There was a time when grilled cheese was not a choice. It was the plan.
I’m not being dramatic. There was a real season of my life — three jobs, a business on the side, a budget that left no margin for anything resembling luxury — where a grilled cheese sandwich was dinner because it was what I could afford. I wasn’t suffering. I was building. But I was also learning something important about money that most people don’t talk about:
Getting to financial stability is not the finish line. It’s the starting line.
Last week, we explored the ways we unintentionally waste money — the subscriptions that silently drain us, the habits that cost more than we realize. This week, I want to flip the script entirely.
Because once you start winning with money — once you have a plan, a margin, a system that actually works — you unlock something most financial conversations never get to: the freedom to spend intentionally on a life you actually love.
Money Is a Tool. What Are You Building?
Here’s the frame I want you to hold for everything that follows.
Money is not the goal. Money is the tool. The goal is a life you look back on at 80 and say, with a full chest: “I’m so glad I did that.”
Not “I’m glad I saved that.” Not “I’m glad I was responsible.” Those things matter — absolutely, and we talk about them all the time. But the end game of financial health is not a large number in an account. It’s a large, rich, well-lived life.
What seems like a “waste” to one person is a profound investment to another. The woman who spends $200 a month on massages isn’t being frivolous — she’s managing her body, her stress, and her energy so she can show up fully everywhere else. The man who flies business class isn’t showing off — he arrives rested, present, and ready.
The question is never simply, “Can I afford this?” The better question is: “Is this the version of my life I actually want to be living?”
This isn’t about extravagance for its own sake. It’s about strategic, intentional spending that makes your actual life better — and that motivates you to keep building toward even more.
Inspired by my own experiences, conversations with clients and friends, and a lot of honest reflection, here are the best ways I know to “waste” money on a life worth living.
Your Home & Environment
- Hire a House Cleaner
Time is the one resource you cannot make more of. When you spend your Saturday scrubbing bathrooms, you’re spending something more valuable than money. A house cleaner doesn’t just clean your home — it buys back your weekend. It gives you two hours on a Sunday morning that belong entirely to you. For many people, this is the single highest-return purchase they’ll ever make.
- Hire a Landscaper
Your outdoor space is an extension of your home and your life. A landscaper doesn’t just mow your lawn — it returns your Saturday afternoons, eliminates a source of chronic low-level guilt, and turns your yard into a place you actually want to be. The question isn’t whether you can afford it. It’s whether you can afford to keep trading your time and energy for a task that brings you no joy.
- Get a Closet Organizer
Your morning starts in your closet. When it’s chaotic, your day starts in low-grade stress before you’ve even made coffee. A professional closet organization — one time, done well — eliminates daily friction you may not even realize is draining you. It sounds trivial. The people who have done it will tell you it changed their mornings entirely.
- Host a Dinner with a Personal Chef
Imagine gathering your closest people around a table. Great food appearing from your own kitchen. No one running to the restaurant, no one stressed about cooking, everyone just… present. A personal chef for an evening is not just a meal. It’s a memory. It’s a story your friends tell for years. It’s the version of entertaining that actually feels like you intended.
Your Health & Body
- Hire a Personal Trainer
Here’s the truth most people won’t say out loud: a gym membership you don’t use is a waste of money. A personal trainer who shows up, holds you accountable, and actually gets you results is one of the best investments you can make. Your body is the vehicle for your entire life. Everything you want to experience, create, and enjoy depends on it. Invest accordingly.
- Annual Blood Work with a Holistic Doctor
Reactive healthcare — waiting until something is wrong and then treating it — is expensive, stressful, and often avoidable. Annual comprehensive blood work with a doctor who looks at optimization, not just the absence of disease, is proactive investment in the most important asset you have: your health. Catching something early, or learning what your body actually needs, is worth far more than what it costs.
- Hire a Nutritionist
Most of us know we should eat better. Very few of us know specifically what “better” means for our particular body, lifestyle, and goals. A nutritionist doesn’t hand you a diet. They help you understand the relationship between what you eat and how you feel, how you perform, how you sleep. That knowledge compounds for the rest of your life.
- Regular Massages, Facials, or Self-Care Rituals
Before you scroll past this one, notice the reflex. We are often the quickest to cut the things that restore us. Regular self-care — whatever that looks like for you — is not vanity. It is maintenance. It is the investment that keeps the engine running. A person who feels good in their body moves differently through the world. That is worth something real.
- Have Your Meals Cooked and Delivered
The promise of meal delivery isn’t convenience for its own sake. It’s the elimination of a daily low-grade decision that drains mental energy, often results in poor choices when you’re tired, and steals time from things that matter more. When your food situation is handled, you eat better, think more clearly, and have more space for what actually needs your attention.
Your Mind & Growth
- Hire a Coach — Business, Life, or Financial
Every elite performer in the world has a coach. Not because they can’t figure things out on their own — but because they know that an outside perspective, honest accountability, and expert guidance accelerates everything. A good coach doesn’t just help you solve problems. They help you see possibilities you couldn’t see from inside your own life. This is one of the highest-return investments that exists.
