend, which can threaten the long-term solvency of their retirement. Others underspend dramatically, living in constant worry despite having ample resources.
As Bill Perkins argues in Die with Zero
→ The solution: It’s hard to unwind decades of frugal habits, but here are a few strategies that can help retirees feel comfortable spending after the paychecks stop:
Get a plan – Either DIY or work with a competent advisor. Your retirement plan should take into account your various income sources, including Social Security and pensions. It will also determine how much you can safely withdraw from your investment portfolio and what accounts to withdraw from, in what order, for maximum tax efficiency. Without this basic information about your retirement plan, you’re fumbling around in the dark.Dynamic withdrawals – Use a smarter retirement income plan. One popular strategy is called “guardrails ”, and you can think of it as driving on a winding mountain road. This approach adjusts income over time to help retirees stay balanced and avoid the extremes of overspending or underspending. I’ve found it to be far superior to relying on the “one size fits all” nature of The 4% Rule or a murky Probability of Success score.More stable income – Research by David Blanchett reveals that retirees with more guaranteed income feel significantly more comfortable spending money. His concept of A License to Spend Note: There are good products and bad products, so professional guidance is recommended. Generally, you want the recommendation for an annuity to come from a fee-only advisor who doesn’t earn a commission for selling you one. Use mental accounting to your advantage – People naturally budget money into mental accounts and treat cash differently based on its source or where it’s held. Work with this tendency instead of against it by creating dedicated accounts for “special” spending goals like travel, wellness, or charitable giving. Set up automatic transfers to these buckets each month, then spend freely from them without guilt. This reduces the pain of paying because the money is already earmarked for that purpose, ready to spend. This approach can help you stay on budget for these expense categories, and it won’t feel like you’re “robbing” the money from somewhere else.
Retirement spending isn’t just about math – psychology plays an important role. Using the right tools can give you the confidence to actually enjoy the money you’ve worked so hard to accumulate. Don’t let fear rob you of the experiences and lifestyle your savings were meant to provide. The key is starting this planning process early, so you can cross the threshold with confidence rather than anxiety about money.
3. Be Proactive with Your Health Most jobs provide at least some movement throughout the day. In retirement, you need to intentionally replace this. Make health and exercise a non-negotiable priority because your energy levels and mental clarity depend on it.
The concept of “healthspan” – years lived in good health, free from chronic disease and mobility issues – should be just as important as the health of your financial plan. Invest time into fitness before and during retirement to slow physical decline and maximize your active, independent years.
The reality is that physical decline accelerates as we age, and what seems manageable in your 50s becomes much more challenging in your 70s and 80s. Maintaining strength, mobility, and cognitive function is critical to enjoying the retirement you’ve worked so hard to achieve.
→ The solution: Create a comprehensive health strategy that goes beyond a vague goal like “staying active.”
This means establishing regular, structured exercise routines that include both cardiovascular fitness and strength training. The latter is especially important for women, given their increased risk for osteoporosis.
Consider working with healthcare professionals who focus on prevention rather than just treatment. Build relationships with trainers, nutritionists, and/or wellness coaches who can help you maintain your physical capabilities as you age. Remember, the goal isn’t just to live longer… It’s to maintain your independence and quality of life throughout retirement.
If you want to explore this further, Dr. Peter Attia ‘s book Outlive
4. Prioritize Relationships Careers provide much more than a paycheck. They give you purpose, social connections, measurable impact, and a sense of identity.
I learned this the hard way when I transitioned from the corporate world to running my own solo company. Even though I was pursuing my passion, losing the daily interactions with colleagues and the clear metrics of corporate success was jarring.
The happiest retirees aren’t those with the most money. They’re the ones who solve the “softer” problems like relationships and identity.
Think about it this way – for 30+ years, when someone asks “What do you do?”, you have a clear answer. An answer you’re proud of. That title becomes part of your identity, whether you realize it or not. Then one day, you retire and suddenly that identity is gone.
