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Note: The examples and case studies in this article are hypothetical but represent real situations I have encountered in my practice working with Washington State public employees.
I think about this question a lot when I'm working with clients on their retirement plans. We spend hours running numbers. Pension options. Tax projections. Healthcare costs. Investment allocation. And then, usually near the end of our meetings, someone will say something like: "I guess I'll finally have time to relax." And I wonder: is that really what they want to do for the next 30 years? Because from what I've seen, the people who retire early and are genuinely happy six months later, a year later, five years later... they're not the ones who are just relaxing. They're the ones who figured out what they were retiring TO, not just what they were retiring FROM. The Question Nobody Asks During Retirement Planning Everyone focuses on the money part. Can I afford to retire? What pension option should I take? How do I bridge healthcare to Medicare? When should I claim Social Security? Those are important questions. I spend most of my time helping people answer them. But there's another question that matters just as much, and almost nobody asks it during the planning phase. What am I actually going to DO? Not in the first month. Not during that honeymoon period where you're catching up on house projects and taking that trip you've been putting off. I mean three years in. Five years in. What fills your days when you're 62 and healthy and have potentially 30 more years ahead of you? The Reality of 10,000 Empty Days Let's do some math. If you retire at 58 and live to 88, that's 30 years. 30 years times 365 days equals 10,950 days. Before you retired, your job filled about 2,000 hours per year. Work days, meetings, projects, deadlines, colleague interactions. Now you have 2,000 hours to fill. Every single year. For potentially three decades. That's a lot of golf. I'm being a little flippant, but the point is serious. The transition from a structured work life to completely unstructured time is harder than most people expect. And the financial planning industry doesn't talk about it much because we're focused on making sure you don't run out of money. What Actually Works (Based on What I've Seen) Here's what I've noticed from clients who are thriving in retirement versus those who are struggling. The ones who are happy didn't just plan their finances. They planned their time. They started before they retired. I've seen people who spent their last years before retirement gradually building up volunteer work. One example: someone who started with a literacy program while still working full-time. By the time they left their job, they had a ready-made structure waiting. Three mornings a week. Relationships already established. A place where they felt needed. It wasn't about filling time. It was about creating purpose on their own terms. They have multiple things, not one big thing. The people who struggle are often the ones who put all their identity eggs in one basket. "I'm going to travel full time." (Gets expensive and exhausting.) "I'm going to start a business." (Sounds great until you realize you just gave yourself another job.) "I'm going to finally relax." (Turns out humans aren't wired for endless relaxation.) The ones who are content have a portfolio of activities. Volunteer work two days a week. Hiking group on Thursdays. Grandkids on Tuesdays. Book club once a month. Part-time consulting gig that brings in a little money and keeps their brain engaged. None of it is overwhelming. All of it adds up to a life. They kept some structure. This surprised me at first, but it makes sense. After spending 30 years with structure, going completely unstructured feels untethered for a lot of people. The happiest retirees I know have routines. Not rigid schedules, but patterns. Coffee and reading in the morning. Walk after lunch. Volunteer work on specific days. Dinner with friends every other Friday. Structure by choice feels different than structure by obligation. They found ways to still contribute. This one's big. Humans need to feel useful. We're wired for it. The DRS pension provides financial security. But it doesn't provide the feeling of being needed that work often gave you (even when you didn't always love your job). One LEOFF 2 member I worked with retired from the fire department at 53. Thought he'd love having nothing to do. Hated it. Started teaching fire science classes at the community college two days a week. Not for the money (though it doesn't hurt). For the feeling of passing on what he knows. Now he's actually happy. The Part-Time Work Consideration Speaking of contributing, let's talk about working after retirement. A lot of early retirees end up going back to some kind of work. Not because they need the money, but because they miss parts of work they didn't expect to miss. If you're a WA public employee with a pension, you can work up to 867 hours per year in a DRS-covered position (about 17 hours per week) without affecting your pension. That's enough for meaningful part-time work. There are no hour limitations on private sector work or other non-DRS-covered jobs. Some people do consulting in their former field. Some get completely different jobs they always wanted to try. Some volunteer in ways that feel like work but without the paycheck. The key is that it's optional. You're working because you want to, not because you have to. That changes everything. What This Means for Your Planning I think about retirement planning in two phases now. Phase one: Make sure you can afford it. Pension strategy, investment management, tax planning, healthcare bridge to Medicare. All the financial stuff. Phase two: Make sure you'll actually enjoy it. Most people spend 90% of their energy on phase one and barely think about phase two until they're already retired. That's backwards. The financial part is important. But what's the point of being financially secure if you're going to be miserable? Some Questions Worth Asking Now If you're planning to retire in the next few years, try asking yourself these: What did I actually like about my job? (Not the paycheck. The actual work.) What have I always wanted to try but didn't have time for? Who do I want to spend more time with? What makes me feel useful? What would a good Tuesday look like if I didn't have to work? These aren't easy questions. But they're worth thinking about before you turn in your retirement paperwork. Here's What I'd Suggest Start experimenting now. You don't have to wait until you retire to figure out what you want your retirement to look like. Take some vacation days and live like you're retired. Not a special trip. A regular week at home with nothing scheduled. See what you do. See how it feels. Join something now that you could continue after retirement. A volunteer organization, a hiking group, a community college class. Test drive the life before you commit to it permanently. And think hard about what you're retiring TO, not just what you're retiring FROM. The financial planning will make sure you can afford retirement. But only you can make sure retirement is actually worth having. Sources
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AuthorsBob Deal is a CPA with over 30 years of experience and been a financial planner for 25 years. Archives
March 2026
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