Small Wins Are Offset by Tiny Losses

Self-awareness helps too.

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We humans have limited reserves of self-respect. We build them laboriously by collecting successes, small wins throughout our lives. The reason for that is simple — confidence. The more successes we accrue, the more confidence we have.

But this process doesn’t seem to work that well; according to some statistics, up to 85% of the world's population is affected by low self-esteem.

That’s because there’s more to confidence than collecting small wins (despite what all the self-help articles might tell you).

The other day I was reading about in . Here’s how the author, Nassim Nicholas Taleb, applies the concept to his life:

Instead of adding something positive, Taleb subtracts the negative. By doing so, he improves his (mental) health.

What if the same principle applies to confidence? What if you need not collect small wins as much as you need to avoid tiny losses?

If that sounds plausible to you, read on.

So, what are tiny losses? Here are three examples.

  1. You know you hate being forced to tell even the tiniest of white lies. Yet you habitually tell them to make the other person feel at ease or to avoid an uncomfortable situation.
  2. You know you’re against excessive drinking of alcohol, but you still frequently succumb to the peer pressure of the situation and have “just one more”.
  3. You know you hate it when you don’t finish what you planned for the day. Your to-do is filled, but you procrastinate on [insert your vice here].

The problem isn’t in lying, losing control, or procrastinating , but in how we approach them: we usually wave them off as inconsequential. And if, somehow, they register on our radar as a problem; we rationalize them away — what’s one white lie, one more beer with friends, and a bit of procrastinating? Besides, everyone thinks and acts that way, right?

Maybe, but here’s the thing: Each time we do something that makes us hate ourselves just a bit afterward, our confidence suffers. Each time we let someone else talk us into stuff we rather wouldn’t do, our confidence suffers. Each time we said we would do something (small) but didn’t, our confidence suffers.

But wait, here’s the most screwed-up part:

If the loss was great, we’d address it. But if the loss is too small, we don’t react. Instead, we adapt to slowly decaying conditions. We collect tiny losses until we’re screwed. Jacking up the heat abruptly makes the frog jump from the pot. But increase the heat gradually and you’ll end up with a cooked frog.

We are the frog.

The goal of this piece is two-fold:

  1. Making you notice the tiny annoyances and how they affect you;
  2. And making you jump out of the boiling pot before you end up cooked.

Hopefully, I’ve accomplished #1. Now, let’s get into the #2, shall we?

Self-Awareness Cultivation & Progressive Sensitization

You remember we talked about us being desensitized to these small losses.

The first step, then, is that you cultivate self-awareness.

But self-awareness, on its own, is useless. It’s a vague, new-agey word that really says nothing. So, let’s refine it: what doyou need to be self-aware of? Easy. Stuff that makes you lose self-respect.

That’s narrower, but we can do better.

Think about the examples I listed above. White lies, procrastination, peer pressure. Any of them trouble you?

What about your diet? Do you eat stuff you know is bad for you? What about other lifestyle choices, such as sleep? What you’re looking for is a mismatch between your purported values and your actions.

For example, I just stuffed my face full of delicious cookies, sumptuous peanut butter, and downed it with a freshly brewed espresso. With sensory experience, you can’t do much better (I’ll argue with you on that). But while I relish the dopamine high induced by the concoction of sugar, fat, and caffeine, I know I’ll regret it in half an hour when the sluggishness hits.

I value good nutrition and hold my willpower in high-esteem (in an above-average kind of way, of course). So, I accrued a tiny loss of self-respect.

These are the situations you look for. Every day occurrences that you’d brush off —they don’t happen that often and the consequences are minimal.

As I notice the onset of sluggishness, the tiny voice in my head that loves to question my life choices springs to life: y

Good thing: the voice is there, which means I have some sort of feedback. Bad thing: the voice is whiny and annoying — I can easily justify ignoring it. It’s also too .

But if you’re going to cultivate self-awareness and want to assess the core issue, the challenge is to stay . You need to go one step further.

Here’s where a study by Gregory Hixon and William Swann comes in.

In it, they gave undergraduates negative feedback on a test of “sociability, likability, and interestingness”. Upon receiving the feedback, the students were assigned to two groups. The first group was given time to think about they were the person they were. The second group got asked about kind of person they were.

The results? The “why” group focused on rationalizing and denying the results. The “what” group focused on what they might glean from the new information.

is the droning voice of your negative self? gives you the necessary distance to assess the situation properly. And while both help you become self-aware, the former often leads to depression and anxiety.

is subjective. is objective.

