Paid Help as Infrastructure

Hello, (Less) Lonely Money Community!

Welcome to this month’s (Less) Lonely Meetings drop—a practical toolkit designed to help you turn each (Less) Lonely Money article into real conversations that deepen trust, insight, and client engagement.

Inside, you’ll find two advisor-ready tools:

• Client Companion — a thoughtful newsletter you can send to clients and prospects that opens the door to talking about paid help as a real part of financial planning—not as an indulgence, but as infrastructure for the lives they’re trying to build.

• Meeting Ready Guide — a practical, non-scripted outline to help you ask clients about capacity, anti-goals, and the cost of running without the support they need.

This month, we explore something the financial planning profession has historically treated as a lifestyle expense to be scrutinized: paid help. The nanny, the housekeeper, the personal trainer, the assistant, the coach, the eldercare coordinator. The list goes on.

Some clients resist this kind of help because of cost. Others can easily afford it but resist anyway—because the resistance isn’t really about money. It’s about identity, guilt, the sense that they should be able to do it all themselves, or the worry that paying for help means they’ve failed at something.

Sending this piece to clients does two things. First, it normalizes the idea that help is a legitimate planning category, not a luxury to be apologized for. Second, it signals that you, as the advisor, are someone they can talk to about it—without judgment, and with a real plan in mind.

Let’s begin.

What Do You Want to Stop Doing? The Case for Paying for Help

• For clients navigating burnout, caregiving demands, or capacity strain

• During career, family, or work-life transition conversations

• When a client seems stretched thin but resists the idea of outsourcing

• As a permission-giving piece for clients who have never considered help as part of their plan

• What Would You Stop Doing If You Could?

• Help Isn’t a Lifestyle Expense—It’s Infrastructure

• The Question Most Financial Plans Forget to Ask

What Do You Want to Stop Doing? The Case for Paying for Help

Most financial planning conversations start with what someone wants to do. Buy a house. Retire by sixty. Send the kids to college. Start a business. Travel more.

But there’s another question that often matters just as much—and rarely gets asked: what do you want to stop doing?

Not the meaningful hard things. Not the work you care about and the people you love, nor the responsibilities that matter to you. The other stuff. The friction. The tasks that take up (too much) time and give very little back. The things you keep doing because you feel like you should, or because nobody else will, or because it feels indulgent to hand them off.

Brian Portnoy, in his book The Geometry of Wealth, calls these anti-goals: the things you want to avoid, the situations you’d pay to never be in again. His point is that money is often more powerful as a pain reliever than as a happiness producer. It’s frequently better at protecting us from the things we hate, bore us, or can’t stand, than at delivering the things we love.

That reframe matters, because it changes what we ask money to do for us.

Paid help shows up in lots of different shapes. A house cleaner. A childcare arrangement that lets both parents work without the weekly schedule becoming a second job. An assistant who handles the inbox so the actual work can get done. A trainer who knows what they’re doing in the gym so we don’t have to figure it out alone. A coach for a project, a career, a hard transition. A care coordinator who manages doctor appointments and pharmacy calls for an aging parent.

All of these can look, at first glance, like luxuries. And there are absolutely versions of them that are, but there are also versions of them that are something else entirely: infrastructure. The kind of structural support that makes the rest of a life functional.

What is more, research backs this up. A study of more than 6,000 people across four countries found that those who spent money to save time reported greater life satisfaction than those who did not—across income levels, and for purchases large and small (Whillans et al. 2017). The dollar amount mattered less than the act of buying back time.