Why You’ll Never Achieve Your Goals — The Progress Paradox

Why You’ll Never Achieve Your Goals — The Progress Paradox

As an executive coach, this^ is the most common cognitive bias I find in the founders/CEOs I coach.

The deep-rooted belief that progress should be linear.

If I keep working hard, my results should keep increasing

Lol. If only…

But the linear progress fallacy is at the heart of so much frustration and failure.

And it’s something we pick up very early on in life, reinforced by society’s artificial “tick-box” systems:

Education: follow these steps to get right answer. Get 90 right answers for an A. Get this many As and go to university…

Corporate careers: do this repetitive task 40 hours a week for 12 months for positive appraisal. Get three positive appraisals and you’ll get promoted. Suck enough corporate d*ck and eventually you’ll make partner….

These artificial tick-box systems create the illusion that life follows a neat linear progression.

Tick ✅

Tick ✅

Tick ✅

Result 🐶

But as soon as you step outside these artificial systems, into what I like to call “real life”, the tickboxes suddenly disappear.

And progress stops looking so linear:

Yes, that’s right — it doesn’t just go up…

But (counter-intuitively) you are still making progress even when your results are decreasing 👀

Switching your progress expectations, from linear to non-linear is the key to making progress in difficult real-life challenges.


To make consistent long-term progress, you have to consistently do new things.

Play the same piano piece 1,000 times and you’ll plateau fast.

But play new pieces, improvise existing songs, switch between scales & rhythms, you’ll 10x your long-term progress.

But in the short term, your results will (ironically) decrease.

When I first learned how the foot pedal works in piano (the thing that adds reverbs to songs and makes it flow), my piano play crashed hard.

It was horrible.

Whereas before I’d just concentrated on playing with my hands, now I was trying to sync up my hand movements with my right foot.

Songs I previously found easy became almost impossible to play.

I immediately wanted to give up and go back to 2 hands, no feet.

By my piano coach (Olivier Ruthersfield IV) told me it’s normal.

The new knowledge of how to use the foot pedal was just interfering with my brain’s old knowledge of playing without. I needed some time for my brain to integrate the old and new.

And lo and behold, after a few days’ suffering through Einaudi à la Tarzan, my brain had worked it out, and “two hands, one pedal” became effortless.

The same for all learning.

When I learned Spanish, I was getting by just fine conversationally.

Then I stumbled across the “subjunctive tense” on YouTube; a bizarre quirk of the Spanish language I had completely ignored up till then.

When I finally started using the subjunctive in conversation, guess what? It interfered with my existing Spanish: I had to start consciously thinking about my grammar, doubting whether or not this was the right time to use the mysterious subjuntivo.

Previously fluid conversations became stuttery and awkward; but as always, after riding out the progress curve, I reached a new peak in my Spanish learning journey and finally understood why people kept telling me to “tengas” a good day. (Instead of “tienes”)

Art is no different: I’ve frequently had to rip up 80-hour portraits because an eye was 2mm off, go back to zero, but then redraw to a much more beautiful final product.

But the lesson of non-linear up-down progress extrapolates to almost all walks of life.

Entrepreneurship is wildly non-linear.

My first company won every award at the Young Enterprise finals when I was 16. But then shut down because the team wanted to focus on their A Levels.

After a few more up-downs, I co-founded a startup at university, and scaled it to 100k signups + lots of money.

But then had to leave after growing increasingly disillusioned with the company’s mission to help middle-class students do slightly better in zero-sum exams (not to mention my co-founder’s increasingly delusional/deceptive belief in the product’s efficacy)

It took me months of clueless bumming around before I found my calling as a startup coach and my new (current) mission to build a globally campused Netflix-style university.

But now, even on my current mission, it’s still a constant up and down.

Things were going great until launch, then our conversion rate came out 6x lower than we’d tested for.

Devastating. But after a small pivot, we were back on track for an easy six-figure first-year ARR…

Until I woke up in the middle of the night with a crazy idea that would 10x even the best-case scenario from our previous business model.

It was too good to ignore and so we had to discard our progress, say bye to our cushy six-figure passive income stream, and ruthlessly focus on the exciting but windy new road ahead of us.

And finally, the most polynomial of all progress curves: relationships.

In an instant, you can go from happily married to “my husband cheated on me with my cousin.”

But if you can endure the pain, keep searching and developing your own self-awareness, there are always brighter opportunities round the corner. (Is what I keep telling myself at night…)

When I broke up my with wonderful ex-girlfriend, it was devastating.

I spent months ruing the decision and made several quixotic/pathetic attempts to get back with her.

But ultimately, I came out of it much happier.

It forced me to learn how to be happy, on my own — without relying on partners, validation or material objects; how to make new friends in new countries when you don’t know a single soul; and how to be myself where there are no tick-boxes to complete or hierarchies to climb.


Whatever you’re working towards, accept your progress will not be linear.

When things go “wrong” for me at work or life, I no longer get mad, or depressed, or throw a tantrum.

I laugh. It’s just part of the game; if it was only ever up, I’d get bored and stop playing.

Expect the ups and downs, ride out the progress curve, and enjoy the rollercoaster ✌️❤️

PS: I’ve now had quite a lot of requests for exec coaching but no capacity to take on new clients until (at least) June. If you’re interested, please register your interest here and I’ll get in touch when new slots open up!

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