It’s a question I hear often — sometimes with a laugh, sometimes with hesitation: “When is it okay to actually enjoy my money?”

This question runs deeper than numbers on a page. It’s about habits, beliefs and emotions built over decades of working and saving. And for those entering retirement, it can feel surprisingly hard to shift from saver to spender.

Why It Feels Hard to Spend In Retirement

For years, you’ve worked, saved and put money away for “someday.” But when retirement arrives and the paycheck stops, spending those savings can feel uncomfortable.

Instead of adding to your accounts each month, you’re drawing them down. That change can bring fear — what if that one big purchase or unexpected expense throws everything off and jeopardizes the security you’ve worked so hard to build?

The Emotions Behind Spending

Spending decisions in retirement often come with mixed emotions. There’s excitement in finally taking the big trip of your dreams or updating your home. But there’s also worry: Will this affect my future security?

This is where financial planning can be a game-changer. We run the numbers and model different scenarios to show how today’s choices can affect tomorrow’s security. Often, seeing the impact in black and white gives people the confidence to say, “Yes, I can afford this — and still meet my long-term goals.”

Balancing Needs, Wants and Timing

When I work with clients, we start by making sure the essentials — housing, healthcare, daily living expenses — are covered. From there, we talk about “wants,” like travel, remodeling and generous gifts to family.

This is where flexibility matters most. Sometimes it makes sense to move forward with a big expense right away. Other times, especially in a volatile market, it may be better to wait or spread the cost over multiple years.

The goal isn’t to limit spending, but to help you understand your options and weigh the trade-offs so you can make confident, informed choices.

When Spending Becomes Too Easy

Interestingly, some retirees start out cautious, then swing the other way. Once spending becomes comfortable, it’s easy to blow past the budget.

There’s no judgment here — just a reminder that overspending today can eliminate some opportunities for your future self.

Retirement is About Opportunities

The truth is, you’ve saved for a reason: to create freedom and opportunities later in life. Retirement is that moment.

So, when the plan supports it, give yourself permission to enjoy what you’ve worked so hard for. Take the trip. Remodel the kitchen. Make the memories. Just be mindful. A solid financial plan can help you enjoy today while protecting tomorrow.

My Advice

There’s no single “right” time to start enjoying your money. The best time is when:

• Your essential needs are covered.
• Your plan accounts for both today’s wants and tomorrow’s needs.
• You can say “yes” to something today without creating regret later.

If you’re unsure whether you’re in that place yet, that’s when a financial advisor can help — by running the numbers, modeling different scenarios and weighing the trade-offs, so you can feel confident enjoying your money — knowing your future is secure.

Because after all, you didn’t work this hard just to not enjoy it.