Time is running out, and you should be doing something about it … but you don’t know what.

That’s what this post is about: something called time anxiety. I’ve been dealing with it for years, and maybe you have, too—even if you’ve never heard the name.

I believe that time anxiety is the most pressing problem of the modern world. Once you work your way through Maslow’s hierarchy and your basic needs are taken care of, you start worrying about time—and you never stop.

• You worry that time is passing you by
• You worry you’re too late or you missed your chance for something important
• You worry there’s something you should be doing right now, but you’re not sure what it is

If you don’t relate to this feeling, consider yourself fortunate. Many people feel this way all the time. And it’s not just a conceptual idea, it’s truly a felt sense. You can experience physical symptoms, even real distress, from time anxiety.

This feeling is often identified as FOMO, but time anxiety is different. FOMO is focused on the present (“Something is happening without me!”), whereas time anxiety surfaces around all three parts of time: past, present, and future.

You experience regret about the past, a lack of clarity about the future, and general disorganization in the present.

The sense of disorganization presents itself even in people who are generally accomplished or “productive.” In fact, time anxiety may be even more common for these people. Part of the reason they’re working so hard—yet frequently changing their focus and getting tripped up—is because they aren’t sure what they should be doing!

In other words: the same people you see as being confident and skillful may actually feel hesitant and clumsy.

This, in a nutshell, is time anxiety. We know we should live as though we’re running out of time (because we are), but we don’t always know how. Therefore, we become anxious.

What can be done—there any solutions? This is a topic I’m actively studying, and I don’t think there’s a simple answer. Still, here’s what I’ve got so far.

First, never underestimate the power of self-awareness.

Once you understand what the problem is—or even once you have a general understanding that there is this thing that affects you—reminding yourself of this basic knowledge can help.

Many people with ADD/ADHD (or Asperger’s, Bipolar, or any number of other conditions) have clear memories of being diagnosed for the first time. Being diagnosed is like being seen or recognized. You realize that the thing you’re experiencing has a name. It has common, identifiable characteristics. There are other people who’ve had similar experiences as you—there are keys that can be discovered.

I mention ADD specifically because it’s the condition I’m most familiar with. I was first diagnosed as a child, but I didn’t seek treatment as an adult until I was thirty-five and struggling to write a book. Once I started actively managing my ADD, I was able to finish the book and also be much more focused all-around.

The list of conditions doesn’t need to be comprised solely of disorders. Understanding your personality type and characteristics also brings some relief. If you’re an introvert, for example, you know that having lots of meetings tires you out, so you learn to plan for them.

So too is it with time anxiety. Without a diagnosis—or at least, without naming it—you’re always at its mercy. With some understanding, you learn to cope, adjust, and maybe even thrive.

Second, be wary of quick fixes.

Beyond self-awareness, I think it’s important to be cautious when identifying “the answers.” People who struggle with time anxiety tend to be good at coming up with answers that make them feel better without creating much in the way of real change. 

Perhaps that’s a long way of saying “Sometimes I come up with answers that make me feel better without changing much.”)

Time anxiety is not something you hack. It’s something you come to terms with.

No amount of improved to-do list apps will solve this problem. There is no bullet journal or magic method. You could invent an alarm clock that physically drags you out of bed two hours before sunrise and forces you to work even harder, but will you really be better off?

The rise of #StudyWeb on TikTok and YouTube fits this description perfectly. Millions of students want to study better, yet many of these same study connoisseurs are deeply worried about spending their time in the most efficient manner.

At the end of the day, this fact remains: there’s always more to do, and there’s never enough time.

Third, stop trying to “manage” time.

Becoming aware of time anxiety leads to another conclusion: our obsession with productivity and “time management” is misaligned. In fact, the whole field may be doing more harm than good!

Plenty of people have criticized the Getting Things Done crowd, but they tend to do so from a “do less” perspective. Their criticism, perhaps oversimplified, is “Live your life and don’t worry about being efficient.”

Of course, telling someone not to worry about something they are worrying about is not very helpful. Besides, what if you do want to improve—you want to do more and do it better?

The person who understands that is who I’m writing this long post for. You want to improve, but you feel stuck and you need more than a list of hacks to make progress.

