So – you are thinking of taking a leap.

Leaps come in varying sizes. Some leaps are relatively small, like joining a gym or starting a blog; some are bigger, like asking out your crush or quitting your job. But whatever the size, the decision really comes down to two questions: what are the pros and cons, and which one outweighs the other? This will predict whether you end up in a net loss or net gain.

What is a pro or a con and how much something matters, is, of course, circumstantial and subjective. The gym fees might not matter so much if you are already rich. The ordeal of learning an instrument might sound fun to one person but a put-off to another. Despite this, I want to argue for why taking the leap is generally a better idea than you might expect, and in many cases, quite a sensible thing to do.

Let’s begin with a story: the birth of this blog.

When I started my blog, I wrote out a pros and cons list. My pros list looked something like this:

1. Something fun
2. Will make me write better
3. Might be useful to other people

My cons list looked something like this:

1. Fear of social judgment
2. Have nothing worthwhile to share

When I started, the pros that I predicted would happen, happened. Indeed, I had some fun, started to write better, and occasionally received a few encouraging comments. But then, over time, something weird occurred. Stuff I didn’t predict started happening.

First, I started realising that writing made my thinking much clearer. You can’t write a good post if it is not already clear in your head. Second, I found that writing more made reading much more enjoyable. When you are constantly editing sentences for clarity and elegance, reading clear, beautiful sentences becomes inspiring. And third, in the process of writing online, I began to connect with a network of readers and other writers that I could learn and draw inspiration from.

In summary, after a few months, my pros list looked something more like this:

1. Something fun
2. Will write better
3. Might be useful to other people
4. (!) Make thinking clearer
5. (!) Reading will be funner
6. (!) Connect with readers and writers

And note that there are countless more pros I could list, almost none of them I could’ve foreseen before taking the leap.

Through it all, the main concerns I had pre-leap – that I might be socially judged and I would have nothing important to share with the world – remained the main concerns post-leap. Despite the unexpected pros, there were no cons that arose after I started writing that I hadn’t considered already and couldn’t prepare for. This leads to my main point:

While you can easily predict the cons of making a leap, there is no way to predict the countless rewards that await you on the other side. There is a fundamental asymmetry of risk and rewards at play.

Provided the chief concerns you predict you can manage, it thus makes a lot of sense to make the leap. By not doing so, you are giving up unimaginable future rewards for a few concerns you can predict and prepare for today.

I have used starting this blog as an illustration of this asymmetry, but there are many other examples I could’ve used as well: my YouTube channel, starting a running club, or asking my partner out. In each of these examples, the challenges I experienced I had largely predicted, but the rewards from these far exceeded my expectations. There was an asymmetry of manageable concerns and unimaginable rewards.

With this asymmetrical nature at play, taking the leap, then, is no longer an emotional jump characterised by reckless passion, but a logical next step toward a more intentional life.

Credits to More To That for this idea.