Being uncomfortable is such a common occurrence for me - it’s natural when I’m working on ambitious goals, or when I’m feeling impostor syndrome. It’s hard to know when to push, how much to push, and when to stop pushing myself.

If you want to achieve a lot, it helps to be deliberate about the amount of “uncomfortable” you accept in your life, and manage the cost of that. For me, that means accepting and reframing this feeling.

The optimal threshold

When does comfort become discomfort? In my experience, discomfort happens with pushing a bit past your boundary.

A work-out intensity that’s sustainable for 1 hour or 15 minutes (1). Anything that you can do for longer than an hour, like a jog, is probably not that uncomfortable. If you’re trying to maintain a pace for only 10 minutes, then you’re probably pushing too hard.

Academic questions where you’re making mistakes about 10-30% of the time (2). Make mistakes more than that, and you’re probably wasting time on questions you’re not really equipped to answer; less than that, wasting time on questions you already know the answer to.

Being “in the zone” at work, where you’ve got the right mix of challenge and skill (3). Even if we can’t quantify it as easily, it’s easy to recognise the feeling of a long easy task (slogging through), or a task so far out of our depth.

Finding motivation

As humans we can be proud of succeeding - but perhaps we’re more often afraid of failing. That fear creeps in before and often during a challenging activity. It’s always easier, safer, to come back to it later.

I’m still struggling with this - even writing this post, I’ve gotten stuck and decided it was time to cook, or do chores, or write another email. I’d love to get better answers - but for now, here are two approaches that work for me.

At a high level, I do things to improve because it comes from the kind of person I want to be. Honest conversations about life with close friends and family anchor my long term goals. Inspiration can come from anywhere - ancient greek phronesis (4) or anime (5).

At a very practical level, the most helpful framing for me is tiny goals that are meaningfully on the critical path: 100 seconds on the bike, or just one more idea into a paragraph.

Watch outs

Being uncomfortable definitely drains my batteries. Being deliberate about being uncomfortable also means making sure I have corresponding time to recharge my batteries.

Be very careful about any commitments. When I’ve over-committed, pushing myself a bit past my comfort zone quickly becomes something I dread.

The environment matters. Fewer restrictions on time, space, and energy stacks the odds in my favor. Breaks are good, but interruptions can really trip you up.

Close the loop, and celebrate effort. Stopping at the point where we’ve achieved the most difficult part of the task. In some ways, the final step is the easiest, and easiest to skip - whether it’s stretching, or writing a good comment when sharing code. I’ve found it helpful to treat these moments as part of celebrating effort.

Conclusion

Does this approach resonate with you? I’d love to hear your thoughts!

(1) Peloton Power Zone training in Zones 3 and 4. https://www.onepeloton.com/blog/power-zone-training/

(2) https://www.psychologytoday.com/us/blog/brain-waves/201911/the-right-level-struggle-learning

(3) https://asana.com/resources/flow-state-work

(4) https://en.wikipedia.org/wiki/Phronesis

(5) I enjoyed “Philosophies from Shounen 101: Becoming a Real-Life Protagonist”, a talk on this topic at Toronto Comic Con from Concussion Cosplay.