Setting personal goals for 2021 was tricky: should I set the bar low to guarantee some success, or go big and ambitious and risk failure? What would the government do?

The bigger question

In my previous two posts, I described how I track my habits and how I keep habits small to keep them achievable.

What I’m now trying to fathom is how to tie the systems of doing little achievable things to longer term goals.

After all, those little achievable things are not ambitious by design – they’re designed to allow consistency while fitting around whatever life might throw at me.

But I’ve heard a lot about organisations setting “stretch goals”. What are they and how do they relate to actual daily practice and systems of work? Does the same logic apply to personal goals?

What are stretch goals?

I read a Harvard Business Review article on the “stretch paradox” recently which both defined stretch goals and described a problem with the way organisations use them:

We’re not talking about merely challenging goals. We’re talking about management moon shots—goals that appear unattainable given current practices, skills, and knowledge.

The language of “moonshots” has been in the news in the UK recently – the UK government even called its same day mass Covid-19 testing programme “Operation Moonshot”.

It’s a neat name – the “shot” part is a play on the word “jab” or “injection”, and it wouldn’t surprise me at all, given Boris Johnson’s colourful/controversial use of language, if the “moon” part was an allusion to something else.

But the word also tells us something about stretch goals.


There are two features which make stretch goals different from more earthbound or paperplane goals:

  • Extreme difficulty
  • Extreme novelty

The Apollo programme which actually landed men on the moon was a stretch goal that succeeded – extremely difficult and novel. The resources, both material and mental, required to make it happen are lovingly depicted in Damien Chazelle’s 2018 film First Man.

The UK Government’s Operation Moonshot had both these features too – a target of 10 million tests a day (a sixth of the entire UK population), realised through novel testing technology called Transcriptase Loop Amplification (LAMP). But it famously failed – the project was quietly subsumed into Dido Harding’s NHS Test and Trace programme.

Stretch goals have led to great success in some areas – so much so, in fact, that it’s still tempting for organisations to simply conclude that one only need adopt them in order to succeed. The failures tend not to be recounted so much.

Past performance, current conditions

The article I read states that problem with setting stretch goals is often down to a lack of self-awareness:

[…] stretch goals are not only widely misunderstood but widely misused. Organizations that would most benefit from them seldom employ them, and organizations for which stretch goals are probably not a good strategy often turn to them in a desperate attempt to generate breakthroughs. Neither approach is likely to be successful. This is what we call “the stretch goal paradox.”

The article then outlines a way to approach whether or not you should use stretch goals:

  • Are you successful or unsuccessful?
    1. If successful, do you have uncommitted resources available?
    2. If unsuccessful, do you have uncommitted resources available?

It’s only if you can get to and answer yes to question 1 that you should pursue stretch goals.

A quick check

Based on the article, here’s what the logic looks like when you lay it out on the table:

  Resources to spare All resources committed
Recent success Thriving but complacent – You are the perfect candidate for stretch goals. Confident but constrained – Your constrained resources mean stretch goals are unlikely to work for you; pursue a strategy of incremental success, or “small wins”, instead.
No recent successes Discouraged but capable – Skip stretch goals and aim for “small losses”, running modest, mildly risky experiments. Most will fail but you’ll learn from them, and the few that work will lay the groundwork for future success. Failing but grasping – Resist the urge to go for broke. Pursue “small wins” until you dig yourself out.

Should I set personal stretch goals?

The table above is interesting for me in thinking about my team and also thinking about the organisation in which I work and the goals set there.

But what does it mean for my own goals?

When it comes to “resources”, I have to think of my time and my energy. Circumstances matter.

If you’re currently furloughed, are sleeping well, and feel you’ve already achieved a lot in lockdown, then setting a stretch goal is probably for you.

Many people in the UK have worked longer hours during lockdown and I think I might be one of them – so I’m probably more in that top-right quadrant. But even if I’m in the bottom right, the strategy the Harvard Business Review proposes is the same: pursue small wins.

This is a good key insight:

Bear in mind that although they’re very useful, small wins are not an automatic gateway to a predetermined stretch goal. By its very nature, a stretch goal requires novel approaches. Because the path to it is uncertain, organizations cannot map out a series of simple, intermediate milestones.

Surely, there’s got to be a way to still aim for those big ambitious achievements?

I’ll keep pondering – my main personal goal this quarter is to put in place a good system for good habits. According to the logic of that article, if I’m to embrace stretch goals, I need to keep accruing those small wins (like publishing this blog post) so that I feel I’ve had recent success at the point where I also find I have some time and energy to spare.