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- The “When, Then” Fallacy
If you’re lucky, you’ve got around 83 years of life to live.
Most people split those 83 years into the same 6 chapters.
Chapter 1: Infancy.
Chapter 2: Childhood.
Chapter 3: Teenage years.
Chapter 4: Young adulthood.
Chapter 5: Middle age.
Chapter 6: Senior years.
And each chapter has different societal expectations of what story is meant to be told.
Chapters 1 through 3 tell stories of:
Playing.
Growing.
Learning.
Enjoying.
Exploring.
Experimenting.
Trying (and failing).
These chapters are stress-free.
Responsibility-free.
Work-free.
Then, in Chapters 4 and 5…
The story takes a drastic turn.
Your life goes from “All play, no work” to “all work, no play” before you can even catch a breath.
Chapters 4 and 5 tell stories of:
Working.
Hustling.
Grinding.
Planning.
Prepping.
Saving.
Going. Going. Going...
People see these chapters as a necessary suffering.
A rite of passage.
A one-way ticket to the retirement of your dreams.
And that’s where Chapter 6 starts.
Perception vs. Reality of Retirement
Chapter 6, the final chapter of the Story of Life, is all about the senior years.
The old age — and the retirement — that you’ve worked so hard to achieve. To “earn.”
In this chapter, we hear stories of:
Happiness.
Relaxation.
Enjoyment.
Exploration.
Quality time.
Family time.
…or at least that’s what people expect.
Tons of people head into retirement expecting fulfilled dreams.
A haven filled with hobbies, travels, and completely checked-off bucket lists...
Golden years of perfection.
But that’s the thing about expectations, isn’t it?
Sometimes — often — they’re not met the way you thought.
In March 2023, the Wall Street Journal explored the idea of retirement.
Of real retirement, and what that looks like for real people.
And here’s what they found:
Yeah.
It’s mostly sleeping, relaxing, and watching TV.
Not the sexy, dream-chasing life you thought it was, right?
That’s precisely the problem with waiting and glamorising your future.
It usually leads to disappointment.
And that’s because of the “When, Then” fallacy.
The Mirage of "When, Then?"
The “When, Then” fallacy is a reasoning error… but it’s also a mindset.
A mindset that says happiness — or adventure, financial security, relationships, etc. — can only come after achieving a certain milestone.
Only when you achieve X can you then experience Y.
You have to achieve something good before you can get what you want — no ifs, ands, or buts.
It puts the onus of long-term happiness and gratification onto an external achievement.
A success.
A checkbox.
Anything that makes you feel like you’ve “earned” it.
So, where does retirement come into this?
Well, retirement is the best damn example of “When, Then” that you could ask for.
“When I retire, then I’ll have more time to relax.”
“When I retire, then I’ll spend more time with my kids.”
“When I retire, then I’ll try that hobby I’ve been thinking about.”
“When I retire, then I’ll travel to visit my bucket list destinations.”
Applying “When, Then” to your retirement sets you up to enjoy life… but only once you retire.
Now delaying gratification in this way — “I can have good things later on” — isn’t inherently bad.
Too much gratification at one time can be a slippery slope to risky, harmful behaviours.
A life of hedonism and excess, and only ever “living for the now”...
You can absolutely have “too much of a good thing.”
But the risk with delaying gratification (until tomorrow, until next month, until retirement) comes when it’s done at the expense of gratification now.
And that’s exactly what “When, Then” does.
It forces you to see “joy now” and “joy later” as two mutually exclusive things that you could never have at the same time.
It delays gratification by robbing you of joy right now.
And that breeds disappointment, unmet expectations, and a lot of wasted time.
If you ask me, the problem with choosing gratification “later” with the “When, Then” fallacy is that it fails to consider one mind-numbingly simple question.
The philosophy that The Wild Goose Chase is all about.
The concept that I live my life by, every single day.
Why can’t you have happiness and fulfilment now and later?
An Integrated Life
If you’re not keen on waiting to be happy and fulfilled, then welcome to the club.
The first step in ditching the “When, Then” perspective on retirement is easy.
It’s a mindset shift that focuses on an integrated, designed life.
An Integrated Life moves you away from thinking of life as a “before and after,” and thinking about it as an evolving experience.
A life filled with continuous growth, freedom, and happiness throughout every stage.
