Mar 29, 2020

Photo by Mike Petrucci on Unsplash

I have some news to share: I just left my full-time job.

With everything going on with the world right now, I would be lying if I said I didn’t pause before pulling the trigger. Even so, I moved forward with confidence in my decision, because the underlying principles I was basing it on still held true. In this newsletter, I will share a few of them.

Going forward, I’ll be spending the majority of my time working on creative projects! You’ll be seeing a lot more writing, drawing, coding, and general creative play from me. I’ll also be spending part of my week working remotely with a startup led by some of my best friends, which will provide additional outlets for creativity and collaboration, as well as injecting some structure into my week. It’s an overwhelming time right now, but I’m excited for this new phase.

As I embark on this adventure, here are five key principles I’m doubling down on:

1) Embracing My Inner Polymath

Our societies and industries tend to direct us toward specialization. Over time, we focus more and more on specific skill-sets and industries, and are rewarded for doing so. By contrast, someone who tries to dip their toes in many different fields will find it difficult to “fit in” with a typical career template. There’s a quote on this which often makes the rounds:

“A jack of all trades is a master of none.”

But that isn’t the whole story. Here’s the original full quote:

“A jack of all trades is a master of none, but oftentimes better than a master of one.”

The difference in meaning is night and day.

Once I discovered this, I suddenly felt validated. Perhaps my tendency to constantly pursue different arenas was actually a fruitful endeavor after all? While the terminologies have changed over time (e.g. “renaissance men”, polymaths, generalists etc.), the fundamentals all prescribe the following:

On the surface, it’s a simple idea. Yet, following it goes against much of the typical career advice we get. It also goes directly against the “10,000 hours rule” made famous by Malcolm Gladwell (thankfully, that theory has been soundly debunked). There are certainly challenges and downsides to this approach — you are not going to have a clear path to follow, and you will have more difficulties relating to others / fitting into communities since you are not easily categorized into a simple archetype.

But should humans really be categorized so easily? Isn’t it our diversity and uniqueness that truly makes us human?

For more on embracing a polymath lifestyle, check out my essay The Polymath Playbook.

2) Making Space for Serendipity

I tend to be a hyper-productive animal. I love building plans and to-do lists, and powering through them. There’s certainly a lot of benefit to doing this — organization, goal-setting, feeling of accomplishment, and so on.

But when it comes to creativity, we often need to allocate some empty space. We can’t plan everything, and we definitely can’t plan creativity. The most impactful things we make often emerge from unexpected places, and we often don’t even know how we got there.

As a good reference point, I often think about a bunny I drew a while back. I did not plan to draw the bunny. I just sat down, took out my iPad, and started drawing. An hour later, there was a bunny. Someone might look at it and ask me: “How did you decide on that nose? Why are the ears down and not up?” I have no idea what I’d tell them. If you asked me to draw it right now, sight unseen, I’m sure it would turn out completely differently.

So, one thing I definitely plan to do (ha!) is ensure I don’t fill up every waking hour with plans. I’ll always be tempted to do so, but I must resist. I must embrace emptiness.

Boredom always precedes a period of great creativity. —Robert M. Pirsig

3) Conversational Energy

Nobody likes meetings, and it’s a particularly stressful time right now with the overwhelming impact of so many video calls in our day. That said, I have come to believe that one-to-one conversations are one of the most powerful sources of energy.

The right conversation, with the right person, at the right time, can completely change your life.

I wrote some thoughts on this topic as part of a thread summarizing an ebook I read called Friendly Ambitious Nerd. The book includes the best lessons from Visakan Veerasamy, with a lot of great suggestions on embracing conversations, your inner passions, and much more. In this tweet, I talk about how it’s important to develop some kind of filter to find the right kinds of energy in your conversations. You can also check out my full thread about the book.

4) Self-Awareness

If you’ve been following my newsletter for a while, you’ll know I’m a strong believer in the power of tools like meditation. They help sharpen our lens into our own minds, and reflection enables us to make much better decisions about how to move forward.

Of course, simply becoming self-aware isn’t enough. You also need to act. To do so, you’ll need to overcome your inner fears, and give yourself permission to make change. In a sense, this becomes a negotiation between you and yourself.

Ask yourself: What specifically am I afraid of?

In my case, one major thing I realized was the importance of having some form of part-time work alongside my creative projects. Yes, the financial piece is key, but more than that, I realized I felt strong anxiety with the idea of not earning. It’s just something I’ve been so used to doing my whole life — I knew it would affect me mentally, even if it was something I could manage financially.

In particular, I knew that if I had a massive weight/burden/anxiety on me, it would affect my creativity. So even if I had all the time and space in the world, I would have a much harder time actually producing anything while was carrying that weight.

5) Working In Public

I’ve been very lucky in my career. I’ve had the privilege of playing many different roles across a number of industries, seeing startups from foundation to acquisition, building coding bootcamps in South Africa… However, most of the knowledge, stories, and lessons from all those experiences lives solely in my mind. Undoubtedly, much of it has faded from my memory.

I don’t have many regrets, but not sharing more during my career so far is definitely one of them. Even if you ignore the benefits of feedback, writing helps you improve your own thinking in so many ways – I wrote a thread on this recently.

If you write entirely for yourself, it’s still worth it.

That’s all for the principles! Now that you think about it, are there any principles of your own that come to mind? Let me know, I’d love to hear from you!