“The Constant ‘Should’”: The Stress of Feeling Like You Should Constantly Be Productive
The pitfalls of flexible work, and how constraining flexibility can actually reduce stress
If you’re fortunate enough to have some control over when you work, you probably struggle with some degree of what I call “the constant ‘should.’”
Work that doesn’t need to be done by a certain time each day has this amorphous quality that allows it to bend around the rest of life. That flexibility is an asset to be sure, but the trade-off is that it can also feel like it constantly looms over your head. Particularly in fields of work like research or writing, there is always more you could read to inform your work, so you’ll never be able to check off a set of discrete tasks on your to-do list and be ‘done.’
“I should be working right now. I should have gotten more done this morning. Should I work tonight or should I let myself relax?” This is “the constant ‘should’” that went unnamed in our household for months before my partner finally called it out. “Somehow the flexibility of your work feels more like a constant weight.. you always say you should be working, so you’re never fully relaxed.”
This constant sense of pressure is often due to two pitfalls:
Unmanaged Flexibility Makes Work Expand
Parkinson’s Law, an idea first noted in a 1955 article by Cyril Northcote Parkinson, states that work expands to fill the time it’s allotted. Without some level of structure, we become slow, lack focus, and fail to prioritize our most important tasks. We could allocate every waking hour to work, but our actual output may not change much. What increases the most when we spend more time working is procrastination.
Some elements of work — especially creative work — call for ample time spent just thinking and imagining. This is not the kind of wasteful fluff that needs to be constrained, rather it’s the 15th check of your email in a single hour or the Google rabbit hole you go down when researching an article.
Inefficiencies feed on time, they multiply if not constrained. Boundaries are their kryptonite.
Setting limits on your work hours keeps inefficiencies to a minimum, pushing you to progress on the core tasks that really matter.
Unmanaged Flexibility Leads to Haphazard, Reactive Living
Because I used to allow my work to be fully (excessively) flexible, it often didn’t get the focused time it deserved. By having no solid criteria for when or how much I’d work at a given time, I got lazy about my schedule.
While there were several things that I rightly prioritized like being available with and for my daughter and doing things to maintain my mental health like therapy and exercise, I wasn’t being strategic about it all. I scheduled appointments and meetings at random times throughout the day and week. I woke up each day with no routine so a slow breakfast led to prolonged teeth-brushing while watching YouTube videos, which led to tidying the house while on the phone with my mom until it was somehow 11am and I’d yet to begin my actual work. Add this up over the weeks and months and you get a ton of wasted time and a lack of progress.
If the question of when and how much to work is left to be decided on the fly, there will always be urgent competing demands that could cause you to not invest enough in your meaningful work. Conversely, your sense of obligation to work could itself become a demand that distracts you mentally and drains the quality from your leisure time.
If every day you present yourself — and your partner or kids if you have them — with the question of “do I work today? if so, when? for how long?” your work will very seldom get done to the extent or quality it should. Not only that but your time with family or friends will also be tainted with the sense that you should always be working. That silent pull towards something else is a strain you’ll all feel.
How to Manage Flexibility Without Losing its Benefits
Constraints are a way to help us thrive, to bring order and positive pressure to our lives and our work, rather than leaving every decision up to the unpredictable demands of the day and our changing moods.
Removing the guesswork about your work hours is crucial because we have limited decision-making capacity. Your most essential tasks get shortchanged when left until after you’ve already had to make hundreds of insignificant yet cognitively draining decisions, like picking out what clothes to wear, what to eat for breakfast, or what type of workout to do.
The more you can systematize, the more mental energy you reserve for the things that matter.
Deciding in advance what amount of work during the week is acceptable to us provides a guide on how to allocate our time that’s driven by our values, needs, and resources, rather than by the whims of the day.
By imposing a schedule or set of constraints, you can keep the benefits of flexibility, but limit its ability to create stress. Constraints make our work — both professional and creative — fit into a pre-determined amount of time we feel is reasonable (and that fulfills external requirements like a job if needed) without letting the sense of obligation to work seep out across our every waking hour.
As a mom of two littles, I used to feel guilty when working. I didn’t feel guilty about having a job in general, but in the moment I still felt like I should be at my family’s disposal. What I now know though is that making myself essentially off-limits while working means I get more done quickly, and allows me to be fully present when not working.
What should your constraints look like?
Maybe a schedule works for you in the form of, for example, “every day I will write at my desk, undistracted, from 7–10 am.”
Or maybe you require or prefer more flexibility in the timing and/or location of your work. That’s fine. A schedule can also look like this “I will write for 3 hours per weekday. It doesn’t matter what part of the day or where, but it will be 3 hours.”
Or perhaps you require day-to-day flexibility. Also fine. Try this- “I will spend 15 focused hours writing this week. It doesn’t matter how those hours are allocated across the days, but it needs to add up to 15 by Sunday.”
The key aspect to play around with is the daily flexibility. If you thrive with more structure and consistency from one day to the next (and if your lifestyle supports this), then you might benefit from a “I write daily from 7–10 am” type of approach. If instead you value or need flexibility for each day to take its own shape, consider setting a weekly set of expectations.
Think of your schedule as simply a set of expectations or standards you set for yourself. There are no other rules than that. Design it however it serves you best. Try out one approach for a week or two and if you feel smothered by it, then try something else.
I do find it useful though to conceptualize this as a set of expectations or standards, rather than ‘goals’ for two reasons.
1) ‘Goals’ implies that it’d be nice to accomplish these things, but it’s optional. If your work is required, or not required but just very important to you, let’s assume it’s a step above ‘goal’ status and it’s just a thing that will happen, one way or another.
2) ‘Goals’ is a somewhat loaded term. They tend to be larger, more conceptual aspirations that develop over time via habits. While many people might say “my goal is to write every day,” I think it’s more accurate to say “my goal is to be a prolific writer. I will write daily to work towards that goal.” Given that distinction, your daily and weekly work routines are better described as habits that benefit from structure, rather than goals.
You might experiment with other constraints to see what best feeds your work. Perhaps you need to use the Pomodoro method to ensure bursts of hyper-focus during your designated work hours. Or maybe you decide you can’t indulge in certain comforts (e.g. TV, texting, social media) until you’ve finished your daily work. Find the boundaries that push you into a rhythm that satisfies your professional or creative objectives while also enabling you to fully enjoy the time you’re not working.
If you’re lucky enough to have the freedom to dictate your schedule, be deliberate and create one that brings out the best in both your leisure and work time.