The perils of deferred happiness

Why we need to rethink how we look at milestones

Dear Rethinkers,

The Rethink newsletter is back this week - and it’s a very special edition (more below!).

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Photo by Jon Moore on Unsplash

Are you good at celebrating important milestones? I used to be terrible. I’d look back on the achievement for well, a nanosecond and then think “What’s next?” Hitting milestones has become a part of our “when, then” obsessed culture. “When I get to (x), then I’ll be happy/successful/content…”

A milestone has become a thing to cross off on a list – that you need to get through to feel that your business, health, and life at large are moving in the right direction. Milestones need a big rethink - from a constantly moving finishing line that we never really cross to a celebration to enjoy the progress we’re making right now.

More on the topic of milestones below, after a weekly Rethink Recap:

• I enjoyed reading this piece by

  Anne Helen Petersen
  author of the Culture Study on why the “workday dead zone is a fake problem.”

• What would you ban from youth sports to make them more enjoyable for kids? Parents? Leagues? This Revisionist History episode with Malcolm Gladwell made me rethink the crisis in girls’ sports.

• If you’d like to meet other people in the Rethink Community, please introduce yourself here. (I love reading your little intros by the way 😊)

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I’m relatively new to Substack but this, in fact, is the 100th edition of the Rethink with Rachel newsletter! Hoorah.

The Rethink community has been steadily growing over the past three years and recently reached 75,000 subscribers. But, although I am extremely grateful, I have to admit something: the satisfaction of reaching these milestones only lasted about an hour. Why?

The milestones trap

Milestones that are based on the belief that some external future achievement will drive lasting happiness are a trap. Getting [x] number of followers or subscribers. A quarterly increase in earnings by 20%. Growing to [x] number of employees. Hitting any kind of number.

Believe me, I’ve fallen into this trap many, many times.

Learning how to reframe meaningful milestones has helped me immensely professionally and personally. Let me share with you how this reframe could be useful to your workplace culture:

• Some milestones should play a similar role to physical landmarks – a monument, a signpost, a bridge, or a say towering oak tree. They help structure our representation of space. For example, how far do we need to get to achieve a goal?

• Other milestones should play a similar role to important yearly landmarks in our lives such as birthdays, anniversaries, or religious festivals. They help structure our perception of time.

• But the most meaningful milestones to motivate yourself and others are known as ‘temporal landmarks’. They help organize our lives into “chunks,” like episodes or even seasons. 

Reframing milestones in this way allow us to think through how we want to progress or what we want to change within stretches of time. Milestones become dividers, not endpoints.

T.S Elliot reportedly said that “Every moment is a fresh beginning.” However, research into temporal landmarks has shown that some moments are better than others for setting milestones. You want to pick significant points that in some way signal a break from the past and a sense of renewal moving forwards.

• The start of a season is a good one.

• The return from a holiday or break.

• The end of a project.

• The start of a school year (even if you’re not at school)

Research by Wharton professor Katy Milkman (and author of the fantastic book How to Change) has shown how temporal landmarks boost motivation because they create what is known as the ‘Fresh Start Effect.’

I often tie these milestone dividers to the start of a new season because the weather impacts how I think and work.  It looks a bit like this: “During the fall months (one of my favourite times of the year) I’m going to focus on X and re-ignite Y.” There is still a completion time, but the milestone is based on the during, not the after.  It’s bounded by a landmark and that can be as simple as the leaves changing colour and falling off the trees.

If people at work often say things like “I have no idea where last year went,” it can be a powerful sign that you need more temporal landmarks. Good milestones help people to know where they are, not just where they’re heading. They help commit you and your team to a shared journey, not just an end goal.

The ‘before and after’ trap we fall into

Workplaces (and society at large) glamorizes the ‘before and after’ milestone. But it’s based on a broken assumption – the perils of deferred happiness.

We’ll get this done and then we’ll do this. I’ll wait for this to happen and then I can focus on this. And then, and then, and then…

If you think in this way, it can feel for yourself or others that milestones are a set of tasks to get through or to cross off. You never really arrive.

A sign you’re falling into this trap:

If you reach an important milestone and after a few moments, you start to wonder, “Hmm…maybe now I can hit a bigger, better, or more shiny milestone.”  Catch yourself! 

Question: What milestone have you enjoyed celebrating? Any that you’ve struggled to recognize?

If you enjoyed this piece, I think you’ll like this newsletter on ‘The power of thinking like Shakespeare.’

Warmly,