In the end, time anxiety is a real problem—truly the most pressing problem of our modern age, at least for many for us. But it doesn’t need to be a crippling disease.

You can incorporate this understanding into your life and move forward, full of the knowledge that time is running out—and yet, there is still time now.

More to come…

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I finished an Annual Review! A full and proper one, for the first time in a while.

Over the past three years I’ve mostly been living vicariously through other people’s reviews, having completed only an abbreviated version of my own. I’m glad the process I created so many years ago has been helpful—but it’s also great to get back to my own review.

In this post I’ll share some of my goals for next year, as well as the overall narrative and focus that I’m going with. Naturally, there are some private items I don’t post about, but I’ll try to be as comprehensive as possible.

Why Share Your Personal Goals?

For me it’s not really accountability so much as that I believe there is value in publicly declaring your intentions.

This started long ago when I was like, “Hey, everyone, I’m going to visit every country in the world”—and I’ve just kind of continued in that fashion ever since. I’ve also combined the process of finishing the review and posting about it, so I tend to see them as one complete project.

So here we are! As mentioned last week, I had a rough couple of years where I was particularly depressed towards the end of the year. Then, I had another couple of years that were fine but not terribly exciting.

Now I’m ready to level-up again.

Grading My Future Self

As I was moving posts over to the new blog (check it out if you haven’t seen it already!), I came across a post I’d completely forgotten about. It’s called Giving the A Grade for the Person You’ll Become, and it’s about an activity where you write a short letter to yourself from the perspective of “future you.”

In this exercise you’re only allowed to give yourself an A, but you have to be specific on what you did to achieve it.

Here’s how the activity’s creator described the process:

In writing their letters, I say to them, they are to place themselves in the future, looking back, and to report on all the insights they’ve acquired and milestones they attained during the year as if those accomplishments were already in the past. Everything must be written in the past tense. Phrases such as “I hope,” I intend,” or “I will” must not appear.

I’m going to use this as an exercise in the online course I’m building (more on that shortly), but I thought I’d mention it now in case anyone wants to work through it on their own.

Despite writing about the exercise before, I’m not sure I’d ever actually done it myself. It was helpful!

Anyway, let’s move on to how the actual review works.

How It Works (skip this part if you’re familiar)

I’ve written many times before about how the review process works. In short, I set a number of goals and sub-goals for specific categories. Then I create an overall narrative (“outcome statement”) for the coming year. Sometimes I have a specific word as well.

I tend to do the review towards the end of December, but you can do it anytime. So if you happen to be reading this post during some other part of the year, there’s no need to wait.

My broad categories tend to be what you might expect: writing, business, finances, travel, wellness, and relationships, for example.

Some of the categories also have sub-categories. With finances, for example, I like to set goals for income, savings, and charitable giving. With wellness, I have goals for running as well as mental health.

Roam Research: New App + Process

About a year ago I began using a tool called Roam Research for daily notetaking. I used this app for the Annual Review this year, so the process came out slightly differently than it has when using a spreadsheet.

Ultimately, the tool you use isn’t that important. You could also complete a review using Notion, Evernote, or any number of other apps. What matters most are the goals you set.

Goals for 2022

All that said, here are a few things that emerged as key goals for my year to come.

• By the end of 2022, I will have written a new book and created an all-new business model in the form of a popular cohort-based course.

There are a lot of reasons why the course is important. Mostly, I believe in the value of the course (much more on this next week). But secondly, I want to reduce my reliance on podcast advertising income. I didn’t start a podcast to make money, but it ended up bringing in more revenue than anything else I do—which is cool, but I don’t want to count on it continuing!

• Speaking of the podcast, I’ll produce another 365 episodes of Side Hustle School. This will take us to more than 2,000 consecutive daily episodes. And I hope to highlight many listener success stories along the way! It’s my favorite part of working on the show.
• I’ve always struggled with being consistent with social media, but this year I’ll figure something out: a new daily sharing process. Combined with a weekly newsletter that goes out every Tuesday morning without fail, I’ll rebuild some momentum and feel more connected with readers.
• I’ll continue to care for myself through daily exercise. I’ll complete another 365-day streak of Move Points. (“It’s harder to quit than to keep going”) and run at least one marathon.
• I’ll host WDS for the first time in three years, bringing that chapter to a close with an epic adventure—and looking ahead to something new. (Join the waiting list for tickets.)
• I’ll take more financial risks and at least half my income in non-traditional assets, especially projects like Tokemak, Alchemix, and DeFi Kingdoms.

