Labor Day can mean more than a three-day weekend. Happiness researcher and author Gretchen Rubin recommends that we use it as a yearly opportunity to stop and reflect on our work.
Signed into law in 1894 to honor the American worker—following years of poor working conditions, strikes, and riots at the height of the Industrial Revolution—Labor Day has since become nothing more than a transition point. When most of us think Labor Day, we think school supplies, end-of-summer cookouts, and the unofficial start of fall—not work.
But what if we used it as an opportunity to stop and reflect on our careers, our work life—our labor?
That’s what happiness researcher and author Gretchen Rubin advocates.
“September is the other January,” writes Rubin. “It feels like a fresh new start to the year, and a good time to re-evaluate. So it’s helpful to have an external prompt to ask ourselves, ‘What could I do to make my work life happier, healthier, more productive, and more creative? What do I want to accomplish in my year of work?’”
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This three-day weekend, let’s honor our own work lives—by taking a few minutes to sit and reflect.
On a macro level
It may not be comfortable to think about, but sometimes we all need a change—a big change.
If you have recurrent thoughts of going back to school, switching jobs, or even trying a new career, now is a good time to bring those to the fore with a few reflection questions:
When people ask you what you do, how do you respond? What emotions do you notice?
Which specific aspects of your job do you like? Are they what author and business consultant Clayton Christensen would call hygiene factors (e.g., work-from-home flexibility, job security, a good manager) or motivation factors (e.g., alignment to company mission, sense of growth)? Which type of factor is more important to you?
Similarly, which specific aspects of your job don’t you like?
If you could go back in time to choose a totally different career, 1) would you, and 2) what would you choose? If you wish you’d chosen differently, can you find an outlet in a related hobby? If you are seriously considering a career change now, can or should you pursue it first as a side hustle?
What skills would you hope to gain if you were to go back to school? How would those help you in your current or future job (e.g., more interesting work, pay raise) and at what cost (e.g., student loans, stress)?
Do you find yourself susceptible to burnout? What factors in your work life and personal life contribute to that?
If you’re confidently happy in your current job or don’t plan to change your situation anytime soon, consider:
Is there a one-word theme you might adopt in your work life for the coming year?
Are there any hobbies you’ve been meaning to pursue as a side hustle or freelance project?
- Imagine it’s Labor Day weekend next year. What one goal do you hope to have accomplished?
Are there skills that you’d like to develop? What might help you sharpen them (e.g., asking your boss to expand your job responsibilities to include something new, subscribing to a service like LinkedIn Learning or Coursera)?
Whom do you admire in your field? Is there a way you can learn more from them from afar (e.g., videos of lectures they’ve given, books they’ve authored) or even personally (e.g., connecting via Twitter, emailing a question related to their work)?
On a micro level
While we can use Labor Day to reflect on the big arc of our careers, we don’t necessarily need to, writes Rubin: “It could be something as big as switching careers or something as mundane as cleaning out your desk.”
Review a few old Verily articles. Are there any habits you meant to implement but didn’t?
What inefficiencies or annoyances in your routine might you be able to fix (e.g., getting a much-needed software update, delegating a recurring task to someone who can more easily manage it, choosing an audiobook for your commute)?
What “school supplies” need refreshing (e.g., a new planner, working pens, personal touches for your desk)?
Is there anyone you might want to collaborate more closely with (e.g., a coworker, someone aiming for the same goals in a different nonprofit or even field)?
Are you maintaining effective boundaries between your work and personal life? If not, is there a way that you can limit what emails and other communication you see while you’re off the clock?
These lists of questions are not exhaustive, and they are not meant to intimidate; they’re meant to inspire productive introspection. Any action you may decide to take need not happen immediately, but intentionally thinking about things is a great step.












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