How to put the knowledge to work? Try the following:

  1. Identify what exactly it is that you want to be self-aware of. Start tiny (more on habits later) and focus on one thing for a week.
  2. To do that, ask yourself “what” instead of “why” questions. These help to elicit a more accurate, objective assessment of yourself.

Moving on.

No More Tiny Losses. Here’s How You Build a Lasting Change.

Self-awareness is a solid short term solution. But to achieve lasting change, you must build habits.

In what follows, I’ll use James Clear’s framework. Within this framework, a habit consists of four things. Cue, Craving, Response, and Reward.

Cue is any situation or an event. In this scenario, it might be something someone has said (external) or your reaction to it (internal). Cue makes you Crave a certain Response. And Response delivers a Reward.

Back to the cookie example.

  1. Cue: Queasy feeling of broken willpower after I stuffed my face with cookies, PB & coffee.
  2. Craving: the need to get rid of the feeling.
  3. Response: Self-serving interpretation: “I did 10 push-ups today already, ergo I deserve this goodness.”
  4. Reward: Feeling better about myself.

5. Actual Reward: Tiny loss of confidence.

To address the “actual reward”, Clear recommends four simple principles.

Cue: Make the cue disappear.

Craving: Make the behavior undesirable

Response: Make the behavior difficult to do.

Reward: Make the behavior dissatisfying.


Addressing cue is often the most effective and simple of all the tools you can use — you remove it. If I didn’t have any cookies at home, I wouldn’t have gorged on them. Peanut butter and coffee alone I can handle, but cookies are the culprit that makes the combination just too good to pass up. Similarly, if you can remove whatever nibbles away at your confidence, you’ve won.

The goal for you: Can you identify something that you can remove?

Though, you often can’t remove the cue or it’d be impractical to do so. Which brings us to…


With craving, Clear recommends making the behavior undesirable. I can’t see that happening anytime cook with my cookie-PB-coffee combo of awesomeness. I’ll crave that no matter what (the same way I’ll always crave sex, communion, or any other of the basic needs people have).

But let’s look at the white lie example again. To reduce craving, you can use reframing. Instead of a desirable way of getting out of an uncomfortable situation, you can see white lies as dishonest treatment of someone else.

But what if making the behavior undesirable doesn’t cut it, and it’s still way too enticing?


For the Response, Clear suggests making the behavior hard to do. Were I to be stupid enough to buy cookies again, I could put them somewhere I can’t get to them so easily. I could ask my partner* to hide them for an even stronger effect.

Similarly, telling white lies is an easy behavior. It doesn’t take much energy — it’s nearly automatic, and it doesn’t involve any physical strain. Introducing difficulty here can take the form of payment, for example. The same way there are swear jars, you could introduce a white lie jar (or I could introduce a cookie jar, mmmmm). If you’re into sports, you can make yourself do push-ups or pull-ups each time you tell a white lie. The consequence will make you think twice. For this to work, you can also implement an accountability contract.

that option is, sadly, unavailable to me: were I to give the cookies to my girlfriend, I’d never see them again.


As for the Reward, Clear suggests making the behavior unsatisfying. Pointless with the cookie example, but let’s stick with white lies again: the “phew” of relief needs to change into a “phew” of dissatisfaction. Through self-exploration, this might occur on its own. At one point, as your values slowly shift, you won’t perceive the outcome as rewarding as it was before.

How to put the knowledge to work? Try the following:

Identify what cues elicit unwanted behavior. If you can’t avoid the cue, focus on increasing friction in the following stages: Make the behavior undesirable, the response hard to do, and the reward unsatisfactory.

All You Need to Know

It’s not just ‘collect small wins & win big eventually’ that helps you gain confidence. It’s also avoiding all the tiny losses — Via Negativa.

To do that, you must first become self-aware. You must identify what poses trouble and focus on that. Start tiny to avoid overwhelm. Use “what” questions to maintain objectivity.

Once you’re aware, you can start building habits. Use Clear’s framework and get rid of the root cause of the confidence loss. Remember: Cue, Craving, Response, and Reward. Apply pressure where needed.

Maybe what you need isn’t a bunch of small wins, but avoiding a bunch of tiny losses.

Your confidence will thank you.

Notes:*take it with a grain of salt, as it's not an actual study. That said, I still think the number is quite high.

On a journey to make my writing suck less.

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