168 Hours: What I’ve Learned Tracking Every 15 Minutes of My Week

Time Tracking Bitches

For the past two weeks I’ve been tracking every 15 minute interval of my life. I borrowed this time-tracking practice from Laura Vanderkam, who writes helpful books including 168 Hours, which outlines the practice in a lot of detail.

One of Laura’s principles is that “you have more time than you think.” Through her research, she’s found that most people who claim to work more than 50 hours a week tend to over-report their work hours, sometimes dramatically so. In other words, a lot of the time they think they’re working, they’re not. It’s not just that their priorities are out of order; they also waste a lot of time.

I was happy with my productivity and work habits until a year or two ago. Then I began feeling frustrated, constantly carrying the sense that there were never enough hours in the day—though of course I had access to the same amount of hours as everyone else. Even more, being self-employed I have a lot of freedom in how I plan and spend those hours. I’m careful about commitments that aren’t rewarding, I try to have no more than two meetings or extended phone calls a day, and so on.

Still, like I said, I’ve been frustrated.

I don’t have all the answers yet, but I’m pretty sure that some of them will be found through this time-tracking process. (If you’d like to try it for yourself, download a free spreadsheet from Laura’s site.)

What I’ve Learned So Far

A few early observations:

1. Time tracking takes time! But mostly it takes mindfulness.

Learning to monitor what you’re doing every 15 minutes takes some getting used to. I often find myself looking up and suddenly realizing I’m not sure what I’ve done for the last 40 minutes, sometimes longer—which of course is notable in itself.

On the positive side, I like seeing the columns fill up. I can tell there are patterns to be deciphered and improved upon.

*There’s an option to track your time every half-hour if fifteen-minute intervals feels excessive, but so far I’m thinking I’ll stick with fifteen.

2. The mere act of tracking my time helps me be more intentional.

When I know I have to account for my time, even if only to myself, I find myself making wiser decisions. I plan my days more carefully. I started writing this post a few days ago, but I’m finishing it while waiting for a replacement driver’s license at the DMV.

It’s not unusual for me to productively use waiting time. I think what’s different is that today I made this my default state instead of just looking at my phone or zoning out. I knew I’d need to account for what became a 30-minute wait, so I made sure to use it well.

3. Momentum matters.

Week I of tracking my time flew by and I only got behind a couple of afternoons. With a trip to New York City and a few other things that threw off my schedule in Week II, I got much more behind. There’s definitely a sense of momentum or inertia to this process: stay on track and you’ll want to keep it going, lose a few hours and you’ll feel discouraged.

Laura notes that most people have irregular weeks, but you shouldn’t wait for a “regular” week to start tracking. Disruptions happen in every week. I always have different projects to work on and I typically travel every week, so if I waited for a “normal” week at home I’d be waiting a long time. If I continue this discipline beyond another couple of weeks, I’ll need to make sure I integrate it into my traveling life.

4. I don’t feel guilty about intentional time that isn’t spent productively.

I don’t really have hobbies (I’ve tried!) and I sometimes say that relaxing stresses me out.

There are a lot of intervals I filled up with items “reading,” “walking to gym,” “phone call with a friend,” or even “search for mistake fares for post-WDS Asia trip.” And I liked that! I don’t feel that these things detract from my other goals at all. I don’t want to avoid or minimize them; in some ways I’d like to do more of them.

What I want to avoid is wasted time. Almost every day I have numerous 15-minute intervals that I don’t know what to label because I don’t remember what I did. This, at least for me, means that I frittered away the time without doing anything productive or taking time for myself in an intentional way.


So what do I do with this info—or to rephrase, if you try it out, what do you do with the info you gain? Well, I’m not completely sure yet. Like I said, simply paying attention to it as I go is helping a bit on its own. I’d like to do more analysis with the data once I have another couple of weeks of good reporting.

In other words, I’m hoping to rally for Week III and gain more insight.


Image: Eder Pozo

Decide for yourself what you want, then find a way to make it happen.

The Truth Is a Terrible Thing, But Not Compared to Falsehood

Screenshot 2018-03-17 08.33.05

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.

This story from Sheila does a great job of showing how our expectations can create an inner world that is too far removed from reality. Sheila, from Chicago, begins to dream of moving to another city. After some online research (but not, however, actually visiting), she convinces herself that she’s found the perfect place.

“All summer, I’ve felt my excitement growing about Raleigh-Durham… even though I didn’t even understand if they were one city or two.

As June, July, and August passed, the story I told myself about utopian Raleigh grew.

I noticed it happening. I cautioned myself from starting to feel certain about anything before visiting, but it’s a very human tendency. In the absence of real information, we tell ourselves stories.”

Do read the whole post, but the short version is that the story she told herself about the potential move wasn’t based on reality. When she actually goes to visit North Carolina, a place she’s set up in her mind to be a sort of paradise / source of renewal / big next step, she ends up disappointed. It’s a nice enough place, sure, but it wasn’t her utopia.


