You’ve already changed so much over the course of your life that you’re an entirely different person. So why do you keep planning your future as if you’ll be so similar to who you are today?
Look at a photo of yourself from ten years ago.
Not a flattering one, but a “real” one. The kind that makes you wince a little because it feels like it’s a stranger wearing your face.
Now think about what was in that person’s head.
What they thought was important. What scared them. What they thought their life was going to look like. The plans they had. The certainties. The blind spots that look obvious now but felt like solid ground.
You probably barely recognize them. And in some ways, you’re glad.
Now zoom out and go back in time even farther. Twenty years. Thirty.
If you’re being honest, that person isn’t really you anymore. They share your name, your family, and some memories – and that’s about it. Same hardware (albeit a bit aged), but a completely different operating system.
A question that should mess with you:
Who designed all of those changes?
Did you sit down at 25 and plan the person you are now? Did you consciously choose the priorities you carry today, the relationships you keep, the work you do, and what things feel important? Or the values you’ve quietly traded out?
Or did most of these changes just… happen? While you were busy planning the small stuff?
You changed. Radically. But odds are, you didn’t author most of it. The world acted upon you. The years acted on you. Crises rewrote you. Jobs molded you. People came in and out and left their fingerprints all over your operating system. And one day you looked up and realized you were running a version of yourself you never installed.
That’s the real pattern.
You are constantly changing, but the changes are happening to you, not by you. You’re along for the ride, but aren’t the one driving.
Meanwhile, you try to plan for your future, but the planning you do is so small. Very incremental in nature. Little tweaks to your calendar. Job moves. Routine optimizations. Side hustles.
You keep busy with tiny improvements, patching the OS – all while your next major OS version gets rewritten in the background. And you call yourself free.
The patch trap
Most people’s conscious planning runs on autopilot. They take who they are right now, extrapolate forward, and call it a strategy.
- Similar job, but with a promotion or two.
- Same body, but slightly older, hopefully ten pounds lighter and a bit more toned.
- Same relationships, but a bit more connected and loving.
- Same identity, but now with a side hustle.
Patch, patch, patch.
These plans feel safe – because they are. The “current you” can easily imagine the “patched you”. That next version of you threatens nothing. They eat the same breakfast, work mostly the same way, and believe mainly the same things as you. It’s still you, but with a bit more shine and polish, slightly more refined.
So you direct your conscious effort at the small stuff — the stuff that doesn’t actually change you — while the big stuff, the real reshaping, happens without you even being consciously in the room.
The version jump you keep avoiding
The trick is to make the major version jump a transformation you author, not something that just happens to you.
Not the one life imposes on you when something breaks. Not the one that arrives by attrition at 55. The one you intentionally design, with thought and care.
You end up with different priorities by choice, not because circumstances finally forced your hand. Your relationships changed because you worked at them, not because the old ones burned down. And you have a different definition of success because you decided what success means to you now, not because you got tired enough that the old definition simply collapsed.
It’s the difference between waking up at 50 and saying, “How did I get here?” versus being able to proudly claim, “This is who I built.”
Both versions of you differ from who you are now. Only one of them is yours.
There’s a reason we don’t tend to intentionally design major transformations of ourselves – the current you doesn’t get to come along untouched. Habits, beliefs, identities, relationships, sometimes even values get rewritten or blown up. Not by accident, but on purpose. By you.
Parts of you will need to die, at your own hands.
That’s what most people hide from. We say we want transformation, but we don’t mean it. What we actually want are upgrades that leave us intact.
But that’s not how version jumps work.
Why this matters for your Work
Your Job runs fine on patches. Your Job was designed by your current OS, for your current OS. The patches are even useful — better systems, better boundaries, a raise, a bigger title.
But your Work? The thing you’re actually here to do?
There’s a real chance your Work belongs to a version of you that doesn’t exist yet. A version of you with different fears, different appetites, and different definitions of what’s worth doing.
Which is awkward because right now, you’re trying to figure out your Work using an operating system that hasn’t done it yet.
Of course you can’t see it clearly. The you who can see it is the self you haven’t created yet.
So you keep patching. Reading another book. Tweaking another routine. Adjusting the title on your LinkedIn. Waiting for clarity to arrive on this version.
It won’t. Not because you’re broken. Because clarity is a feature of the next release. And the next release will not install itself, at least not in any direction current you would choose.
The honest question
Look at your current plans. Career. Money. Health. Relationships. All of it.
Then ask:
Was this designed by who I am now, for who I am now?
If yes, you’re patching. The OS is still going to rewrite itself in the background — it always does — but you’ve handed responsibility for planning the next big version over to forces that don’t have your best interests at heart.
A version jump starts the moment you take back control of the plan. The moment you let yourself plan for a self you can’t entirely imagine yet and stop demanding that the current you be the one who gets to keep the keys.
You’ve already changed many times. Which means you know you’ll continue to change.
The only real question is whether the next major change happens by accident or by design.
Quotation I’ve Been Pondering
“Every act of becoming is also an act of letting die.”
— Carl Jung
Journal Prompt
Look at the version of me I am right now. How much of this did I actually author — and how much just happened while I was looking the other way?