The Wisdom and Freedom of Failure


It may feel odd to start a new year writing about one of the most dreaded F-words: Failure.

We’re still in celebration mode, welcoming a new beginning with renewed optimism.

Here is the thing. We’re wired with a bias towards the negative. For each loss, we need two successes to bring us back to neutral. So, we tend to avoid the pain of loss like the plague.

To move forward intentionally and truthfully—and not give ourselves the same load of superficial pep talk—we need to work with failure, not avoid it.

Let’s look at the deeper intimate feedback of failure, beyond the generic clichés—what doesn’t kill you makes you stronger, learn from your mistakes, it’s the journey that counts, at least you were brave enough to try.

I’ll share with you some of my failures as examples that I hope will be helpful to you.

Two types failure

We fail in one of two ways.

  1. Actions taken not producing the desired results
  2. Not taking action, or giving up on action

Let’s look at both in more detail.

The wisdom of disappointment

If we don’t get the expected results, we usually examine what we’ve done in order to do things differently in the future.

Let’s think about the failed experience from another angle.

Instead of asking what I did wrong, let’s ask why did I choose to do this?

Failure is disappointment. Disappointment is based on expectations. And expectations are based on motives.

  • Why did you choose to take this action?
  • What were you trying to achieve?
  • How would your life be different had you achieved your goal?

Sometimes what we want to achieve is shallow and ego driven. Trying to take a different action is unhelpful.

Instead, we need to examine our motivation for doing something in the first place.

  • Did we want a relationship to succeed out of desperation?
  • Did we want this job, or promotion, because we fear we don’t have enough money?
  • Did we want a certain result to look good when we share it on social media?

You might say: What’s wrong with doing something, even for the wrong reason, if it makes me happy?

It’s a fair question. I’ll answer with another known cliché: If you do something for the wrong reasons, you’ll never be happy.

Having a relationship based on insecurity will breed more insecurity. If you can’t manage your money based on what you have, you’ll always fear not having enough. If you do things to look good, you’ll always be looking for the next hit of approval.

Fear and approval based motivations might bring some temporary pleasure, but not long-lasting satisfaction.

Sometimes we fail because we do things for the wrong reasons.

Here is a personal example. Over the years, I complicated my finances out of fear and greed (the worst motives). I created many accounts thinking I’m proofing my money against loss. And I got greedy and started trading and taking shortcuts to generate more money. Both strategies were a complete failure.

The accounts were a drag on my time and energy. I needed to fill many forms and comply with more tax requirements—only to realize years later that it was all pointless. Having one, or fifty accounts, wouldn’t affect the amount covered by the investor protection fund. I acted out of fear and didn’t do my homework.

As for investing, I wrote about making irrational decisions, and achieving mediocre results here and here.

This year, I dealt with both issues after facing my motives. I canceled all the subscriptions and started a different approach. And as I write this, I’m in the last step of eliminating eight accounts.

Failure stings. But it also helps us heal (or at least face) deep emotional wounds—especially fear.

If you do something and you fail, look beneath the action and face your truth. Then move forward with a different action, or let go of the entire experience.

The freedom of unfulfilled desires

Another form of failure is associated with inaction. We fail to act on our goals and resolutions. Or, we start and give up. I’ll also include in this category doing less of something that you want to do more of.

We beat ourselves up over the things we didn’t do and wallow in regret and what could’ve been.

But we don’t think of the things we did in this free time. Good, or not so good, we got to experience something else.

I failed this year in accomplishing many things, including maintaining a consistent writing schedule. I felt uninspired, lacked discipline, procrastinated and struggled.

I kept nagging myself till I realized a personal truth: I didn’t write because something else was more important.

By not doing some actions, I created space for other things. I deepened my financial knowledge, and dealt with other failures. In the span of one year, I untangled the financial mess I created over the last ten years.

I also spent time doing things that might be considered unproductive or unimportant, like binge-watching shows and cleaning my home. But it was fun and I enjoyed the conversations with my family about the shared experiences. And a clean home always gives me peace.

Our priorities change as we change, and failing to do something is simply a reminder that it’s not the most important thing right now.

If you didn’t do something, look at what you did instead, and look at the motivations driving that behavior.

Beyond intentions and priorities

What if you had a good motive, but you didn’t work on your goal out of fear or overwhelm?

Most likely fear of failure is the biggest culprit. In this case you failed already by not taking action. What do you have to lose? Once you come to this realization, you can start again.

Overwhelm means you’re taking on too much, or you’re not clear about what you want. Clarify and simplify, then start.

Failure is not an adversary. And it’s not an identity either—we’re not our failures.

We don’t need to beat ourselves up or feel ashamed that we failed. Just like success provides valuable rewards (money, social connection, or personal satisfaction), failure reveals unhelpful motives, unrealistic expectations, and confused priorities.

I invite you to closely explore past failure. It’s an essential part of a well examined life.

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