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Why Everyone is Obsessed with Milestones (and Achievements)?

Do you catch yourself recalling: “A year ago today” or “It has been 10 years since...”.

You are not alone. In fact, most people mark a significant event that has occurred in their life in a special way to them; and those who have been involved in project management will be more than familiar with the term ‘milestone’ in their career.

Whilst the generic term ‘milestone’ was once a specific measuring tool in Roman times, marking the defined distance of a mile with cast iron ‘mileposts’ the term we use today is used to measure progress and a sense of achievement as well as for a negative event that we have endured.

So why do people obsess over milestones that have passed which may or may not be related to a person’s achievements?

In December 2019, The Office for National Statistics “revealed that the typical milestones experienced by young people were happening later than they used to - and sometimes in a different order. Is the same true for the significant moments that happen later in life?”

It is clear to see, in sociological terms, the expectations of a, may I say, ‘older’ generation are not being met by younger ones as they might not necessarily adhere to the more traditional route of: finishing school, going to college or university, meeting a partner, introducing him or her to their parents, moving in with them, getting married, having a baby, maybe getting a dog, having another child.

The traditional route has been upturned, shaken around and possibly discarded, for any order to be followed as and when the individual feels comfortable enough and ‘ready’ to do what might make them happy.

Life is a journey and we, as humans, naturally set ourselves targets and objectives to aim for. A sense of achievement will motivate and encourage, the constancy (moving forward and) progression creating new milestones.

Developmental milestones in a child’s early years are significant and any parent in the UK will be familiar with their child’s ‘Red Book’ in which all the ‘stats’ are logged: a medical record including: vaccinations received, height, weight, even the order of teeth appearing. I bet most parents with older children will still have their child’s Red Book tucked away safely somewhere.

What milestones are significant to you? How do you record them?

First Kiss

For most people, their first kiss is a memorable event. Whether it was a positive or negative experience, I bet you remember the name of the person you first kissed, how old you were and where it took place.

First boyfriend / girlfriend

Did you play it down and try to convince your parents that you ‘were just friends’ so there was less pressure felt in the hope they ‘passed the parental test’ (or, more likely, that you felt your parents didn’t put you new ‘special friend’ off?)

Leaving home

I left home for boarding school at the age of 10 and although I returned home three times a year, the fact that I travelled across the world on an aeroplane without an adult, it made me independent at a very early age. I felt a little sorry (and perplexed, if I’m honest) for the 18 year olds around me at university who felt so homesick they couldn’t enjoy themselves fully.

Moving in with someone

An important event in anyone’s life, one which could ‘make or break’ their relationship. Ground rules on the toilet seat, toothpaste trails and spoonfuls of milk left in the carton are all great discussion points to evaluate how successful cohabiting might be...

Getting married / divorced

I recall congratulating someone on their marriage and they thanked me with sincerity but corrected me because their ‘new’ surname was as a result of their divorce! I was young and naïve and have never again presumed a change of name means anything!


“It would have been 10 years today that we would have been together.” Negative memories to some, but milestone for others so they can celebrate how far they have come and how much they have learnt and developed since their loss.

First payslip

It didn’t last long, did it? I started my career before the minimum wage was introduced but it was still some feat to spend my weekly wage in one pub outing! I had to get a second job to buy my food!

Milestone birthdays and anniversaries

Sweet 16, Legal 18, Adult 21, 30, 40, 50 and so on. Celebrating my loved ones’ birthdays has always been important to me – and I always try to make a fuss on their special day. What I can say is that the older I have got, the more low key the celebrations have been. Where I hosted a small dinner party for friends on my 18th, I chose to spend my 40th at LEGOLAND.

Achieving something on your bucket list

I truly believe you should never give up hope on achieving your dream and seeking out the opportunity to do so. I was told I would never play competitive sport again when I was at school due to injury. My stubbornness and determination gave me the strength to disbelieve the consultants and I went on to represent England in sport. A dream that I had had since I could run and one which I will never forget!

