Are You Working Hard Enough?

At some point, we’ve all beaten ourselves up wondering, “Am I putting in enough work to reach my goals?”
I’ve been there. I might be there tomorrow. That never-ending thought - am I doing enough? am I working hard enough? - creeps in when things feel still, like you’re falling behind while everyone else is sprinting ahead.

You lie awake at night, head full of ideas for things you’re definitely going to start tomorrow - only to wake up, check your phone, and slip right back into your usual loop.

We’re surrounded by people telling us to grind harder, to wake up earlier, to squeeze more productivity out of the same 24 hours. That “5 to 9 before my 9 to 5” trend? I remember watching those clips - cold plunges, gym sessions, smoothies, journaling, all before the sun’s up - and feeling this weird mix of inspiration and exhaustion. Like… good for them, honestly. But also, when did living become a competition of who can do the most before breakfast?

So how do you know when you’ve done enough? How do you quiet that voice that says you could’ve done more?

Maybe I’ve been thinking about this too much because I’ve been watching Severance lately. (Don’t worry - no spoilers.) Ben Stiller described the show as an exploration of “work-life balance.” The characters literally split their consciousness in two: one version that only exists at work, and another that only lives outside of it. What fascinated me wasn’t just the concept - it was the emptiness in both lives. The “innie” never gets to feel the joy of finishing something, while the “outie” never experiences the satisfaction of creating. Both halves are stuck chasing something they can’t fully reach.

That hit me. Because when you think about it, most of us do a softer version of that. We switch between our “working self” and our “real self,” trying to keep them separate, trying to balance output with peace. But sometimes that balance doesn’t exist. Sometimes, the more you push in one direction, the more the other side starts to fall apart.

I’ve noticed it in my own life, when I feel good about my personal life, my creative drive slows down. When I’m locked in and producing, my social life starts to fade into the background. And so the cycle begins: feeling guilty for resting, then feeling burnt out from working too much.

The truth is, “working harder” doesn’t always mean “doing better.” Especially in creative work, effort has a strange curve. There’s a point where putting in more hours stops helping and starts hurting. Push too far and you stop making, you just start spinning. That’s where burnout sneaks in, disguised as discipline.

I’ve learned (the hard way) that the key is to find your personal limit - that spot where your energy, focus, and output overlap in a way that feels sustainable. You’ll slip past it sometimes, and that’s fine. But once you’ve felt the edge of burnout, you start to recognize it early. You learn to pull back before the crash.

The problem is that limit isn’t fixed. It shifts with time, seasons, your mental state, even the people you’re around. Some months you can work twelve-hour days and love it. Other times, just showing up for a few hours is enough. The goal isn’t to be constantly “on.” The goal is to know yourself well enough to tell when pushing harder helps and when it doesn’t.

And then there’s the other side - when you’re not burnt out, but you’re barely working. You sit down to focus, and half the time disappears into your phone, your fridge, or your thoughts. You convince yourself that being “busy” counts as being productive. But it doesn’t. And in those moments, that voice in your head - the one that says you’re not doing enough - might actually have a point.

Because doing the work is the only real antidote to doubt. Not thinking about it, not planning it - doing it. Most great ideas start as sparks that only become real through hours of unseen effort. It’s not glamorous, and it’s rarely rewarding in the short term, but the process itself is where the meaning lives.

That doesn’t mean the work has to consume you. It just means you have to commit to showing up. Get organized. Make systems. Set deadlines. Build momentum.

And once you’ve done that, once you’ve found that rhythm - the final step is rest.

Not the kind of “rest” where you’re still checking emails or half-watching a movie while thinking about tomorrow’s to-do list. Real rest. The kind that feels like stepping outside of yourself for a day. One full day each week where you don’t think about creating, fixing, or producing anything.

Go outside. Let yourself be bored. Sit in silence long enough for your thoughts to settle. Boredom feels useless at first, but that’s often where your best ideas are hiding.

By the way, I uploaded a new video this week. It’s not tied to this letter, but if you’ve ever questioned your work or yourself, I think it might speak to you.

Keep going. Keep resting. Keep finding that middle ground.

See you on the next stair,
Alastair