When you tell yourself a story that might not be true, in some ways you’re protecting yourself. In other ways, though, you’re denying yourself the possibility of something greater. If you discover that the thing you so very much wanted to believe wasn’t true, what does that realization produce? It brings disappointment and pain, most likely, but it can also introduce you to a strength you didn’t know you had.

It can help you see that you don’t need an imaginary security blanket. That blanket wasn’t ever real to begin with, and you’re still here. What can you do now that you’re free from believing in an illusion?

Also, maybe you’ll learn from acknowledging the pain of the truth. True strength isn’t necessarily forging ahead, come-what-may, but rather accepting where you need to pause and consider if there might be a better path forward.


A question that’s rarely asked in these situations: What if Sheila had never gone to visit her imaginary utopia? What if she’d simply chosen to live with the fantasy, imagining a better life in another state that may or may not actually exist?

Maybe that would be okay. We derive a lot of value from anticipating situations and experiences—so much so that I suppose you could argue that remaining in the dark is sometimes better, if it helps you get through other parts of life.

All things considered, however, maybe it’s better that we choose to illuminate ourselves. Even if it’s hard. Even if we don’t fully know what this acceptance will mean.

The truth is a terrible thing, but not compared to falsehood. Open the door and let the light in. You’ll be alright.


Image: PParnxoxo

Decide for yourself what you want, then find a way to make it happen.

To Win the Lottery, Buy a Ticket and Never Check the Numbers


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 convenience store, 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.

Then, for the price of a single dollar, I was given a slip of paper containing a series of numbers.

I understood that this slip of paper had a value that was yet to be determined. Most likely it was worth $0, but there was a chance—however slim—that it could be worth much more. When the winning numbers are announced, hundreds of thousands of tickets like these would immediately become worthless. But of course, one or more tickets could be worth millions.

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.


“You Can’t Win if You Don’t Play…” (But You Also Have to Check the Numbers)

When most people buy lottery tickets, they aren’t doing so because they are compulsive gamblers. They aren’t investing their life savings. Most of them have no real expectation of winning, and only a vague hope that they’ll ever stand on a stage with an oversized check for millions of dollars.

What they’re buying is a fantasy, a brief time of thinking, “What if?” You know how the fantasy goes: What would you do if you have more money than you’d ever imagined?

Spending a dollar on a dream is hardly an irrational investment. Look at what people spend on Netflix each month, or concert tickets, or admission to Disneyland. There’s nothing wrong with those things. Choose your own entertainment without judgment.

But when I bought my first ticket in 15 years, I wasn’t thinking about the lottery fantasy at all.

There’s another old expression about contests of all kinds: You can’t win if you don’t play. If you don’t buy your ticket, you’re not in the game.

Well, I bought my ticket. I got in the game. But then I cheated the system. By refusing to check the numbers, I opted out of the chance to win a random drawing.

At first I wasn’t sure why I felt the urge to buy my first lottery ticket in 15 years. Then, as I handed over my dollar and realized my subconscious motivation, I smiled.

See, I don’t want random. I don’t want external forces controlling my life. I have agency. I AM ENOUGH. I don’t need a miracle, I need my inner compass.

Maybe you need to say some of those things to yourself, too:

I don’t want external forces controlling my life.

I have agency. I AM ENOUGH.

I don’t need a miracle, I need to learn to trust myself.

So that’s why I’m now carrying around this lottery ticket in my journal. Not out of a vague hope that my number will come up, but as a reminder to create my own future.

I know that not all of it is up to me—even without playing the lottery, luck and circumstance affect all of us every day. Some of us experience pain or grief sooner or more profoundly than others. Privilege or the lack thereof plays a role, too. Some of us begin our lives with a head start for no good reason.

Still, because we can’t control everything, it’s all the more important to assert our freedom of choice over the few things we can.

As for me, the lottery can keep its algorithm and bestow its winnings elsewhere. I’m tired of waiting for something to happen. I want to make something happen.

I’d like to think it was a dollar well spent.


Images: NeonBrand, Carlos

Decide for yourself what you want, then find a way to make it happen.

Don’t Feel Pressured To Find Your Life’s Purpose At Age 21


I got an email from a reader who wrote in with a question I’ve heard many times in different ways. Here’s how Andrew, this reader in particular, phrased it:

“I just graduated from college, but still feel entirely lost on what I want to do and where I want to be. I’m only 21 and graduated high school and college a year early, but I just feel like I’m pushing my life along without learning what I want and enjoying the process of it all .

I’ve had my highs and lows throughout these years, and I’m starting to get nervous that I’m going to slip low again because I don’t know how to find what I truly want. I’m done with college, but feel more lost than when I started. I’ve been taking the steps to try to find my true passion, but I just get frustrated when I feel like I’m not getting any closer.

