It’s OK to Take a Break

I just got back from hiking in the Dolomites. Two weeks of steep trails, high passes, and, best of all, no signal.

What I love most about these trips isn’t just the views. It’s the silence.

No Slack. No group chats. No endless scroll of people telling me what I should care about. Just my boots, my breath, and my thoughts.

I’ve come to realize these breaks are a real life reset button. 

But getting there—really unplugging—is harder than it sounds. Because let’s be honest: stepping away from work feels tough, almost impossible in high-stake businesses.

There’s the phone in your pocket whispering, what if they need you? Or worse, your own boss (or inner critic) subtly signaling that taking a break is fine, but could you just do this one last thing.

I’ve felt that tension many times, even caused it for others. I’ve learned the hard way: glorifying hustle and staying “always on” isn’t leadership. It’s burnout masquerading as productivity.

But in the stillness of the mountains, without the algorithm feeding me what’s urgent, I can finally listen to what’s important. That’s where clarity lives. 

That’s where I remember what I actually want, who I want to build with, what I want to create, and the kind of person I want to be.

The Problem with Always Being “On”

In our hyperconnected world, being reachable is often confused with being responsible. Phones in our pockets, Slack in our palms, meetings booked wall-to-wall—it all creates the illusion of progress. But more often than not, we’re just reacting, not reflecting.

There’s a deeper cost to that kind of overload: it drowns out your inner voice. It leaves no room for curiosity, clear processing, for long-term thinking, or deeply considering the question, “What do I actually want?”

I’ve felt that pressure myself, both internally and from others. The anxiety of stepping away. The guilt of a delayed reply. The subtle signals from bosses or peers that “real leaders” are always available. I’ve even been that leader at times too, someone who unintentionally rewarded burnout and lacked boundaries.

But I’ve learned (and am still learning) that constant connectivity is not the same as consistent leadership. In fact, they’re often at odds.

A Conversation That Changed My Perspective

In an upcoming episode of my podcast Unlearn, I sat down with Brad Feld, co-founder of Techstars and author of Give First. We talked about the power of giving without expectation, the long game of relationships, mentorship, and most unexpectedly, how stepping back is often the way forward.

Brad shared his own experience of burnout. After years of public visibility, constant travel, and always being available, he just stopped. No announcement. No explanation. He unplugged, disappeared from the public eye, and took time to reflect.

What stood out to me was how natural it sounded yet how rare it is in our world. The courage to step away without fear of irrelevance. The wisdom to pause even while others are accelerating. It echoed something I’ve discovered on every long walk I’ve taken: when you’re not overwhelmed by outside noise, your true priorities finally speak up.

As Brad put it, “This is the shot we have. Why spend it chasing the wrong things?”

The Hardest Part: Letting Go

Unplugging doesn’t come easy. I’ve resisted it. I’ve rationalized my way out of it. I’ve snuck down to hotel business centers at 5 a.m., refreshing my inbox while my wife and kids slept in the room upstairs.

For years, my self-worth was tied to being responsive, being needed, being productive. And even now, the voice in my head says things like, “You can’t afford to take a break.” Or worse, “Other people are moving faster, don’t fall behind.”

But I’ve learned to challenge that voice. Because I’ve seen the results of stepping away.

When I return from these hikes, I’m not behind, I’m ahead. I’m clearer, calmer, and more focused. I make better decisions. I reconnect with the deeper “why” behind what I’m doing. 

And most importantly, I remember who I am without all the external pressure shaping my identity.

The world doesn’t collapse when I disconnect. But I’ve come close to collapsing when I don’t.

Why Taking a Break Matters

Taking time away isn’t about luxury, it’s about longevity. It’s not a weakness. It’s wisdom. Here’s why stepping back is vital for founders, leaders, and builders:

• Mental Clarity: Constant information streams make it hard to think deeply. Stepping back resets your cognitive bandwidth.

• Rediscovering Inner Desires: When you disconnect, you stop reacting to what others want from you and start hearing what you want.

• Pattern Recognition Reflection: reveals patterns—what’s working, what’s not, and what you’ve been avoiding.

• Realignment: The only way to know if your current path is the right one is to stop walking long enough to check the map.

• Perspective: Disconnection provides altitude. It helps you see the bigger picture—and what really matters in the long run.

What I Learned From the Mountains

Coming back from the Dolomites, I noticed a subtle shift. The same work was waiting. The same challenges, frustrating behaviors and situations at work. 

But I felt different.

What I wanted was different too.

All those undesired content pushes and prompts I’d absorbed unconsciously: Grow the business faster, earn more, be more visible… they no longer held the same weight. 

In their place were quieter truths: Be present. Make things that matter. Work with people you love. Stop chasing what doesn’t help you grow.

That insight didn’t come from reading another business book or attending another strategy session. It came from walking through fog, surrounded by peaks, hearing nothing but the sound of my breath and boots.

Letting Others Take the Wheel

Part of the fear of taking a break is feeling like everything will fall apart without you. I get it. I’ve been there.

But the truth is, your absence can be a gift—to your team, your company, and even your ego. It allows others to step up. It exposes weak points in your delegation. It forces systems to function without bottlenecks.

Stepping away is leadership. It’s how you build resilience, not just in yourself, but in the people around you.

Your Reset Doesn’t Have to Look Like Mine

Not everyone’s reset is hiking mountains or going off-grid. That’s not the point.

The point is: Find what brings you clarity. Carve out time for it. Protect it. Practice it often. And don’t apologize for needing it.

As Brad said in our podcast, “Generosity fuels the ecosystem.” That includes being generous with yourself—your rest, your reflection, and your energy.

You can’t give first if your tank is empty.

Because sometimes, the best way to move forward…is to stop, listen, and ask yourself where you truly want to go.

What’s Your Reset Routine?

If you’ve read this far, thank you. And now, a question for you: What’s your reset routine?

How do you step away, unplug, and reconnect with what truly matters to you?

I can go hiking in the Dolomites every weekend. But we can build in regular practices to reset. Here are a few strategies I’ve integrated into my life (some the hard way):

1. Half-Year Disconnects

My wife and I agreed recently that we’d take one week every six months completely off—no phones, no laptops. Early on, I hated it. 

Now, I crave it.

2. Digital Detox Days, even Weekends

From Friday evening to Sunday morning, I try not to engage with work or tech unless it’s an emergency. No email. No Slack. No social.

3. Walking Without Devices

Some of my best thinking happens on long walks—no music, no podcasts, just space. Try it.

4. Solo Reflection Time

Book time with yourself. An hour. A day. A long weekend. Journal. Think. Dream. Let the silence do its work.

5. Decide What Not to Do

Sometimes, taking a break means stepping away from commitments that no longer serve you. Make space by saying no.

I’d love to hear your routine—and maybe borrow a few ideas myself. 

Let’s normalize taking breaks as an essential part of doing great work.

Written by: Barry O’Reilly for the Barry O’Reilly Blog.