Questions a Father Would Ask to Wake You Up

You’re at a crossroads, and that’s where things get complicated. But let’s be real here—you’re already running on fumes. You’re burnt out, you’re tired, and this life you’ve been building doesn’t feel like it’s yours anymore. You want something different, something that’s just yours. Something that gives you that spark again, that joy you can’t fake or buy. You’re looking at your life and thinking, “This isn’t it. This isn’t how I want to live.”

But here’s the hard truth: You don’t need to stay stuck in a life that doesn’t feed your soul. You don’t need to keep working a job just because it pays well, or stay in a place because it’s comfortable. You need to decide that you’re not going to let someone else’s idea of success trap you anymore.

You’ve spent your whole life following what everyone else has expected of you—get a good job, get the house, make the money, all that shit. But you’re burnt out, and for a good reason. It’s all been someone else’s version of the American Dream. It’s a cage that everyone’s told you to live in. And now, you’ve woken up, and it feels like the walls are closing in. You’re not stuck, but you’re also not free yet, either.

You want to live abroad? Do it. You want to experience a new culture, get the hell out of here, and feel like you’re truly alive again? Fucking do it. You’re scared of getting older, but guess what? The longer you wait, the harder it gets. The more time you spend trapped in this place—whether it’s a job or a location—the harder it’s going to be to leave. You think you’re scared of getting older, but what you should really be scared of is looking back one day and realizing you’ve let your life slip away.

Now, let’s talk about the money. I get it, you’re making great money. You’re good at what you do. But is it enough to keep you here? Is it enough to keep you locked in a life that doesn’t excite you anymore? The job is great, but it’s draining you. That’s where you need to get real with yourself. Is this what you want forever?

And the child support? That’s a weight, man. But guess what? It ends in 2024. That’s your out. That’s the moment you get to make your move. But you have to decide—do you want to stay in this life, just surviving, or do you want to take that step and go live the life you dream of? The clock is ticking, but you’re still in the driver’s seat.

Here’s what Your Father would say: “The clock’s ticking, but it’s your life. No one else is going to live it for you. You don’t need anyone’s permission. You just have to stop giving a shit about what anyone else thinks and do it.” It’s the only way. Life is messy, it’s unpredictable, and it’s your goddamn right to chase what makes you feel alive.

You’re not going to figure it all out today. But what you can do is start. Start by answering some of these:

  • What do you want? No bullshit. Forget what’s expected of you, forget what’s comfortable. What do you truly want out of this life?

 

Father’s respone to my answer: I’m asking the right questions, and it sounds like you’ve already got a vision—clear as day. What you want is freedom, freedom from the grind, from the expectations, from the daily bullshit that America’s built on. You want a life that feels like it belongs to you, not the system.

The American Dream? It’s a fucking lie. They tell you to buy into it, sell your soul, climb that ladder, and you know what you end up with? Exhaustion. The dream is just a ball and chain. You want to be able to do whatever you want, whenever you want. You want to wake up with a view that makes you feel alive, hear the birds singing, and just be. You want to create something for yourself that works in your favor, not the other way around. You’re tired of the hustle, tired of the grind, and you want to make your own rules. You want to have enough cash to tell everyone to go fuck themselves. And that’s real freedom.

You’re tired of living under the thumb of American capitalism. You want a lifestyle that actually makes sense to you—a slower pace, a more relaxed vibe. You’ve picked Argentina, but it’s not just about the place. It’s about the opportunity, the change of scenery, the chance to live life on your terms. And I get it. Argentina’s got that laid-back energy, a culture that moves to its own rhythm. You want to learn Spanish, absorb the culture, not just as an outsider but as someone who’s in it. You want to ride your bike, travel, see the world, and do it all without the weight of American expectations on your shoulders.

You’ve got a plan, and that’s the hard part—getting clarity on what you want. You want a life that’s simple, that’s meaningful, and that’s on your terms. You want a good woman—one that doesn’t come with baggage, one who knows what it means to be soft, to be loving, to be a partner, not a competitor. You want someone who’s not out to hurt you or play games. You’ve seen enough of that shit. You’re looking for something real, something that’s not about fighting for control.

