When the storm hits, will you be building your ship or bailing water?
Your gut has been screaming at you for months about what you really want to do with your life. September’s chaos is about to drown out that voice completely – unless you do something radical first.
Forget January 1st. The real new year starts after Labour Day, when summer’s lazy haze lifts and that hectic back-to-school energy kicks in. There’s something primal about September that January just can’t touch – that feeling of wrapping yourself in a cozy sweater, all while sharpening your sword for what’s ahead.
This is the season of preparation. Of getting serious. Of trading summer’s “whatever happens, happens” for fall’s “It’s time to demolish my goals.”
But remember – while you’re feeling that September energy, winter is literally coming.
The Wake-Up Call Nobody Wants to Hear
I’m not just talking about the weather. Economic uncertainty is brewing. AI is reshaping work. Look at this chart:
Before, workers were playing a game of musical chairs where there were more chairs than bums. Made it a whole hell of a lot easier to move around. Now, the game has shifted, and for the first time since peak pandemic, there are less chairs than workers.
People are desperately searching for meaning while companies are cutting costs. The world got harder while you were on vacation, and the cost of playing small just went through the roof.
While you’ve been thinking about your dreams – maybe someday, when things settle down, when you figure it all out – the landscape shifted beneath your feet. The comfortable middle ground is disappearing fast.
The Truth You Already Know (But Won’t Admit)
Stop pretending you’re confused about what you want. You’re not confused. You’re scared.
You already know what you’re here to do. Your gut has been screaming it at you for months, maybe years. That thing that lights you up when you think about it, then immediately makes you spiral into “but what will people think?” and “how would I even make money doing that?”.
Harsh fact: “someday” is where dreams go to die. It’s the most comfortable prison ever built – no risk, no judgment, no failure, and no damn life worth living.
September’s Perfect Storm
And now September’s about to make it worse. Your calendar is about to explode. School schedules, Q4 deadlines, holiday planning – the perfect storm of legitimate excuses is brewing. Everyone’s about to get insanely busy juggling other people’s priorities.
You’ll have every reason in the world not to deal with your own dreams right now. The chaos will feel urgent, unavoidable, and even completely justified.
There will always be a reason NOT to build your dream life. In January it’ll be New Year overwhelm. In spring there’ll be something else. The chaos isn’t a bug in your system, but a feature of a life that you didn’t design and isn’t really yours.
The Fear That’s Running the Show
What’s really keeping you stuck isn’t the chaos. It’s the fear.
What if people think you’re nuts? What if you can’t monetize whatever this thing is? What if you try and you suck at it? It’s just so much easier to keep it locked safely inside your head where it can’t be judged, can’t fail, and can’t disappoint anyone. Especially yourself.
The problem is, it also can’t live.
Your Counter-Cultural Revolution
This September, while everyone else drowns in busy, I’m daring you to go the opposite direction. To be radically counter-cultural and actually slow down long enough to remember who the hell you are.
Stop being a mindless robot. Start paying attention to your feelings for a change; they’re not inconveniences, they’re data. Stop thinking your way to clarity and start feeling your way there.
You know what this looks like: Sitting in silence. No phone, no distractions, just you and your thoughts. Journaling without an agenda. Walking without podcasts. Just time to reflect, not focused on a particular goal or outcome. The scary simple stuff that actually cuts through years of mental noise.
Winter is coming whether you start building your dream life or not. The economy might shift whether you play it safe or not. People might judge you whether you hide your dreams or not.
The only choice you get is this: Do you face uncertainty while building something that actually matters to you, or do you face it while still living someone else’s life?
This fall, choose courage. Your future self is counting on it.
Time to get going.
Quotation I’ve Been Pondering
“A ship in harbor is safe, but that is not what ships are built for.”
— John A. Shedd
Journal Prompt
“Which dream keeps calling me, and what part of that dream terrifies me the most? How might leaning into that fear become the path to living it?”
Until next week!!
Work and live well.
Tim
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