An Unhelpful guide to your quarter life crisis

In this guide, we’ll take a lighthearted look at the struggles of your late twenties, from career confusion to relationship dilemmas, and offer some practical tips to help you navigate this wild phase of life. A reminder that you’re not alone in the chaos.


Phil Knight is the Co-founder of Nike

I don’t need to give any more of an introduction than that

A self-made man hailing from little old Oregon in the United States

Building one of the biggest and most influential companies in all of history

I was recommended Phil’s autobiography, Shoe Dog by one of my great friends, Rudy Taylor

Everyone needs a Rudy Taylor in their life—his ability to seek out opportunities while truly enjoying life is exactly the energy I love being surrounded by.

Rudy & I met at my old Corporate Job In Melbourne, after many trips to the gym at lunchtime, games of table tennis & post work VLSs, it was clear that we were going to have a friendship that would span decades

The book is essentially a tell-all memoir from Phil about his life before & during the early stages of building Nike

Before starting Blue-Ribbon (which later became Nike), Phil was just like anyone else growing up in post-teenage life

Where to now?

The structured teenage years behind you with two main options in front of you

  • The well-worn path of a secure 9-5 job, slowly ascending the corporate ladder
  • Or venturing into the unknown

The options always seem limited & unlimited simultaneously during these years.

For two weeks during my travels in Northern Colombia, I’ve been enthralled by Phil’s writing

It is so casual, so engaging, like your uncle telling you a story at a family get-together

The way he has approached his entire life is something I’ve recently taken great inspiration from

Phil put it succinctly, about life in your youth

“I’d tell men and women in their mid-twenties not to settle for a job or a profession or even a career”

“Seek a calling… Even if you don’t know what that means, seek it”.

In his earlier years, at a similar crossroad to many of us, Phil chose the unknown

A backpacking trip traversing the globe to find out more about the world & also himself

Without giving you a book club summary of the book (I’d encourage you to read it yourselves) this trip ultimately paved the way for all that was to come with Nike

Your Twenties are a strange time

It’s the exact sweet spot we’re able to cringe at our early twenties

While still being young enough to pretend we’ve got enough time to figure it all out

Around this age, you start to realise what being an adult is, rather than when you first legally became one

It’s not driving your car without your parents, cracking your first legal beer or working your first shift at a fast-food resturant

Unfortunately, being thrust into adulthood when you turn 18 is just the beginning of it

Attempting to be an adult has looked like the following:

  • Try to see a large portion of the world
  • Try to save enough money to live, eat food & do some nice things occasionally
  • Keep my social life alive with close friends
  • Learn as many new skills as possible like a new language, (trying) to start businesses & Investing
  • Try to save for a house (I’ve given up on this one)
  • Making time to stay relatively fit and healthy
  • Accepting that life’s curveballs – like unexpected career shifts, personal setbacks, or global events—are just part of the ride, and the best you can do is roll with it.
  • Redefining what ‘successful’ is. Not necessarily meaning I want a high-paying job, a nice title, or material wealth—it might just mean feeling content with who I am, how I spend my time, and who I share it with.
  • Talking to new people as often as possible
  • Learning to say no and disagree with people
  • Realising that no one, and I seriously mean no one has it entirely worked out


I will leave this series open-ended, because I think there is a lot to breakdown and explore

But I will share some knowledge that has helped me navigate this time in my life

  1. Your timeline is your own

The great comparison game of our generation

It’s easy to start believing you’re a failure when the top 1% of people globally are being flashed across phones in front of you every day

Millionaires, athletes, and businesspeople all ascending to the highest echelons of existence

And all I’ve got to show for it is a declining bank account and an almanac of great memories

It’s an easy comparison game to play

What you define as success in your life doesn’t have to abide by any set timeline or regulation

Any milestones you think you have to meet by a certain time period are arbitrary

You don’t have to pay a penalty for going slower or in a different direction to everyone else

It’s a self-flagellating system to measure your progress against someone else’s highlights—they’re walking their own path, and so are you.

Whether it’s career advancement, buying a house, or finding a healthy relationship

The best things come to those who wait and work on their own backyard first

I’ll reach over to a poet from Brazil – Mario Quintana for a succinct quote that encapsulates the above

“O segredo é não correr atrás das borboletas… É cuidar do jardim para que elas venham até você.

