Figuring Out What to Do With Your Life: The Modern Day Dilemma - Part 2

This is the second part of a series on figuring out what to do with your life. If you’d like to read part 1 of the series, you can read it here. This part is a curation of my favourite resources on understanding how the world works in the context of work and success, from the perspective of those who have deeply reflected on it.

But if there is only one thing to take away from this post, it is that figuring out what to do with your life is a journey not a destination. Everyone will experience doubt about whether they are on the right path or not; many times over. As new industries emerge, we all have to reinvent ourselves more than once. And managing one’s own career becomes a job in itself. The resources laid out here and in the last post, serve as tools to a) view things from a different standpoint and b) implement some sort of a system that feels natural to you.

“We do not rise to the level of our goals; we fall to the level of our systems.” - James Clear

Now on to the resources…

1. On Work:

👉The End of Job Book - ⏱️~5 hrs

The End of Jobs Source:

It may sound cliche, but this was one of those books that absolutely shifted my thinking. Depending on where you stand on entrepreneurship, you might already know the message of this book, which is, technology has made entrepreneurship “safer, more accessible, and more profitable than ever before”.

Taylor Pearson, the author of the book, argues that with tools such as cloud computing, Alibaba, and the ability to easily hire affordable talent as and when you need it on sites like Upwork, you no longer need huge upfront capital to get up and running. The biggest shift for me was learning that employment is now riskier than entrepreneurship, as Naval says “If society can train you, it can train someone else, and replace you”. This takes us to the next recommendation.

2. On Creating Wealth:

👉How to Get Rich (without getting lucky), Tweetstorm - ⏱️~10 mins

How to Get Rich (without getting lucky) Source:

I believe the title is intentionally provocative but the premise is how to create wealth and achieve financial freedom. Regardless of what your goals are, money is an inescapable aspect of modern life. Most of us exchange time for money, but this is mostly unsustainable. The moment you stop working, for instance due to a long term sickness or a career break, your income stream comes to a halt.

To break out of this cycle, you need to build a system where your income is not directly dependent on the number of hours you work. In such a system, your “work” compounds over time, and works for you when you’re not. An example is an app that is built once, but is distributed to thousands of people. Or a podcast that attracts opportunities while the host is asleep. The key is not to obtain money, but wealth. But really, the key is not even to obtain wealth, but freedom.

3. On Focus:

👉Antifragile Planning - ⏱️varied

Antifragile Planning Source:

Taylor Pearson has devised a system to get stuff done by maximising focus. It rests on the notion that doing 10% of 10 things is far less fruitful than 100% of 1 thing. Focus is everything. But how do you know what to focus on? When you have a couple of spare hours, how do you know how to best utilise this time? It’s far too easy to end up on YouTube for example. Taylor’s system is based on the concept “vertical coherence”, the idea that if you know where you want to be in the long run, you can determine how to spend your time today by connecting it to your long term vision.

First, you work out your long term goals, imagining yourself in 25 years time. Of course no-one could plan that far in the future but the goal of the exercise is to place you in a mindset where you allow yourself to dream big. Then you work your way back down and set goals for the next 90 days, 1 month, 1 week and 1 day. Ultimately, it helps you to determine what to say yes/no to on a daily basis.

If you’d like to dig deeper or prefer a more interactive learning experience, I recommend Taylor’s online course The Effective Entrepreneur. If you end up implementing this system, you will naturally come away with a number of goals, but goals are hard to stick to. And depending on your personality type, you respond to goals differently. For this, I found the ‘Four Tendencies Framework’ by Gretchen Rubin, mentioned in part 1 to be very helpful. For instance, if you’re an Obliger meaning you’re more likely to stick to goals when you have external pressure, then finding an accountability buddy is a good way to help achieve the goals.

4. On Success:

👉How to be Successful - ⏱️~10 mins

How to be Successful Source:

Sam Altman is a successful entrepreneur and angel investor, he is also a chairman at Y Combinator and OpenAI. I found his blog post about “success” a great read. In a way it summarises most of what is covered in this series. “As your career progresses, each unit of work you do should generate more and more results. There are many ways to get this leverage, such as capital, technology, brand, network effects, and managing people.”

Let me know your thoughts on Twitter, did you find any of these resources useful? Are there any other resources you think should be on this list?

I’ll leave you with this quote:

“Use courage and wisdom, not labor, to make money.” - Nassim Taleb