I can’t spend money properly and it’s driving me crazy.

I am terrible at spending. Time or money, it doesn’t matter which. I suck at it. Absolutely suck.

By this I don’t mean that I don’t spend a lot of it—time or money. I do, on both counts. Too much, in fact. The problem is that I don’t really make it work for me, or know how to make it work for me.

What I mean is that I don’t have the first clue how to invest my time or money wisely, even after all these years.

— § —

I did not grow up in a wealthy household.

Now we weren’t poor, exactly. The bills were paid. We had a car, and we had a television, and we had heat, and nobody ever really went hungry or wanted for anything. But that was accomplished, in general, through an ethos of not-spending, not through an ethos of wise-spending.

© Aron Hsiao / 2007

As is the case in many households that belong to a particular class, the in the household that I grew up in, there were two rules:

1. Spending money is always bad. Money spent is lost, gone forever. The most important thing you can do with money is hang onto it at all costs. Never, ever, ever spend unless your balls are in a vise and a gun is to your head, because money is rare and precious and a lifeline and spent money ain’t never coming back.

2. Time is free, and has no value. Time is the opposite of money, in fact. Money is rare and precious and never coming back, but time is everywhere, laying around in regrettable piles. So don’t spend money, ever, but do instead spend time, because it’s free. Whenever you’re tempted to spend money, or it seems as though you need to spend money, be smart and get around this need by spending time instead.

We can call this approach to time and money the lower-middle-class-and-below understanding of time and money. To people in these classes, the old adage that “time is money” has a much more nuanced meaning. It doesn’t mean that time and money are fully commensurable and exchangeable, but rather merely that money is invariably and formally limited, so it’s a smart idea to always try to spend time first, in order to save money.

So, background out of the way, back to my problem.

— § —

First facet of this problem is that I have no idea how to spend money in a profitable way. It’s embedded in my soul that nothing is ever “worth the money.” What is therefore not embedded in my soul is a list of anything that might actually be “worth the money,” much less any tools for identifying such things.

Now I do understand intellectually by now that there are good ways to spend. My understanding goes something like: You can be like Tim Ferriss or Penelope Trunk and hire an assistant. You can be like a white-collar salaried employee and buy training. You can be like a company are purchase services that provide leverage to your labor—that multiply your efforts and work in ways that produce a return—that is, a surplus of value relative to what you’ve spent.

But… Having grown up without any examples of this ever actually happening, I can’t locate or evaluate these kinds of possibilities to save my life. What services are the right services? When is the right time to hire? At what level? What could I earn by spending wisely? How would I even measure that?

Most of them time when I try to “spend wisely” or “invest in myself,” I get it catastrophically wrong. Because I did not grow up seeing this happen, ever, and I have no idea what criteria ought to be in play, what sorts of spending opportunities are likely to be good investments and so on. I don’t see where I ought to spend, and where I do spend, I oughtn’t have because the return isn’t there. I’m an easy mark. Hence, for example, massive student loan debt (yes, count me amongst the members of the lower classes that couldn’t make this calculation well).

Just as badly, I have a tendency to overspend whenever I do crack the wallet open. Because if spending is inherently bad, but I’m going to spend anyway, then I may as well make the most of it—sort of like the idea that if you’re going to fly to Paris from Utah, you’d be an idiot not to also make London and Berlin a part of your trip. After all, you’re going all that way, and you don’t know when you’ll be back again.

So—where other people can be frugal and buy the base model of something that they need, I’m always tempted to buy the luxury model. Why? Because I’m not supposed to spend anyway. And I don’t want to have to spend on this particular thing again. And I’m breaking a rule, committing a violation, “wasting” money already. Why take the massive, massive risk of spending something, then only spend on the subpar edition of the product?

If you’re going to have heartburn for buying a blender or a roll of paper towels, you’d better buy the best blender or the best paper towels, particularly if you have the money in your account.

Now I know intellectually that this is not a good way to spend. But I also don’t have a lot of framework or infrastructure in my head for doing it in other ways with any skill. I’m trying to learn it, but it’s slow to come, and I’m making a lot of mistakes, even by middle age. A lot of mistakes.

— § —

Now for the second facet of the problem—the time dimension, which is the converse of the money dimension. I have no idea when not to spend time, but to spend money instead.

