• The Silent Grief of Remote Work

    I’ve always believed in the immense benefits of remote work—the flexibility, the freedom, the ability to connect with brilliant people from all over the world. I’ve had the privilege of working alongside colleagues from diverse backgrounds, cultures, and time zones, and these digital connections have enriched my life in ways I never expected. Remote work allows for a kind of collaboration that transcends borders, and in many ways, it’s become my ideal work environment.

    But, as with any system, there are costs that we don’t always talk about, and one of the most difficult challenges I’ve faced working remotely is the loss of colleagues due to layoffs. Recently, nearly 300 of my colleagues were let go, and the impact was profound. It wasn’t just a professional shift—it felt personal. These weren’t just coworkers; some of them were people I had built deep, meaningful relationships with, people who had become a part of my remote “family.”

    What’s unique about remote work is that our relationships are built through digital spaces. We don’t have the spontaneous, in-person moments that often create bonds in a physical office. There are no coffee breaks or impromptu chats by the water cooler. Instead, our connections form through Slack messages, video calls, and shared projects. We celebrate wins, we support each other through challenges, and we often lean on each other in ways that go beyond work.

    When those bonds are severed, the void left behind is stark. The absence of a colleague, a friend, or a mentor is felt deeply, even though the only thing we shared was a screen and a sense of purpose. It’s a loss that doesn’t fit neatly into the conversation about remote work’s advantages. There’s no physical office to return to for closure, no in-person goodbye that marks the end of a chapter. It’s just the silence that follows when someone who has been a part of your work life is no longer there.

    And yet, even with this emotional cost, I still stand firmly behind the overall benefits of remote work. The flexibility it provides, the opportunities for collaboration, and the ability to connect with incredible people all over the world far outweigh the challenges. Remote work has changed my life for the better, and I believe it’s the future of work for many.

    But this loss—the silent grief that comes with losing colleagues who were once integral to your daily rhythm—is one of the real costs that we need to acknowledge. It’s a challenge that doesn’t have an easy solution, and it’s one that I think is often overlooked in the broader conversation about remote work’s many benefits.

    When we talk about remote work, we often focus on the positives—productivity, work-life balance, global collaboration. But the emotional impact of losing people who have become family is something we don’t always address. It’s not a flaw of remote work itself, but rather a reality that comes with the territory. The relationships we build in this digital space are real, and when they are lost, it’s a grief that doesn’t fit neatly into the usual narratives.

    I believe we can continue to make remote work better, more inclusive, and more connected. But in doing so, it’s important that we don’t forget the emotional cost of these virtual connections—because in some ways, they are as real as any physical relationship, and their loss can leave a lasting impact.

  • Please Be Patient

    I recently read a daily devotional that really stuck with me. It told the story of someone pulling up behind a car at a red light and noticing a bright sticker on the rear window that said: “New Driver. Please Be Patient.”

    Simple, right? But powerful.

    The devotional went on to wonder—what if people walked around with signs like that? “New Parent.” “Grieving.” “Still Figuring It Out.” If we knew what others were going through, would we respond with more grace, more patience, more compassion?

    That reflection made me think about product management—about how often we operate at full speed, chasing deadlines and KPIs, without pausing to consider what others (or even we ourselves) might be navigating behind the scenes.

    Here’s how that one line—Please be patient—translates into building better products, better teams, and better habits of leadership.

    Be Patient with Your Users

    Not every user is an expert. They didn’t build the product. They might be stressed, confused, in a hurry, or learning something new.

    Design with that in mind. Write helpful error messages. Offer simple onboarding. Make space for second chances. Assume they’re doing their best.

    Sometimes, we treat users like they’re doing something wrong—when really, they’re just trying to figure things out. That’s your cue to show up with clarity and kindness.

    Be Patient with Your Team

    That engineer might be ramping up. That designer might be in the middle of a tough critique cycle. That marketer might be balancing multiple launches. We’re quick to notice missed deadlines—but slower to see silent struggles.

    Create a culture where “Please be patient” is more than a platitude. Normalize asking for help. Celebrate growth over speed. Make it okay to not be okay.

    If someone’s learning, support them. If someone’s overwhelmed, notice. People do better when they feel seen.

    Be Patient with Yourself

    Product management is messy. It’s storytelling, prioritization, psychology, herding cats, and playing translator between worlds. You’re not going to get it all right all the time.

    And that’s okay.

    Give yourself grace. You’re still learning. You’re still growing. Some days will feel like wins. Others will feel like survival. Keep going anyway.

