Designers / Interviews

Balancing the Grind with Filippo Di Trapani, Design Lead at Automattic

Filippo Di Trapani is the Design Lead at Automattic, where he manages teams and projects to deliver improved payment experiences for

Partner up with Balance the Grind to showcase your brand’s story and promote healthy work-life balance. Get in touch with us about sponsorship opportunities.

1) To kick things off, could you tell us a little about your career background and current role?

I’m a designer based out of Ottawa, Canada, and work for a company called Automattic. I started my career as a graphic designer a little over 16 years ago focusing on print and brand design.

I slowly transitioned to web and then digital based products working at SAAS based products like, Shopify, and now

In my current role, as a design lead at Automattic, I run teams and projects to deliver improved payment experiences for our flagship product

2) What does a day in the life look like for you? Can you take us through a recent workday?

Well, I’ll start by saying that my day-in-a-life now is very different to what it was a couple months ago before COVID-19 hit.

My wife works for the Canadian federal government and is directly involved in the response to this crisis. She’s working full days from home and we also have our three kids at home so I’m taking care of them. 

One of the positives sides of this crisis is that our mornings aren’t as hectic as they used to be. We get up a little bit later than we used to and are in less of a rush to get out the door. I start my day with 30 minutes of physical exercise and then grab a breakfast before taking on the day with the kids.

Thanks to the weather, we have made it a habit to go out for a long walk around the neighbourhood or on a scenic trail. Sometimes we take food with us and have a picnic or get back home in time for lunch. 

Thankfully one of my kids still naps so I put him down after lunch and then have about an hour to hop on a video chat or do some work while the kids get some screen time. When my son wakes up, I wrangle the other two and we find some activities to keep us busy or just play outside. 

When my wife is done work for the day, one of us prepares dinner while the other entertains the kids. After dinner, I hop on the computer for about an hour to reply to work emails and messages so I can clear my way for more productive work after we put the kids to bed. That leaves me with 3-4 hours to get some work done and then to get to bed before we start it all over again the next day.

3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?

Automattic is a distributed company that has employees located all over the world. It has been operating as a remote company for over ten years and is very well suited for a flexible work schedule.

I feel very lucky to be working at Automattic through this pandemic because it has allowed me to rearrange my work schedule in such a way that I can take care of my kids while my wife works and then work later at night.

It hasn’t been easy but I’m not alone and we’ve all found a way to make it work and keep business going as usual. 

4) What does work-life balance mean to you and how do you work to achieve that goal?

To me, work-life balance means being flexible and taking care of yourself. There are always going to be times where you have to work more than others but, in the end, I find it all balances out.

What’s most important is that you make the time you need to take care of yourself. I am a big believer that experiencing life outside of work always benefits the workplace.

Whether you’re travelling, working on side projects, or investing in your hobbies, you learn through your experiences and those lessons are what make you a more well rounded person which, in turn, allow you to better face the challenges at your workplace.

Personally, I work really hard to set clear expectations for my work and do everything I can to deliver on my commitments. Over time, this has allowed me to build a level of trust with my colleagues that makes it easy for me to step away from my work and invest in my family, side projects, and personal interests. 

5) In the past 12 months, have you started or stopped any routines or habits to change your life?

The last couple of months have seen an unprecedented change in my routines and habits but I’m generally always working at it to keep up with my trade as a designer.

I have experimented with journaling, making art, coding, and other artistic expressions but I think the biggest change for me over the last year has been prioritizing my physical and mental health.

This has resulted in me dedicating 30-45 mins a day, for up to five days a week, on exercise. The results have been very positive on my mental health and the effects are very noticeable when I don’t do it for extended periods of time.

While it used to feel like a chore earlier in my life, I have come to embrace exercising and very much look forward to those couple minutes alone every day. 

6) Do you have any favourite books, podcasts or newsletters that you’d like to recommend?


I’m a big fan of reading biographies/autobiographies. Some of my favorites include Nelson Mandela’s Long Walk to Freedom, Steve Jobs by Walter Isaacson, Elon Musk by Ashlee Vance.


I recently got into podcasts and found it really interesting how great of a medium it was for learning. Here are some of my favorites: NPR’s How I built this, Distributed by Matt Mullenweg, and Solid Steel by Ninja Tunes. 


I’m not terribly into newsletters but there are two that I really like and follow religiously.

Creative Samba by Miguel Ferreira (about writing, advertising, and creativity) and Codrops (about web design and development).

7) Are there any products, gadgets or apps that you can’t live without?

Music plays a very big part in my life and so the combination of my music app (which is currently YouTube music), my Sonos, and my Google home are at the top of my list. 

I’ve also been really happy with my Google pixel 2 phone. It’s the best phone I’ve ever had and after three years, it’s still working really well. 

My Nespresso coffee machine holds a special place in my heart. The convenience it offers and great taste make me very thankful I own one everyday. 

8) If you could read an interview about work-life balance by anyone, who would that be?  

As a father of three kids, I’d be interested to read how Tobi Lütke, also a father of three and CEO of Shopify, manages his time. I’m also a big fan of Erykah Badu and so I’m always interested to hear about her life and how she produces her art. 

9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?

If there’s one thing I’d like for people to take away from this interview, it’s how important it is to make time for yourself. In my option, it’s so critical to put your interests and health first because then you can be your best version for everyone else.

Before you go…

If you’d like to sponsor or advertise with Balance the Grind, let’s talk here.

Join our community and never miss a conversation about work, life & balance – subscribe to our newsletter.

This conversation is brought to you by the Walkolution Treadmill Desk, work healthier with a treadmill desk. Sustainably manufactured in Germany.

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.