It’s been very fun to learn about these things over the past year. It started as research for the book I’ll be writing, but I ended up enjoying it much more than I expected. #wagmi

• In short, I thought the years of 2014-2017 would be my second phase of business, but they turned out to be more preparatory. The real “second phase” starts now!

As I said, that’s a selection of my most important goals for the year.

For the first time I can remember, I’m looking forward to the next few years, and I believe they can be better (at least in their own way) than what came before. I hope you’ll join me for 2022!

How about you? Have you started an Annual Review yet?

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Have we really come to the end of another year? It seems that way! What a crazy twelve months it’s been.

In this post I’ll share a bit about my upcoming Annual Review, as well as a few highlights of the year. In fact, let’s start with the highlights!

My 2021, In Brief

What I Didn’t Do

• I had my second year in a row of very limited travel, mostly because of the obvious limitations, but also because I’ve now adjusted to a different routine. I also didn’t publish a book, which feels strange.
• I didn’t do a lot of speaking, events, or meetups. After postponing the ten-year anniversary of WDS last year, in 2021 we had to postpone again. Frustrating! The good news is, it’s finally going to happen next year—guaranteed. Join the waiting list to be the first to hear about tickets.

What I Did Instead

• I may not have published a book, but I sold one (!) that I’ll be working on a lot in 2022. Or at least, I sold a new book concept. With nonfiction, you usually sell a proposal, and then you write the book—so there’s still much to be done.
• I recorded a podcast episode every day for the fifth year in a row. I just renewed for season 6—subscribe and join in! You can follow from Spotify, Apple Podcasts, or wherever you like to listen. (Every single episode from the archives is also freely available for streaming or downloading.)
• Towards the end of the year, I started working on a secret project that’s required a lot of quiet, intensive creative work. The project won’t remain secret for long—I’ll announce it the first week of January. I’m very, very excited about it, in a way I haven’t felt for a long time.
• I ran more in 2021 than I’ve ever done. I got up to an average of 40 miles/week, then did 50 miles/week several times, and even made it to 60 miles for one week. I’m not trying to go further than that (~40 is a good base for me) but it’s been fun to challenge myself. I also set a PR (1:33:51) for the half-marathon, my favorite distance.
• When I got an Apple Watch a few years ago, I started working on a streak of achieving my move points on consecutive days. I got close to 100 and then lost the streak by accident when I went to Thailand and crossed the international dateline. I got to 100 and kept going, then decided to try for a year. Long story short, I got to 365 and kept going—and last week I hit day 1,000!

 

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• Finally, we redesigned the blog! I’ll say more about this the first week of January, but it’s been a long, long time coming. After three previous efforts fell short, I finally found a concept that felt right. The whole site is new (and some of it still needs a bit of work), but the blog section is the main focus. I wanted to make something that was more topically oriented, as opposed to the typical chronological navigation of blogs.

There’s more to be done, but I think we’re 90% there. Big thanks to Anna, the designer, and Nicky, my longtime digital magician, for their hard work on this project.

• Along with the new blog, I got back on track with publishing a weekly newsletter (sign up here or at the bottom of any post). It goes out every Tuesday morning at 9am Eastern time, rain or shine. Now that I have the habit back, I don’t think I’ll slip again. It feels good.

Those are just a few highlights, of course. It wasn’t an amazing year for me but it was pretty good all around. And honestly, when I think back at how I’ve felt during this season in some other years, I have no complaints.

Annual Review, Latest Version

Over the next week I’ll be completing my Annual Review.

I’ve modified this process over the years, and a couple of times I didn’t share a lot of detailed posts about my own goals.

But guess what? I’m going to change that this year!

Expect a long post from me next week. Things are good, so I’m taking advantage of long-delayed momentum.

