Why is Age 27 the Critical Point in Our Lives?

5 years after graduation is the year you are young enough to take big risks while old enough to have the life experience to make critical decisions for your future life.

9 min readMar 26, 2023

👋🏻 Dear stranger, Harris here. Born and raised in Hong Kong and now based in London. Co-founder of Jupitrr, an AI Video Maker that creates B-roll 10x faster for content creators!

27 is such a weird age. It’s like the middle child.

Everyone talks about being a fresh graduate or being a parent, but nobody EVER talks about what happens 5 years after we graduate, as if we have all figured out what we want in our lives already. Unfortunately, that’s something far from the truth.

In this blog, I am going to share with you the truth nobody taught you about being a young adult at 27, and what methods I used to deal with it.

27 is the age when we have already started something for 5 years. Even though some of us are comfortable with what’s on our plate, most of us are unsure whether it’s something we want for the rest of our lives.

It’s not just the career that I’m talking about, it’s also about our own value set, our habits, which country we live in, and maybe even our life partner. At age 27, we start to set the tone for the life we’re living in the coming 60 years.

Of course, I do believe changes are, and should be made at any age of our lives, but I’ll say 27 is the sweet spot we should make important decisions.

27 is when we started to drift apart (「人生分水嶺」)

In Chinese, there is a term called 「人生分水嶺」 (literal translation: ‘the watershed of our lives’). I try not to make a ‘proper translation’ here, let’s keep it authentic.

Watershed is a land area that channels rainfall to streams and rivers, and eventually to outflow points such as reservoirs, bays, and the ocean.

Stage 1 — Rainfall: When we were a kid, we were like raindrops that arrive in the big pool. We all started studying somewhat of the same subjects. In college, we studied different majors. But still, we all are in the same stream in the river, flowing ahead in the same direction. We faced mid-terms and finals and aimed for a good GPA.

Stage 2 — Streamflow: When we graduate and got our first job, every decision we make drifts us apart. Although we somehow start to do different things, we are still early in our life stage, and most things don’t matter.

Stage 3 — Divergence: We have been like unconscious raindrops that follow the flow. We believe we’ll eventually be somewhere great. However, we aren’t aware that we are approaching stage 3 of the divergence in the watershed already. Every decision we make matters more. Who to marry and which country to live in matter more than which graduate job we took. Not that they are 100% irreversible, they just incur higher costs to reverse.

The effects of decision-making are exponential. Every decision has to ride on the previous one we made.

After graduation, we all flock to big companies, they pay the most competitive package. If it’s a company we like, we got a perfect match! However, in many cases, we’re stuck in the spiral of needing the job while hating the job.

The 5 years after graduation is like a one-size-fits-all lifestyle. We go to the same companies. We do the same leisure activities. We buy the same handbags. It’s totally awesome if we simply love these. However, many of us are doing so under auto-pilot mode.

In the first 5 years after graduation, it’s like this:

Life is hard. No worries, we somehow look forward to the weekends! We visit the fanciest restaurants and buy the fanciest products we don’t need to ‘compensate’ our effort during the weekdays.

Sunday evenings are the worst. Fear creeps into our bed on Monday mornings. We hate our job, but ironically, we’re too busy to quit too.

We tried out all sorts of things and somehow settled many things too after 2–3 years. Repeated patterns start appearing from that point, and finding ourselves somewhat similar to the world of the movie ‘Free Guy’.

We have slid into an auto-pilot mode in this stage — where we don’t think to act. We do the same things over and over again until we’re too numb to realize it.

Until a moment, we’re like ‘Wait, is this something I really want?’ Should I stay on my path to gauge my advantage for ‘success’ or start out a new path?

At 27, I left my home and started living abroad.

If you’re interested in my story of moving abroad from Hong Kong to Toronto to London, read my blog here about how living abroad changed my life.

Perhaps I am just being fortunate, I didn’t encounter many struggles with which career path I should be in. The coincidence that I started Freehunter during my final year in college saved my life. It is still a miracle how many people helped me in my journey when I had no track record at all. I haven’t got a proper chance to thank them.

However, I’m no different from anyone, I still go through ‘the watershed of life’. But to me, it’s about knowing who I am, where I wish to live in, and tuning the mindset, worldview, and habits that suit me.

