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

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