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Spend Once, Benefit Forever - Investing for Perpetual Returns

Published or Updated On: 
January 15, 2023

🤖 Evil Healthcare Robots

When it comes to health insurance, I’m a cheapskate. I buy the bottom of the barrel. Three years ago, I bought from a health insurance company that was so crappy, they didn’t even offer online bill pay. This meant that every month, I had to call them to pay by credit card over the phone. Even worse, it was an automated phone payment system, which meant I could only pay as fast as the malevolent talking robot would allow. A typo while entering my credit card number started the whole process over, which I imagine made the company giddy with perverse delight.

Even though it didn’t take that long to do each month, the process was so annoying that the following year when choosing an insurance, I selected a slightly more expensive option just so I could pay automatically online. Honestly, it was 100% worth it. I made the change once, and have reaped the benefits every month since then for years.

Like this bill pay example, there are ways you can “spend once” and benefit forever. In this blog post, I’ll walk through a conceptual framework for thinking about your spends & returns. I’ll argue that for life-changing results, you should be investing in things that can offer you perpetual returns. I’ll provide examples, and some questions to ask yourself to make this all actionable. Let’s get into it.

🧾 Costs & Returns

Everyone has a finite amount of time, energy and money. These are your currencies. How you spend them is up to you. When you spend them, you get a return, some kind of benefit. For example, if I spend some time and energy doing the dishes & tidying up, my return is a clean kitchen.

When your return exceeds your cost, it’s a good investment. In this dishes example, it’s a good investment but not a great one. Notice how the return circle isn’t that much bigger than the cost circle. Here’s a different example. Say I decide I want to flip a house. I buy one and renovate it at significant cost but I’m able to sell it for even more.

As you can see, flipping a house is way more work than doing the dishes, but it’s a much better investment. Not only is the difference between the size of two circles bigger, but notice the sheer size of the return circle. It’s big! So it makes more sense to “spend” a bunch on flipping a house than on cleaning your kitchen (though hopefully you can do both).

1️⃣ One Time Returns

This might all seem like common sense so far, but there’s a dimension here that many people miss. If I flip a house, I only get a big payday once. Flipping gives me a one time benefit. I can flip another house, but it will require the similar costs. I might create some additional efficiency with my new experience, but the cost is still going to be high. This becomes a lot more obvious if we add a new dimension to our graphics: time.

♾️ Perpetual Returns

There are ways to spend your currencies that can produce a perpetual return, meaning you spend once and get a benefit forever.

A classic example is my wife, who was a nurse (RN) going to back to school to become a nurse practitioner (NP). The cost is pretty big: at least 2 years of school, plus $20,000 - $35,000+. But the return she gets from this investment is perpetual. The hourly wage she can command goes up by 60%, permanently, and she receives durable lifestyle gains too: NPs usually work 4 days per week instead of 5, get more paid time off, and have more autonomy. In about half of all states, she could even open her own practice. 

Because the return from NP school is perpetual, the value is far greater than that of a single house flip.

Spend once, benefit forever.

I can think of 3 categories of investments that deliver perpetual returns: skills, systems, and assets. Check out the list below for some examples of each.


  • Reading an outstanding book on productivity
    ➡️ improved work output for the rest of your career
  • Learning how to program in Python
    ➡️ opening the door to higher paying jobs
  • Being taught a great coping tool by a therapist
    ➡️ enjoying your life more


  • Automating your bill pay
    ➡️ no forced interaction with evil health insurance robots
  • Setting up a saving schedule for early financial independence (FIRE)
    ➡️ freedom from the requirement to work for a living
  • Creating a practice for groceries where you buy online & re-order the same cart from 4 weeks ago
    ➡️ easy meal planning
  • Organizational habits, e.g. always putting your personal items in the same place
    ➡️ less time spent searching for stuff
  • In your business, defining your work & hiring someone else to do it
    ➡️ create leverage & free up your time


  • Building or buying a business
    ➡️ the classic example, a way to get huge perpetual returns
  • Creating a stellar reputation
    ➡️ opportunities find their way to you that aren’t available to others
  • Starting a community
    ➡️ you have an audience to learn from & sell to
  • Making a new friend
    ➡️ enjoying the companionship of shared experiences, maybe for life

Of the 3, I think assets are the heavyweight. I spend time, energy and money on all 3, but I spend the most on assets. The opportunity for perpetual returns is one of the main reasons I started Paragon, my activewear brand. It’s also one of the main reasons I started this blog. Here’s how I think about it:

Writing high quality articles is a big time cost. If I write for someone else, I could get paid some cash, maybe $5k-$10k/year depending on the quantity of articles. But for each article I write, I’d only get paid once. Alternatively, I can write for myself. My short term return is $0, but what I’m doing instead is building an asset. Over time, the return for each article I write can potentially become very high with good SEO, and because of the way SEO works, it can be perpetual. Same goes for my email list. I know of people who have made several hundred thousand dollars off their blogs, just looking at cash & not other benefits returned.

This can’t be the whole picture though, or else everyone would be creating successful blogs, right? Notice I mentioned the return on a blog can potentially be very high. Unlike the perpetual returns offered by NP school, my returns are not guaranteed. 

🍞 You've gotta risk it to get the biscuit

That leads us to a new element for our framework: risk. My blog is risky because it’s going to take so much effort, with no return up front. There’s the chance that all my work will all be for nothing. Here’s a more realistic visual:

Either this is a really good idea, or I'm an idiot

Particularly for assets, the more life-changing the potential returns are, the more risk tends to be involved. So as the header says, you've gotta risk it to get the biscuit.

🧠 How to use all this

If you’re reading this blog, you’re probably a savvy investor. For life-changing perpetual returns, you should prioritize investing in skills, systems, and assets. Keep this framework in mind as you consider new spends. For your current spends, here are some questions to ask yourself.


  • What are the main things that take up your time? What projects are you working on? What’s got your attention?
  • If your plate is full, what has a high “cost” but only a modest or one-time "return"? How could you get that off your plate? Can you delay, delete, or delegate? Can you solve it by spending some money?


  • What skills can you develop? What sounds fun to learn that would be useful to you, increase your earning power, improve your quality of life, or open other doors?
  • What systems can you create? What can you automate in your life? What could be done more quickly, or with lower effort if it had a standard practice, habit, or plan that you simply stick to? 
  • What assets can you build? How can you take something you’re good at, and turn it into a business? How can you earn goodwill from an important community? How can you meet interesting people?
  • If you are already investing in a skill, system or asset, how can you lean into that more? How can you allocate a greater spend to that investment?

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