- Attend Personal Growth Conferences
There is something that happens when you put yourself in a room full of people who are intentionally working on themselves, their businesses, or their ideas. Energy shifts. Possibilities expand. You come home with one idea, one connection, or one reframe that changes the trajectory of something important. The investment in getting in the room almost always pays back more than the ticket price.
- Take a Sabbatical
This is the one that feels the most impossible and is often the most necessary. A sabbatical — a real, intentional break from the grind — is not laziness. It is the kind of reset that allows you to return to your work and your life with clarity, creativity, and renewed purpose. Many people who have done it describe it as one of the most transformative decisions of their lives. “I’m glad I did that” is almost universally the verdict.
- Take Time Off to Volunteer
There is a particular kind of fulfillment that comes from giving your time — not your money, not your expertise from a distance, but your actual presence — to something larger than yourself. The research on this is consistent: people who regularly volunteer report higher levels of happiness, meaning, and life satisfaction. Sometimes the best investment is the one that gives you something money can’t buy.
Your Experiences & Adventures
- Luxury Travel
Travel — real travel, the kind that takes you somewhere unfamiliar and changes how you see the world — is one of the most frequently cited sources of life satisfaction in retirement reflections. And yet it’s one of the first things people defer. “We’ll do it when the kids are older.” “We’ll do it when we have more money.” The thing about travel is that your body has a timeline. Go now. Go well. Go intentionally.
- Extended Trips and Slow Travel
There is a fundamental difference between a vacation and immersion. A week in Italy checking off tourist sites is not the same as spending three weeks in a single neighborhood, learning the rhythms of a place, eating where the locals eat, letting the pace of somewhere different recalibrate you entirely. Slow travel is not more expensive than fast travel — it is often less so. But it requires the most valuable thing: time. Which is exactly why it’s worth protecting.
- Flying Private
This one is genuinely not for everyone, and that’s completely fine. But for the person whose time is worth a significant amount per hour — the executive, the entrepreneur, the person managing a complex life — the calculation on private air travel is not always as irrational as it sounds. Four hours of uninterrupted, productive, comfortable work versus a crowded airport and a middle seat is a real trade-off worth examining with clear eyes.
- Front-Row Seats to a Concert or Sporting Event
You know the difference. You’ve sat in the upper deck, and you’ve sat close. The experience is categorically different — not marginally better, but a completely different event. For a show or a game that genuinely matters to you, the front-row version is not a splurge. It’s the real thing. The other version is a photograph of the real thing. Buy the real thing sometimes.
- Own a “Just for Fun” Vehicle
The motorcycle you’ve always wanted. The vintage truck. The convertible for the summers. There are purchases that are purely, unapologetically about joy — and that is reason enough. A life that has no room for the thing you’ve always wanted just because you wanted it is a life lived too practically. Financial freedom isn’t just about security. It’s about saying yes to the joy version of your life, occasionally, on purpose.
Your Style & Presence
- Get a Color Consultation
It sounds like a small thing. It isn’t. Understanding the colors that work with your natural coloring — and confidently removing the ones that don’t — simplifies your closet, elevates how you present yourself, and removes a source of daily low-level uncertainty that you may not have realized was there. Looking and feeling put-together is not superficial. Confidence is a tool. Use it.
- Hire a Personal Shopper
The personal shopper is not just for people who hate shopping (though if you hate shopping, stop torturing yourself immediately). It’s for anyone who wants to show up to important moments — a speaking engagement, a meeting, a first date, a family photo — feeling exactly right. A stylist who knows your life, your body, and your goals removes the friction and the guesswork from something that, for many people, consumes far more time and mental energy than it should.
The Bigger Truth: You Built This
I think about the grilled cheese years often. Not with regret — with gratitude. Because those years built the discipline, the clarity, and the appreciation that make intentional spending actually meaningful.
The massage means something different when you’ve gone without. The business class seat means something different when you’ve done cross-country in a middle seat, exhausted, for years. The personal trainer means something different when you’ve watched your health suffer under the weight of a life with no margin for it.
Financial freedom is not about spending recklessly. It’s about spending consciously — with the full knowledge of what you’ve earned, what you’ve saved, and what you’ve decided your one life is worth.
You get to decide what your best life looks like. Define it. Plan for it. And then, when you get there, actually live it.
“I’m glad I did that” is the goal. Not just for the big moments — the trips, the milestones, the adventures. But for the ordinary Tuesday where you came home to a clean house, ate a meal you didn’t have to cook, and had the energy to actually be present for the people you love.
That’s what the money is for.
Now I Want to Hear From You
What is the best way you “waste” money — the thing that other people might raise an eyebrow at, but that genuinely makes your life better? And which item on this list are you most excited to add as you build your financial freedom?
Drop it in the comments, reply to this email, or bring it to our next conversation. Because this — the part where money starts working for your life instead of the other way around — is my favorite part of the whole journey.
And if you’re not there yet? That’s exactly what we’re building toward. Together.
