In a world that no longer tells you exactly what to do, how do you decide what’s next?

Are you truly the architect of your life, or are you unknowingly shackled by the ghost of "supposed to"?

What if the biggest question we should be asking isn’t "What should I do now?" but "Who told me I should be doing anything at all?"

When the Gatekeepers Vanished

We find ourselves in an era of unprecedented freedom, yet many grapple with a profound sense of being adrift. As Seth Godin points out, society once readily answered the question, “What should I do now?” dictating everything from our careers to our hairstyles.

Those clear, albeit restrictive, paths have largely dissolved. The gatekeepers, we're told, have left the gates unlocked. However, the deep-seated indoctrination of what we're ‘supposed to’ do, be, and achieve lingers powerfully.

The Map Is Gone, but the Compass Is Faded

This creates a jarring disconnect: the promise of boundless choice clashing with an internal compass still trying to navigate by old, faded maps, leading to a paralysing fear of not measuring up or getting it all "wrong."

For generations, society handed us a map and a script. It told us what was acceptable, what was respectable, what was successful. From the haircut on your head to the degree in your hand to the car in your driveway, life was a paint-by-numbers kit.

And then, almost overnight, the rules disappeared. Or rather, the gatekeepers forgot to lock the gates. Suddenly, you were free. So free that you had no idea where to go. Now, those clear paths have dissolved. The freedom to choose your own way is exhilarating but it comes with a catch: uncertainty.

Paralysis of Choice and Its Hidden Costs

This newfound freedom can paralyse you. Without a roadmap, you might feel lost, second-guessing every decision. The pressure to optimise every choice can spiral: your career, your hobbies, even your downtime.

This isn't just a fleeting discomfort; it’s a recipe for chronic anxiety and dissatisfaction. The chasm between this newfound autonomy and the persistent echo of external expectation can, as Chris Williamson highlights, turn us into insecure overachievers.

We struggle to distinguish between the few areas demanding our utmost vigilance and the many that don’t, believing everything is a high-stakes battle. We try to "win" at everything, even activities meant for relaxation, like the person passing out in a breathwork class by pushing too hard. What, exactly, are we trying to win?

This relentless pursuit, often fueled by impractical idealism and a failure to appreciate reality's complexities, as Ray Dalio might suggest, transforms the potential joy of living into an exhausting series of tasks. We're so busy trying to perfect and control, we forget to simply be.

The ennui and fear that Godin speaks of become our constant companions, exacerbated because, as Shane Parrish’s insights on relativity show, our perspective is inherently limited, yet we treat our subjective experience as the absolute truth, overlooking the vastness of what we cannot see.

Spinning in Every Direction—Burnout Beckons

This isn’t liberation. For many, it’s low-key existential dread. That blank canvas can feel like a void. We mistake infinite choice for direction, mistaking "possibility" for "clarity." And worse, the voices of the past whisper still: "You should be doing more." "You should know the way." "You should be better."

You're spinning in a thousand directions because you’re trying to optimise, win and perform, even at rest. Even when you're just being. You’re measuring your life against frames of reference you inherited, not ones you chose.

You might push yourself to perfect everything, from your morning routine to your life’s purpose, only to find you’re not enjoying any of it. It’s like holding your breath too long, hoping to “win” at life, only to collapse under the strain.

The result? Burnout masquerading as ambition. Anxiety dressed up as aspiration.

When the Cage Is Only in Your Head

But what if the cage isn't the world, but our perception of it? What if, as Chris Williamson radically suggests, there is actually no problem to be fixed? The game changes entirely when we dare to challenge this ingrained notion of constant self-improvement as a solution to a non-existent core flaw.

Imagine embracing what Ray Dalio terms "hyperrealism." This isn’t about abandoning dreams; it's about grounding them in the fertile soil of things as they are, appreciating even the harsh beauties of reality.

It's about understanding, as Shane Parrish explains, that while our experiences shape our unique vantage points, these are relative, not absolute. This doesn't mean all views are equally valid, but it’s a call to courageously examine our assumptions and actively seek out what others see that we can't.

"Figuring out what to do next," a core challenge identified by Godin, starts not with finding a perfect, pre-ordained path, but by first seeing the landscape clearly. But what if the goal isn’t to fix something that isn’t broken?

What if there is no singular right move, just a series of increasingly honest ones? The hyperrealists among us have learned to stop worshipping idealism and start revering reality.

Building a Relationship with Your Own Truth

And the reality is: You don't need a perfect plan. You need a relationship with truth. Yours. You need to realise that your experience, your lens, your position are valid, but not absolute. There's power in seeing your perspective as a perspective. Ask what others see that you can't. Update your worldview. That’s growth, not flaw.

Your perspective, shaped by your unique experiences, isn’t the only one. Others see the world differently, and that’s not a flaw; it’s a chance to grow. By grounding yourself in what’s real, not idealised, you can choose dreams that align with who you are, not what you think you’re supposed to be.

Dancing with Freedom Instead of Fearing It

The resolution isn't to find the right answer from an infinite list of choices, but to embrace the privilege of owning our choices, as Godin beautifully puts it, and learning to "dance" with them.

This dance is best performed when we are, as Dalio advocates, hyperrealistic – choosing our dreams wisely by understanding the terrain. It involves recognising the relativity of our own perceptions and having the humility to seek out diverse perspectives to illuminate our inevitable blind spots.

Ultimately, it’s about redirecting our finite time and energy away from the exhausting pursuit of perfecting and controlling every facet of life, and as Oliver Burkeman, advises, pouring it into "something infinitely more absorbing than trying to keep life under control, which is actually living it.”

