Podcast 237: #HappierLaborDay—How Can We Make Our Work Lives Happier?


We’ve been talking about #HappierLaborDay to use the Labor Day holiday as a milestone to remember to step back, to reflect on how to make your work life happier, healthier, more productive, or more creative.

Here in the United States, Labor Day is a holiday that takes place every year on the first Monday in September. It was established as a way to make sure that we all  remember and honor the contributions and achievements of American workers, and everything they do to support the strength, prosperity, and well-being of our country.

It’s a great reminder to be grateful to all the work done by so many people that contributes to our daily lives.

And it can also be a great reminder to think about our own work lives. Also by “work,” we don’t necessarily mean paid work. It’s whatever you do that shapes the work of your life. I clerked for Justice Sandra Day O’Connor, and she once told me that she thought the secret to a happy life was “Work worth doing”—but that doesn’t necessarily mean getting paid for it. (You can listen to this two-minute episode of “A Little Happier” where I talk about that conversation.)

We talked about this topic last year, too, in episode 184.

Elizabeth and Sarah talked about #HappierLaborDay in episode 120 in their fascinating conversation with Sheri Salata—author of  the memoir The Beautiful No, co-host of the podcast The Sheri & Nancy Show, and former executive producer of The Oprah Winfrey Show.

Using this holiday is somewhat arbitrary, but the date’s not important; it’s just a catalyst to step back and think about the big picture of our work lives.

One thing we often discuss, and which is very relevant to #HappierLaborDay is: Choose the bigger life.

For us, #HappierLaborDay got us thinking.

Elizabeth is focused on starting a scripted podcast company along with her work in TV. She and her writing partner Sarah Fain love writing and producing for TV, and doing their podcast Happier in Hollywood, and they’re also very intrigued by the possibilities of this newer kind of story-telling.

Elizabeth mentions the outstanding podcast and TV show Homecoming. Elizabeth reminds herself of her mantra: “Step into the future.” Do you have any helpful work mantras?

As for me, last year, I talked about how I wanted to do something with TV. And it’s happening! Elizabeth and I worked on the WETA pledge show together, which was such a great adventure.

Now I’m thrilled that I’ve joined CBS This Morning as a Contributor. The first segment aired on August 26, and now it will be the last minute of every Monday’s show. Tune in, watch!

Elizabeth really helped me. She gave me so much encouragement, reminders, and insider information about TV.

On the writing front, for #HappierLaborDay, I thought a lot about what I’m planning to write next. But as I thought about that, I noticed a pattern in my writing life that I hadn’t really quite grasped: I’m starting to work on side projects as well as major projects. There are good aspects to this, but it could also be a problem. I want to keep an eye on that. 

Drumroll…my next “big” book will be about the five senses and the body. I’m so excited about this subject! I need to do some much research, note-taking, and so on, I became intrigued with the idea of writing something about Why and How I Quit SugarI’ve also started working on aphorisms. I love aphorisms, proverbs, paradoxes, koans, and Secrets of Adulthood. I can’t stop researching, note-taking, and writing aphorisms. Send me any of your favorite examples! I’m collecting them.

As I have realized this pattern, I think: This all immensely enjoyable and feels productive, and these two smaller projects are related to the big project, but I worry that I’m developing a pattern that over time, might not be good, of becoming too fragmented and not making enough progress on my main priority. Speaking of aphorisms, here’s one I wrote: Working is one of the most dangerous forms of procrastination. I need to make sure that my big book idea, about the body and the five senses, doesn’t get delayed.

Many, many people mentioned resolutions related to creating more outer order in their work lives. Very gratifying to me, as the author of a book called Outer Order, Inner Calm! Some repeated themes: cleaning out drawers, organizing shelves, clearing out junk, creating better systems to remember what to bring to the office and what to bring home, and making a change to make a work environment more pleasant: more comfortable chair, better light, etc.

Happiness Hack

One thing we heard from many people is that if you’re working in a job that for whatever reason isn’t fulfilling, it can be great to start a side hustle.

We wanted to talk to the expert on side hustles! We decided to call our friend Chris Guillebeau. He’s the host of the terrific daily podcast Side Hustle School—which is part of the Onward Project family of podcasts, along with Happier in Hollywood and Do the Thing with Whole30’s Melissa Hartwig Urban. He’s also the author of many NYT bestsellers such as Side HustleThe $100 Start UpBorn For This, and his latest book 100 Side Hustles. I will note that he’s also a Rebel in the Four Tendencies framework.

If you want to hear more from Christ, on the Side Hustle School podcast he’ll explore #HappierLaborDay in episodes 974 and 975.

Also, Chris will be our special guest when we do our live show in Portland on September 13.

Gretchen’s Demerit

In my work life, I have too many moving pieces to rely on my brain—and I’ve been doing that far too often. I need to write things down!

Elizabeth’s Gold Star

Elizabeth gives herself a gold star for hosting a cocktail party in her backyard, with her Happier in Hollywood co-host Sarah Fain, to do a q-and-a session for Happier in Hollywood listeners.


  1. Want to get an email when tickets are on sale for live events in your area, so you don’t miss it? Sign up here.
  2. September is the other January! Get a free chapter from my book, Happier at Home, or listen to an excerpt of the audiobook here.




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