Do you have any advice? I know you hear this all the time, but I’m not afraid of hard work, I’m just struggling to find out what to pour my motivation and drive into.”

I’m no expert on life—your answers to his questions are just as valid as mine—but here’s what I said:

I don’t think most of us know our true passion or purpose right away. It tends to emerge as we embark on different paths.

It’s good that you’re feeling a bit 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.

Since I wasn’t sure what to do or where to turn, I just began to pursue challenges and “zones of learning” in whatever I was interested in. I learned to play a lot of different musical instruments. I learned about entrepreneurship, or at least how to make enough of a living that I didn’t have to work for someone else.

At some point I heard of an opportunity to volunteer in West Africa, and that changed everything. But I didn’t really seek any of these things out—I just followed paths as they opened. Later I became more intentional, moving back to the U.S. and starting this blog, but none of that could have happened without all that came before.

The classic Steve Jobs quote comes to mind:

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”

I’m not one to correct Steve Jobs, but I guess I’d add less of a deterministic bent to it: Where do you want the dots to connect? What steps can you take to best position yourself for the most well-connected dots? And so on.

If you’re not sure where to begin, consider these questions:

  • Is there anything you’ve always wanted to do, but held back on for some reason?
  • If the world was ending in 3 months, how would you spend your time?
  • If you could change one thing about yourself, what would it be?
  • If you could change one thing about the world, what would it be?
  • What are you afraid of right now?

Finding your passion or purpose doesn’t have much to do with age, but experience matters. And because experience comes from active choices, go get some experience!

Do keep searching, but don’t feel so much pressure. It will come if you let it.


Image: Jack

Decide for yourself what you want, then find a way to make it happen.

The Importance of Having a Breakdown, AKA “What Happened to the Annual Review”


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 wistfulness.

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.

More on that in a bit too. For now, here are the two principles I’ve been looking to as guideposts:

A crisis represents an appetite for growth that hasn’t found another way of expressing itself. Many people, after a horrific few months or years of breakdown, will say: ‘I don’t know how I’d ever have gotten well if I hadn’t fallen ill.’” –The Book of Life


When we make a decision, whether it’s good or bad, at least it’s motion. That motion is what moves us forward. Ironically, whether that motion is in the right or wrong direction, at least it’s giving us some better visibility of the terrain around us and helping us learn.” –Scott Belsky

In other words: you didn’t ask for this thing, but maybe you need it. And for the best odds of success, choose the direction you feel is best even if you’re not certain, and then hit the trail.


So First, a Word on Breakdowns

Clinical depression and anxiety are hard to explain to people who haven’t experienced them. It’s not just being sad or feeling worried.

When you’re in a depressed state, you can’t usually see a way out. You don’t believe it will ever get better. You can’t just tell yourself, “Self, get it together.”

Nothing feels soothing. The only thing that brings relief is forgetting about it, which happens once in a while for a brief period of time. But then you remember that you’re sad, whether circumstantially or just as a state of being. And when you remember, you go straight back to ground zero.

This isn’t merely an observation from afar, of course. I’ve been feeling this way for quite some time now. And then, at a point when I thought it was getting better, it got much worse. Damn. Don’t you hate it when that happens?

Here’s another point from the article I referenced above:

“In the midst of a breakdown, we often wonder whether we have gone mad. We have not. We’re behaving oddly, but beneath the surface agitation, we are on a hidden yet logical search for health.

We haven’t become ill; we were ill already. Our crisis, if we can get through it, is an attempt to dislodge us from a toxic status quo and an insistent call to rebuild our lives on a more authentic and sincere basis.”

It might be nice to avoid the process of becoming so broken, but call me if you figure that one out.

Anyway, in recent seasons this has been my state of being on more days than not. I’m somewhat functional but I’m also unwell. Some of it is circumstantial and some of it isn’t. It’s all a jumbled mess that I’m trying to figure out.

Speaking of being authentic and sincere, lately I’ve realized that I’ve missed some key opportunities to demonstrate both of those attributes.

For someone who built a brand around non-conformity, I’ve cared a lot—way too much—about what other people think of me. For someone who encourages people to make big changes, I’ve delayed or postponed my own for too long.

I’m correcting those mistakes now, and guess what? It feels good! Even in the midst of the shadows and storms, taking major steps in the bravery department has helped significantly. I’ll continue in this direction, trusting the process even if some parts of it remain uncertain.

Until then, what do you call the time between the breakdown and the “getting well” part? I think you call it the wilderness. That’s where I’m at now, wandering about and looking for the off-ramp.


And Then, the Review

This was my state of being going into the Annual Review. Despite its name, the review is much more about the future than the past. I typically spend about 20% of the time looking back at the year that’s ending, and 80% selecting various goals and a theme for the next year.