Keep in mind that it’s not just your individual identity at risk. Retirement is a major life transition that can strain even the strongest marriage. “Gray divorce” – divorce among couples over 50 – has doubled since the 1990s , and retirement is often a contributing factor. When couples spend decades focused on careers and raising children, they may discover they’ve grown apart once those shared structures disappear. Suddenly spending 24/7 together can expose incompatibilities that were hidden by busy work schedules. The spouse who defined themselves through their career may struggle with depression or aimlessness, putting additional stress on the relationship.
→ The solution: Systematically replace each non-financial benefit your job provided while also strengthening your most important relationships:
Social connections: Join professional organizations, volunteer groups, or clubs related to your interests. Consider mentoring roles where you can share your expertise while building new relationships. The key is finding regular, scheduled interactions with people who share your values or interests – not just casual acquaintances, but meaningful connections that provide intellectual stimulation and accountability.Marriage and partnership: If you’re married or in a long-term relationship, start having honest conversations about retirement expectations now. Discuss how you’ll each find individual purpose and maintain your connection as a couple. Consider couples counseling sessions that address the emotional aspects of this transition. Plan separate interests and shared activities. The goal is to enter retirement as partners in this new chapter, not strangers who happen to live in the same house.Family and old friendships: Retirement gives you the time to invest in relationships that may have taken a backseat during your career-focused years. Reach out to old friends you’ve lost touch with as many are probably dealing with similar life transitions. Plan regular trips or activities with adult children to deepen those relationships beyond holiday visits. Consider being more present for grandchildren if you have them. These relationships require intentional cultivation, but they often become the most meaningful part of retirement when professional accomplishments fade into the background.
Start building these replacement activities while you’re still working. The goal is to have them already established when you retire, not scrambling to find meaning afterward. Think about developing your “retirement identity” years before you actually retire. Maybe you become known as the neighborhood expert on local history, the person who writes thoughtful investment analysis, or the mentor who helps young professionals navigate their careers.
5. Build Adaptability Into Everything The most valuable retirement asset is flexibility. Markets crash. Health situations evolve. Tax laws change. Family dynamics shift. Global pandemics happen. You need to be able to adapt your plan when life throws curveballs.
→ The solution: Build flexibility into every aspect of your retirement planning:
Develop a retirement income plan and investment strategy that are prepared for bad markets, not derailed by them.
Maintain a “war chest” with several years of living expenses in cash and short-term bonds to ride out market events and provide uninterrupted retirement income.
Plan for variable spending needs – distinguish between essential expenses (housing, healthcare, food) and discretionary spending (travel, entertainment) so you know where fat can be trimmed if needed.
Build healthcare cost buffers into your plan – medical expenses often increase with age and can be unpredictable.
Address major risks that could torpedo your plan – inflation (which erodes purchasing power over decades), long-term care events, changes in tax laws, etc.
The retirees who struggle most are the ones who assumed everything would go according to plan. A resilient strategy acknowledges that retirement rarely unfolds exactly as expected and builds in the flexibility to handle whatever comes your way.
The Bottom Line Retirement isn’t all rainbows and butterflies just because you don’t have to go to work anymore. In fact, for many high-achievers, the transition from structured, purposeful work to unstructured “freedom” can be deeply unsatisfying.
But here’s the good news: you don’t have to leave this to chance. By proactively planning around time, spending, health, relationships, and adaptability, you can create a retirement that’s genuinely fulfilling rather than just financially secure. The goal isn’t just to buy yourself 7 Saturdays a week – it’s to build the retirement of your dreams and make the most of this next chapter.
In late retirement, you want to be able to look back and say “I’m glad I did” instead of “I wish I would have.”
Start building these systems now, while you still have the income and structure of work to support the transition. Your future retired self will thank you!
About the author: Allen Mueller, CFA, MBA is a self-described “engineer turned finance nerd” and founder of 7 Saturdays Financial.
