Why the Best Teams Learn to ‘Be Comfortable Being Uncomfortable’

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Have you ever told yourself “No pain, no gain!” as you try to build muscle or run just a little further? 

We know that some discomfort is the path to strength and fitness. I think this applies to business, too. 

No, I don’t mean you need to live in pain in order to be successful. But I do think “mental muscle development” within an organization and its people requires moments of discomfort. 

That’s why I encourage my team to “be comfortable being uncomfortable.” I don’t want them feeling anxious. Far from it! But if your stress level is at a 2 of 10, you’re not being challenged enough, and that can actually lead to turnover because people are bored and then seek something fresh. 

Before you rush off to shake things up, let me save you from a costly mistake: discomfort without trust is just chaos. When you tell your team to “get comfortable being uncomfortable” like I do, you need to emphasize that you’re talking about inner growth and development. 

You’re not trying to provoke anxiety. You’re looking for that sweet spot where people are stretched just enough to grow but supported enough not to panic.  

Here are five ways to help your team embrace productive discomfort: 

  1. Audit for Autopilot

Your one-on-ones are where this shift really starts. Most of us use these meetings for status reports, but they’re actually your best tool for spotting where people have gone into maintenance mode. 

If you’ve got a top performer hitting every target without breaking a sweat, try asking: “If you had to hand off everything you could do in your sleep, what would be left? What’s the one thing that still makes you a little nervous when you wake up in the morning?” 

This question instantly separates maintenance work from growth work. If they can’t name something that challenges them, they’ve probably stopped stretching. Your job isn’t to punish efficiency. It’s to find their next uncomfortable level. 

  1. Use the Big Win Framework

Once you’ve identified where someone’s hesitating to take a swing, help them calculate the risk like an owner. Instead of letting them list all the reasons it might not work, ask them to play out the extremes. 

“Let’s assume this goes exactly right. What’s the biggest win we walk away with?” 

Push them beyond the numbers. What positive impacts hit customers? What stresses does this resolve for the team? How does this move you closer to your vision? 

After they’ve lived in that successful future for a minute, ground it: “And if this totally misses, what’s the biggest problem we’ll need to clean up?” 

You’re looking for moments where the worst case is manageable but the best case is a game changer. That’s where real growth happens. 

  1. Reframe Anxiety as Excitement

Here’s something I practice myself: when nerves hit, I frame it internally as excitement, not anxiety. Because that’s actually what it is. It’s an opportunity to deliver and prove something to myself. 

If you see someone physically tensing up at the thought of a big project, ask them to think back to their greatest professional win. “How’d you feel the week before that launched? Was it that same knot in your stomach?” 

Our greatest successes usually start with that exact feeling of being out of our depth. That discomfort signals we’re onto something. Help your team see that nervous energy as fuel instead of a warning sign. 

  1. Embed Your Mission, Vision, and Values

Unless you teach your team to problem-solve through their own discomfort, they’ll never truly own their work. You’ll stay stuck as the bottleneck in your own company. 

Drive home your mission, vision, and values regularly enough that they feel like second nature. When your team has these deeply embedded, they develop a shared gut instinct. They understand the boundaries of their roles and where the real goals lie. 

Your values act as the safety net. They give your people permission to be uncomfortable because they know exactly which risks align with where the company is headed. They can weigh risk and reward for themselves because they know the direction you’re going. 

  1. Model It Yourself

To keep your organization from getting lazy, you’ve got to be willing to challenge the status quo yourself. Ask your team: “What’s one process we’ve got right now that’s working fine but is actually holding us back? If you had to break one thing today to make us better tomorrow, what would it be?” 

And here’s another important question: “What’s one thing I can do, or stop doing, that would make this discomfort feel a little safer for you?” 

Leading from the front proves you’re willing to live in the same discomfort you’re asking from your team. You’re building an organization that doesn’t just survive the next market shift but actually looks forward to it because your people have the grit to handle the pivot. 

The bottom line? If your team isn’t feeling at least a little stretched, they’re probably not growing. And if they’re not growing, your business isn’t either. 

Want to talk about building a team that can handle this kind of growth? Click here to schedule a free consultation. 

Anne Lackey

Anne Lackey is the Co-Founder and CEO of HireSmart Virtual Employees, where she helps businesses scale with full-time, highly trained remote staff. With decades of experience in business operations and systems, Anne is a recognized expert in virtual staffing, process efficiency, and team building.


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