This time, though, I couldn’t get past the first part. In fact, I withdrew every time I tried to approach it. When I considered accomplishments, they seemed insignificant in comparison to the failures.

Even when I understood that I couldn’t have changed some or another particular circumstance, I still fixated on what felt like utter defeat.

Avoiding the past and looking ahead to the future was also hard, since one year is connected to another. For the first four days of the weeklong trip, I had a hard time even thinking about goals—an odd experience for someone who’s otherwise highly motivated to identify objectives and work toward accomplishing them.

In the end I did manage to set some goals, both personal and work-wise. At this point I can’t say too much about the personal goals—all in due time, I hope.

But for now…


In the Midst of This, I Still Have Work to Do

I realize that some parts of this report may not sound that encouraging. I think that’s where authenticity and sincerity come in—I wouldn’t be honest if I listed achievements and various work projects without providing more of the story. Still, I should also provide some balance. I’m not just sitting around moping all the time—I have work to do. And the work is good!

Publishing a podcast episode every single day in 2017 has been a wonderfully purposeful goal for me. So purposeful, in fact, that I’ve decided to do it all over again in 2018.

1. 365 More Stories of People Creating Freedom

Season II of Side Hustle School debuts on January 1, 2018.

You can listen in Apple Podcasts (iTunes), Spotify, or wherever you usually listen to podcasts. You can also subscribe directly on the site.

I’m excited to build on what we started this year. Expect more improvements, more listener contributions, and, naturally, more crazy stories. For example, the first two weeks alone will feature (among others):

  • An accountant who earns $233,751 reselling items he buys at Walmart
  • A designer who earns an extra $5,000/month posting logos on Instagram
  • How to make extra money using Merch by Amazon (without taking any risk or stocking inventory)
  • Two finance professionals go gorillas for bamboo fiber socks

And so many more… it’s gonna be good.

2. Side Hustle Society: My First Training Program in Several Years Basically Forever

When I launched Side Hustle School in January 2017, I said that a training program and online community was “coming soon.” Well, it was technically in the works, but not exactly coming soon.

Guess what: it’s now actually on the way! I spent much of my Annual Review trip working on content and structure for the course. I’m looking forward to sharing it with whoever’s interested—perhaps even you.

It’s called Side Hustle Society, and it launches on January 9, 2017… whether I’m ready or not. Watch this space. 🙂

3. An All-New Project That I’ll Talk About at Some Point

I’m taking on a new editorial project, and it will be different from every one I’ve done before. But first I’ll go into a cave and make it happen, and I don’t think I’ll say much more about it until it’s very close to being ready to go.

This is similar what I did with Side Hustle School last year, where I worked on it for several months before saying anything about it publicly. I’m starting to think this is a better model, all things considered. Less hype, more quality.

4. WDS 2018 (#8!)

Every year since 2011, I’ve welcomed a group of friends and explorers to a global gathering called World Domination Summit. 2018 will be year 8, and we plan to build on the theme of “Team Everybody” that we started this summer.

This definitely isn’t a solo project: I’m fortunate to work with a wonderful team on making this happen. Never been before? Well, save the dates! WDS 2018 will take place from June 26-July 2, and I’d love to see you there.



On the Possibility of Lights Appearing in Tunnels

These projects and duties serve as anchors. They don’t provide complete comfort, but they do give me something to keep my mind on while I’m trying to find my way.

Every day I have to make the show—or as I prefer to say, every day I get to make the show. I really do enjoy it. Being able to write books and speak to audiences is a “job” that I never take for granted. Even when I’m sad, I know for sure that work-wise I’m doing exactly what I’m supposed to.

Is work a distraction from other issues? Perhaps it could be at times, but overall I don’t think it’s that simple. I’m actively doing everything I can to care for myself and make progress, but that’s not really a full-time job. I also know that what I do in the career space matters, and that feels good. I just want to be better off otherwise.

So for now and for next year: connection and relationships will matter more than ever.

Travel will continue but more purposefully. The calendar will be clearer to allow for more possibility. And most of all, I’ll be making a big change even if I don’t have complete confidence in the outcome.

One other thing I know for sure: 2018 will be very different. It has to be. And so it will.

To new beginnings,


Chris Guillebeau

P.S. I’ll be okay eventually, so you don’t need to worry. I just wanted to provide an honest report instead of pretending that the shadows blocking my view don’t exist. Maybe in the end, the shadows will prove the existence of the sunshine.

Images: Clark, Oliver, Austin, Braden, Andreas

Decide for yourself what you want, then find a way to make it happen.

2017 Annual Review: How to Evaluate Your Life Even When You’re Feeling Sad


UPDATE: The Importance of Having a Breakdown

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.

Still, there are several reasons why I’m going to proceed with the review:

First, the unexamined life is not worth living—at least according to a wise person like Socrates or Bill Murray. Only by looking at things the way they are, not the way we might wish them to be, can we truly set an intention and ensure that anything within our realm of control is aligned with that intention.

