If you really want to build a life you don’t feel the need to escape from, ask yourself these 5 questions

I still remember a quote I stumbled upon back in my startup days that really shook me awake. It was from Seth Godin: “Instead of wondering when your next vacation is, maybe you should set up a life you don’t need to escape from.”

I found those words when I was knee-deep in spreadsheets, trying to grow my tech company, barely sleeping, and drinking too many cups of coffee to count. It hit me hard: Why was I building something I was craving an escape from?

Eventually, I exited that startup and began my path as a writer—a shift that surprised a lot of people, including me. But I felt drawn to this next chapter because I wanted to structure my life in a way that felt fulfilling, not suffocating. Over time, I realized there are a few questions we can ask ourselves to ensure we’re creating a life we actually want to live, not one we have to run from.

Below, you’ll find five questions I consider pivotal. They’re the same ones I revisit whenever I sense my life or career drifting off track. If you’re looking to build a life that doesn’t have you eyeing the exits—this might be your checklist, too.

1. What does ‘success’ actually mean to me?

Back when I was in founder mode, I had a very specific image of success: scaling fast, landing funding, hitting headlines. And for a while, chasing that vision gave me direction. But somewhere along the way, I forgot to ask whether that version of success was mine—or just one I had absorbed from startup culture, investors, or comparison traps on LinkedIn.

After stepping away, I realized that I had never truly defined success on my own terms. I had been running full speed toward a finish line I hadn’t chosen.

Now, success looks different. It’s more about time freedom than title, more about impact than optics. It includes quiet mornings, creative flow, and work that aligns with my values.

It’s worth pausing to ask: Am I striving for something I genuinely want—or something I think I should want? Redefining success might be the most liberating thing you do.

2. What would I do if money were no object?

There’s a powerful question the philosopher Alan Watts once posed: “What would you like to do if money were no object?” I first heard it years ago, but it only truly landed after I left my startup. 

When you’re in the thick of trying to survive or scale, it’s easy to measure your choices in dollars and ROI. But when the noise quieted, I had to face a deeper question: What would I choose if I wasn’t choosing based on income?

This question isn’t about being irresponsible or pretending money doesn’t matter—it’s about getting to the core of your desires before practicality starts editing them. Because when we start from a place of authenticity, we often find that our “impractical” dreams are more doable than we thought—and more sustainable in the long run.

For me, the answer led to writing. Not because it was the most profitable path, but because it felt true. And ironically, that honesty opened doors I never could’ve forced with strategy alone.

So ask yourself: If money weren’t the deciding factor, what would you spend your time building? That’s where the gold is.

3. What would a good week look like?

Deciding on a career path, a business idea, or a whole life direction? That can feel impossibly heavy—like standing at a fork in the road with no map and too many voices in your head. I’ve been there. When I left my startup, people kept asking, “What’s down the line?” And honestly, I had no idea. The big picture felt too big.

So I zoomed in.

Instead of asking what I wanted my life to look like, I asked: What would a good week look like? Not perfect. Not Instagram-worthy. Just good. Grounded. Aligned.

For me, that looked like a few deep-focus writing sessions, meaningful conversations, time outside, less urgency, more presence. When I started designing my weeks around those elements, something shifted. Clarity came—not from some grand plan, but from living small moments that actually felt like me.

If you’re feeling stuck or overwhelmed, forget about your five-year plan for a minute. Try designing one good week. Then, build from there.

4. What would I like to think on my deathbed?

I know, I know—this one sounds a bit heavy, maybe even cliché. But honestly? It cuts through the noise like nothing else.

When you strip away the to-do lists, the KPIs, the followers, the milestones… what’s left? What will you actually care about when you’re looking back at your life, not planning it?

This question has quietly shaped some of my biggest decisions. Not because I want to live every day like it’s my last (that’s a bit much), but because I want to live in a way that future-me would be proud of. Would I be glad I pushed through another 80-hour week for the sake of some metric? Or would I wish I’d taken that walk, written that piece, told someone how much they meant to me?

When the end comes—whenever that is—I don’t want to be left wondering why I waited to enjoy the life I worked so hard to build.

So ask yourself: What kind of memories do I want to replay? What kind of impact do I want to have made? The answers tend to recalibrate everything

5. How much is “enough”?

Let’s get real for a second: passion is great. Purpose is important. But not having enough money? That’s stressful, exhausting, and honestly—not noble.

I’ve been on both sides. I’ve experienced the financial uncertainty of building something from scratch, and I’ve also felt the trap of chasing endless growth, thinking more money would fix the feeling of imbalance. Spoiler: it didn’t.

What has helped is sitting down and getting brutally honest about what I actually need. Not some arbitrary revenue goal. Not what looks impressive on paper. Just:

• How much do I need to live comfortably?
• What does financial stability look like for me—not in theory, but in numbers?
• And how do I balance that with everything else I’ve said matters—freedom, fulfillment, time?

If you don’t ask this, you risk swinging between two extremes: chasing money at the cost of your well-being, or chasing your dreams without a sustainable plan to support them.

There’s nothing glamorous about living in survival mode. Defining enough helps you build a life that’s not only meaningful—but actually livable.

Wrapping up

Building a life you don’t need to escape from is no small task. It requires honesty, consistent self-reflection, and the courage to make course corrections when you realize you’re off track.

But it’s worth it.

These five questions aren’t a magic formula—they’re a compass. A way to regularly check in with yourself and make sure the life you’re building actually feels like yours. Some answers will shift over time. Others will stay surprisingly steady. What matters is that you keep asking.

Because the goal isn’t perfection, or constant passion, or financial abundance at all costs. It’s alignment. It’s building a life where you can exhale, show up fully, and feel proud of how you’re spending your time here.

Start with one question. One honest answer. And go from there.

Until next time, friends.