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Balancing the Grind with Lance Willett, Chief Product & Technology Officer at Tumblr

Lance Willett is the Chief Product & Technology Officer at Automattic, where he leads the product and engineering teams for Tumblr.

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

I lead the product and engineering teams for Tumblr, where we connect people and their interests via a social blogging network.

Inspired to come to work each day to participate in the rich history of creative people publishing their best work to the web, plus soak up the visible passion my coworkers bring to every product feature, bug fix, and community interaction.

My decade with Automattic spans several roles including product management to front-end development to software quality and testing. I thrive in leadership roles, whether teams or projects and programs, where I help define and deliver amazing products and experiences for people all over the world.

A trend over the last 5 years is a move from leading teams to groups and now to groups of
groups — leadership at scale.

This brings both intellectual and tactical challenges to manage personal relationships for collaboration, groups/teams for accountability as I communicate constantly with a wide array of leaders, peers, teammates, and partners.

Recently I’ve shifted to even more direct coaching and mentoring, which brings direct rewards from activating the strengths of those around me, including people I’ve kept in touch with over the years.

The conversations teach me so much, too — I still have lots to learn across technical topics, business and management, and the human behavior side of things.

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

My daily routine starts early with a “20/20/20” session, adapted from Robin Sharma’s The
5 AM Club
book, where the first hour of each day is split into three categories: “Move, Reflect, Grow.”

By 6 am I’m doing 20 minutes of intense body workout, 20 minutes of meditation and stretching, and 20 minutes reading a book or the news. Favorite workouts are an outside run, bursts on my stationary bike with NPR News on my phone, or a set or two 7-minute bodyweight workouts.

Breakfast follows, as I prepare coffee and tea for my family. I adapt my wake-up time based
on the season: earlier in summer, later in winter. In darker, colder months I split my day into two halves with a longer, outside break to get some sunshine in the early afternoon.

As my home office is in a separate room, I’ll go in and close the door, turn on my iMac, and dive right in. There is no such thing as “quiet time” in the morning here due to active teammates already online many hours in the Eastern and Central USA, Europe, Africa, and the Middle East. (I’m based in Tucson, Arizona; 7 hours behind London and 3 off New York.)

My next 8 to 10 working hours are broken up by frequent breaks for water, food, stretching. For video and audio calls I raise my Jarvis standing desk to its full height, feet on a rubber mat for comfort. I use LED lights to brighten my video calls since my desk isn’t near a window.

During “deep work” sessions, my best heads-down focus comes when sitting down with electronic or jazz music on my headphones to block distractions.

I attempt to keep Mondays and Fridays a bit more free from scheduled events and meetings to allow flexibility for my focus work sessions. Wednesdays are the longest days with several hours-long meetings to catch up with teammates.

A typical weekly view of hours at the computer, tracked in RescueTime, looks like a bell curve: Monday to Wednesday ramp up, then back down to fewer hours into Friday and the weekend.

Automattic uses quite a bit of written communication, so my day is spent reading and writing and collaborating with teammates via Google Docs, Slack, and P2s (our internal blogging system). We tend to use Zoom or Google Meet for meetings.

I structure my day around check-in and check-out zones, too: what’s most important today? What do I need to do tomorrow? Each one includes a checklist so I catch loose ends.

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

Yes, Automattic is a globally distributed company with no official offices, and I’ve worked
remotely since I started, with 5 years before that when I ran my own web development
company.

When I joined the company in 2010, my entire life fit inside a house on wheels (motorhome / RV / caravan), as I wrapped up 4+ years working from the road. Anywhere, USA.

Today the flexibility isn’t as much the split of hours each day, because as a senior executive, most of my time is dedicated to others’ schedules. I’m able to take time for family events, appointments, and get rest as needed.

I see strong benefits from the flexible work style in at least two other areas: the ability to create my own space how I work the best, and gained time for family, exercise, reading, learning, sleeping rather than dictated by a long commute to a physical office.

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

The balance means Lance-at-work and Lance-at-home are not treated as separate selves;
health, rest, and energy are closely tied together.

My philosophy here is, “Use energy to get energy.” I first read this in the book Mastery by George Leonard, put it into practice with frameworks like 7-Minute Exercise and such.

