Stop Feeling Like You Should Be Better With Money

When I begin working with a new client, almost inevitably, a moment will come where they express regret over financial mistakes they’ve made in the past. This regret most often manifests with the phrasing, “I should have…” or “I wish I would have…” As Albert Ellis famously said, “Stop ‘shoulding’ on yourself.” Everyone feels they should be better with money, including some of the most financially successful people you can imagine.

Here are a few popular financial “shoulds”:

  • I should have more money than I do at my age.
  • I should have avoided investing in that thing that didn’t pan out.
  • I should have put more into my 401(k).
  • I should have bought a more affordable car.
  • I should have paid off my credit cards by now.
  • I should have less debt.

The list could go on and on.

Warren Buffett Made Financial Mistakes

Warren Buffett is widely recognized as one of (if not the) preeminent investors alive today. Yet, he has admitted to making plenty of investment mistakes along the way – including his purchase of Berkshire Hathaway!

As it turns out, Buffett purchased the controlling interest of Berkshire Hathaway in anger after the firm’s management attempted to low-ball him when they offered to purchase his stock. Instead of renegotiating, he got pissed, bought a controlling interest in the company, and fired the management. It was an emotional reaction that, in his estimates, cost him $200 billion.

He should have made an unemotional decision, but he didn’t.

Buffett’s blunders aren’t limited to the faraway past. Indeed, he’s admitted making investment mistakes as recently as last year.

If the Oracle of Omaha can’t avoid making financial mistakes, why would you expect to do better?

You’re Not Good Enough

If you feel that you should be better with money, consider that your feelings may stem from a comparison between the real you and the ideal you. Where the ideal you may have shredded abs, the real you still needs to lose a few pounds. These kinds of comparisons can create feelings of stress and make us believe that a part of our lives isn’t living up to expectations.

Worse yet, you may be comparing the real you to an ideal someone else. Do you have a friend that always seems to be in fantastic shape and has their life completely together? Chances are, at best, you’re getting the highlight reel. At worst, you may only be seeing a façade. Social media is not our friend in this regard. Other people have different journeys and different challenges. It’s unfair to yourself to make those comparisons.

If there’s some way you feel like you should be better with money, stop and pay attention to those feelings. Notice what comparisons you’re making. Question them.

As we cling to our “shoulds”, we trust ourselves less and see ourselves in a more negative light.

What Do You Want?

This excellent article in Psychology Today describes how to confront the feelings of “should” by asking, “What do I want?” It’s a powerful mindset shift that allows you to see the differences between the fictional ideal you and the real you.

If you feel you’re failing in some way financially, ask yourself if you’re doing (or not doing) something you “should”. If so, where did you get these beliefs? What do you fear would happen if you stopped?

These questions can give you perspective about the areas that are creating stress in your financial life. After some reflection, you may realize that all the things you thought that you should be doing were never really your ideas in the first place. Quite often, many of our “shoulds” were inherited from our families and friends.

When you instead ask what you want, you may find that you’re able to let go of some of the areas in your life where you feel you should be better with money.

Stop Feeling Like You Should Be Better With Money

If you’d like help talking through any ways you feel you should be better with money, then click here to set up a quick, complimentary introduction call to see if Prana Wealth is a good fit. We do still have the capacity to take on new clients.

As a fee-only financial advisor in Atlanta, we can (and do) work virtually with clients all across the U.S. and we’re here to help you when you’re ready.


The information contained herein is intended to be used for educational purposes only and is not exhaustive. Diversification and/or any strategy that may be discussed does not guarantee against investment losses but are intended to help manage risk and return. If applicable, historical discussions and/or opinions are not predictive of future events. The content is presented in good faith and has been drawn from sources believed to be reliable. The content is not intended to be legal, tax or financial advice. Please consult a legal, tax or financial professional for information specific to your individual situation.
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