You don’t need to optimise or win every moment. There is no universal "doing this wrong." True fulfillment and a successful life may well be the potent alchemy Dalio describes: Dreams + Reality + Determination.

You don’t need to chase perfection or decode the master plan. You need to live. Not everything matters equally. Not every breath needs to be held longer. You are allowed to care deeply about what calls to you and release the rest.

The real privilege isn't knowing what to do next. It's owning that the choice is yours. Not as a burden. As a dance. And you learn the steps as you go.

Life doesn’t need to be a flawless performance. Ground your dreams in reality, like a builder who knows the terrain before breaking ground. Listen to others to see what you might miss, and let go of the need to control every outcome. Pour your energy into what truly matters—living, not perfecting.

So, step away from the illusion of ‘supposed to,’ embrace the beautiful, sometimes harsh, reality, and consciously choose your next step, knowing it’s the living that matters, not an unattainable perfection.

Freedom to choose is a privilege; dance with it, imperfections and all.

The Essential Concepts

The Illusion of Unfettered Freedom: While we live in an era where societal norms are less prescriptive, the ingrained sense of what we 'should' be doing still heavily influences our choices and can lead to a feeling of being adrift despite the apparent freedom.

The Fading Map and the Unreliable Compass: The clear paths of the past have largely disappeared, leaving us with a sense of boundless choice that clashes with an internal compass still guided by outdated societal expectations, resulting in a fear of not measuring up.

The Paralysis of Over-Optimisation: The newfound freedom to choose can be paralysing, leading to constant second-guessing and the pressure to optimise every aspect of life, which ultimately breeds anxiety and dissatisfaction.

The Internal Cage of 'Supposed To': Often, the limitations we experience are not imposed by the external world but rather by our own internalised beliefs about what we are expected to do or achieve, hindering us from pursuing our genuine desires.

The Art of Hyperrealism: Instead of chasing an idealised version of life, grounding our dreams in the reality of things as they are, and appreciating our subjective perspective as just one view, can lead to more authentic choices.

Building a Relationship with Personal Truth: True direction comes not from a perfect pre-ordained path, but from understanding and aligning with our own values and experiences, while also being open to the perspectives of others.

Dancing with the Privilege of Choice: The resolution to the anxiety of infinite choices lies in embracing the freedom to choose our own way and learning as we go, rather than seeking a single 'right' answer or striving for unattainable perfection.

I am a Knowledge Worker...

What does it mean for me?

This post suggests that despite the apparent freedom in career paths today, you might be operating within the internal cage of 'supposed to', driven by ingrained expectations of what a successful knowledge worker should be or achieve.

This can lead to the paralysis of over-optimisation, where you feel pressured to excel in every aspect of your work and professional development, causing anxiety and burnout.

The fading map and the unreliable compass metaphor resonates, as the traditional, linear career paths have dissolved, leaving you navigating with an internal compass still pointing to old societal norms of success, rather than your own genuine aspirations within the corporate landscape.

Embracing the art of hyperrealism means grounding your career goals in the reality of your skills, interests, and the actual opportunities within your organisation, rather than an idealised version of what you think you should want.

How do I action this?

• Challenge Your "Supposed To" Beliefs: This week, identify one aspect of your career aspirations or daily work where you feel a strong sense of "I should be doing this." Question the origin of this belief. Is it genuinely aligned with your values and interests, or is it an inherited expectation?
  
• Practice Hyperrealistic Goal Setting: Instead of focusing solely on an ideal outcome, take one of your career goals and analyze the current reality: your existing skills, available resources within the company, and potential obstacles. Adjust your approach to be more grounded in these realities.
  
• Seek Diverse Perspectives on Your Path: Have a conversation with a colleague whose career trajectory or work style differs significantly from yours. Ask about their perspective on professional growth and what guides their choices, opening yourself to viewpoints beyond your current frame of reference.
  
• Experiment with "Dancing with Choice" in a Small Way: In an upcoming task or project where you have some autonomy, consciously choose an approach that feels more authentic to you, even if it deviates slightly from the "standard" way of doing things. Reflect on the outcome and your experience.
  

I am a Freelancer, Solopreneur, Entrepreneur, Independent Worker...

What does it mean for me?

As you forge your own path, this post highlights that the absence of a predefined entrepreneurial roadmap can be both liberating and daunting.

You might feel the pressure of the paralysis of over-optimisation, believing you should be mastering every marketing channel, networking event, and tech stack simultaneously.

This stems from the illusion of unfettered freedom, where the lack of gatekeepers doesn't automatically equate to clarity.

The internal cage of 'supposed to' can manifest as adhering to outdated business advice or comparing yourself to seemingly perfect online personas.

Embracing the art of hyperrealism means grounding your business strategy in your actual skills, the market's real needs, and your genuine vision, rather than chasing an idealised version of solopreneurial success.

How do I action this?

• Identify Your "Shoulds" in Business: Make a list of 2-3 things you feel you should be doing in your business (e.g., a specific social media platform, a particular type of content). Question where these "shoulds" come from and whether they truly align with your strengths and business goals.
  
• Practice Hyperrealistic Business Planning: Take one of your business goals (e.g., client acquisition, product development). Instead of focusing on an ideal scenario, honestly assess your current resources, time constraints, and market realities. Adjust your plan to be more grounded in these factors.
  
• Seek Diverse Perspectives from Other Independents: Connect with a solopreneur or freelancer whose business model or niche is different from yours. Ask about their biggest challenges and how they navigate the freedom of being their own boss, gaining insights beyond your immediate circle.
  
• Experiment with "Dancing with Choice" in Your Approach: In an upcoming business decision (e.g., a marketing strategy, a new tool), choose a path that feels more aligned with your authentic style and values, even if it's unconventional. Reflect on the process and the results.