Here’s what that can look like:
The Status Quo Life
Infancy to teenage years: Enjoy life
Young adulthood to middle ages/early senior years: Work 60-hour weeks and hustle hard without making room for enjoyment or fun, because work > everything (including happiness).
Senior years: retire and finally enjoy your life
The Integrated Life
20s: Discover your talents, passions, interests, and what makes you “tick” … then start doing it
30s: Turn your passions into profits, establishing the foundation you need to start (and continue) living your ideal life
40s: Start increasing your freedom, re-evaluate your passions and interests, pivot if you want to (because you can)
50s: Evaluate, evolve, and prioritise the work, tasks, and people that are most important to you and make more time for them
60s: Focus completely on whatever you now know is the most meaningful to you
When you’re following the Status Quo lifestyle, there’s a lot less freedom.
A lot less growth.
A lot less happiness… (at least until you’re 65, then, as the data shows, you'll probably just sit on the couch)
Crafting an Integrated Life — and sprinkling every life stage with passion, happiness, and joy — offers continuous growth and development.
No waiting until you’re retired to start to be happy and fulfilled.
(Or, more realistically, waiting to be disappointed that you’re not magically happy and fulfilled).
You’ll also see that the Three Core Pillars — Location Independence, Financial Freedom, and Self-Actualisation — are woven throughout the Integrated Life example.
There’s Location Independence at every life stage.
Prioritise your passions → develop a flexible work model → work from anywhere and everywhere.
There’s Financial Freedom at every life stage.
Turn passions into profits → balance delayed gratification with real-time gratification.
There’s Self-Actualisation at every life stage.
Identify and evaluate your goals → refine them whenever you want → grow.
And I can guarantee you that’s not a coincidence.
Each of the Three Core Pillars is crafted with an Integrated Life in mind, and embodying them throughout your entire life journey positions you for this new trajectory.
Society might tell us that a Status Quo life is what we should want.
But that’s only because it’s what we’re used to.
An Integrated Life is how we can actually thrive.
Not everything is about giant wins and massive achievements.
There is incredible beauty in small, continuous growth.
And that’s the best way to foster ongoing happiness and fulfilment.
Achieving The Integrated Life
Crafting the life you want doesn’t mean sacrificing happiness for hustling…
Choosing stagnancy over moving…
And constantly making massive, stress-inducing changes in the name of “success.”
That doesn’t guarantee late-life enjoyment or happiness.
It guarantees burnout and regret.
Weaving happiness throughout your journey — before and during retirement — is the way to go.
That seems like a big shift, but like I’ve said before…
Making changes to reprioritise growth and happiness doesn’t need to mean only hustling and stressing.
Change-making steps can be small and digestible, like:
Taking time to reflect, understand, and acknowledge your current place on the Status Quo arc.
Working to understand and articulate your most authentic desires, values, and priorities.
Outlining what you need to launch a Freedom Business and leverage new opportunities.
All of those tasks can be done from the comfort of your own home, with nothing but you, a pen, a piece of paper, and some time for self-reflection.
But don’t let the simplicity cloud the importance of the work.
One good decision can have a life-changing ripple effect.
So just start with one small thing.
Take the time out of your day today to complete this exercise, considering how you can craft your Integrated Life in just a few steps:
Write down the vision of your ideal life in 25 years, and include as much detail as possible. Where are you? Who are you with? What are you doing with your time?
Considering your dream future, think of 1 or 2 things you can start doing today to launch yourself in the right direction. This can include things like:
Writing down an updated list of your values and goals.
Considering how you might alter your career to be more fulfilling.
Identifying areas of your life that you’d like to improve, and fi out how
Start doing one of the things today. Not tomorrow, not next week, not next month. Today.
I know from experience that your dream life can be achieved in a number of years.
I turned my life around in less than 5.
But you have to start with something, even if it’s small.
Just one thing.
One small change that ditches the traditional concept of life trajectories.
One small action that can propel you forward into a reality that’s designed for your happiness.
One small mindset shift that grounds you in the present instead of waiting for the future.
A future when you can finally be happy.
A future that rejects the tyranny of “When, Then” and embraces the magic of an Integrated Life.
Ultimately, the question isn't about when you'll find happiness.
It's about how you're cultivating it for yourself right now.
Until next time,
Stay Awesome, Stay powerful.
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