The Don’t Work series marks the end of another chapter in my life. Just as Work in Progress chronicled my career-building years, this series covers the unraveling of my working identity.

A year ago, I took time off work, expecting it to go one way. It didn't, but I’m grateful for the twists and lessons along the way.

Through my writing, I hoped to convey my own experiences and lessons learned during this time. In particular, I focused on the contrast between the old me and new me, and how the concepts and ideas that worked for me before, now were flipped on their heads.

I recognize that some of these ideas might not resonate with everyone. What worked for me might not fit your situation. That’s okay.

But almost every lesson I learned was a blindspot for me only 2 years ago. So a big part of this is advice to my former self: “hey dude, you think you know life? Well, things are not always what you think. Get ready, because change is coming.”

Also, check out my recent discussion with Michael Karnjanaprakorn, where we discuss sabbaticals, finding meaning outside work, and more: Scaling Down to Find Meaning

Before I turn the page on a new chapter, I wanted to revisit some of the big picture ideas embedded throughout this series.

Most popular article: How to be unproductive

Most polarizing article: The very easy, not-painful-at-all, 5 super simple steps to changing your career

Favorite joke: “Some of you might be thinking, basically anything could be rationalized as hard work. ‘Hitting this bong is hard work, dude!’” (from The “Hard Work” Delusion)

Favorite reader comment: “I've read ur latest piece more times than I'd like to admit, really powerful, well done.”

Summary from the last series: 10 Takeaways from a 'Work in Progress' (or, how to build a career

Here are the big picture takeaways…

1. Careers are fluid, not fixed

I believe the classic model of careers is largely dead. Even professions like lawyers and doctors, who in the past, benefited from start-to-finish stability will experience significant ups-and-downs over the span of a long career.

We forget that modern careers are largely a function of circumstances. Not long ago, the working world looked very different. And not far in the future, it will look much different as well.

Rather than trying to hold onto these outdated models, we benefit when we recognize the fluidity of life. Especially the fluidity of our own careers.

Careers go up-and-down. Our ambitions change. Circumstances change. Life has seasons, where certain things make sense in one versus another.

I don’t buy into any of the bullshit that people sling about life being simple and straightforward. Your career won’t have a clean narrative. Instead, life is a muddy swamp, filled with ambiguity and tradeoffs.

Accept the fluidity.

2. At some point, every work virtue becomes a vice

Hard work, productivity, ambition, scale, callings, and a strong work-identity…

I used to believe these principles were all universal virtues. And in many ways, they worked well for me before.

We are always drawn to these seductive ideals. That there is “one way” to do something. As if the working world had natural laws as permanent as gravity.

But every virtue, at some point, loses its merit. Maybe we move into a new stage of life. Or we realize what got us here, won’t get us there. Or we realize these were naive delusions to begin with. For example:

• Hard work creates blinders about what you should be working hard on.

• Productivity only works when the destination and path to get there is clear.

• Ambition is unambitious when it’s stuck at a narrow level.

• Scale can leave us disconnected from the work that matters.

• Callings are great when you have one, but worthless when you don’t.

• Work identities distance us from who we really are.

Whatever it is, I’m now more careful about having rigid rules that don’t bend to circumstances. If there is a meta-rule, it’s: “the only constant is change.”

3. Scramble your patterns

I liked how Derek Sivers put it recently in an interview, describing what he did after leaving his company (emphasis mine):

“I started doing things the opposite of whatever I had been doing at any moment on a day-to-day basis. If every instinct was telling me to turn left. I would turn right. And if everything in me was telling me to stop, I would go. And I did that to deliberately scramble my patterns and force exploration.” - from the Never Enough Podcast

That largely explains my journey over the last 12 months.

To many people, what I did was unrecognizable to the person they used to know. They think I’ve gone off the deep end. For example:

• I used to be a hardcore operator with goals, plans, metrics, etc. But instead, I tried going without any of them.