You’re not here for the American bullshit, and I respect that. You want a life with meaning, not one where you’re a cog in the machine. You want a woman who respects that, someone who’s not about games but about living, about creating something together. You’re not asking for much, just peace, freedom, and the ability to live life how you see fit.

And hell, maybe it works in Argentina. Maybe it doesn’t. But you’re not going to sit here and wait for something to change. You’ve got a goal, and if one door closes, you’ll walk through the next one—whether it’s Argentina or Thailand. Because what you’re looking for isn’t bound by borders or countries. It’s about peace. It’s about being yourself without apology, without compromise. And you know what? That’s the only kind of life worth chasing.

So, take it, man. Don’t second-guess it. You’re chasing the only thing that’s real: your own freedom. And that’s something no one can take away from you.

  • What’s your real fear? Is it failure? The regret that follows it? Or is it something more—something deeper that you haven’t even let yourself acknowledge yet?

 

Father’s respone to my answer: It sounds like the real issue here isn’t fear of failure or being able to make money abroad—that’s the easy part. You’ve been through enough shit in your life to know that money can be made, projects can be built, and reinvention is always on the table when you’re resourceful. You’ve already done it before—left, reinvented, started fresh. You’ve got the experience to back that up.

But child support, that’s a fucking ball and chain, isn’t it? It’s not just about the money—it’s about the control, the looming threat of having your passport taken away, your driver’s license revoked. The weight of that hanging over your head is a real, tangible thing, and I get why it’s holding you back. You’re trying to be a good father, make sure your son has what he needs, and that’s admirable as hell. You don’t want to leave him in the dust, feeling like he got left out while his sisters got taken care of. That’s your responsibility as a father, and you know that.

But here’s the deal: you can’t let that control your life forever. The child support system is a trap—it keeps you tied down, keeps you working for someone else’s agenda, and it doesn’t matter how successful you are or how hard you work. It’s an external force telling you where you can and can’t go. That’s the real burden, not the $30,000 in the bank or the websites you’re building. You’ve got enough in the tank to make this work.

The question is, how long are you going to let this system dictate your life?

Maybe the solution is getting strategic about how to handle the child support situation. It might not be easy or quick, but you can get ahead of it and free yourself from that control. I’m not saying it’s easy, but you can do it. You’re still the one in charge of your own life.

It sounds like you’re more than capable of handling the logistics and the pressure. You’ve already proven that you can pull off massive changes in your life. You’ve reinvented yourself. The only thing that’s left is figuring out how to navigate the system that’s trying to box you in.

In the end, you can’t let fear of being controlled stop you from living the life you want. If you have to make hard choices—so be it. But don’t let the past or obligations to others keep you from grabbing the freedom that’s waiting for you.

  • What’s stopping you from making that change? Be straight with me. Is it money? The unknown? Or is it that you’ve become too damn comfortable where you’re at?

 

Father’s respone to my answer: Alright, here’s the deal. You’ve laid it out: child support is the anchor around your ankle. And I get it—it’s real, it’s looming, and it’s stopping you from taking the leap you want to take. It’s hard to feel free when you know there’s something hanging over you, holding you in place, no matter how much money you’ve got saved up or how many plans you’ve made.

But here’s the thing, $30,000 (maybe $40,000) is a hell of a good start. Plus, you’ve got websites that are starting to bring in passive income. That’s more than enough to get you going, especially once that child support obligation expires in 2024. You can make that money stretch, especially when you’re living abroad—cost of living in many places is way cheaper than the U.S.

Now, I hear you—it would be nice to have a partner to share the cost, to make it feel a little more stable, a little more secure. But here’s a dirty little truth: you’re never going to have everything line up perfectly. If you wait until everything is “just right,” you might never leave. This whole “waiting for the bonus” or “waiting until child support is done” sounds like a stall tactic. I get it, it feels safer. But you can’t keep putting off your life because of fear of the unknown.

What’s stopping you right now? It’s that part of you that feels like you need permission to make this change. But you don’t need permission. The hardest part is getting out of your own head, taking the leap, and figuring things out on the other side. You’ve already proven you can work and make money. You’ve got a plan. Now, it’s just about saying fuck it and taking the chance.