If you’d like to do your own review, these tools and links might be helpful:

• • • Annual Review (original post from 2008!)
    • What Is Your Personal Moonshot?
    • Decide Now How You’ll Evaluate Yourself Next Year
    • Being Able to Ask “What’s Next?” Is a Sign That You’re Happy
    • “The Success I’m Having Now is What I Planned For Three Years Ago”

As mentioned, I had a couple of challenging years and then a couple of “pretty good” years, including this one. I can now see that I was regrouping during those “pretty good” years, and planning for a big year to come.

Well, now I’m ready for an amazing year! Or at least, you know, a better-than-pretty-good one. Expectations are everything, but I’m going to give it everything I have.

More to come next week. Onwards!

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Somewhere along the way, however, I fell off the learning wagon. I just stopped learning! Or at least, I stopped actively learning. I had so much to do that I no longer took time to study and absorb complex topics. During the first few months of the pandemic, I decided to regroup.

What else was I going to do? My 40-city tour for The Money Tree was canceled, and it wasn’t like I was going to start baking or something. (I did, however, eventually get into plants. I grew a whole rain forest in my living room! Or at least that’s how I like to think of it.)

It started with the realization that I mostly consumed information that had a direct correlation to my work or for entertainment. A third, important category was missing: information that I didn’t necessarily need, but that was interesting and potentially helpful.

A lot of it came down to the simple rule of forming an exercise habit, or probably any other number of habits: you just have to make yourself start doing it, and everything else tends to fall into place. Watching a long series of lectures on world history might not be as entertaining as a typical TV series, but when you take the time to do it, you’ll go away feeling enriched and wanting to learn more.

In this post I’ll give you two things: a list of free and low-cost learning platforms where you can access world-class courses, as well as a few tips to make learning stick. (Spoiler on the last part: the single most important thing is to write down what you learn.)

Where You Can Learn for Free or Low-Cost

If you want to learn online, you have an abundance of options. Too many options, most likely, so you’ll need to narrow it down or you’ll be overwhelmed. To start, here are a few good starting points, all of which I’ve tried.

These are some places you can learn for free:

• Coursera – I really enjoyed The Modern World: History from 1760-1910
• edX– especially strong with technology topics, like this course on computer science for lawyers, or this one on blockchain from Berkeley
• YouTube – get a premium membership to avoid ads and download videos for offline viewing

These are some places you can learn for small amounts of money:

• Udacity – watch for sales, where courses drop to just 10-20% of their usual cost
• LinkedIn Learning – available for free to all LinkedIn Premium members (check out my classes on entrepreneurship
• CreativeLive – for $13/month you can get a “Creator Pass,” which provides access to the entire catalog of hundreds of courses
• Blinkist – some authors hate book summaries, and I agree they aren’t nearly as helpful as reading books—but for topics like the sciences, where I’m not going to read a ton of 400-page books, I like it

Notetaking Is Essential

Alright, so you’re learning new things—awesome! But this is only the first part.

If you don’t take notes on what you learn, you’re essentially just entertaining yourself. There’s nothing wrong with entertainment, of course, but your goal is to learn. If you’re not actually absorbing the material in a way that you can easily recall later, you’re not really learning.

There are a lot of habits that can help with knowledge retention. Spaced repetition is one, where you create a system of flash cards (digital or otherwise) that you then use to revisit and recall key facts.

The single most important habit, however, is synthesis in the form of notetaking.

Synthesis in this case just means “summarize in your own words.” After you read, study, watch, or listen to something you’d like to recall later, write down the key points in your own words.

Research has shown that writing is much more effective than highlighting. When you highlight something in a book (including Kindle or online), you trick your brain into thinking you’ll remember it later, but really you won’t. There’s something about the synthesis process that helps makes things stick.

For example, if I was reading this article, I might synthesize it as follows:

It’s important to learn actively. If you don’t have a plan for regular learning, it will never happen. The single most important habit to retaining what you learn is to rewrite core concepts in your own words.

You might say it differently, but those are the essential, critical points of this post. If you remember and apply them, you’ll be better off every day of your life. But of course, remembering and applying is not easy! That’s why you need a plan.