Second, joy and sorrow can co-exist. Looking back, I know I can I feel proud of some of the work I did this year. And it’s not just work: I also feel proud of a lot of personal growth as well. I do feel more self-aware than ever, for better or worse (or maybe for better and worse).

Last, in recent weeks I’ve been thinking about this quote a lot:

“You cannot protect yourself from sadness without protecting yourself from happiness.” -Jonathan Safran Foer

Let’s not sugarcoat it. I’ve long chosen highs and lows instead of a mediocre flatline. So for all these reasons, on with the review.

Here’s How It Works

If you’d like to learn about the approach I use for the review, here are a few starting points:

1. Read the original post

2. Download this free tool (more about this in a moment)

3. Before doing anything else, make two lists consisting of a) what went well and b) what didn’t go well this year

Revised Spreadsheet Template (Download for Free)

The main phase of the review is forward-looking, not retrospective. I spend most of my time thinking about goals, values, and decisions.

For the whole eight nine ten years I’ve used the same simple spreadsheet to set goals in various life categories. It’s a very basic tool. It won’t win any design awards, but it will help you to think more clearly about your life, which is probably more important.

We’ve recently tweaked the formatting and added a few more data points, so be sure you have the current version:

—>Download the Updated Annual Review Template

Some have questioned whether a spreadsheet is sufficient to truly devise what matters to you and plan your life accordingly. This is a valid concern—we first need to ensure that our goals match up with our values and overall vision.

No amount of goal-setting will help if you’re pursuing the wrong goals. However, I do believe (strongly!) that being specific about our intentions and tying them to measurable milestones is good for us.

If you haven’t done it before, give it a try. And if the template structure doesn’t work for you, don’t hesitate to modify it however it serves you best.

In the next few posts I’ll share some of my reflections on 2017, as well as a look ahead at the next year. Stay tuned…


Image: Andrew

Decide for yourself what you want, then find a way to make it happen.

Feeling sad on the holidays? Me too. Here’s all I know how to do.


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!

If you’re wearing matching sweaters while stringing lights and singing carols with your family, good for you. I really do mean it. Take joy whenever and however you can.

The thing is, not everyone feels joyful this season. In fact, not everyone likes the holidays in general. Some of us actively dread this season, because it tends to correspond with seasons of sadness.

Sometimes these seasons of sadness are connected to specific events, and sometimes they aren’t. Sometimes we feel alone, even if we’re around good people who love and care for us.

Sadness like this isn’t usually simple. You can’t just tell someone, “Cheer up!” and witness their transformation in front of your eyes. (And unfortunately it doesn’t usually work when you say it to yourself either.)

There isn’t an easy answer for these things, at least not one that I’ve found. Mostly I want you to know that even if you feel alone, you’re not the only one who’s struggling. And there will be a better season at some point, hopefully soon and “just around the corner,” but even if not, it’s still on the way at some point.

In the meantime….

Having some perspective is good. You don’t sleep on the street, do you? You have access to clean water, right? And presumably you’re not fleeing Syria or another war-torn country. To be clear, thinking of other people in need doesn’t mean you shouldn’t be sad. Don’t feel guilty about how you feel—you already have enough negative feelings. It just helps to have a little perspective.

Giving to others and helping however you can is also good. It won’t solve all your problems, but it can help other people with theirs. Give however you can, wherever you can, and in whatever way feels right to you. If nothing else, you’ll make someone else’s life a little better.

Keep doing things you know are good for you. Is exercise helpful? For most people it is, so try to stay active. Listen to music you like. Go for walks. Do something you enjoy, and if it doesn’t feel enjoyable now, that’s okay too.

Know yourself and do what’s best for you. Some people shouldn’t drink alcohol during extended times of sadness. Others can handle it in moderation, and it may even help. The same is true of caffeine, sugar, or other substances. You know yourself best.

When something good happens, appreciate it! Sometimes a reprieve arrives in an unexpected surprise. Well, don’t ask too many questions! Just like the happy people in the ridiculous sweaters, take joy however you can.

Make a gratitude list. The other day I wrote down a list of 10 things I appreciated even in the midst of a season of sadness. Then the next day I did it again. Even in the worst of times, there’s a list waiting for you to write it, too.


Once again, remember that everyone you meet is fighting their own hard battle.

The holidays aren’t a joyous time for everyone. If you’re struggling, hold on till a new year comes around. Keep believing that the best is yet to come, even if you can’t see it.


Image: Clem

Decide for yourself what you want, then find a way to make it happen.

When You’re Stuck in a Hole, Look for Someone to Join You: A Lesson in Empathy


Happy Thanksgiving to all, and not just those in the U.S.! Thankfulness is available no matter where you live. Hopefully pie is available where you live, too.

