Balancing the Grind with Tiffany Sun, Chief Content Officer at Twill

Tiffany Sun is the Chief Content Officer at Twill, where she leads a team of 17 FTE and 50+ freelancers responsible for creating global content across Twill’s web and mobile apps: Twill Therapeutics, Twill Care, and Happify.

Let’s start with your background! Can you share with us your career journey and what you’re currently up to?

I’m currently the Chief Content Officer at Twill, a mental health tech company based in NYC. I spent nearly a decade as an editor, initially in magazines, before quickly moving on to digital media for brands like Oprah and Martha Stewart Living.

In 2013, I got the start-up itch and joined my current company, which was called Happify at the time, as the 5th employee. I was excited by the prospect (and mission) of improving people’s mental health and well-being by blending evidence-based research with innovative content—over the years, seeing the direct impact our app has made on people’s lives, from their relationships to their health challenges, has been one of the most gratifying parts of my career.

We eventually scaled the company to hundreds of employees and started to offer Twill’s mental health solutions to Fortune 50 employers, health plans, and pharma companies.  

We’d love to know what a typical day is like for you. Could you describe a recent workday?

Since I work in health tech, I wish I could say I woke up every morning at 6 a.m. for a 15-minute meditation and a workout prior to diving into the workday. Alas, while there are days I’ll turn to a meditation on the Twill Therapeutics app before launching into the day, I typically eat a quick breakfast (always with some protein) before starting my morning meetings.

I lead the content team and work cross-functionally with colleagues across sales, product, marketing, and research so my days tend to be pretty filled with Zoom meetings. Unlike many people, I do my best and most focused work between the hours of 5 to 7pm, when I have more distraction-free time. And my best ideas usually come to me at 1 a.m.—not in the shower!  

Can you define work-life balance for yourself and share with us your approach in maintaining it?

When I find work thoughts creeping in when I’m spending time with friends or family, this is usually a sign that the balance is off. If I’m distracted and checking work emails or Slacks when my husband is trying to tell me a story about his day, that’s another sign.

Over time I’ve gotten better at recognizing when the scale is tipped a little too far in the work direction, and I have to set a real intention to disengage. Sometimes that’s physically moving my laptop or phone to another room so I don’t have to be tempted to check them. And without fail, every night, I reset by unwinding with a good book in bed.

I tend to choose fiction so that I can be transported into another place and time. (I have nothing against a productivity book, but it will inevitably make me think about work just before bed, so I try to save those for my subway commute!)

Change is constant, and it’s essential for growth. Have you made any lifestyle changes in the past year to improve your work-life balance?

Last winter, I realised with a rather significant amount of shame, that there were several stretches of days where I had not left my apartment at all, since I work from home most days of the week. My husband and I started to go on regular walks around our Brooklyn neighbourhood, typically after dinner, even in cold weather.

Hopefully I will break that cycle this upcoming winter! I also received a keyboard as a gift a couple birthdays ago, and this past year I started using the Flowkey app to improve my chords and to learn some fun pop songs. Playing piano has been a great release and stress reliever for me because you literally have to empty your mind of everything else in order to find your flow.  

We’re always on the lookout for new resources! Can you recommend any books, podcasts, or newsletters that have helped you in your journey towards balance?

I love Deb Liu’s Perspectives newsletter—she’s a tech exec and current CEO of, and her Substack is always filled with valuable lessons about leadership and management, while keeping it all in, well, perspective.

I’m also a big fan of wellness podcasts, including Dr. Mark Hyman’s “The Doctor’s Farmacy”, “the Mindbodygreen Podcast”, and “On Health for Women” with Dr. Aviva Romm.

In terms of books that have helped me gain perspective on what truly matters in life, I’d recommend Man’s Search for Meaning by Viktor Frankl, The Art of Happiness by the Dalai Lama, and anything by Sharon Salzberg.  

Before we wrap up, do you have any final words of wisdom or insights on work, life, or balance that you’d like to share with our readers?

We’re never going to have perfect balance all the time—there are moments when it feels like there’s something blowing up in every sphere of our life, all at the same time. I’ve learned from folks much wiser than me that we have to be kind and gentle with ourselves, and simply notice when things are skewed in one direction or another. It’s the noticing that counts. Then you can decide what to do about it.

About Author

Hey there! I'm Hao, the Editor-in-Chief at Balance the Grind. We’re on a mission to showcase healthy work-life balance through interesting stories from people all over the world, in different careers and lifestyles.