***

I’ve started making much more time for active learning. I feel like a lifelong learner again—just one who got off track for a while. I think it’s going to stick this time, at least as long as I keep taking notes.

What have you been learning recently?

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Among other things, the German philosopher Friedrich Wilhelm Nietzsche was known for an outrageous mustache that frightened away potential soulmates. He also said a lot of outrageous things, which caused him to be shunned by much of society at the time.

Before publishing Thus Spoke Zarathustra, his best known work in which he proclaimed “God is dead,” he wrote a book titled The Joyful Wisdom (originally: The Gay Science).

In that book, he posed a question that may be even more interesting than the death of God. Well over one-hundred years later, this question is so provocative that it can still cause you to lose sleep … or maybe that’s just me.

Nietzsche’s question was: “What if I had to live this life over again—would I be able to stand it?”

“What if some day or night a demon were to steal after you into your loneliest loneliness and say to you: ‘This life as you now live it and have lived it, you will have to live once more and innumerable times more; and there will be nothing new in it, but every pain and every joy and every thought and sigh and everything unutterably small or great in your life will have to return to you, all in the same succession and sequence – even this spider and this moonlight between the trees, and even this moment and I myself. The eternal hourglass of existence is turned upside down again and again, and you with it, speck of dust!’”

I think of this as a long way of asking, “Would you willingly choose to relive the life you’ve lived in its entirety, or would you be so tormented with regret that you’d rather have anything else?”

If you’ve never sat with this question, it can be quite an experience. Many people go to great lengths to avoid thinking about their lives, for all sorts of reasons. Thinking about your life can be a burden! You’ve got plenty of other things to do, and besides, where do you even start?

Moreover, you might have a sneaking suspicion that you already know your answer to the question, and it doesn’t feel great. Would you like to live exactly the same life over again? No! You’d do many things differently. Regret is a byproduct of being human.

That’s not the question, though. The question is, “If you HAD to experience it all the same way, how would you feel?” There are three possible answers:

1. You’d feel exuberant. You’ve done everything right! Congratulations, enlightened soul.

2. You’d feel tormented with regret. Everything is meaningless.

3. You’d think, wow, that’s interesting. I would definitely relive some parts of my life, and others I might want to change. I wonder if this insight might cause me to change something now?

In case you feel tormented: it’s okay, I get it. I used to feel that way more than the other answers. Day after day, I felt trapped, scared, and upset with myself. But something changed … specifically, I did.

Though I hesitate to use the unconditional past tense—it’s more of an ongoing practice than a one-and-done decision—I can say with confidence that I WOULD live my same life over again now. I still have more to work on (etc. etc.) but I no longer feel tormented.

That’s why, while it’s probably nice to feel exuberant with the knowledge that you wouldn’t change anything at all, I think the third answer is the best.

All of us still have work to do on ourselves—to live better, to love and experience more, to make the most of the time we have left. Better to know that than to bury your head in the sand. And better still to be willing to do the work.

The way to transform this sense of despair is to understand its logical conclusion: not to cause you to be tormented with regret, but to help you change the future.

Try to change it right now!

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One time, Will Smith was working on a film set in Toronto. It was the middle of winter and they were shooting night scenes, so the actors and crew worked 6pm to 6am. Brrr! 

During breaks, Smith could have huddled in his trailer, complaining about the bitter cold. Instead, he ran around making jokes and delivering hot chocolate to crew members. He acted on a question that he later explained is constantly on his mind: “How can I make this experience more magical?“

Working in the cold sucks, but the job had to be done. Rather than complain about it, and rather than just endure it, Smith set out to make the experience better (or “more magical”) for everyone else.

That question—How can I make this experience more magical?—is an example of a dominant question. It’s a question that guides your decision-making process. We all have dominant questions, whether we’re consciously aware of them or not.

Do you know your dominant questions?

In my case, I spend a lot of time having conversations with myself or otherwise being lost in thought. After hearing the anecdote about Will Smith, I started thinking about my dominant questions.

It turns out they’re pretty easy to categorize as positive or negative. Let’s start with the negative ones:

• Why am I continuing to struggle?
• Why can’t I get my act together?
• Why is [this thing I’m doing] not working as well as I’d like?
• Why is my perceived social status lower than I think it should be?