• I used to be all about productivity, inbox zero, etc. I was a taskmaster. But instead, I tried doing all the things that felt unproductive to me.

• I used to be a hard worker in the traditional sense. But instead, I’ve chosen a path that to many, seems lazy.

We love the idea of pushing through with discipline, willpower and habits. But sometimes growth comes from trying something entirely different.

As I’ve said: “to the workaholic, working is easy. Not working, on the other hand, is hard work.”

4. Create your own definitions

There are definitions of “Work” and then there is the socially acceptable definition of “Work.”

Work actually means many things. But our society’s view of Work is pretty narrow. Which do you choose?

Others will seek to define you with a label. It’s how they understand you. But you are much more complex than one label. Which do you choose?

One feature of writing is that I can do whatever I want. I can swear like a fuckity fuck. I can play with words in ways that are contradictory (e.g. “being unproductive was the most productive thing I could have done”). And, most importantly, I don’t need to cite my sources using MLA format. What freedom!

Yes, there are always practical consequences and restrictions to decisions. I may have more freedom than you. But you, like me, can create your own version. Don’t take outside ideas at face value. Question them. And manipulate words to fit the definition that works best for you. You decide.

5. Take a break, will you?

If it’s not clear, I highly recommend sabbaticals. Taking time off at some point in your career—whether it’s a year or only a few months—can be incredibly valuable. You don’t need to follow the same path I did, but I believe most people would benefit from some version of stepping away.

Especially if you’re locked into the work grind and can’t see life beyond it. Especially if you’ve been operating at scale, but feel disconnected from your work. Especially if you’re burnt out, stuck, or starting to wonder if there are other paths out there.

So how do you take a sabbatical?

• Plan ahead: Even if it’s years from now, think about when you could carve out time. Consider how long it could be, whether that’s a month, a quarter, or more.

• Build a financial buffer: treat it like you would any big purchase—a car, a vacation, a house downpayment. Give yourself as much runway as possible to reduce the financial pressure during the sabbatical (e.g. if taking off 3 months, plan at least 6 months of savings). And remember, you will always leave money on the table by stepping away. Get comfortable with that.

• Get creative: Consider ways to reduce expenses or simplify life during your sabbatical. Could you stay with family? Take a cheaper route, or explore alternative work setups like part-time freelancing?

Worst case, you take a break and return to your old path, refreshed and renewed with energy. Or, like me, you discover that your old path isn’t the right one anymore—and you give yourself the freedom to make a change. In both cases, you win.

Are you climbing the wrong mountain?

For many of us, work is where we find meaning in life. Or indirectly through the byproducts of it (e.g. money and status). Work is our vehicle to get there. Or so we believe.

We’ve discarded and ignored all the other sources of meaning along the way: relationships, community, causes, philosophies, and faith.

We try to force meaning through the narrow funnel of work, hoping that this is where we find salvation. It appears to work for some other people, so why not us?

But I feel like a mountain climber who now sees an entire landscape of mountains to be climbed (and more along the horizon that I barely even understand myself). Yet, most people seem to be standing in line at the base of one mountain, believing it’s the best—or only—one worth climbing. They’ve been indoctrinated into believing that reaching the summit of this particular one is where they’ll find salvation.

I’m not here to convince you to abandon the mountain you're currently climbing. But I am here to tell you to lift up your head and notice the other mountains.

Are you climbing this one simply because everyone else is? And if you’ve never looked up to see the others, how can you be sure this one’s right for you?

Life is too short to stand in line for someone else’s mountain.

Series Credits

Special thanks to the following people for their contribution to this project.

➤ For supporting me every day, providing the ultimate sounding board, and never pushing me in a direction I didn’t want to go (plus, being my editor): my wife.

➤ For being models of balanced ambition, and proving you can have a successful career and then do something completely different: my mom and dad.

➤ And for everyone who gave me space or offered little nudges of support or shared their own story with me: I will never take your support for granted.