Let's be real. When you first started your business, you didn’t set out to work 60-hour weeks. But, if you’re like most founders, you’re probably spending around 18% more time at work than you believe you should, clocking around 15 more hours a week than the national average just to try and get everything done. That’s almost two full workdays added to an already packed schedule.

None of us wakes up one morning and decides to make our lives more difficult, so how did things get so off track?

The honest answer is, it has less to do with bad habits or poor planning and a lot more to do with how our brains are wired.

So, let's take a look at the psychology behind this common founder trap, learn how to recognize when you're caught in it, and, more importantly, find ways to steer clear of it entirely.

The science behind getting stuck in our ways

It’s easy to assume that people stick with tedious routines just because they’re being stubborn, but research suggests there’s a deeper reason.

In a recent study involving more than 4,000 people, participants were given the chance to switch from a dull, repetitive task to one that was more enjoyable and stimulating, without any difference in pay or time required. You’d think most people would jump at the chance, right? Surprisingly, about 25% chose to stay with the boring task. No extra reward, no hidden catch.

Why?

The answer lies deep in our brains.

When we repeat the same task over and over, our brains create "cognitive shortcuts" for it, which ultimately makes it feel easier and more automatic. It might not be the fastest or most effective option, but it feels smoother because we’re not thinking as hard about it.

Psychologists call this "entrenchment."

And the longer we do something a certain way, the more "entrenched" we become. Change demands effort, even when it promises something better. So when it comes to shaking up our routines or trying something new, the mental friction can be surprisingly strong.

Why founders are especially vulnerable to this trap

While this tendency affects people across all walks of life, there's something about the entrepreneurial mindset that makes us particularly susceptible to getting stuck in our own particular patterns, even when those patterns have outlived their usefulness.

You learned to do everything yourself

In the early days of bootstrapping a business, there’s no team to lean on. It’s just you and whatever tools you can get your hands on. So, you wear every hat: marketer, salesperson, customer service rep, tech support—you name it. If something needed doing, you rolled up your sleeves and figured it out.

And because that approach got you this far, it’s easy to think, “If it ain't broke, don't fix it.”

You've repeated your early processes hundreds of times

When you first started out, you were building systems from scratch. Maybe you hacked together a way to onboard new clients, send invoices, follow up on leads, or manage your inbox. You didn’t have time to perfect it; you just needed it to work.

And once it worked? You stuck with it.

Now, those scrappy first-time solutions have become your go-to routines. You know the clicks by heart. It’s second nature. And that mental muscle-memory makes it easy to keep doing things the way you always have.

Your identity is tied to being hands-on

There’s real pride in being able to say, “I built this with my own two hands.” And rightfully so.

You’re the one who knows the ins and outs of every process because you built the processes. Every decision, every detail, every hard-earned win… it all has your fingerprints on it.

But here’s the tricky part: when your sense of worth or value gets tied up in doing, it becomes incredibly hard to step back. That emotional connection to your current way of working makes it harder to embrace new approaches, even when, deep down, you know they could be better for your business and your well-being.

You've been rewarded for persistence

Persistence is one of the reasons you made it this far. When things got tough, you didn’t walk away. When people doubted you, you proved them wrong. When the odds were against you, you showed up anyway. That kind of grit is baked into the business world, and it’s often what separates those who succeed from those who give up too soon.

However, the same mindset that helped you push through rejection, cash flow issues, and sleepless nights can also make you push through bad systems, clunky processes, or low-value tasks, just because you’re used to enduring things instead of fixing them.

Common signs of founder entrenchment

Entrenchment doesn't storm into your office and announce its arrival. It's far more insidious. It quietly seeps into your daily operations, masquerading as diligence, as quality control, or simply as "the way things have always been done."

So, if you’re wondering whether entrenchment has crept into your work, here are a few common signs:

• You’re still handling manual tasks that could be automated.
• You’re involved in every single decision.
• You rely on outdated tools because “they got us this far.”
• You hesitate to hire or delegate because “no one knows the business like I do.”
• You’re working more hours but getting less done.
• Your team constantly asks for permission instead of taking initiative.
• You feel uncomfortable stepping away from the weeds.
• You often say, “It’s quicker if I just do it.”
• You’re excited about big ideas but never have time to explore them.

What it’s really costing you

Hanging out in your comfort zone and sticking with what you know can feel like the smartest choice, especially when it’s worked in the past.

But here’s the thing: staying there often comes with a price tag that gets steeper over time.