Here’s a story for anyone wandering in the wilderness—or in this case, anyone stuck in a hole:

A man is walking down a street when he falls in a hole. The walls are so steep he can’t get out.

A doctor passes by and the man shouts up, “Hey you! Can you help me out?” The doctor writes a prescription, throws it down in the hole, and moves on.

Then a priest comes along and the man shouts up, “Father, I’m down in this hole. Can you help me out?” The priest writes out a prayer, throws it down in the hole, and moves on.

Then a friend walks by. “Hey, it’s me,” the man calls out. “Can you help?” And then the friend jumps in the hole.

The man says, “Are you stupid? Now we’re both down here.”

The friend says, “Yeah, but I’ve been down here before … and I know the way out.”

Everyone you meet is fighting a hard battle, and sometimes we need a companion who’s fought the battle before.

Are you stuck in a hole? Hang tough! Can you help someone who’s stuck? Jump in and join them.


-From The West Wing with hat tip to Peter Shankman

-Image by Simone

Decide for yourself what you want, then find a way to make it happen.

A Field Guide to Wandering in the Wilderness of the Soul


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.

Amenities are limited in this wilderness. You sprain your ankle on those picturesque cobblestones. Cafés serve overpriced, burnt coffee, and the servers are rude. All you want is to get back on the path, but it’s not so simple. The teacher appears when the student is ready, so they say, but you’re ready to drop out of class.

You curse the landscape, your traveling companions, and most of all yourself. You try to fight your way out, but any opponent you select is a straw man, any battle a proxy war that only ends up delaying your exit further.

No one chooses the wilderness; the wilderness chooses by its own logic. And once you’ve entered, your ability to determine the time and location of exit is beyond your control.


Let’s say you’ve recently arrived in this unpleasant no-mans-land. Perhaps this isn’t your first time here, so you try to get your bearings. You survey the landscape, recognizing familiar signs and features. With a shrug of your shoulders, you think, Well, I’ve done this before. I just need to lace up my boots and start hiking.

But each wilderness of the soul has some unique shape or challenge to it. You notice that the tools you used the last time have become rusty, or maybe even defective. The wilderness is mocking you, telling you that if a quick fix was available, you wouldn’t have encountered each other again.

As you ponder your options, you think, Where am I? And, How did I get here? And most of all, Where’s the off-ramp from this wilderness?

But that’s where you find yourself frustrated again. The off-ramp isn’t on the map! The very definition of a wilderness is a place where you find yourself wandering, most likely going off in the wrong direction multiple times. Your path out will be anything but direct.

Eventually you sink in and accept your fate. Damn. I guess I’m officially lost in the wilderness!

It’s at this point, or soon thereafter, that you finally learn something. First, you learn that you are not in control. The longer you fight this lesson, the longer you remain in one place.

It’s not that you have no autonomy whatsoever. You have skills, and you have life experience. You can draw on those times in your life where you had to do hard things. These memories and experiences won’t take you all the way, but they’ll help.

When you stop panicking, it gets easier. It’s hard to make wise decisions when you feel so desperate.


Speaking of decisions, somewhere in the wilderness there’s a decision you need to make. Before you can escape and get back on the path, you need to find your way to that decision point.

That choice you must make is not obvious or easy. Whatever the decision is, there are no two ways about it. Trying to have it all only leads to a muddy compromise that further delays you.

Once you navigate that point of no return, it gets easier still. You find a rest stop somewhere. You find an unexpected guide or companion. You see the beginnings of a trail.

Note: try not to get too excited at this point, because it might not be over yet. There’s always that “Darkest hour before dawn” thing to look out for.

Clues appear that lead you along the way, bread crumbs drop from the sky to give you sustenance. At first these feel like the bare minimum of rations, but somehow the crumbs lead you to a place of comfort. You begin to take joy in small pleasures again. The coffee becomes much better, and the servers even smile once in a while.

Finally you emerge from that wilderness, dusty and haggard, face set toward the sun and the path that leads you forward. Maybe you look back for a moment and feel grateful for the lessons you’ve learned. Maybe you shake off the dust and vow never to return.

Or maybe you just pause and say, “What the hell was that about?”


There’s no “5 ways to escape the wilderness” guide. If it were that simple, it wouldn’t be a true wilderness.

But understand this: acknowledging that you are in the wilderness is oddly empowering. Admitting your powerlessness can build resilience.

You probably know the quote well, having seen it on bumper stickers and Instagram captions the world over: Be kind, for everyone you meet is fighting a hard battle.

Where does that come from? Oh, right, it comes from the human condition. The reality of life, love, and adventure. The choice to truly live, and to risk with no guarantee of return.

When you find yourself lost, release control but never give up hope. Always know that life is worth living no matter how hard things get.

And never doubt that there’s an off-ramp from the wilderness, even if that exit seems impossibly far away.


