Newsletter #20

Authentic Success: A tool to help you define your own version of success

Hi there,

Before we dive into the theory, let's start with something practical.

I've created a tool called the Authentic Success Quiz – a short online assessment that will help you map your personal definition of success. It takes about 10 minutes.

Here's how it works: You'll see 32 statements. All of them sound positive because they're all legitimate versions of success. Your job isn't to identify which ones are "correct." Your job is to notice which ones resonate with you.

"Success means finding inner peace regardless of external circumstances." "Success means building something that outlasts you." "Success means living authentically, even when it's uncomfortable."

They all sound good. But which ones resonate most deeply? Which ones feel like they were written about you specifically?

Be honest. Don't score everything highly just because you think you should value it and you’ll get to what actually matters to you.

After you complete the quiz, you'll receive your personal Authentic Success Profile with tailored insights to guide your next steps toward lasting fulfillment.

Take the Authentic Success Quiz →

Discover your unique Authentic Success Profile when you take the quiz.

The Problem with Most Success Advice

Now, let's talk about why this matters.

Most success advice assumes you already know what success means. It then sells you tools to get there faster.

The morning routine. The productivity system. The investment strategy. The mindfulness practice.

But that assumption skips the hardest question: What kind of success are you actually working towards?

The productivity methods, the mindfulness practices, the wealth strategies – they all point in different directions because they serve fundamentally different visions of a life well-lived.

Inner peace or outer achievement?

Accepting your nature or transforming it?

Taking bold leaps or playing it safe?

Accumulating resources or living simply?

These aren't details to figure out later. They're foundational choices that lead to radically different lives. And here's the uncomfortable truth: You can't pick all the "good" answers because they genuinely contradict each other.

The Eight Philosophies of Success

This assessment presents eight distinct philosophies of success drawn from history's great thinkers. Stoicism. Buddhism. Existentialism. Aristotelian virtue ethics. And so on. Each one captures something real and valuable about human flourishing. (NOTE: I’ve actually created a much deeper assessment based on 15 philosophies if you’re interested. But that was too complicated for the online tool!!!)

None of them are 100% right. None of them are 100% wrong.

But here's what generic success advice obscures: You're probably trying to pursue conflicting definitions simultaneously, creating an incoherent mixture that leaves you exhausted from chasing goals that work at cross-purposes.

Think about it.

You can't simultaneously seek inner detachment and worldly achievement with equal commitment. You can't completely accept your nature while working relentlessly to transform it. You can't maximise individual excellence and collective contribution without sometimes choosing one over the other.

The tension between these philosophies isn't a bug. It's the feature. It reveals what you actually value versus what you think you should value.

Where Are You Contradicting Yourself?

I spent years trying to succeed on all fronts. Thinking all forms of success were relevant to me. Because those were the forms of success I saw around me. The ambitious entrepreneur. The present parent. The mindful meditator. The adventurous risk-taker. The stable provider.

I was following advice from all directions, not realising that some of it pointed north while other advice pointed south.

The result? Exhaustion. Confusion. And a nagging sense that I was trying to do all the "right" things but somehow still felt “wrong”.

The breakthrough came when I stopped trying to reconcile competing visions of success and started getting honest about what actually mattered to me. Not what should matter. Not what mattered to people I admired. What mattered to me.

That required a good dose of honest clarity about my internal contradictions.

Why was I chasing outer achievement while also trying to cultivate inner detachment? Why was I accumulating money while also claiming to value simplicity? Why was I playing it safe while also beating myself up for not being bold enough?

It turned out that these contradictions weren't internal character flaws. They were navigation errors I’d made. I was following maps that led to different destinations.

The Goal Isn't to Find the "Right" Answer

This assessment won't give you the answers to instant success. It won't tell you which philosophy is correct. That’s because A) it’s a simplified tool and B) because there is no correct philosophy.

The goal is to clarify which tensions matter most to you and where your actual life contradicts what you genuinely value.

But the assessment will help you ask better questions: which success philosophies have you been unconsciously following? Where are your internal contradictions creating confusion? What would success actually look like if you stripped away borrowed definitions and got honest about what matters to you?

Some people will discover they've been chasing career advancement while genuinely valuing inner peace above all else. Others will find they've been trying to accept themselves while simultaneously running self-improvement programs that suggest they're fundamentally insufficient.

Both patterns create suffering. Not because you're doing something wrong, but because you're trying to walk two paths at once.

You Can't Pursue Authentic Success If You Don't Know What It Is

Here’s my thinking in a nutshell…All the productivity hacks in the world won't help if you're climbing the wrong mountain. All the mindfulness practices won't create peace if you're pursuing a definition of success that requires constant striving. All the wealth accumulation won't create security if what you actually value is freedom from material concern.

The tools matter. The hacks, the practices, the methodologies all work (well some of them do). But they only work when you're clear about where you're trying to go.

That clarity doesn't come from adding more advice. It comes from stripping away everything that isn't actually yours. From getting quiet enough to hear what you genuinely value beneath the noise of what you think you should want.

That's what this assessment is designed to help you do.

[Take the Authentic Success Quiz →]

It won't solve everything. But it will give you something more valuable than a quick fix solution. It will provide a bit of clarity about what you're actually trying to solve for.

Because the truth is, you can't pursue success if you don't know what it is.

Until next time,

Simon