I run most mornings through Germantown before the sun comes up. Same routes, same rhythm, same pace. It's comfortable. I know every turn, every hill, every place where the streetlights cut out.
And it’s nice. But it isn’t growth. Still exercise? Of course. Still valuable? Undoubtedly. But will it push me to the next level? Not exactly.
Business is no different. When everything feels easy, when you can operate on autopilot, that's usually when you're in the most danger. Not from external threats, but from your own complacency.
I've seen it happen to myself. I've watched it happen to other entrepreneurs. And I've learned to recognize the warning signs before they become serious problems.
8 Warning Signs You’ve Grown Complacent
#1 – You Haven't Lost Sleep Over a Decision in Months
Remember when you used to lie awake at night wrestling with tough choices? When every major decision felt like it carried real weight? If those nights are gone, you might not be making hard enough decisions.
The decisions that keep me up are the ones that matter most. When I'm sleeping soundly every night, I check whether I'm actually pushing the business—and myself—forward or just maintaining the status quo.
#2 – Your Calendar Looks Identical to Last Year
Pull up your calendar from 12 months ago. Does it look essentially the same as today? Same meetings, same people, same activities?
Your time reflects your priorities. If your schedule hasn't evolved, neither has your business. Growth requires new conversations, different relationships, and activities that challenge what you know.
#3 – You Can't Remember the Last Time You Said "I Don't Know"
Expertise is valuable. But the moment you think you have all the answers is the moment you stop learning.
I'm 53 years old and still a perpetual student of real estate trends, leadership development, and athletic performance. Not because I have to, but because the moment I think I’ve mastered it all is the moment I become irrelevant. Every course reminds me how much I still don't know—and that keeps me hungry.
Your business deserves the same humility.
#4 – Your Team Stopped Bringing You Problems
This one's subtle but critical. When your team stops bringing you challenges, it doesn't mean everything's running smoothly. It usually means one of three things: they've stopped expecting you to help them solve difficult things, they're avoiding problems altogether, or they're not encountering real challenges in the first place.
If they're handling problems without you, that might be good. If they're avoiding problems or never facing meaningful challenges, that's a red flag. Either way, you've lost touch with what's really happening in your business.
#5 – You're Turning Down Opportunities Because They're "Too Much Work"
I get it. You've earned the right to be selective. But there's a difference between strategic focus and avoiding hard work.
When I signed up for the Keys 100 Ultramarathon, I knew there was a real chance I couldn't finish. That's exactly why I signed up. I wanted to challenge myself in a way that scared me a little.
Your business needs those same challenges. If you're only taking on opportunities that fit comfortably into your existing systems, you're not growing.
#6 – Your Competition Surprises You
When was the last time you studied what your competitors are doing? Not just glanced at their website, but really examined their approach?
If you're constantly surprised by what others in your space are doing, you've lost your edge. Comfort makes you inward-focused. Growth requires you to stay aware of the landscape around you.
#7 – Your Morning Routine Never Changes
I love my morning runs. But when I'm training for a specific event, I have to shake things up. Different distances, different paces, different types of training.
The same principle applies to how you start your business day. If you're doing the exact same things in the exact same order, you're optimizing for comfort rather than results.
#8 – You Can Explain Your Business in Your Sleep
This might sound counterintuitive, but stick with me. When you can rattle off your business model, your value proposition, and your differentiators without thinking, you've stopped questioning them.
The best businesses evolve. The story you tell about your company should be getting sharper, more refined, more compelling. If it's exactly the same as it was two years ago, you've stopped adapting.
Breaking Past Complacency
Michelle and I have five kids, and I've learned that parenting requires constant adaptation. What worked with our oldest doesn't work with our youngest. What was effective last year might not be effective today.
Your business is the same. Comfort isn't inherently bad, but it shouldn't be your default state.
If you recognized yourself in some of these signs, don't panic. Awareness is the first step. The real question is: what are you going to do differently tomorrow?
Because the distance between where you are and where you want to be isn't measured in miles. It's measured in the decisions you make when no one's watching, the challenges you choose when you could choose comfort, and the willingness to feel uncertain again.
What signs of comfort have you noticed in your own business? How do you push yourself out of that zone?