The problem with these questions should be obvious: they reflect a sense of frustration, fixation on ego, and low self-worth.

By contrast, here are the positive ones:

• How can I make the best use of this day?
• How would I like to feel today?
• What can I do to be helpful?
• What should I do next?

My favorite is the first: How can I make the best use of this day? It reminds me of Did Today Matter?, another question I ask myself, typically in the evening as I wind down.

Asking this question has less built-in ego attachment while still allowing me to be myself without judgment.

The question “How can I make the best use of this day?” incorporates the limitations and constraints that any particular day comes with. It suggests that I consider a wide range of possibilities, along with the limitations and constraints, and come up with the best possible answer.

What can I do today? How am I able to use the time I have right now to the best of my ability—ignoring (as much as possible) the myriad of problems that are beyond my influence?

When I find myself feeling sad or discouraged, I try to think more about this question.

Do you know your dominant questions? What would you like them to be?

*I first heard the story about Will Smith in the audio version of Limitless, a book by Jim Kwik.

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Strategy: To increase your risk tolerance, remind yourself of risky decisions that have turned out well.

As with the list of things you’ve done that few other people have, this is not merely a list of accomplishments. The key point is to identify risks you’ve taken, bold moves, and other decisions you made that could have gone south but ended up paying off.

Of course, what’s “bold” for you may be different from me, and vice versa. But here are a few of mine:

Traveled to Pakistan and Saudi Arabia without a visa

I was especially nervous about these trips, and for good reason. In both cases I had tried extensively to get the visa in advance with no luck. In Saudi Arabia, there was no such thing as a tourist visa at the time. After much discussion (I was taken to some sort of holding room and left by myself for an hour) they decided to let me stay but held on to my passport for the duration of my visit. Pakistan was a little less intense, but it was definitely an issue upon arrival at immigration in Karachi.

I should note that I also made this risky decision with Eritrea (again after many failed attempts to get the visa in advance) and it didn’t work out so well. There I was deported in the middle of the night on an Egypt Air flight, leading to a heated discussion on my blog as to whether this counted as a country visit or not.

Still, all’s well that ends well!

Rented an art museum for a conference before anyone had registered

While I was traveling to meet readers in all fifty states on my first book tour—another risk, now that I think about it—I had the idea to invite many of them to a conference in Portland, Oregon.

I had never produced an event before, nor did I know much about event planning. The few friends I asked to join the team also had no background in running events.

But it all worked! Far, far better than any of us expected, in fact.

One of the scary parts was going to talk to the people in charge of venue rentals at the Portland Art Museum. I loved the space and thought it was perfect. It was also expensive. The event team asked a lot of questions that I had no idea how to answer, and in retrospect I’m sure they thought I was in over my head—and they weren’t necessarily wrong.

I had to commit to the venue rental, A/V rentals and crew, catering, permits, insurance, and a ton of other expenses before anyone had registered for the event.

But again, it worked. People came: 440 of them, in fact. And then they came back the next year and then the next. Good decision!

Since then, more than 10,000 people have attended the World Domination Summit. I lost something like $28,000 that first year, but in retrospect it was one of the best investments I’ve ever made.

Committed to record a podcast episode every day for a year (I’m now on year 5…)

Here the biggest thing that was risky was that I committed to tell a different story in the form of a case study every day. When I started I had five stories recorded and maybe another fifteen in mind. What would happen after week three?

It was a gamble, and thankfully it paid off. The show debuted at #2 on iTunes and ended up being downloaded millions of times. Even better, I kept going after a year. We’re now passed 1,700 consecutive daily episodes and I’m planning to renew for another year.

But let’s go back to the risk: I trace much of the successful outcome to the commitment to do it daily. Very few shows were published that frequently when I started Side Hustle School, and I think many early listeners appreciated the consistency of it.

And it’s not just the listeners. For me, it’s easier to do it every day than it would be to do it two or three times a week. When something has to happen every day, it gets done. Once you start playing loose with the schedule, everything falls apart.

