The One Risk You Should Take Right Now

Three stories about saying yes to uncertainty.

Peranakan Museum in Singapore 📷

If you skim this post and remember nothing else, don’t forget this part:

Right now, there is at least one small risk you can take that will make your life better.

Go away and think about that.

Okay, here’s the post (live from Singapore! More on my trip at the end.)

My life has been better because I’ve taken more risks. I often ask, “What risks am I taking right now?”

It’s another way of asking “How am I challenging myself?”

Here are three short stories of risks I’ve taken that have paid off. I don’t think I’ve told these stories before, at least not in this way.

1. Traveling to meet people I respected

Very early in my career as a blogger (back in 2008 that's how people described it) I would travel to faraway cities specifically for the purpose of meeting another author or colleague or someone I respected.

As one notable example, I went to meet with Seth Godin and hang out with the first version of what became his popular alt-MBA program. This was an incredible visit! A decade later, I remember it well and I'm still in touch with several of the people I met that day. Seth has also been present in my life ever since, sometimes with direct advice, but mostly just parasocially through his posts and other writing.

This is just one example. I traveled to meet with lots of people and it often ended up being incredibly worthwhile, even life-changing in a few instances.

Sometimes the biggest returns come from simply showing up in person.

2. Writing The Money Tree

In 2019, I had the idea to write a very specific type of novel. I read fiction all the time, but even after having written many nonfiction books, I really didn’t know much about how to write a novel. But all of a sudden, I had this one strong idea, and I latched onto it.

The finished product became The Money Tree, one of the books I'm most proud of and feel best about.

I know that writing a novel probably doesn’t sound like a big risk, but at the time I was exclusively a nonfiction author. I could get paid well to write more traditional business books, but I wanted to do something different. It was well worth it!

Strange ideas are often worth following up on.

3. Moving to San Diego

Here is an even more personal one.

After many years of living in Portland, Oregon, I moved to San Diego within less than a month of first thinking about it. I was very depressed at the time and wanted to start over in a place with more sun. I didn't tell many people about my change in location, and never wrote a post saying “Hey, I’m in California now!” I just went and did it.

Over the next few months, I tried to get to know new people, often in ways that felt slightly silly to me at the time. For example, I would go to random meetups, even for topics or hobbies I had little interest in just to see what it felt like to connect with strangers.

At 40 years old, the first six months I was there ended up being a formative time in my life.

Change of place can lead to change of perspective.

If you think about it, you probably have some risk-taking stories of your own—right? You can draw on these memories to take more risks.

In fact, that’s a core principle: most people are too risk-averse and would benefit from taking more risks.

This doesn’t mean you should go out and be reckless. But there is a broad range of things you can do that could end up having a very high rate of return on investment.

A rainy walk in the National Orchard Garden 📷

In Other News: Notes from Singapore!

This week I’m in Singapore, a place I used to visit often but haven’t been to for several years. It’s a special place in my mind: my first trip here in 2006 is when I officially decided to visit every country in the world. (I was actually on a ferry in Hong Kong when I made the decision, but it was the same trip.)

• On another visit, I was with my friend Stephanie and we went for a run but got caught in a huge rainstorm. Like, massive! It was pouring and pouring and there was no way to avoid getting completely soaked—but we loved it. Fun times.

• Another time I learned I could sneak into a particular hotel to exercise and shower when I was just passing through in transit. For some reason I really liked the sense of subterfuge. A free gym!

• It’s also the place where I first became vegetarian, following that initial trip in 2006.

Anyway, I’m back in town this week and going on long walks every day and that’s fun.

I arrived at 6am local time after flying the long way around, from JFK to Frankfurt, with a two-hour layover that I spent walking around the terminal to get some steps in, then another twelve-hour flight from FRA to SIN.

I keep my watch on eastern time, and I need to close my circles every day, so naturally I went for a run straight upon arrival. (Thankfully, my hotel let me check in early.)

I’m also jet lagged, which is no longer as fun and mysterious as it feels to a young traveler, but that’s okay. I’m happy! I get to do this!

It’s not really a risk, I suppose, but it’s a nice change of scene.

Back to risk-taking: what is the risk you’ll take this year??