#30 Why your calendar doesn’t match your priorities and how to fix it
Break free from the 9h-to-5h schedule and start living the life you want
What are your top priorities in life? Family? Kids? Health?
Now, take a look at your calendar. Do you spend most of your time on what truly matters to you? Or is there a disconnect between what you say is important and where your attention actually goes?
It is mind-blowing to me. I see this all the time. Business owners who have control over their schedule yet still work 11-hour days, barely seeing their family, friends, or making time for exercise. Parents who say their kids are their top priority, yet at 17:30, parks are full of nannies.
Your calendar should be a reflection of your priorities, but for most people, it isn’t.
As we grow up and start building a family, life inherently gets more complex. How do we expect to manage if we keep doing the same things we did before? The reality is, the old way of working no longer fits the life we say we want.
Who decided that 9h to 5h was the sacred work schedule? Some ancient productivity overlord? The first step to real freedom is realizing this “default” way of working is just a mental cage. There’s no law. The only thing keeping you stuck is the mental handcuffs. As Naval says:
“Forty-hour workweeks are a relic of the Industrial Age. Knowledge workers function like athletes — train and sprint, then rest and reassess.”
― Naval Ravikant
And now, you’re probably thinking: But how else am I supposed to sustain myself and my family? Money is the problem.
Yes, money is important. But I am afraid it’s not the only reason people are stuck in 9-to-5 jobs.
The 5 reasons why you're stuck (and how to break free)
There are many reasons why people remain stuck in a routine that doesn't align with their priorities. Here are some of the most common ones:
Fear of uncertainty and fear of rejection
Even the thought of quitting can trigger a fear of uncertainty. And once you move past that, the next step—finding a new job, starting a business, or looking for clients—often comes with a fear of rejection. Most people prefer a predictable, stable life, even if it means sacrificing their freedom. The unknown feels riskier than staying put.
Question to think about: what is more risky, a corporate job where you can get fired anytime or working as a freelancer with multiple revenue streams?
Social conditioning and status
From a young age, we’re taught to follow a linear path: study, get a good job, work hard, and retire at 65. Anything outside of this feels “wrong” or “risky,” even if it makes more sense for personal fulfillment.
Quitting a high-status job or choosing an unconventional path often leads to judgment from family, friends, or peers. Many stay stuck because they don’t want to deal with criticism.
Question to think about: Who do you admire and who do you want to become? The partner at a firm who never has time for their family, or the business owner who sees their kids every day?
The identity trap
For many, their job isn’t just what they do—it’s who they are. Leaving a corporate career can feel like losing a part of yourself.
In your 20s, when your priority is paying your bills, it’s normal for your job to be 80% of your identity. But here’s the big realization: your identity should not be fixed.
As you grow, your identity can—and should—expand. Family, relationships, health, and personal growth should become part of the equation. People who break free realize this: your work is what you do, not who you are.
Question to think about: What defines your identity now? and how do you want to evolve over your lifetime?
This is my identity graph over time. What is yours?
Lifestyle inflation & status games
As people earn more, they spend more—on bigger homes, better cars, expensive vacations. These financial commitments make it impossible to step away from high-income but time-draining careers.
Question to think about: what “enough” looks like for you? Every time you spend money remember that you are trading future freedom for whatever you are buying.
Misunderstanding financial freedom
Many believe they need millions to retire, but true financial freedom is about having enough to cover your needs with minimal stress.
More on this in our next post. Subscribe below to read it. We will break down the real numbers about “how much money do I need to retire”
That’s the catch: as we grow up and start building a family, life gets more complex. How can we manage if we cling to the same old habits? The old way of working doesn’t fit the life we want anymore.
Now that we’ve seen the traps, here are three keys to unlock your time.
Three levers to help you break free
Lever 1: Growth vs. Fixed mindset
A fixed mindset is the belief that your abilities and talents are static—you either have them or you don’t. A growth mindset, on the other hand, is the belief that skills and intelligence can be developed through effort, learning, and persistence.
Applied to careers, a fixed mindset sees career setbacks like a rejection, a failed project, or a missed promotion, as proof that you’re not good enough. A growth mindset sees them as opportunities to learn, adapt, and refine your approach, knowing that progress comes from persistence, not perfection.
When you get rejected by a client or potential employer, what does it mean?
A fixed mindset says: I’m not good enough. I’ll never find another opportunity.
A growth mindset says: This is a chance to refine my pitch, improve my skills, and find a better fit.
This shift in perspective changes everything. Carol Dweck’s book Mindset explores this in depth. It’s a must-read if you struggle with fear of failure.
But mindset alone isn’t enough, you need action.
Lever 2: Agency is the seed of everything
One of the biggest obstacles to breaking free is lack of agency. Agency is the ability to act intentionally, to shape your circumstances rather than just reacting to them. (as we explained in our post about education, is one of the biggest failures of the education of our time)
Someone with agency doesn’t just accept their job’s demands as unchangeable. They ask: Can I negotiate more flexibility? Can I transition to a different role that aligns better with my priorities? Can I build a side project that lets me take control of my time?
Without agency, work runs your life. With agency, you start designing your own reality.
Fostering agency starts with shifting from a victim mindset to an ownership mindset by asking "What is within my control?" instead of "I have no choice." Small decisions reinforce control, like setting boundaries at work or saying no to misaligned commitments. Most importantly, action creates momentum. Whether it’s reaching out to industry contacts, publishing content, or attending events. The more you move, the more control you gain over your life and career.
Lever 3: Breaking free is a journey, not a switch
People think of breaking free as a sudden moment. One day you’re working full-time, the next you’re in a fully flexible set up. But that’s not how it works. It’s a sliding scale. The ones who break free make intentional changes, small at first, but compounding over time.
It is time to start.
Most people wait for the "perfect moment" to take control of their time, but the truth is, that moment never comes. The ones who break free aren’t necessarily the smartest or the wealthiest—they're the ones who decide to start.
So, what’s the one thing holding you back from reclaiming your time? Drop a comment below. We would love to hear your excuses thoughts ;).
And if you want tailored advice for your, copy paste the following prompt into the AI chat of your choice (chatgpt, grok etc) and attach this article and your linkedin profile to the prompt:
“You are now a career advice expert. Based on the attached article and my LinkedIn profile, I need your help. I’m currently a [your job title] at [your company], and I want to transition out of my full-time role. Can you provide three career path options that align with my expertise, along with a step-by-step plan on how to execute each one?"
Thanks for reading 3x!
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