The Dream Life You're Almost Ready For
Why pretending to go for it is more damaging than doing nothing.
I’m worried you’re trapping yourself in a life you don’t want.
It’d be one thing to really go for itt half pretending to is doing more damage than doing nothing at all. This is just a hunch… but it might explain why you’re not actually trying to get better.
No, no—no judgement here. It takes one to know one. I did that. Many times, in many ways. So I know what it looks like. You’re in good company, friendo. And, well, here’s why I bring it up: you’re only trying to prove to people you’re not lazy.
I just wish you knew—
No one thinks that.
Except you.
But if you did know, maybe then you’d follow your curiosity for you. Like you used to. Instead of locking it away, focused on one-upping yourself for them. And maybe the stuff you don’t know wouldn’t feel like an accusation, but like an invitation to enjoy learning… instead of trying to secretly pretend you don’t need to. And for a life that doesn’t fit anyway.
This kind of thing always starts with some kind of spark. A good one. Full of exciting possibilities. Which, just as quickly get smacked by rationality.
This is the most insidious part.
We take it upon ourselves to build practical maps to places we’ve never been.
I’m all for dreaming.
In fact, I used to give a keynote called Mission: Permission. It was about the unlikely skills that I learned for getting through mental health’s lowest points. And, how to use those skills to reframe risk, manage stress, and build a life beyond survival mode.
Starting with telling yourself it’s ok to do so.
This requires big dreaming and radical acceptance. At the same time. You need a willingness to think huge. And you also need the ability to then make it bite sized, but without letting go of that big picture.
“Ohhhh, you gotta try SMART goals”, your coworker will suggest.
So you do.
That’s when you go buy some new notebooks and sign up for that new AI time-management software—the stuff that will TOTALLY work better than last time.
Can’t forget to color code your gcal.
You even hear your boss’s confident voice in the back of your mind, “let’s start with the low hanging fruit” (I f*cking hate this one, personally. But you’re 1000% going to hear it more than you’re happy about).
“Ok”, you think, “if I actually want to quit my job and try to do this—to really go for it—I’ll need at least six months of savings.”
Here come the budget templates…
“LOOKOUT, HE’S OPENING EXCEL… ON A SATURDAY NIGHT”
You start customizing dashboards, tinkering with formulas, and tell yourself that once the system is jussstttt right, you’ll do it—you’ll hand in your resignation and buy the plane ticket to Spain.
It’s me… I’m we.
All this stuff gets built on the idea of a life you’re not even living yet.
I used to spend whole weekends perfecting workflows I never use.
…I still do, but I used to, too.
Sometimes it’s just flat out fun. Color-coding dashboards or rewriting morning routines. Reading books, listening to podcasts, and watching videos about the frameworks or methods other people have already outgrown…
But then it tips into procrastination disguised as preparation.
And that’s because it’s missing two important puzzle pieces:
Small steps that don’t actually fit the bigger structure (yet).
It didn’t leave room for wonder.
If we’re going to do this thing and keep you from getting trapped in a life you don’t want, we need to inject some wonder back into it.
For a long time, snowboarding and the places it took me fueled that fire.
It’s a hard thing to explain to people. I’ve tried many of them, “it’s like flying, or surfing, or that moment on a swing set before you start coming back down to earth.”
None come close to what Of a Lifetime explains without actually saying any of it.
Because it’s not actually about snowboarding. It’s a film by Jérôme Tanon that celebrates discovery and adventure in Antarctica, sailing across the Drake Passage with the legendary De Le Rue family.
It reminded me how important it is to be open to the wonder that exists in this world. Xavier and his daughter, Mila, go looking for it. Brothers, Xavier and Victor, share moments of gratitude for reconnecting in a new phase of life.
I’ve never seen a more spectacular outdoor film.
The story is told through Mila’s diaries, and follows her growth while she openly stares down her fears and also invites wonder.
Watching it reminded me of one of my favorite quotes:
“I always wonder why birds choose to stay in the same place when they can fly anywhere on the earth, then I ask myself the same question.”
― Harun Yahya
Structure and wonder create rhythm… whereas structure and control create limits.
That’s how you get stuck in the version of yourself that’s only ever “almost ready.” But not quite. For so long, I wanted structure to be the answer. It isn’t.
Good systems keep things open.
Bad systems keep things hidden.
That’s the difference between finding clarity, and only ever almost finding clarity. Rhythm is what helps you go with the flow when clarity disappears, and then jump back in to find it again. But it only shows up after you start moving.
Seven years ago, i suffered a traumatic brain injury in a snowboarding accident. It sent me into a sustained depression. Months spent in a dark room, working on physical therapy for my eyes that couldn’t track properly and resulted in constant blurred vision.
I did a lot of planning during my recovery. Career aspirations, financial goals, bucket list items…
Routine and structure are what brought me back to life.
But looking for wonder is what helped me start living it again.
This was one of my first big-days in the mountains after my traumatic brain injury. Days later, I was sailing on a boat in the Caribbean after an instagram message exchange. But that’s a story for another time.
I spent years making sense of purpose and fulfillment.
Searching.
Thinking that earning the “thing” would allow me to do meaningful work and structure the life I wanted.
In reality, the whole things flipped.
So I worked backward in order to move forward.
It went like this:
Start with structure & good habits.
Build momentum using those habits.
Create purpose from the momentum.
Fail, adjust, try again, and repeat.
Get results/ the “thing” you wanted.
1-4 are the whole game.
I’ll leave you with this: gaining competence is good if you intend to go use it in response to lived experiences. But it can easily become a habit of only learning about competence in theory without practice if you let it.
Build your structure so you can wave buh bye to your boss and go buy that plane ticket. But then keep going—look for wonder and find your rhythm.
“If you don’t do it this year, you will be one year older when you do!”
– Warren Miller
onward.
-dmac
Here are my favorite resources for becoming unobstructed that you can use this week.
watch.
What It's Like to "MAKE IT" by Van Neistat.
The Fear of Starting by Mark Soderwall at TEDxRedding.
How Micro-Adventures May Save Your Creativity & Drive by Goth Babe.
listen.
The Cure for Nihilism with Suzy Welch and Simon Sinek.
How to say no with Vanessa Bohns, Topher Payne, and Adam Grant.
From shop kid to leading Patagonia Snow's marketing engine with Colleen Quigley.
read.
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What counts as "work" when your work feels like... your art? by
.The Shift Has Already Begun—Now What Are You Choosing? by
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Welcome back or welcome to Becoming Unobstructed.
I’m Derek, a former outdoor guide climbing my way through the tech world.
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