How to Measure Success Accurately

The Not Good Enough Measurement Problem

A common issue I encounter with my coaching clients is that they are actually doing well in life –  objectively speaking – but according to their own self-measurement they are failures.

This stems from childhood trauma and harmful parenting techniques. Sometimes even well-intentioned parents can do serious damage with how they teach their kids to self-measure.

While this happens in lots of different ways, the general problem is that kids are taught to measure themselves by comparing to unreasonable data points, namely other people who are doing better than them, or imagined better results that seem possible.

A friend of mine recently complained that her mother in law constantly makes comparisons with the other daughter in law, saying things like, “They just bought a new Tesla, why can’t you earn more money like they do?” I was shocked! I can’t believe people still say shit like this.

Childhood Conditioning

When you were younger, you might have found yourself constantly being compared to kids who are doing “better” than you by some arbitrary measurement, such as a sibling who learned how to read quicker than you did, or your friend who’s “always a good boy”. 

This means you were compared with someone who’s completely different to you in terms of life experience, genetic advantages, training and education, support and encouragement, and so on.

Not only that, you’re not taking in the whole picture of the other person, and instead just cherry-picking one small area of achievement, e.g. a kid might be a faster runner than you but doing worse academically, socially, and emotionally, but you only look at running.

Maybe you were constantly reminded that better results always seem possible, such as a client of mine who scored 99% on a spelling test and his father’s only response was “Where’s the other 1%?” It’s like no matter how well you did – even if you were better than all your competitors – the feedback was always, “You should have done better”. And even when you do the best that’s objectively possible, the feedback is just, “That’s what you should do every time”.

This gives you the impression that perfection is the baseline; anything less than the best is a failure. It also teaches you to measure yourself based on imagined results rather than what actually happened. Even breaking a world record can be undermined by imagining an even better result, despite no evidence it’s actually possible.

This system of using imaginary measurements also trains you into believing that you are somehow slacking off. If it’s possible for you to do better, but you don’t, then you assume somehow you must have sabotaged your effort and you didn’t try hard enough. If you measure yourself like this all the time, you’ll quickly form an identity of a person who’s lazy, ungrateful, and just generally a bad person.

Teachers are notorious for giving the feedback of, “He’s not living up to his potential”. It gives the impression that you are deliberately under-performing. You can imagine how confusing this is to a kid who feels he’s trying his best. And yet, you could give anyone this feedback and they’d never be able to challenge it – how’s anyone going to be sure they’re living up to their potential when you can always imagine more??

I’ve already done pieces of content on how to measure success and how to measure self confidence, so today I want to offer something a bit different: a mindset shift when it comes to making comparisons.

Measuring Success Accurately

Firstly, you must accept that if you want to measure by comparison to others, it’s only fair, reasonable and accurate that you compare with all available data points. 

If I was to say “I’m the best chess player in the world” because I only compared myself with a few chess amateurs who I beat in a game, you’d say that’s not an accurate measurement, and that I need to compare with more chess players. Fair enough. Well that means you can’t compare yourself to a few people “better” than you and then claim to be a failure! You must compare to all other players.

Further, you aren’t allowed to compare with imaginary data points if you wish to be accurate. You must measure upwards from measurable baselines, i.e. measure what you’ve done rather than what you can imagine doing. If “better” is always hypothetically possible, then it’s not tangible as a falsifiable fact, i.e. you can’t use it as a measurement reference.

I don’t measure my climb up Mt Everest by how far I have to go to get to the top, because it’s only imagined that I could reach the top. I measure how far I’ve climbed from the bottom, because that distance has actually happened. Your baseline must always be zero: the starting point of the activity; and your progress must only be a measurement of what you’ve actually done. It just makes sense!



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Practical Measurement System

So here’s an exercise to open your mind to more accurate self measurement:

Using whatever technology you have available, try to determine the entire spectrum of human achievement that’s actually happened regarding the activity you’re measuring, and then identify where you sit on that spectrum.

This will make more sense with some examples…

I used to think that my podcast wasn’t doing “well”. I measured that by saying I “only” had a few hundred listens on average per episode. I was comparing myself to higher-performing podcasts without looking at any “below” me, and I was imagining having more listeners. This is not an accurate measurement of how well my podcast is doing compared with others.

So I did my research. Turns out the average number of episodes for all podcasts ever launched is 14; I have over 200. According to the data, only a “slight fraction” of all podcasts make it that far. When I looked at all data that might measure success – number of plays, downloads, longevity – I came to the conclusion that I’m in the top 50th percentile at the very least.

I have a chess rating of 1000 ELO. The ratings go to 3000 and beyond, so it looks like I’m not doing well. But the average rating is about 600, so I’m doing better than most. And if you then include all the hundreds of millions of people who have never been rated because they don’t play chess – people I can be reasonably sure I’d beat in a game – then I’m technically one of the best players on earth!

I thought I wasn’t earning as much money as most of the people I knew, which is probably true. However, the average yearly salary for the whole world is estimated to be between $10K-$20K US. With that in mind, my “small” income is probably in the top 10th percentile globally.

Does this give you an idea of what accurate comparative measurement would look like?

If you’re going to compare yourself to others, then compare to all others. Make it accurate by including as much data as is available. Sometimes you can’t get all the information, but with some creative thinking and rational estimation, you should be able to make an informed guess about where you stand.

What you’ll notice right away is that even participating in an activity places you in a high ranking. If you run even a few hundred metres per week, you are running more than most people. If you have even one genuine friend or a partner, you’re more socially connected than most people. If you’re above the poverty line, you’re doing better financially than most people.

So use this measurement system frequently whenever your brain (or your parents etc.) start comparing you to others. Find out where you actually stand as a comparison with all humans.

And when your mind (or again, your parents) start making up imaginary reference points, like how well you “could have” done, stop and measure from the baseline. How far have you come? What have you actually done? How does this compare with zero?

I don’t measure my Brazilian Jiu Jitsu progress by how well I “could” be doing. I measure it by how many hours I’ve trained, how long I’m surviving in sparring, how many techniques I’ve learned to apply when rolling, and so on. My reference baseline measurement is “zero BJJ experience” – I measure upwards from there.

Measure how far you did run rather than how far you “should have” run. Measure how much you’ve learned at school rather than how much you “should know by now”. Measure how many answers you got correct on the spelling test rather than measuring answers you didn’t get.

Self-Abuse Doesn’t Help… Duh!

You might believe that unfair, negatively skewed, and impossible-to-please measurement systems are somehow helpful, like they motivate you or keep you accountable. This is total bullshit. They do the exact opposite. Your success is in spite of this abusive measurement system, not because of it!

Constantly measuring yourself as not good enough is like drinking poison.

You will actually perform better when you don’t burden yourself with the weight of never being good enough, never being satisfied, never feeling like you won, and always having the sense that you are a failure. It should be obvious to you – confident people perform better, and confidence comes from encouragement, optimism, and accuracy, not from abuse!

Make It Real

Lastly, make sure you actually write these measurements down on paper rather than trying to do them in your head. Your negative-conditioned mind will undermine them with “Yeah, but…” complaints if you just think about them. 

Write them down, and then when your mind complains and argues and tries to twist them into failures, calmly point to the data and ask your mind, “What part of this measurement is factually inaccurate? Where’s your proof that this is not a fair measurement of my actual standing in this activity?”

Keep doing this repeatedly for as long as it takes to sink in and replace your old measurement system. Be prepared for needing to do this manual override for many months before your brain changes.



Learn to build your confidence with integrity, contact Dan about coaching



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