The personal price you pay:

• You’re running on empty. Doing all the things, day after day, leads to burnout before you even know it. It’s exhausting, and that constant grind wears you down more than you probably want to admit.
• You miss out on the benefits of growth. Avoiding new challenges might feel safer, but it means you’re not stretching yourself or your business in exciting ways. Growth often comes from stepping outside that comfort zone.
• Your brain doesn’t get the space it needs. When you’re stuck in the daily hustle, there’s less time for dreaming big, thinking strategically, or getting creative with new ideas.
• You fall out of love with your work. When every day feels like a slog of putting out fires, it’s hard to feel the joy and passion that got you started.

What it does to your business

• You become a bottleneck. When everything has to go through you, progress slows. That makes it tough to scale, no matter how strong your vision is.
• Your team members get frustrated. When your team feels micromanaged or stuck waiting on your green light, morale dips and momentum stalls.
• Opportunities slip through your fingers. While you’re buried in the day-to-day grind, chances to innovate, partner, or expand just pass you by.
• Innovation takes a back seat. Rigid thinking and outdated processes limit creativity and stop you from adapting to change.
• Growth is limited to how much you can personally handle. If everything depends on your time and energy capacity, there’s a ceiling on how far you can go.

How to break free from entrenchment

Recognizing the patterns and costs of entrenchment is the diagnostic step. What comes next is the cure. Don't mistake the goal as simply working fewer hours. The real aim is to shift your effort away from draining tasks and onto the work that truly drives growth and creates exponential value.

1. Ask yourself the right questions

Self-awareness is the first step to change. Try asking:

• When was the last time I changed how I approach a big task?
• What am I doing just because “that’s how we’ve always done it”?
• Where do I feel nervous about handing things over?
• If a coach watched me work for a day, what would they tell me to stop doing?

You don’t have to have all the answers right away, but they can help you spot the patterns that are keeping you stuck.

2. Rotate your tasks

Switching between different types of work keeps you mentally flexible. For example, you might spend Monday focused on operations and Tuesday on growth. This kind of rotation keeps you from going too deep into autopilot.

3. Time-box your responsibilities

Give yourself a set amount of time to handle certain tasks, then stop. Whether it’s checking your inbox or reviewing a document, setting time limits helps you avoid going down rabbit holes.

4. Schedule regular pauses

Put reminders in your calendar to step back and reflect. Even a 10-minute check-in once a week can help you catch inefficiencies before they take over.

5. Bring in accountability

Founders are used to answering to themselves, but even the most independent and driven among us can benefit from having someone in their corner to check in regularly.

Find a coach, mentor, or peer who will ask the tough questions and keep you honest about how you’re spending your time. Sometimes all it takes is an outside perspective to see what you’ve been missing.

6. Use a decision framework

Create clear criteria for when to stick with current approaches versus when to switch to new methods.

For example:

Stick with your current approach when:

• It’s working well, and change would cause more disruption than it’s worth. If the system isn’t broken, and it’s delivering what you need and it’s helping you meet your goals, it might be smarter to leave it alone—at least for now.
• You’re still learning and you need to master it. Repetition builds skill. If you’re in the learning phase, consistency can help you gain confidence and efficiency.
• The timing isn’t right. External factors like limited runway, volatile market conditions, or major transitions can make now a risky time to overhaul anything big.
• The alternative isn't clearly better. Change for the sake of change can be exhausting. If a new approach doesn’t offer clear benefits, it’s okay to hold steady.

Consider making a change when:

• You’ve become the bottleneck. If everything grinds to a halt without your direct involvement, it’s a sign your current systems aren’t scalable.
• There’s a clearly better way. If a new tool, system, or strategy can save you time, reduce errors, or free up mental space, that’s worth exploring.
• The current method is draining your team—or you. If something’s consistently causing stress, burnout, or friction, that’s a red flag that needs your attention.
• You dread the work. If you find yourself putting off certain recurring tasks, that’s often a signal that something needs to change—either how it’s done or who’s doing it.

Having predetermined criteria removes the emotional decision-making that often keeps us stuck, and writing it down makes it easier to follow when your schedule gets hectic.

What's the bottom line?

As a founder, you’ve weathered uncertainty, solved impossible problems, and shown up even when it felt like everything was on your shoulders. You’ve powered through hard seasons, made tough calls, and learned more than most people ever will.

But here’s the truth: you don’t have to carry it all to prove your value. You are the heart of your business, not because you do everything, but because you had the vision and courage to start. That doesn’t go away when you step back from certain tasks or build systems that don’t revolve around you.

The habits that brought you here were about survival. The habits that will take you forward? They’re about sustainability, and having space for what truly matters to you, to your team, and to the life you’re trying to create.

Ready to stop doing it the hard way?

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