Knowing You Can't Spend Money Yourself

Recently, I hit a milestone in my journey to overcome what I like to call “the disease of not having money.” I spent $160 an hour on private lessons for my two children. In the past, I would not have paid such a price. I've always been the type to teach them things myself, like swimming and cycling.

But after seeing how much my kids enjoyed their group parkour lessons, I decided that this is one of the best ways to accumulate wealth. Nothing makes me happier than seeing my children happy—nothing. Also, group lessons are hard to find on weekends and I don't have the equipment.

After the private lesson, I didn't feel much of the usual pain of “losing” $160. I know they won't be college athletes with scholarships, let alone go pro, but the joy they got was worth it. Still, I couldn't help but think that fresh crab and lobster can be bought for $160—at least three pounds!

Despite this small victory in spending more money, I realized that I couldn't spend the money me. And this is where the struggle continues.

Inability to Spend Money on Me

I have long believed that pain and discipline are necessary to achieve your goals. Being handed things on a silver platter often inhibits growth.

Embracing a “broken mind” can make you rich, and feeling hungry—both literally and figuratively—keeps you going. Whether it's maintaining your weight by remembering those less fortunate or grinding away to escape a bad job, sacrifice is necessary.

So when it comes to spending money for me, it feels like a betrayal of the sacrifices I've made to achieve financial freedom since 1999. I've been saving and investing for so long that I don't buy things. the need he feels completely shut out.

Let me make an example.

New jacket with zip pockets

I wear the same kind of clothes every day—pants, sneakers, a t-shirt, and a gym jacket with zippered pockets. Basically sports wear. Since I no longer go to the office or meet with clients, convenience is king.

However, now that I attend my children's school functions and birthday parties almost every week, I have started to notice something: stains on my clothes accumulate, even after I have washed them. I don't want to look boring in front of my peers, at least not to embarrass my children.

Earlier this year, instead of buying a new jacket for $110, I took my four-year-old to a tailor to have the zipper repaired for $25. Saving $90 sounded great! But after five months, the jacket faded, and I wanted to buy a new one.

Hoping to be sold, I went to Nike's website and found the same thing. But when I saw that there was no discount, I didn't pull the trigger.

Tennis shoes with holes

While on site, I also noticed my tennis/pickleball shoes did not improve, but two holes in the front soles! These shoes were only three months old and were given to me by a pickle friend who ordered the wrong size.

I usually spend $140–$160 on tennis shoes that last about six months. So while I was shopping for a jacket, I started browsing for new shoes. But when I was about to leave, I stopped.

Although I had just spent $160 on private lessons for my children, I couldn't spend $110 on a jacket or $160 on new shoes. me. What's going on?

The Solution to Spend More on Yourself

After two weeks of not buying a jacket, I decided enough was enough. My anxiety disorder had once again started to take its toll on my health and happiness.

But instead of buying it for myself, I asked my wife to buy it for me! This way, I could avoid the guilt of buying something I didn't really need. Sure, I wanted to look good at school events, but I didn't the need a new jacket.

That's the solution: If you are struggling to spend money on yourself, ask your significant other or a close friend to do it for you. Having a gatekeeper adds a layer of accountability, and you avoid the personal pain of spending money.

You've already tricked yourself into viewing the investment as an expense in order to justify investing more. Now, get yourself out of the spending routine completely!

That said, I still I couldn't afford new tennis shoes. Why? Because I have a pair of vintage Agassi tennis shoes sitting in my closet. They are new, but I see them as a collection and I can't wear them.

Things You Can Say to Get the Most Out of It

For those who have been saving for decades, changing spending habits can seem impossible. The opportunity cost of not including that money can be huge. Or you can just convince yourself that you don't need it.

But if you have money and are already providing for your loved ones, you should be able to indulge yourself from time to time. Here are a few things you can say that help you feel better about spending money:

1. I am successfully supporting my family – If you put your family first, you should feel free to enjoy what is left for you. Supporting your family is like paying yourself first. The rest should be innocent.
2. I work hard to earn my money – If you put in long hours, you deserve to treat yourself. What's the point of working hard if you never enjoy the fruits of your labor?
3. I have worked for a long time for my money – In your 20s and 30s, saving is wise if you are building an income. But once you've worked for 20 years, continuing to cut corners may not be healthy.
4. I will die with more money if I don't spend more – If you die with a lot of money, it means that you have not fully enjoyed the wealth you have built. You will be wasting your healthiest years for little reward.
5. I only buy things I really value – If you spend money on things that really improve your quality of life, that spending is worth it. Stop thinking that any money you spend goes to zero—it doesn't. Instead, you'll get a big return in the form of improved well-being and happiness.
6. I donate money to help others – If you donate money regularly, you are a thoughtful person. And thinking people deserve to be rewarded once in a while.
7. I actively track my finances – If you know where your money goes every day, you will see that the spending you do is within your control. There's no need to feel guilty about spending money on something that won't have a negative impact on your financial situation.
8. I save and invest religiously – If you save more than the average savings rate of ~5% and invest more of your money, you are already doing much better than the average person. It's okay to live a little and enjoy the fruits of your discipline!

Still Not Spending Money on New Shoes

Even after telling myself it's okay to use, I still haven't bought new tennis shoes. Instead, I make do with what I have, using minimalism as a way to reduce. Retirement and simplicity go hand in hand, and having fewer things brings me more peace.

For now, I'm content to enjoy my new spotless running jacket, which cost me $110. If my new investment in Nike stock grows 10 times the cost of a new pair of shoes—$1,600—then I'll probably use the profits to finally buy them. This is my 10X Rule of Use: I only spend on unnecessary things if the corresponding investment grows 10 times its cost.

But there is another challenge that may be the cause of my reluctance to spend my money. After buying a new house in 2023 that we didn't need, I already feel enough financial guilt to not get another thing I don't need. It took a lot to convince my wife to move. Furthermore, it is too early to say whether the move was the right decision.

As a result, I am more careful about how I spend money. While I know spending $160 on new shoes won't break the bank, it doesn't have to. I am focused on achieving financial independence by December 31, 2029, and nothing will distract me from that goal.

Student Questions and Suggestions

Do you have a hard time spending money on yourself but have no problem spending on your children or loved ones? Why do you think that is? What strategies have you used to free up your spending?

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