Am I Allowed to Enjoy My Money Before Retirement? A New Way to Think About Retirement Lifestyle Planning

What if the old way of thinking about retirement is the thing keeping you stuck? Let me tell a story about what I mean… I had a client named Dave. Dave was 61. He’d spent his entire career as an engineer, methodical and careful with every dollar. After we first met, he shared a spreadsheet with me. On it was a list of everything he hadn’t done in the last decade: the fishing trip to Alaska he’d been postponing. The kitchen renovation his wife had quietly stopped mentioning. The weekend place up north they’d looked at three times but never bought. He looked at me and said, “I don’t need these things. My wife and I can make do without them.” Dave had done everything right. He had saved diligently, invested consistently, and was on track for a genuinely comfortable retirement. And yet, there he sat, holding his life at arm’s length, waiting for some imaginary permission slip to arrive in the mail. That conversation became a turning point for me. Because I realized that my job isn’t just to create and manage the structure of people’s money. It’s to help people like Dave understand that money is not the destination. It’s the vehicle. And retirement lifestyle planning is how we make sure the vehicle actually takes you where you want to go. At Pleasant Wealth, it’s what we call connecting the structure and soul of your money. 

The Responsible One’s Dilemma

If you’ve spent your life being the responsible one, you may have developed a complicated relationship with spending.  You’re the one who saved, planned, thought ahead, and put everyone else’s needs before your own. So it can feel like a moral conundrum to spend money on yourself. You get an uneasiness about it in your body (you might get that feeling in the pit of your stomach just reading this). It’s like you’re trying to go in separate directions. Especially on things that feel like luxuries. Especially when retirement isn’t quite here yet. So you wait. You defer the trip. You keep driving the car that’s fine (wouldn’t it be cool if I could get to 200k miles?).  You tell yourself: “After retirement.” “When I feel more secure.” “When I know for certain it’s okay.” But here’s what I’ve seen happen to people who wait too long to give themselves permission: retirement arrives, and the habit of deferring is so deeply ingrained that spending still doesn’t feel okay. The anxiety doesn’t go away on its own. The permission slip never comes unless someone helps you write it.

Retirement lifestyle planning isn’t about spending recklessly (you wouldn’t ever agree to that anyway). It’s about spending intentionally on the life you actually want to be living.

What Retirement Lifestyle Planning Actually Means

Most people think of financial planning as a series of restrictions: 

• Don’t spend too much
• Don’t retire too early
• Don’t outlive your money. 

These are fiscally sound guardrails. But they’re not a starting point. If we envision retirement as a path, we first need to understand the two most important points: where you are now (the structure) and where you want to be (the soul). We start with your life and ask questions like: 

• What does a good week look like for you? 
• What are the experiences that make you feel most like yourself? 
• What have you been postponing that you’re ready to stop postponing? 
• What would you do differently if you knew, with confidence, that your finances could support it?

These aren’t soft questions. They’re the scaffolding of genuine retirement lifestyle planning. A financial plan that doesn’t account for how you actually want to live isn’t really a plan. It’s another stack of papers for a dusty, seldom-opened filing cabinet.  When we understand your values, your vision, and your definition of a well-lived life, we can build a financial strategy that actively funds it. Not someday. Now, and later.

Back to Dave

After our first conversation, Dave, his wife, Laura, and I spent a few sessions on something they had never done. These exercises weren’t just about compiling numbers that added up neatly. We mapped out what their retirement was supposed to feel like.  We looked at their cash flow, their savings rate, their projected Social Security income, and their investment accounts. We stress-tested the plan against market downturns and longer-than-average lifespans. And then I was able to tell them, with real confidence: Dave and Laura, you can book the Alaska trip. You can renovate the kitchen. You’re not going to run out of money. You could see them both wrestle with several emotions as they took in this information: Momentary relief that this was really possible, disbelief that this can’t really (italics) be possible, and ease as they began to integrate these ideas into their vision for the future. He booked the trip the following week. His wife cried when he told her. That’s retirement lifestyle planning done right. It’s not permission to be reckless. It’s a clear-eyed, evidence-based answer to the question: “Can I actually live my life?”

Ask Your Financial Advisor If…

Are you feeling unsure of whether your current financial plan is built around your life or only the dollars and cents? Here are some questions worth bringing to any advisor conversation:

• Ask your financial advisor if they’ve ever asked you what a good week looks like in retirement. If the answer is no, that’s a gap worth closing.
• Ask your financial advisor if your plan includes a “joy budget,” an intentional allocation for the experiences, travel, and treats that make life feel worth living right now, not just in some future version of yourself.
• Ask your financial advisor if your retirement projections account for how you want to spend your early retirement years. Many women are at their healthiest and most active in their 60s. Those years deserve to be funded well.
• Ask your financial advisor if there is a specific, defensible number you could spend per year (not a vague “be careful”), so you can make decisions from clarity instead of anxiety.
• Ask your financial advisor if your values and your financial strategy are actually aligned. Your money should reflect what matters most to you. And if it doesn’t, that’s something worth fixing.

You’ve Earned This

There is a version of financial planning that keeps you anxious, cautious, and permanently waiting for life to begin. And there is a version that meets you where you are, understands what you’re building toward, and gives you the clarity to live fully in the present and far into the future.  At Pleasant Wealth, we practice the second kind. We believe that retirement lifestyle planning should feel like a conversation, not a lecture. That your financial strategy should expand your life, not restrict it. And that you deserve an advisor who asks what you actually want, and then helps you get there. You can learn more about how we work with women navigating these questions on our financial planning for women page.

Want to Grab Coffee? 

If Dave’s story sounded a little familiar,  if you’ve been keeping a mental list of things you’ve been waiting to do, I’d love to talk. Not a sales call. Just a conversation over coffee about where you are, what you’re hoping for, and whether your financial plan is actually built to support the life you want to be living. I’m easy to find. Let’s find a time that works for you → Find time to grab coffee