Image: Bradley, Glen

Decide for yourself what you want, then find a way to make it happen.

Pandering Never Builds a Legacy


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. I wrote about Paula in the appendix of SIDE HUSTLE—she’s my go-to expert on rental properties, a topic I know little about, but one that often comes up in the small business world.

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.

Here’s some of what she said that resonated with me:

“The revolutionaries who came before us – the people who shook the worlds of architecture and music and food and art and technology – they thought bigger than the crowds, and that’s why their work … outlives them.

Do you want your grandkids to remember you for writing articles on “5 ways to save on car insurance?”

If your goal is to leave a legacy – not just make a buck or two, but to leave behind work that represents your time on this earth – you cannot follow the crowd.

You must ignore the crowd and serve the craft. I’ll repeat that: You are here to serve the craft, not the crowd.

Pandering never builds a legacy.

As online content creators, our legacy will not be the number of Facebook likes we’ve left behind.”

By the way, I heard her say this at Fincon, an event I also spoke at. I spoke after Paula and before Darren Rowse, another friend. Small world!


Image: Nathan

Decide for yourself what you want, then find a way to make it happen.

For All the Things You Can’t Control, Remember “This Too Shall Pass”


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.

You might have a lot of influence, all the autonomy you could wish for, and independence for days—but when it comes to things you can’t control, none of that matters.

I was reading a thread on Quora recently and noticed a recurring theme in what people mentioned as being outside the realm of control.

What other people do.

This is the biggest one. Even if you maintain complete independence for yourself, with no boss and no other accountability, that freedom doesn’t extend beyond yourself. Ultimately, people with free will like to exercise it. You might wish for someone to change, you might even desperately want them to (or feel like you need them to), but their decisions on how to proceed are their own.

What other people think of you.

You can’t control anyone else’s thoughts at all. You may want someone to like you, to think well of you, to earn their favor in some way—but this too is outside your control. Alas!

If you’re seeking approval from someone, never forget that approval is theirs to give or withhold. So since you can’t force someone to think well of you, be attracted to you, or whatever positive sentiment you’d prefer, it might be a good idea to worry about it a lot less.

The rest of the world as it unfolds around you.

The world and environment we live in influences the options available to us. One time a flight I was on had to divert for a medical emergency and I missed an important connection. It’s always the right thing to make sure someone else gets the help they need, of course. But in this case it meant that I had to make a number of unexpected changes that affected the next 10 days of a busy travel schedule.

When feeling frustrated by any of these things, one of the most powerful remedies is to remember the timeless wisdom of “This too shall pass.” No matter the difficulty, it won’t be there forever. The same is true for all the good things in your life: This too shall pass.

Therefore, if you can come to terms with the things you can’t control, or at least stop worrying about them so much—and at the same time, learn to appreciate the good things while there’s still time—perhaps you’ll be much happier.

Via: Quora

Image: Elijah


Decide for yourself what you want, then find a way to make it happen.

Going Back to a Hard Place


Imagine revisiting a place you’d been long ago during a hard time in your life. Maybe that time was long, long ago, and the place far, far away. Or maybe it was last week, and the place is the coffee shop down the street.

Whatever the story, you experience an unpleasant flashback as soon as you arrive or walk into this place. You remember what happened when you received terrible news, or you relive that thing that someone said to hurt you. Maybe your time in this hard place was even traumatic, and you can’t help but by reminded of it.

And it’s not just about the memories. You can feel it. The anxiety tightens, and maybe you’re short of breath. Perhaps this was a good place for other people, but for you, it sucked.

There’s no doubt about it: that thing was hard! Not just a little hard, but hard in a life-changing way. Back then, during the time of the hard thing, you had no idea how you’d recover. You couldn’t fathom ever being “okay” or normal again.

But maybe there’s also something good about this experience, the one that feels so unpleasant at first.

That hard time is in the past—maybe not entirely, but a big part of it is. Some of it has made you better, wiser, stronger. You made it through, even though you didn’t feel like you ever would. (It’s okay if you’re still making it through. It’s a process.)

And now when you revisit the place of the hard thing, it has less control over you. Now you can see it through a different perspective. Here’s the BEFORE, where you were last time. Look at how weak you were; feel compassion for the self you were then. But look, as well, at the self you are now. This is the AFTER. See how so much is different?

How does it feel to wake up at 3am and not be terrified? Sure, you wish you could sleep, but insomnia without anxiety is just jet lag. You stay awake for a while. You eventually fall asleep. It’s life.

This place can not control you. That person can not hurt you anymore, unless you let them in or are unable to let them go. Now is the time of feeling proud. Now is the season of the new you.


Image: Grace

Decide for yourself what you want, then find a way to make it happen.

Why Ideas Are Not Enough (Or: How to Sell Out Like Iron Maiden)


Link: Perennial Seller

“What if I’m not good at making ideas happen? I just like to have ideas!”

