Hey everyone,

Today’s post is a little different to my usual Sunday format.

What was meant to be a concise idea quickly exploded into a lengthy draft that felt too nuanced to edit down.

I was surprised by the rate at which the words spilt onto the page. Clearly I’ve been thinking about this more than I thought.

And for good reason, because it is one of the most critical questions we must answer.

Today at a Glance

• There is an age-old debate, still raging online today, between people who believe that to achieve success, one must sacrifice everything to pursue that goal (including their relationships, their social life, and even their health) and people who prefer to optimise for work-life balance.

• Most of us overlook the key factor in this argument: how each individual defines success and what it looks like in their life. This is one of the most deeply personal questions we all have to answer.

• Real problems arise when we have a disconnect between our definition of a successful life and how we actually live life in pursuit of that goal. The smaller the disconnect, the bigger the probability of living a fulfilled life.

Success

The most personal decision you’ll ever make

Never bet on a founder who doesn’t work weekends

I’ve seen this phrase floating around the internet recently.

Everyone was getting triggered no matter what side of the debate they fell.

This feels like an age-old debate in our hypermodern society:

Should you sacrifice everything to build a breakthrough startup or optimise your life to balance your work, family, and health commitments?

While each side’s argument is convincing, there is a severe lack of nuance.

This is unsurprising considering the platforms (X, LinkedIn etc.) where debates occur today.

I completely get the founder who is so busy from Monday 9 am to Friday 1 pm with Slack, email and meetings that the only time they have for deep work is Friday 3 pm to Sunday midnight.

But I also completely get the founder who priorities work-life balance and only works weekdays, 9-5 pm.

Define your version of success

The thing that we overlook in this argument is how each individual defines:

1. What success means to them.

2. What success looks like in their life.

This is our most personal decision (there are literally 8 billion different ways it could be defined). Yet people continue to fight about it online, comparing apples with oranges.

In the essence of time, and sticking to the confines of this argument within startup world, let’s say people’s definition of success broadly falls into two categories:

1. I want to start a global multi-billion-dollar company that lists on the NYSE.

2. I want to run my own business that earns enough for me to provide for my family and which allows me to do what I want when I want to do it.

We can all agree that starting a startup can achieve both of the outcomes above. Naturally, the startup in each category will look slightly different.

Depending on how you’ve defined success from the options above, your life is going to look a certain way to achieve that outcome.

Option 2 is easy to envision. It’s comfortable. You get to work whenever you feel like and you live a cosy existence.

Option 1 is where the hard-truths lie.

Let’s define this person’s life explicitly:

You sacrifice everything (your sanity, your nights, your weekends, your cortisol, your relationships) to build a multi-billion dollar company.

The most successful entrepreneurs on Earth (Jobs, Musk, Bezos, Zuck, and even the lesser-known but still wildly successful ones) prove that nothing less is required to achieve this version of success.

And even then, once you’ve sacrificed it all—you’ve invested everything you had in the company and spent a decade on it—even then, it’s still not guaranteed.

Therefore, the key challenge is to narrowly and explicitly define what success means in our lives. This might actually be the easy part.

Once we’ve defined our version of success, our job is to map out what our life needs to look like every year, every month, every week, and every day to achieve success.

Once that’s done, it’s time for execution—to put our heads down and stay in our lane.

Unfortunately, people don’t stay in their lane.

My main problem with this whole debate can be summed up in a question:

How can someone who has defined success as Option 2 and lives a life of ‘balance’ shit on the person who has defined success as Option 1 for working on their startup 24/7?

My point: They can’t and shouldn’t (see, staying in our lane). But in reality, they do. It’s all over X and LinkedIn to see.

I’m hesitant to make predictions, but if I were a betting man I’d guess this debate is not going to stop anytime soon.

People are too bad at conflating their version of success, what it takes to achieve their version of success and comparing to how the rest of us are achieving our version of success.

But if you’re still reading this, you’re probably part of the lucky few who can intervene.

Who can go through the years of work (because newsflash: it won’t take a day or even a week) to define success for yourself and design your life to accomplish that outcome.

If you take one thing away from this:

Don’t be someone who defines success as Option 1 but lives their life like someone chasing Option 2.

Questions

We are all seeking answers to the big questions in life. Success and fulfilment are two of the biggest mysteries we strive to solve today.

However, it’s not actually about finding the answer. It’s about framing the question. If we ask the right questions, we can give the right answers.

Some questions I find helpful when thinking through what success looks like in my life:

• Imagine yourself as an 80-year-old on your deathbed, looking back on your life. What will you regret not doing?

• What really matters right now in your life? Is it aligned to your version of success?

• Is your day-to-day life closely aligned with pursuing your version of success?

• What are the things holding you back from achieving your version of success that you can eliminate from your life?

I’m confident I’ll add to this list of questions as I continue to define, refine, and fine-tune what success means for my life.

I hope this might help you do the same.

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Thanks for reading today’s deep dive.

I’ll be back in your inbox on Sunday.

— Luca