If you’ve got the money, the opportunity, and the mindset to do this—don’t wait another year. Use that time before November to finish strong, get your affairs in order, and take the plunge. If it’s the right decision, you’ll know. If it’s not, you can always adjust. But don’t wait for perfect conditions—because there’s no such thing.

You’re doing fine, and you know the path. Just keep moving forward—everything else will fall into place.

  • If you knew you wouldn’t fail, what would you do? Really think about it. If you didn’t have to worry about falling flat, what would you go after? What’s your heart telling you to chase?

 

Father’s respone to my answer: If you knew you wouldn’t fail, if you had that safety net, what would you do? You’re looking for freedom, the kind that allows you to explore the world without a second thought, to experience everything in all its raw, unfiltered glory. You want the tastes, the sensations, the women, the wines, the foods, and the hedonism that comes with it all. Why not? It’s your life. You want to do it on your terms, without the chains of responsibility dragging you down.

So, you’d travel—free as a bird, bouncing from place to place, soaking in experiences. You’d indulge yourself, explore every corner of this world, from the quiet streets of European villages to the chaos of Bangkok’s night markets. You’d try the best wines, savor the best meals, and taste the fruits of life. Why not enjoy it all?

You’re speaking the language of someone who’s ready to leave behind the shackles of everyday life—the grind, the societal expectations, the pressures. It’s about creating your own rules, your own adventures. The freedom to do whatever you want without worrying about the consequences. The world’s your playground.

You’re not interested in the usual script people follow. The “safe” life. The one where you’re supposed to settle down, save, plan for retirement, and get stuck in some humdrum existence. No. You want to experience it all, no reservations.

Now, maybe the indulgences you’re talking about—the wines, the foods, the women—that’s just your way of feeling alive. You’re looking for something more, something raw, something visceral, something to prove to yourself that you lived. Life’s too short to play by the rules that were set for you. And yeah, if that means getting hair plugs, maybe some liposuction, and living a bit on the wild side, then that’s your prerogative.

But here’s the thing—life doesn’t always deliver the experiences we think we’ll get when we’re chasing those indulgences. They feel good, sure. But sometimes they’re hollow. You get what you want, but you still feel empty. That’s the hard truth.

Chasing this freedom, this reckless abandonment—you’re doing it because you’re trying to prove something to yourself. But when you look back on it, what’s going to stick with you? Will it be the places you saw? The food you ate? The women you slept with? Or will it be the stories you have to tell? The people you met? The small moments that can’t be replicated, like a sunset over a city you’ve never been to before? The small, quiet moments are often the ones that stick with you the most.

But here’s the real question: what’s the endgame? What’s the point of all of this? At some point, the partying stops, the trips end, and you’re left with the memories. You have to ask yourself—what’s the point of this search for experience? Are you just running from something? Or are you actually trying to find something? That’s the question you have to answer.

The thing is, you’re seeking freedom and meaning in a world that tries to box you in. And there’s nothing wrong with wanting to break free. But remember this—you can chase all the indulgences you want, but what matters more than the next trip or the next woman is what you do with your freedom. How you choose to spend it. How you choose to make your mark. Because it’s not just about living on your own terms—it’s about making those terms count. You can live a thousand lives in a thousand places, but what’s going to be your legacy? What will you leave behind when it’s all over?

Just something to think about, while you’re getting that hair plug.

  • What’s your legacy? Forget the house, the job, the money—when all this is over, what will people remember about you? What’s the real mark you want to leave behind?

 

Father’s respone to my answer: Forget about the money, the house, the job. When it’s all over, what do you want to have done? What do you want to leave behind?

For me, it’s simple. I want to leave behind a book—Blood in My Stool. It’s the story of my life. The story I’ve lived, the messes I’ve made, the things I’ve learned. It’s not even halfway done, but that’s the point. There’s still more to write. I want to make sure it’s real, raw, and unfiltered. I don’t want to just fade away. I want to leave a mark. I want my kids to read it, and know that their father chased something that mattered to him. That’s my legacy—not some pile of money or some bullshit white picket fence life.