“Don’t waste your time chasing butterflies. Mend your garden, and the butterflies will come”

Watching everyone else’s garden flourish is nice, but by building your own, on your own timeline is where you will reap the rewards


2. No one has it figured out

    When I used to sit on the Frankston line train to university most weekdays

    I’d see Business people, sporting three-piece suits, a coffee in the right hand singing the corporate symphony into their AirPods about what business crisis they were solving that day

    I used to think, “Wow, they’ve got it all figured out”

    “If only my life could be like that”

    As I grew older, I came to realise how little some of these people had their lives in order

    That suit and tie facade is sometimes their armor against dealing with their own internal battles

    You can define ‘it’ by whatever means you like

    A career, family, a house, friends, staying healthy, even life in its entirety

    You shouldn’t aim to solve it all like an algebraic equation

    That is a task that will only leave you sad and confused

    Life is less about having all the answers & more about being adaptable

    Each day there are so many things that will change, come & go & invariably shift your life on a new course

    Sometimes without your control

    Staying resilient & flexible during every stage of your life will serve you well

    Be prepared for things to never turn out as they should

    I’ve always aimed to learn more and more & accepted the impermanence of everything as a way of dealing with this


    3. Failures are the bricks that build the house

      Naturally, no one likes things not working out as they planned

      The resources you’ve put into whatever task, project, plan, or commitment you’ve strived to complete

      All seemingly gone to waste

      I was very risk-averse in my earlier years because of this very notion

      Often trying less to offset the downside risk of something not working out how I’d envisioned

      The true definition of a pessimist

      If I believe things won’t work out before I even attempt them, I won’t be disappointed when they don’t work out

      You can imagine how far this got me

      Every setback, mistake, or failure you experience is not a sign that you’re doing something wrong—it’s an essential part of creating the life you want.

      Just like building a house (your own life), each brick (or failure) forms the foundation of your growth, making you wiser with every misstep.

      What feels like a dead end right now can often be the very thing that guides you toward a better opportunity or a new direction you never would have considered.

      Failure teaches you resilience, adaptability, and what doesn’t work, which are all crucial for long-term success.

      So don’t fear those moments, lean into them, and when they arrive, shake their hand like an old friend

      The lessons you can take from these moments are what define people, and elevate them to the next level

      Without trying to sound like a deranged business or motivational speaker here, failure is an essential part of any process

      Those missteps help you pave the way for future successes

      Nothing that a plan or perfect strategy could have accounted for.

      something slightly comforting is that every single person on earth has them

      Most not publicly of course, but everyone has to deal with these moments of turmoil


      4. Don’t wait for permission to live the life you want

        I’ve got a bad habit of quoting billionaires in this blog

        and I’ll be dammed if I’m going to stop today

        Unfortunately, they are all well-publicized & do have some good wisdom to impart to the masses

        For this one, I’ll go to the founder of Amazon, Mr Bezo’s

        I was listening to him speak on the Lex freidman podcast some months ago

        and he spoke of something he’d fostered in the Amazon work culture that I think translates well to living as well

        It’s basically called the two-door theory

        The idea is that most decisions in life are like a two-way door.

        You pick a door, walkthrough, and if it turns out you don’t like what’s on the other side, guess what?

        You can come back and pick another one.

        It’s not the end of the world, and the key here is that these kinds of decisions are reversible. You don’t have to overthink them—just go for it, and if it doesn’t work out, you can course-correct.

        Similar to many decisions that face younger people

        Should I travel the world?

        Should I go for that new job?

        Should I try and move to that new city?

        Almost all these decisions have a two-way door option if you need it

        You can always go back to your previous life, job, career, or city if the first option didn’t eventuate as you’d imagined

        The alternative, if you never choose to go through the door at all

        Being to scared of the change that might enter your life

        Is never finding out your potential

        The best thing about any of these decisions is that they are entirely devised by you

        If you have an idea, a dream, or just something you’ve always wanted to do

        You don’t have to ask anyone to follow through with it

        Sure there are always third parties to consult

        Parents, friends, partners, bosses & all the rest

        You can be a little selfish

        Everyone who has done something with themselves has eventually put their own lives ahead of all else

        It’s better to ask for forgiveness than permission

        We all lie in bed at night – alone with our thoughts, pondering all of life’s questions and nuances

        The thing is you actually don’t need every answer

        It’s not a high school exam you can merely study a textbook for

        Life is invariably much more complex than that

        It’s more about learning & finding out about yourself along the way

        What brings you joy, finding out what you enjoy learning about, trying new things and sharing those experiences with those around you

        Are all good things to try and find out

        Whether you’re at your own quarter, mid or end of life crisis

        There’s no single answer to your own life—it’s the variety of experiences you collect that give you many reasons to enjoy it.

        LB

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