Bought a small amount of Bitcoin in 2018 when it was priced at $10,000

I didn’t know what I was doing and I’m not sure I could have even explained what a blockchain was at the time, but it seemed like a decent way to achieve some asset diversification. I don’t expect to ever sell it, and my biggest regret (at least in terms of Bitcoin…) is not buying more.

I now think of investing small amounts of money in digital currencies as a classic asymmetrical risk: potentially a high reward with a relatively low downside. Go in on dog money, everyone!

Chose to write a blog full-time instead of pursuing a Ph.D.*

*Longtime readers may recall that this choice was largely made for me—in 2008 I was rejected from nearly every program I applied to!

But I don’t usually take no for an answer, so some version of myself would have shown up at Princeton anyway and just started attending classes. Who knows if that risky decision would have paid off, but I’m glad I chose the other one. In the end, the “risky” choice to pursue full-time blogging (and eventually writing books) has been far more rewarding than I ever anticipated.

—

Aside from these highlights, I can think of a few others that are too personal for this blog. Then again, this post is about risky decisions—so perhaps I’ll do a follow-up.

What risky decisions have you made that turned out well?

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Every so often, a news article that offers “expert advice” on getting upgraded at the airport makes the rounds. Inevitably, the advice includes something about how you should “dress well and ask nicely.”

Real travel experts always roll their eyes at such advice. These days, almost all upgrades are handled through computer systems based on elite status, travel disruptions, and other automated factors.

The travel experts then write their own articles explaining why the advice is dumb, and the process repeats a few months later.

I’m with the real travel experts: the advice on asking for upgrades is just clickbait. Yet I can’t help but remember a time many years ago—way back in 2007, I think—when I was traveling from Copenhagen to Chicago.

I don’t think I was dressed any better or worse than I usually am, but I did approach the gate agent with a cheeky request.

At that point I had flown transatlantic Business Class two times, and another time across the pacific from Hawaii to Japan. Each of those times, I’d been upgraded at the last minute, and I loved the experience.

Once you fly in the front on a long-haul trip, it’s hard to schlep to the back with the rest of Peasant Class.

I walked up to the SAS gate agent with a smile and my request: “Hi there! I just wanted to make sure my name was on the upgrade list.”

I was bluffing—there wouldn’t be any reason for me to be on such a list back then. But she said she’d check, and I thanked her before walking back to the seating area.

I figured nothing would happen, but five minutes before boarding, another agent paged me to return to the counter. That agent swapped my boarding pass for a new one, and I looked at it in wonder. Business Class!!

For the next ten hours, I enjoyed unlimited refills of champagne, a large cheese plate followed by chocolate cake, and a lie-flat seat where I could sleep off my food coma. I’ve been on well over a thousand flights since then, but I still remember that day very well.

Now, whenever I read the lame travel advice on asking for upgrades, I always remember that experience. Yeah, the advice is dumb … and most of the time, following it won’t pay off. Except, of course, when it will.

If You Don’t Ask, You’ll Never Receive

The right kind of risks are asymmetrical, which means that the potential reward far outweighs the potential loss.

If you’re looking for a way to level-up your life, start taking more of these risks. You can do so right now, today, by identifying disproportionate opportunities in your life.

The easiest asymmetrical risk you can take is to simply go through life asking for what you want.

Just think about it: if you ask for what you want and don’t get it, oh well. That happens. Meanwhile, creating the possible outcome of not getting it also creates a possible outcome of getting what you really want.

That morning at the airport in Copenhagen, if I didn’t get the upgrade, no big deal. I might feel a little rejected, maybe slightly embarrassed, but no real harm would be done. I’d still be able to continue on my journey to Chicago, just with less free cheese and wine.

If you don’t ask, you’ll never receive. It’s a winner-take-all scenario.

Take Positive-Value Risks Every Day

Life offers the chance for these “positive asymmetrical risks” every day.*

*Asymmetrical risks can be both positive and negative. A positive risk is betting $1 to win $9. A negative risk is like betting $10 to win $1. Not as ideal!

Take the lottery, for example. Even though the Powerball lottery is mathematically proven to not be a good investment, it’s a classic asymmetrical risk (at least when you’re buying tickets with small amounts of money that you don’t care about losing).