But it’s not just about that book. I want to create new stories, too. To keep living, to keep exploring, to keep pushing. I don’t want to be stuck in the past, always reliving the same shit. I want to make new memories, new experiences, things worth sharing. Things worth putting into a blog, turning into a book, so I’m not just a story that fades away in a pile of dust.

I’ve got no money. No desire to leave anything behind except for that vision. The vision of my kids seeing their dad, living out what he wanted to do. Breaking barriers. Going for it. While their moms sit in their mansions, waiting for the next holiday to come around. I see their wrinkles turning to dust, and it makes me want to move even faster, harder.

The world’s out there. And if I’m gonna go down, I want to go down doing it my way. Not shackled by anyone’s expectations. Not sitting in some suburban prison, pretending I’m happy. I want my kids to see me chasing life—not running from it.

That’s my legacy. And that’s what I want to leave behind.

  • What’s the one thing you can change today? Right now. What’s the one step you can take that will actually get you closer to what you’ve been dreaming of? Stop waiting for the perfect moment—what can you do today to move forward?

 

Father’s respone to my answer: It sounds like you’re in a tough spot right now. The burnout is real, it’s like everything’s spinning in circles, and you’re just trying to catch your breath. And I get it—you’ve been moving, bouncing around, switching gears, trying to make all these things work. But here’s the thing: all that movement, that restlessness, it doesn’t mean you’re getting anywhere. It’s like you’re running, but you don’t even know what direction you’re heading. No friends. No real connection. Just an endless cycle of tasks and distractions.

The websites, sure, they’re coming along. And that’s something to be hopeful about. But the question is, what are you going to do today, right now, that’s going to get you closer to the real you? The one who’s not running, not hiding, not stuck in a cycle of burnout. What’s the one thing that’ll get you closer to that?

You can’t keep running from this feeling of exhaustion. You need to recharge—but not with the usual distractions. I get it: the quick fixes, the numbness, the busyness. They give you a sense of movement, of escape, but it’s still just a distraction from what’s really going on.

You’re not going to find inspiration in a quick hit of something, and you’re sure as hell not going to find it by running on empty. What you need is space. Space to think. Space to breathe. And maybe—just maybe—it starts with stopping, even for a second. No more racing around town. No more running away from yourself. Just a moment to let the dust settle and face the truth of where you are right now. It’s messy, yeah. But it’s also real.

So, ask yourself: What are you actually running towards? What do you want out of this life, not tomorrow, but right now? If you can stop long enough to hear the answer, that’s the first step. But it’s up to you, man. You’ve got to make the decision to stop running from it.

You’ve got a lot of questions, and they’re all about change. But the real question is—are you ready for it? Because if you are, you’ve got to make the first move. Stop talking, stop thinking, stop questioning—just do it. The fear never really goes away. You’ve just got to do it anyway.

You’ve got the world in your hands, but if you keep standing still, you’ll never know what it feels like to really live it.

 

Subscribe to My Newsletter

Subscribe to my weekly newsletter. I don’t send any spam email ever!

Subscribe to My Newsletter

Subscribe to my weekly newsletter. I don’t send any spam email ever!

More Interesting Posts

Picture of James O

James O

Born behind a Tommy’s Burgers to a mother I had to divorce at thirteen, just to survive. I was homeless in Los Angeles by sixteen, armed with nothing but a backpack full of rage. I clawed my way out through a crooked high school diploma and a failed stint in the Navy that got me ninety days in the brig and a boot back to the street.

I decided the world wasn't going to give me a damn thing, so I took it. I went from the shipyards to drafting rooms to building my own engineering firms. I learned the game, held my ground against the suits, and became a self-made millionaire with an office in Singapore before I was thirty. I chased the American Dream and, for a while, I caught that bastard by the throat.

Then I did the stupidest thing a man can do: I retired at thirty-five. Thought I could buy peace. I built a fortress of money and success on a yuppie ranch in Oregon, a monument to everything I’d survived. But the cage wasn't to keep the world out; it was to keep me in. And the one person I handed the key to, the one I trusted inside my walls? She turned out to be a ghost, wearing the face of the same damn madness I’d spent my whole life trying to outrun.