You Will Never Feel Done

Why productivity won’t save you [Not Obvious: Part 3]

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The Way of Work explores stories of where we fit in the world of work. This is part of the series, Not Obvious, exploring why work advice fails us:

• Part 1: Why Work Advice Fails Us

• Part 2: Burnout, Balance, and the Bullshit in Between

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I wish I got more done. I’ve certainly tried.

There’s my to-do list, always expanding and never-ending. But then there’s another, deeper, unwritten list – the ambitions I can’t seem to finish, or sometimes even start.

I tell myself I’ll get to it all. But I know I won’t.

I’ve tried every system: Getting Things Done, Time Blocking, Pomodoro, Inbox Zero, Deep Work, etc.

But none of them deliver what I’m really after: feeling done. Worse, I’m starting to wonder if I’ll ever get there. And whether productivity will ever save me.

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The Obvious To-Dos

My list starts with the visible, legible tasks of daily life:

❏ Answer emails.
❏ Attend meetings.
❏ Finish tasks.
❏ Look busy.
❏ Repeat forever.

Productivity systems thrive here, treating “getting things done” like a logistics problem = break down the world into actionable parts » process them » pump them out. Find the right framework, and we’ll catch up, get ahead, and never feel behind again.

We consult our sacred to-do list religiously, adding, checking, believing. But yet, salvation never comes. Because once we get through the have-to-dos, we’re supposed to reach the want-to-dos. And that’s where things start to get messy.

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The Invisible To-Dos

Beyond the Obvious To-Dos, there are ideas that we never explicitly write down, but are always there, running in the background. And unfortunately, this list is much longer than the other one.

“Beyond the mountains, more mountains.” - Haitian proverb

We think our lives are ruled by the Obvious To-Dos, but it’s here, in the invisible realm, where our sense of being “on track” or “falling behind” is really shaped. Each layer reveals another hidden pressure.

Each of us is different, but most seem to follow a similar framework:

1. The Optimal Self

We don’t just have work to-do lists, we have self to-do lists. And the most important project is ME. This list isn't just about getting things done, it’s about becoming the person we think we’re supposed to be:

❏ Learn more.
❏ Accumulate skills.
❏ Be healthier.
❏ Be more mindful.
❏ Eliminate flaws.

The goal here is to “be the best version of myself.” And the gap between who we are and who we want to be – our unfulfilled ideal – represents our sense of completion. We’ll define ourselves not by what we’ve done, but by what we haven’t become.

2. The Actualized Ambition

Next is The Perfect Career Fantasy: the place where our work aligns with our life’s mission in transcendent harmony. Where the Gods of Jobs “call” us, and we are recruited into the perfect position (one where we can never be fired, btw). This fantasy isn’t written down anywhere, but it’s always front and center in our minds:

❏ Find purpose.
❏ Land dream job.
❏ Make enough money.
❏ Achieve success.
❏ Find balance.

Now, it’s no longer just a list of tasks, it’s about fulfilling our identity. Work isn’t just something we do, it’s how we prove that we’re enough.

3. The Full-Life List

If we’re not totally clueless, we know life doesn’t stop at work. Enter The Full-Life Fairy Tale. Now, our projects aren’t just about our Self or our Work, they extend to our Life:

❏ Have great relationships.
❏ Travel to all the places.
❏ Go on big adventures.
❏ Create something meaningful.
❏ Master a hobby.

The ultimate goal here is to “live a complete life.” A life of excitement, richness, and joy; something impressive sounding for the eulogy at our funeral. These are the dreams we stash away for “someday,” telling ourselves we’ll get to them once we’ve crossed off everything else. It’s our bucket list; we can’t die having not done some of this stuff!

4. Existential Excellence

And now we get down to what we really want – the mushy stuff we try to ignore, but internally yearn for. It’s the final boss, reaching a meta-level mastery over The Game of Life:

❏ Get everything under control.
❏ Achieve clarity.
❏ Find peace.
❏ Be complete.
❏ Feel done.