Most people don’t buy lottery tickets as an investment strategy but rather as a chance to dream. Someone has to win the big prize, right? Whoever it ends up being, that person’s reward far, far exceeds their expected loss.

So what if you went through life asking for whatever you really wanted?

• Ask for the upgrade (or the raise, the promotion, etc.)
• Ask for something for free
• Ask your boss if you can skip work today
• Ask your boss if you can work on a different project that you’re excited about, even though it’s outside your defined responsibilities
• Talk to the person you have a crush on
• Talk to strangers (at least when they want to talk back)
• When you attend an event where questions are welcomed, be the first to raise your hand (have a good question prepared in advance)
• Reach out to a famous person who’s influenced you (when in doubt, try the Gmail trick and write to them at firstnamelastname@gmail.com)

In all these situations, it helps to be prepared for a negative response. (“The answer is no? Okay, that’s fine.”)

In fact, if you start asking for what you want, and you never encounter a negative response, you should consider whether you’re really asking enough.

Identifying and taking asymmetrical risks is a sure-fire way to live more intentionally. The easiest way to practice is to start asking for what you really want. Just be careful what you ask for—you might get it!

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P.S. I originally started thinking about asymmetrical risks in the context of investing. As I mentioned last week, the world of decentralized finance (or DeFi) offers opportunities to earn returns that far exceed what banks are paying. This is just one example of a real-world asymmetrical risk.

Images: 1, 2, 3

Do you find yourself dreading the holiday season, or just not excited about it? If so, I promise you’re not the only one.

One report from the National Alliance on Mental Illness suggests that 64% of people with mental health issues feel worse during the holidays.

Whether you have a diagnosed mental illness or not, you might just be sad, depressed, or anxious during this time. This is … normal.

To be clear, if you’re a person who loves the holidays, awesome! I don’t begrudge your celebration at all. Have fun, be merry.

What concerns me is the universal expectation that everyone MUST love the holiday season. As noted, for many people, this time of year produces more negative emotions than positive ones.

This can be true because of previous experiences—you have bad memories of earlier years—or due to anxiety about the future. If everyone around you is celebrating and joyful, you might feel the need to pretend.

Well, guess what! You don’t have to pretend! Being sad (or anxious, or just less cheerful) is not the same as being a grinch.

And we all know people (perhaps we’ve done it too) who overeat and drink too much alcohol this time of year. Maybe instead of doing this in celebration, it’s more of a coping mechanism?

Like I said, I don’t begrudge anyone else’s holiday joy. What I resent is the expectation that everyone just chooses to be happy about reindeer or religious symbols or some guy from Finland who breaks into people’s homes to eat their food.

Happiness, despite what you’re told, is not always a choice.

You can choose to be content, to accept, to move forward positively as best as you can—all those things are possible. Sometimes you can even choose to be joyful.

But happiness is not always available on demand, and that’s okay. From much experience, I assure you that if you accept this fact, eventually you will actually be happier. Weird how that works!

If the season fails to brighten your day, and even if it brings you down, just know that this is how it goes sometimes, and “this too shall pass.”

Eventually everything will come full circle, and we can all look forward to the decorations coming down.

How to Be Alone

A while back I wrote a post called How to Be Alone on a Holiday.

I’ve spent a lot of holidays by myself, sometimes by choice and other times by circumstance. At the time I wrote that post, though, I was still a year or two away from a Christmas and New Year’s season that was the roughest of all. I guess I was trying to prepare myself!

That year, I wasn’t actually alone for most of the more celebratory days, but I might as well have been. I remember trying to take care of other people, doing my best to pretend to be joyful, all while I wanted to go to my room and take a Xanax and sleep for the rest of the day.

Out of that experience, I wrote a very personal post, The Importance of Having a Breakdown. A month later, I had made some big changes and was in a much better place—but during those long days in December, I was inconsolable.

Thankfully, this year, I don’t need consoling and I’m very grateful for my life. The gratefulness doesn’t come from celebrating any particular day on the calendar, but from a truly new perspective that I’m exactly where I need to be.

So if this is a hard year or season for you, cheer up! It gets better. Or don’t cheer up, because that’s okay, too. Whatever you do, you don’t need to pretend.

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Images: 1, 2, 3

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