How Routines Can Become Ruts – And Destroy Your Success

Want to know what’s keeping you stuck in the status quo?

Your routines.

Wait, what? I know, like so many other people, I’ve written repeatedly about the necessity of having the right habits and routines to make progress on challenging goals. But these habits and routines can also hold you back if you’re not careful.

Let’s explore this idea…

The Dark Side of Routines and Habits

You’re undoubtedly aware of the importance of routines, systems, and habits. They are the heroes of productivity and productivity gurus everywhere sign their praises. There is, of course, a reason for the attention they attract; they work. They are the scaffolding that allows you to tackle increasingly complex and impressive work. When you have a solid morning routine that is optimized for who you are and what you’re trying to accomplish, you start each day in the optimal manner. If you have a well-oiled task management system and ingrained habits that support your goals, you’re going to make amazing progress. These systems and routines push you forward towards your goals and free up your mental bandwidth for tackling more challenging problems and extend what is possible for you.

But they come at a cost. There is a darker side to systems, habits, and routines. They can also create a mental prison, trapping you in outdated patterns that stifle growth. It’s a paradox that many successful professionals grapple with; the very systems that helped you achieve your current level of success might now be the weight holding you back from your next great leap.

Think about it. You’ve optimized your routines for your existing job, your current lifestyle, and your active goals. They’re optimized for the status quo – by definition. They’re the reason you are where you are.

The Challenges

The things that allowed you to achieve your past goals and that brought you to where you are today might just be the very things that are now holding you back.

What if your goals have shifted? What if the path you’ve been on for so long now no longer aligns with your deepest aspirations? This is where your habits and routines can calcify into ruts, leaving you feeling trapped and unfulfilled.

There are two core challenges here:

Recognizing when your habits, systems, and routines have outlived their usefulness. It requires self-awareness to realize your goals have changed and how your routines might limit you. This is tough to do in the thick of the battle of the daily grind in a busy life.
Being willing to adjust – or throw away – what has led you to past success. Your comfort kills your dreams. Your habits and daily routines provide structure and stability to your life, and allow you to be successful in your current state. But they not only got you there, they keep you there, preventing you from hitting the next level. You need to let go of that comfort and success and explore the unknown, knowing only that you will encounter setbacks and challenges with whatever change you’re attempting. You’re going to fail. It’s going to suck at first, and that can be uncomfortable as hell.

So how do we strike a balance? How do we maintain the productivity-boosting power of routines while avoiding the stagnation of ruts?

The Solution

There are a couple of key elements to the solution. The first – and often the most overlooked – is to be clear on what you want (and what you don’t want). It is shocking how many people don’t know what they want to get out of their work or what type of life they want to live. They’ve just got their heads down and keep working, seldom taking the time to reflect on where they’re heading and why.

If you aren’t clear about where you’re heading, you will not get there.

To help get this clarity, I recommend scheduling regular “life audits.” These are moments where you step back from the daily hustle and take a bird’s eye view of your life and career. Are your current habits and routines aligned with where you want to be in five years? In ten? If not, it’s time for some recalibration.

Reflect on how you’d like your future self to be. How would you be spending your time? What habits would you have? Slowly start building up these habits and routines to the extent you can.

Remember to build some flexibility into your systems. While consistency is crucial for habit formation, too much rigidity can lead to staleness. And when you’re trying to form a new habit, you’re going to slip. If you take things too seriously, you might abandon the routine you’re trying to establish. Frequently remind yourself why you’re doing things differently. Keeping your goal top of mind can help make you more likely to form the habit you’re trying to form.

Finally, don’t systemize and make all of your life routine and habitual. You need time to pursue novelty. Our brains thrive on new experiences and by regularly exposing yourself to new ideas, skills, or environments, you keep your mind plastic and adaptable. Perhaps you can introduce “wild card” days into your work week, where you break from your usual routine and explore novel approaches or ideas. This could be as simple as attending a conference outside your field or as bold as taking a sabbatical to pursue a passion project.

Conclusion

Remember, the goal isn’t to abandon routines altogether. That way lies chaos and inefficiency. Instead, aim to create dynamic routines–systems that evolve as you do. Think of your habits and routines not as a fixed track, but as a flexible framework that supports your growth and adaptation.

If you’re feeling stuck in your career, start today by reevaluating your habits and routines. Make small, intentional changes that align with your future vision–and watch as new opportunities unfold. Maybe it’s dedicating an hour each morning to learning a new skill or exploring ideas from a different industry. Small, consistent steps can lead to significant changes.

Ultimately, the tension between ruts and routines is not something to be resolved, but a dynamic to be managed. It’s about finding that sweet spot where your systems provide structure without constriction, where your habits empower rather than entrap.

Embrace the power of routines, but don’t let them define you. Keep one eye on efficiency and the other on possibility. In doing so, you might just find that elusive “something more” you’ve been seeking–not by abandoning your successful systems, but by evolving them to support the next chapter of your journey.

Quotation that I’ve been pondering

I love this quote from the philosopher Albert Camus:

“The only way to deal with an absurd universe is to become so absolutely free that your very existence is an act of rebellion.”

Journal prompt

“Did I have any dreams or aspirations as a child? What did I want to be when I grew up? What might have caused me to give up on those dreams? How might I explore them?”