Ever since I started Side Hustle School on January 1, I’ve heard this question a surprising number of times. And believe me, I know it would be nice if you could just have ideas and then someone else goes out and “handles” them.

That’s not how it works for most of us, though—even people who are successful writers, entrepreneurs, or artists of all kinds. Ideas gain value not through brainstorming but through the getting-it-done phase that all good work needs.

A new book comes out today from stoic-in-chief Ryan Holiday. It’s called Perennial Seller, and I was able to read an advance copy a couple months ago. To be honest, I get a bunch of advance copies in the mail, and I’m not always able to read most of them. This time, though, I brought it on a flight and was instantly hooked. I read every page!

Here’s what Ryan says about ideas and doing the work:

If you’re trying to make something great, you must do the making. That work cannot be outsourced to someone else. You can’t hire your friends to do it for you. There is no firm that can produce a timeless work of art on your behalf for a flat fee. It’s not about finding the right partner, the right investor, the right patron—not yet anyway. If this is your project, the hard work will fall on you. There’s just no way around it.”

He goes on to say that “it’s not that dreaming doesn’t matter or that ideas aren’t important.” Dreaming matters! Ideas are important.

Still, without doing the work… there’s nothing to show for a dream.

The title Perennial Seller refers to the concept of making something that endures, not just a flash-in-the-pan that launches with a sparkle but then quickly becomes irrelevant. Among many other examples, the book points to Iron Maiden—remember them?

I can’t say I follow their work much (I mean, I did in seventh grade but…). However, it seems they’re still selling out arena tours all over the world. They’re a perennial seller, even without a lot of mainstream attention.

What separates the rare enduring successes from the crowd of bands, books, movies, and anything else that is quickly forgotten? Read this book to find out—you won’t regret it.

It’s easily my #1 business book of the year so far… and it’s hard to imagine that something will easily surpass it.*

Link: Perennial Seller

*Okay, well—they aren’t really the same kind of book, but Side Hustle comes out in September and I hear it’s worth a look.


Image: Sam

Decide for yourself what you want, then find a way to make it happen.

The Movie of Your Life, Part II


I used to worry a lot about what people think of me. I felt that I could be damaged or even destroyed by someone’s words, or my failure to achieve an arbitrary level of success.

I tried to present the right image in each encounter. When something went wrong, I would run and hide.

I still worry a lot, of course. But now for the most part I worry about different things. If there’s anything good about getting older, it’s that I care much less about people seeing my faults.

Now—at least sometimes—when I encounter a situation that might bring me down, I tend to think who cares? Get a life, man. I have one.

A while back I wrote about the idea of your life as a movie, with you as the director. When you go through your archives in post-production, you might stumble on a scene that feels particularly surreal.

In those times, you may wonder, “Why did I put this scene in my movie?”

I’ve been thinking about this lately as I continue my journey. With the benefit of perspective, I realize that some of the scenes in my movie are… well, a little surreal. Looking back on those scenes, it’s easy to wonder, “Did that really happen?”

Sometimes the reflection is positive:

“Wow, I still can’t believe I did that! I had an idea and I made it happen. I followed a dream and I’m so glad I did.”

And sometimes it’s negative:

“Wow, that was bad. Was I really that wrong about such a fundamental situation? Was I that wrong about myself?”

It’s only with hindsight that some things make sense, and it’s also true that at a certain point you worry less about the ones that never will.

Still, why do we put these scenes in our lives?


Image: Fabrizio

Decide for yourself what you want, then find a way to make it happen.

The Myth of the Self-Made Man


Arnold Schwarzenegger on being a self-made man:

“I came over here with absolutely nothing. I had $20 in the pocket and some sweaty clothes in a gym bag. But let me tell you, I had this one little apartment and on Thanksgiving, the bodybuilders from Gold’s Gym came to my apartment and they brought me pillows, dishes, silverware, all of the things I didn’t have. None of us can make it alone. None of us. Not even me, who’s been the Terminator and went back in time to save the human race. Not even me, that fought and killed predators with his bare hands.

“I always tell people that you can call me anything that you want, but don’t ever, ever call me a self-made man. It gives the wrong impression, that we can do it alone. None of us can. The whole concept of the self-made man or woman is a myth. I would have never made it in my life without the help. I want you to understand this because as soon as you know you are here because of a lot of help, then you also understand that now it’s time to help others. That’s what this is all about.”

Even though I write a lot about independence and self-reliance, I also try to be aware of other factors that allowed those values to foster and develop, at least in my case. I was fortunate to have parents who cared for me. I also had various privilege—racial, gender, socioeconomic, citizenship, etc.

And then, of course, I had a lot of help… which is why, like the Terminator, I believe that now is the time to help others.

Link: “No One Can Do It Alone”

Image: Paulo


Decide for yourself what you want, then find a way to make it happen.