Because the whole premise is exactly backward as far as my deep, what-I-learned-in-kindergarten psyche is concerned. Spend money instead of time? No, no, no, no, you never, ever do that! Capiche? It’s the other way around! Not money instead of time; time instead of money! That’s what time is for—so that you don’t have to spend money!

Far more often that I’d like to admit, I discover only at the end of a day or a weekend that I’ve invested many or even dozens of hours slowly fixing something that I could have instead spent $20 or $30 to fix. Yes, my time is far more valuable than that. I know this intellectually.

But even when I do spot these things before wasting the entire weekend, bringing myself to spend $30 on something that I could fix myself in three or four hours drives me crazy. I could fix it myself! Spend money? Sputter! Sputter! I mean… I could fix it myself!

And so here comes the overspending problem again. If I do break down and say, “okay, I’ll go to the store and replace this $30 item because my time is too valuable to spend the entire afternoon fixing this $30 item,” I end up walking out not with the $30 version as a replacement, but with the $200 version as a replacement, for reasons already stated.

Yeah.

— § —

To make this set of self-defeating problems worse, I have struggled with this in the workplace, too. In fact, it often comes up in the self-performance-evaluations that I write, and that more senior management sign off on. I don’t know how many times now over the years I’ve written some variant of the same thing.

Under “Areas for Improvement” is where it invariably comes up:

• “Better identify and act on opportunities to spend wisely on products, services, or opportunities that can multiply our efforts, provide an advantageous ROI, and support our strategic and tactical goals.”

• “Learn to recognize more effectively cases in which it will be more cost-effective to hire or purchase outside help or services rather than try to accomplish a task using in-house labor.”

But dammit if after all this time I still struggle. Does it ever occur to me to hire a consultant or a freelancer to do a task? No, I have to admit that even years after my first management role, 99 percent of the time someone else has to suggest it, and my first impulse is always to recoil in horror. Spend money? Oh God no! Especially not the company’s money, OMG, OMG, OMG!

And I routinely get spotted doing tasks that I should not have been doing at my salary level, and that it would have been ten times cheaper to have a freelancer do. I don’t even notice until someone calls me out on it. “Wait, you’ve been working on that for two days? Holy shit, why? Stop it! Hire someone on Fiverr. For God’s sake!”

Because of course, somewhere deep in my imagination or soul, time is still free. Time is still, after all these years, free—and money is not. Especially when it’s not even my money.

— § —

I hate this in particular at times like this, like tonight.

© Aron Hsiao / 2009

Because I am sitting here knowing that there are a million areas in life in which I just plain old need help, and could have it, and it could make my life better and in fact enhance my ability to earn. I’m sure there are a million services that I can pay in a million creative ways to facilitate this, yet I feel:

• Complete revulsion at the thought of actually spending money on intangible things that I could damn well do myself, like “services.”

• Completely out of my depth in the ability to identify what would be a “wise” spend and what would be a “stupid” spend from amongst these services.

• Compulsively tempted to say, “Well if I’m going to spend on ‘services,’ hell, I’ll just hire a personal assistant and be done with it; may as well go the whole nine yards if I’m going to spend money.”

The first is of course incorrect and myopic.

The second is regrettable and I can only hope that sometime down the road, after a lifetime of work, I’ll be able to evaluate spending properly.

The third is an example of how I end up spending more than I can afford on luxuries that I don’t need because I quite simply lack economic intelligence at a visceral level.

— § —

Not sure why I post this. It’s embarrassing, and it’s also possibly myopic and oversharing.

But it’s true that it’s been a while since I posted, it’s true that there are times recently (like tonight) when I’m really struggling to make sense of a lot of things, and it’s also true that I don’t see people delving into these kinds of class-based tendencies very often.

People just act like smart people “spend smart” and dumb people “spend dumb.” Well I’ve got a high IQ and a Ph.D. and I struggle mightily not to “spend dumb,” and in fact don’t really know how to “spend smart,” even after years of trying to learn. It’s like I missed that day in class entirely.

Call it the anti-Tim-Ferriss secret: “How you can avoid spending $20 on an Ikea table by cutting down the one and only mature tree in your backyard, using all of your kids’ Elmer’s glue, all of the staples and thumbtacks in the house, and combining these with 50-100 hours of your time—to finish it all into an amateurish, low-quality piece of furniture that—amazingly—costs you ‘nothing.’ (And other money-saving secrets of the working class!)”