Later, I revisited the learnings in the HBR article “The Corporate Athlete,” which describes the physical needs for knowledge as equally as important to a high performing, healthy career as mental health and emotional intelligence.

Balance to me means paying attention to food, sleep, time alone, time with others — paired with time spent learning and growing. This awareness, combined with frequent reflection, means I notice and shift when things get out of alignment.

I check in with journaling, meditation, and talking with important people in my life to get an honest external opinion. My wife and family, peers at work, and executive coach, Akshay Kapur, act as accountability partners.

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

Yes, I kicked off the 20/20/20 morning routine mentioned above in the last year or so, when I realized my concept of “don’t have enough time for the important things” was not accurate.

The truth is there is always enough time for priorities. I didn’t have my priorities straight when I rolled out of bed and immediately began a workday; the poor results of the lack of discipline were clear.

Lately, I’ve adopted a mindset for “GTD with a high spin rate” where I attempt to unblock myself and others with a fast turnaround on emails, requests, reading, and tasks. “Handle it once” and clear next actions on everything. More time doing and being present for people, less time managing the items and tasks.

For example, rather than starting a “read later” pile, I deleted the entire reading list and jump in straight away to what looks interesting. Combined with free ebooks from my local library, it proves effective in finding the best books and resources to dive into more deeply.

With my role switch to Tumblr, I noticed my time and calendar quickly got out of control with added meetings and responsibilities. For July 2020, to track my progress, I kicked off a monthly “time spent” study to track my time, make adjustments for impact, and notate my best working hours in the day and how that lines up with my attention and progress.

(Format: a Bear app note for each new day, listing tasks, meetings, and actions with short notes inline after they occur — combined with RescueTime hour tracking as a confidence check.)

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

So many! I’ll pick one of each to keep it brief.

  1. Book: Principles by Ray Dalio. Big influence on my leadership style with a focus on learning
    through self-reflection and honest assessments.
  2. Podcast: Distributed.blog – The future of work is here. Insights and stories from
    many remote teams, hosted by Automattic CEO and WordPress cofounder Matt
    Mullenweg.
  3. Newsletter: Blog | Conscious Leadership Group — an absolute gem! Jim Dethmer and
    team bring next-level coaching, psychology, meditation, and leadership resources to the
    forefront. A must-read when it hits my inbox.

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

The Bear app (macOS, iOS) is the centerpiece of my work organization. The paid version is well worth the price with syncing across devices, custom themes (I use Solarized Light), and export to PDF. I love tagging notes to sort them by topic for easy retrieval, using the “Untagged” view as a daily buffer to clear out and process loose ends.

Bose Q35 noise-canceling headphones, previously for travel, now help with privacy and focus at home, where my family members are around more due to the pandemic shutdown, and often all of us concurrently on calls or video meetings.

RescueTime is a must for tracking app/website usage to know where I spend my time. Gives a clear look at my time spent on the computer for accountability and tracking over time.

Headspace, Calm, and Simple Habit for guided meditation.

Goodreads app for tracking books and reviews. This allows me to pick from the best of the books my friends are reading, and share out my reviews and notes for their benefit.

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

Anyone that works with their hands, craftspeople; but also musicians, artists, and especially
poets and writers. I love to learn how my favorite authors work day-to-day, from how they
produce new ideas to their specific office environment and time blocking.

Cal Newport, Louis L’Amour, Neal Stephenson, and Haruki Murakami are great examples of this type of meta-analysis that I find endlessly inspirational.

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

My favorite tip is to pay attention to your streaks, yet in smaller increments. I don’t get hung up on months or years, and often look at a weekly cadence to see how I’m doing with key habits. You’ll be surprised how paying attention to progress motivates a continued strong habit.

During the COVID-19 lockdown, where everyone struggles with focus and distractions and
anxiety, I suggest aiming for just a “1 Day Streak.” Every day is a new chapter!

Make the right steps today first before worrying about the future, focus both your attention and your energy on the present moment. Then, repeat the same cycle tomorrow.

Follow more of my thoughts like this on my blog: The Sensible Leader – Tech, leadership,
productivity, and more
.

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About Author

Balance The Grind gives me a platform to talk to these people about how they're achieving their ideal lifestyle. I'm inspired by the passion, the work ethic, the hustle; and these conversations motivate me to live life the way I want to live it.