After my graduation, I went through ‘Stage 2 — Streamflow’ like everybody else. I tried getting into communities where I don’t belong. I also somehow invested my whole soul into my company and I almost lost myself in it. As I have mentioned in my previous blog, there is a period where I cut off all of my social and leisure time.

I was stuck in the routine of getting up → arriving at the office → work → going back home → sleeping. Even though I still had a certain level of awareness of whether I was improving enough on a daily basis, I lacked the vision of the big picture.

Luckily, founding a startup is like living a year of a normal person in a month. At 26, I realized I want to get more exposure from the rest of the world, and that’s why I left the hometown I have been living in for 26 years last year in 2022.

In May 2022, I left Hong Kong. I flew to London and stayed for 5 months. And now, I’m based in Toronto and growing my second business Jupitrr. Thinking back, it has been one of the best decisions I’ve ever made in my life.

Anyway, I’ll share more about it in my future blogs!

My Personal Learnings in Making Better Decisions

The longer we got stuck in an auto-pilot mode, the more irreversible our unfulfilling life would be in the future.

In 27, we have to learn how to make better decisions. I’m not saying becoming rich and successful and all that jazz, I’m talking about simply having a good life.

The philosophy of stoicism changed me a lot in this area. It basically teaches us how to maximize happiness in our own ways.

If you’re interested to learn more, here is a book recommendation I’ve got for you that changed my mindset a lot: A Guide to the Good Life: The Ancient Art of Stoic Joy

The meaning of ‘good life’ varies from person to person obviously. However, I believe 99.9% of us treasure happiness at the most atomic level.

By the way, happiness is different from pleasure. Happiness is a longlasting enjoyment while pleasure is a short-term spike.
For example, having the freedom to quit your job and travel gives you happiness. Travel itself gives you pleasure.

Here are a few learnings I personally had on making my life happier.

Optimize for what we want, not what society tells us

Optimize for things we believe are the best for ourselves, of course, unless it is illegal or harmful to others.

Society is often wrong. If it is always right, we are all rich and happy individuals today already, right?

Society tells us stability is important, but it doesn’t tell us not taking risks is the biggest risk.

It’s like holding all cash under our mattress — the money becomes less valuable amid inflation. I believe in taking risks that slightly challenged ourselves regularly as if they are workouts to our minds.

Society teaches us to be rich, but it doesn’t teach us how to be happy.

In schools, we are taught to be obedient to authorities but never taught to be obedient to our beliefs. We are taught to calculate Net Present Value in buying a flat but never taught to ‘calculate’ it for our life decisions.

People want to be rich because money buys freedom, and freedom brings happiness. So, optimize for happiness.

Happiness is the umbrella that encompasses the ingredient of a fulfilling life. Striving for excellence, being rich, being famous, or living a laid-back comfortable life, etc. can all be a subset of happiness.

Final words

We all go down paths that are more and more diverging as we age. It is normal and inevitable.

It is common to hear people gossiping about those who went on a ‘weird’ path after graduation. But hey, their path might be weird to most of us but exciting and fulfilling to themselves. Who are we to judge?

I have a high school friend who dropped out of 3 universities and graduated from the 4th. After that, he changed his career path 3 times in 4 years too.

I also met a girl who quitted her job and became a digital nomad. She travels to various countries like Thailand and stayed for several months each. She did not have a so-called ‘proper job’ for over a year.

I might be the outcast here but I am usually the one to defend them when people talk down on those who make special life choices. Before laughing at those who took a special path, why don’t we ponder again and examine whether we have been loyal to our true beliefs?

Last but not least,

Old people on their death bed never regret doing things, they just regret not doing them.

Who am I?

I am a tech startup founder since 2017, where I was still a final year college student.

My first company Freehunter grew to be one of the largest freelance job matching platforms in Asia.

My 2nd startup Jupitrr is an AI Video Maker.

We help content creators make videos 10X faster with AI — e.g automatically generating stock videos, subtitles, and many more!

Full Demo Video (Updated Jan 2024): https://www.loom.com/share/0d9747329cd54efba4c8e489c41f037c?sid=ff6fb3ce-8248-4e2f-993a-c43087a678a8