Read my story about coming back from injury to play for England here:

Starting a business

I am sure any business owner will remember the day they became their own boss. Whilst the responsibility is huge and the work is literally never ending, the day you could decide your own fate will always be a turning point. I had a conversation with someone this week about going back to employed work after owning your own business and we agreed that it could present challenges for many reasons.

Getting that promotion!

Having worked so hard for the same company and team for however long and having had your eye on climbing the career ladder to achieve your ambitions and goals, a promotion gives you a sense of worth and belonging. Not only is it financially rewarding, the recognition of your hard work is almost enough.

Buying your first car

A little bit like your first girlfriend or boyfriend, you will remember their name, what their personality was like and how much freedom they gave you(?!). I lived in cities until I met ‘my other half’ in my mid-20s and he had a car. I can’t deny it felt much better not having to lug bags of cat litter and food shopping every week on the tube by myself.


A really special day for everyone and almost as exciting for parents who may not feel quite as financially responsible for their children as the newly qualified professional that can spend their money in any way they choose (until they realise it’s much harder to earn than spend!)

Having a child or grandchild

The patter of tiny feet is a great milestone for anybody and expecting to welcome a new family member into the clan brings joy, if not a little apprehension, for many. Our recollections of pregnancy, childbirth itself and the immediate moments after it bring some of the clearest and memorable keepsakes that any parent (or grandparent) have the privilege of holding.

Receiving medical treatment or operation

Anyone that has waited for lifesaving treatment that has transformed their lives will know the feeling of the days, and even months, leading up to it. Not only a sense of hope, but a relief, a cautious anxiety and perhaps even guilt might make the person evaluate why they are deserving of the chance ahead of them.

Being cured

The moment the consultant says that a person is in remission of a disease such as cancer will be imprinted in the person’s mind, with the chains that have held them for so long being released with one simple sentence. That day will never become insignificant and every day thereafter is likely to be led to the full, as the fragility of life is all too real.

Raising £X for a charity

A target, with a sense of challenge set, to raise money for a cause close to someone’s heart and succeeding and exceeding expectations will be a cause to celebrate. The total amount raised will always be referred to, as the target to beat the next time round.

Saving £X for a deposit

Spending money is easy, earning money is hard and saving money is even harder. When the money for a deposit for a house or car has been gathered and saved, it makes the purchase so much more special. Buying something, especially something with money that you have earned yourself makes the purchase that more special!

Running # miles in a day

Anyone aiming for a certain fitness level or ideal weight might fixate on covering a certain distance to cover each day so their target can be realistically increased and their overall objective completed. Even apps and gadgets can now help record these milestones.


We can see milestones being both positive or negative.

Milestones and achievements can be logged and saved by memory or writing about them, maybe through journaling, creates a record of them that will often highlight the feelings those milestones bring.

We can even record our Milestones and Achievements under Life Events in Facebook so our network on social media can keep up too.

By recording milestones in a safe place like a scrapbook or memory box, they can be reviewed at a later date. A legacy is left for future readers, handed down through generations, with accuracy as the emotions felt through each milestone is brought back to life.

Whilst subjective, a milestone is significant to an individual to move forward and understanding motivation behind milestones is key.

Do we plan for milestones or do they occur through the achievements and failures that we experience during our life’s journey?

Milestones are important. They form experiences which make up part of our journey in life.

  • They push us forward, even at times in which we struggle. Achievements are rewards in themselves and offer us the motivation to progress.

  • They are important to look back on; to feel a sense of growth when they are not positive.

To recognise the progress from a certain point is healing and should be the biggest sense of achievement felt.

Whilst I use milestones as a sense of achievement as well as direction to progress and develop, I am often found recalling dates to reminisce and celebrate how far I have travelled until this point of my journey.

I celebrate another milestone myself this month.

Happy Birthday to AKA Virtual Assistant who turns 1 on 10th February 2021.


The Office for National Statistics


Is working with AKA Virtual Assistant going to become a milestone for you?

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