Now, what we really want is to be immortal by transcending death in a metaphysical form… but we’ll save that “woo-woo” for a future essay.

We want control over our existence, reaching a finished state where all life’s messes are cleaned up and ordered nicely in their appropriate containers. And maybe we’ll get a shiny certificate (digital, of course) for ‘winning at life’ – one last credential added to the end of our LinkedIn profile.

But here's the twist in all these lists we’ve built: they’re never getting done.

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Coming Undone

All of these lists, the visible and invisible, can feel like a lot. Impossible, even.

But wait! The productivity simpletons have some advice for us…

❏ “Write these things down to get them out of your head.” (GTD)
❏ “Prioritize the Not Urgent/Important to-dos.” (Eisenhower Matrix)
❏ “Focus on the things that put you into the zone.” (Flow States)
❏ “Slow down and do less, but better.” (Deep Work)

And the chorus of motivational overlords echoes:

“It IS possible!
DON’T give up!
You CAN have the life of your dreams!
You just have to WANT it!”

Blah blah blah… acting like getting all of this done is a solvable problem.

But clearly, it’s not. There’s too much. Life isn’t a project plan. Or if it is, it’s the kind of project that’s guaranteed to run over-budget and well past the deadline (i.e. death).

It’s messy, unpredictable, often unfair. Relationships don’t get completed, self-improvement is never final, and even our understanding of ourselves (and life) is in constant revision.

Sure, I might cross off a few items from the bucket list, but there’s no way I’ll hit all of them. And my to-do list reloads daily with things I prepared for and even more I didn’t. There’s a new crisis, an old dream resurfaces, I discover a new one.

And still… we keep making our lists and checking our boxes, as if we can impose order on something inherently chaotic. As if we can just organize, schedule, and systematize enough, we can create certainty where there is none.

Productivity culture bulldozes over this existential unease. It has no room for the deeper questions. Instead, it thrives on feeding us methods and hacks that make us feel in control, even when we’re not. And we wonder why things don’t feel right!

Life isn’t a set of neatly organized tasks. No system can ‘fix’ the feeling that there’s always more to do. Face the music:

You will never feel done. You will never be done. Until, of course, YOU are done.

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Done For

As each day passes, we have less time to do it all. The lists grow, our capacities shrink. Slowly, tasks get deleted… not by us, but by time. That career change? It’s no longer an option. That trip? We no longer have the energy for. The last time we saw a good friend? That was the last time we’ll ever see them.

There will be no grand finale, no moment of triumph where we can say, “I did it!”

The productivity gurus will sell you a color-coded system for organizing your tasks, but they can’t help you confront the open-endedness of life. They can promise that you’ll get everything done, but never teach you to live inside the undone.

Maybe we should aspire to finish it all. Cross off every task. Finish every goal. But then what? What happens after? Am I supposed to just… sit there? A finished human, waiting around until life says, “okay, now you’re done”?

Maybe the real problem isn’t having too much to do, it’s having nothing left to do.

We have to accept that our to-do lists will never be empty. And that’s okay. Maybe even a good thing. Our lives, always in process and in progress. Meaning even emerging in the “undone” – exploring the spaces between who we are and who we think we should be.

There is a lot to do. There is a lot we could do.

Yeah. I wish I got more done. But I’m not done yet.

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Bonus: Ambiguous Advice

▸ “Successful people wake up at 5 AM.”
So do toddlers, roosters, and people who regret last night’s Taco Bell.

▸ “80% of the results come from 20% of the effort.”
Great! I’ll do the 20%, and you can do the 80%.

▸ “Peak productivity happens in flow states.”
That means my best work is done in Mario Kart.

▸ “Multitasking is a myth. Focus on one thing at a time.”
Yeah, the key is to just rapidly move from one thing to the next.

▸ “Done is better than perfect.”
Except if you’re my surgeon.

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Next up, I explore the BS around managing people. Subscribe to stay tuned.

Hire slow. Fire fast. Try not to get sued.

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