One of the best things about having more than one source of income is that it provides security when something goes wrong. You’re not dependent on your employer—so that even if a job loss would be a major problem, at least it wouldn’t be an all-out disaster.
But what if you don’t have that security set up, and you lose your job... what do you do? Read More
Reality isn’t just what someone tells you. They could be lying to you, or they just might be speaking from their own limited perspective. We know this, right? We can't just accept at face value everything we hear.
But reality also isn’t just what you tell yourself, at least not if you're trying to avoid something. You too have a limited perspective. You have weaknesses, insecurities, and fears that can be surprisingly resilient in their pursuit of a false narrative. Reality is at least somewhat objective, at least when it comes to basic facts. Sure, you can interpret those facts as you’d like, but facts are facts. When you choose to persistently believe something that you know, deep down, might not actually be true, you’re lying to the most important person in your life: yourself. Read More
A moonshot, according to the ubiquitous WikiPedia, is a "is an ambitious, exploratory and ground-breaking project undertaken without any expectation of near-term profitability or benefit and also, perhaps, without a full investigation of potential risks and benefits.”
For a long time my moonshot was going to every country in the world. Then I accomplished that goal (without ever getting to the actual moon—it's not a country, after all) and had to figure out what came next... Read More
I recently bought my first lottery ticket in something like 15 years. The purchase happened on a whim, as I was walking down the street in California. When I passed by a minimart, I thought, “I should go inside and buy a lottery ticket.” And so I did.
To a lottery novice such as myself, the process was a little confusing. Apparently there’s not just one lottery... there are many! Not being familiar with the pros and cons of various options, I asked the clerk for the cheapest one. I bought the ticket on a lark and didn’t really have a plan at first. But then, before I left the store, I knew what I would do next: nothing at all. I’d hold on to the ticket but never check the numbers to see if I’d won. Read More
If you’re going through a dark night of the soul, you might as well pass the time in a beautiful place.
That’s what I was thinking as my hour-long Qantas flight from Melbourne began its descent to Sydney. Australia has long been a place of joy and peace for me, and Sydney in particular. Ever since I first stumbled into town five years ago, when I was denied boarding on a flight from Brisbane to Nauru (long story), I’ve been coming back every chance I get. This time felt different because, well, I’m different. I’ve been judging the days on a 1-10 scale, and I get excited—at least moderately so—when I feel higher than a 3. And so as the flight lands in Sydney and I take the airport train to the city, bracing myself against an onset of anxiety, I begin my self-talk. Read More
I don't think you're supposed to know your true passion or purpose right away. It tends to emerge as you embark on different paths.
It's good that you're frustrated—it shows that you understand the importance of the search. But I think the best thing you can do is be open and explore different paths. The truest one tends to appear as you go along, not before you start. At least that's how it was for me. From a young age I felt exactly what you describe: the idea that I was just pushing my life along with no north star. Read More
What can I say about the Annual Review process that I’ve completed without fail for more than a decade?
This year, I gave up on it and walked away. Well, not quite—that would be an exaggeration. But to be fully honest (and we shall return to this phrase again), I had a hard time facing it. Eventually I was able to make some progress, which I’ll note below, but the overall sense was one of sadness. Last year was hard, too. And there have been other hard years. This time, however, felt nearly insurmountable. A challenge became a struggle. The struggle became a crisis, and the crisis became, well, something that approaches a total breakdown. Read More
Last year I resisted my Annual Review for the first time in 10 years. This year, what can I say... I guess it’s the second wave of resistance.
Over the past month I’ve entered a season of wandering in the wilderness. I don’t want to sound overly-mopey, so I’ll spare you the details. I know I’ll get through it at some point; it’s just hard to celebrate accomplishments or feel festive at the moment. There are still several reasons why I’m going to proceed with the review... Read More
Maybe you like hearing Christmas music in September. Maybe you can’t get enough of Rudolph's story of triumph over reindeer bullying. And let's all pour another glass of egg nog!
When you’re wandering cobblestone streets in Europe, stopping at cafes and making unexpected discoveries, it’s fun to lose your way and wander off the well-trodden path. You’re on an adventure! When you’re out on a long run and don’t mind if you take a wrong turn or two, you know that the extra distance is good for you.
But here’s the thing: you’re not really lost in those situations. You’re exactly where you wanted to be, even if you didn’t know it before you took the detour. That’s why "getting lost" feels oddly welcoming. When it comes to wandering in the wilderness of the soul, however, it’s a different situation. This is the wilderness where you feel truly lost. You lack direction, enthusiasm, or purpose—or maybe all three. You don’t know what to do, and every option you can see feels like two steps backwards. Read More
I have a weird memory of my dad explaining math to me when I was a kid. I never actually learned real math, at least once it went beyond how to pocket extra lunch money, and still haven’t learned 30-odd years later.
But my dad was a good storyteller, and often taught me lessons using examples. One time he told me how if you stood across the room and moved halfway toward the wall, and then halfway again, and then kept moving only halfway over and over, you would never actually reach the wall. As a ten-year-old, my mind was blown. You'll never reach the wall if you only move halfway, even if you spend 10 years moving over and over? Read More
Do you ever feel stuck? I'm pretty sure we all do at some point. Feeling stuck is like feeling afraid: it happens to everyone, but not everyone gets past it. You win by getting unstuck, not by skipping the process entirely.
When you feel stuck, asking why is often helpful. But just asking "Why am I stuck?" doesn't always work, because feeling stuck can be more of a general sensation than a specific ailment. So here are a few other questions that might help you figure things out. Ask them to yourself and see what your self has to say. Read More
I’m as guilty as anyone else who says that to build a business, or a blog, it’s good to ask people what they want and then give it to them. It works!
But there’s another side to this thinking, and I heard the counterpoint presented beautifully last week by Paula Pant. For years, she's published a popular blog about personal finance. But as she shared in a talk, after starting down the familiar path of "Hey everyone, what should I write for you?" she realized that maybe it was better to ask herself what she wanted to do. Read More
Just as there are some things that can’t be fixed, there are also some things you can’t control. This fact can be hard to accept for those of us who like to both fix and control things.
Hey everyone, the SIDE HUSTLE book is out!