    Stick your own sign on the mirror if you need to: “Still Learning. Please Be Patient.”

    Leading Like Jesus

    What struck me most about that devotional wasn’t just the sticker—it was the reminder of how Jesus moved through the world. He wasn’t rushed. He wasn’t reactive. He saw people. He stopped. He made time.

    That’s the model.

    In Ephesians 4:1–3, Paul urges us to live “a life worthy of the calling [we] have received,” and that includes being “completely humble and gentle; be patient, bearing with one another in love.”

    That’s not just good theology—it’s good leadership.

    Whether you’re shipping a feature, running a sprint, coaching a teammate, or debugging your own thoughts—remember the sticker:

    “Please be patient.”

    You never know what someone’s carrying. But you always have a choice in how you respond.

  • Imagine a product that evolved as your needs changed

    At a recent product team meetup for WooCommerce I remembered one of the first ‘ideas’ I had after joining Automattic as part of the WooThemes acquisition in 2015. After joining I was intrigued by all the different products Automattic had within the company, but found myself wondering if there was not a way that all these products could work together to create a unique product experience and vision.

    I shared this vision at the 2015 Grand Meetup (a time where the entire company came together for a week in a chosen location) as my flash talk and actually found the notes for it in Simple Note (interestingly enough) when looking for it during that meetup – and thought I’d share it here again for posterity.

    It was written as if someone was recounting their experience to someone else:


    I had so many ideas.

    I just needed a way to keep track of them all.

    I decided to install this note taking app I’d heard everyone talking about. (Simplenote).

    It offered such a clean and simple interface – it was all I needed to help me keep track of my ideas and thoughts. I found I could use it anywhere and anytime, it magically synced everything seamlessly between my phone and my computer. It kept all my information safe, secure and private. (VaultPress).

    I found it made it so easy to start capturing and storing my ideas, when all I had at that stage were lots of ideas and I just needed a way of capturing them for future reference. For a good few years all I did with the app was take notes as well as store and share photos and links with friends (Cloudup).

    Later, after much prompting from friends and family, I decided that some of the ideas I was storing in that little app would be much better shared with the world.

    So I decided to find my voice, vocalise my ideas and share them with the world (.blog). With just a simple swipe I was able to take one of my favourite ‘ideas’, converted it into a draft ‘post’ and had started my my own place on the internet (WordPress.com).

    With what felt like just a “tap of a button” I had published that idea, and now it was out there – for the world to read!

    A few weeks later I received a notification on my mobile phone – an alert that traffic to that post I had published had been unusually high! Apparently my article had been shared on some ‘feed’ (Reader) that curated the best articles of the week I think, and it now been shared all over the internet!

    That idea was no longer just ‘my’ idea! I ended up spending most of that morning looking through various stats and insights (Jetpack) that gave me some clarity on just where all that traffic had come from and where my idea had been shared and I quickly start engaging with all the feedback via the comments (Akismet).

    After fair amount of time and effort, that first post had now become the spark for a thriving blog and community and I was starting to think – where to from here – what’s next? I had seen a lot of people were getting into ecommerce and setting up their own stores online – but the idea of creating an online store was intimidating – the time and money needed, added to the uncertainty of success – that was just scary!

    But, what if I could simply add a product to my existing blog – and start selling to the loyal following I had already spent all this time creating?

    To get started I took five of my most popular ‘posts’ and created a poll (Crowdsignal) which I sent out to my readers to get a better idea of what product might resonate with them – it did not take long and the answers came in. There was interest. There was potential to take this further. It was time to started selling!

    Instead of writing a new post now though I chose to add a product to my blog. After uploading a photo, adding a product description, setting a price and some basic shipping details I was ready to start selling (Payments Block). The best thing about it was that I never had to worry about ‘what was happening in the background’ it just worked.

    I kept adding products to my site and sales kept growing as did the demand for new products. I started to realise that the future of my business lay in adding a fully-fledged online store (WooCommerce) to my blog and to start offering more complex features like earning recurring revenue through creating subscription based products and started putting a bigger emphasis into optimising my site and customer experience to take my business to the next level.

    Now, several years later, I am the owner of a very succcesful company with multiple employees. I still struggle to believe where it all started – with that simple ‘app’. I am now considered a VIP customer apparently (WordPress VIP) – which gives me access to a team that have come alongside me to help me grow and scale my business to meet the continuously changing demands of my customers and stay ahead of my competitors. All this would not have been possible without that app it feels – it just worked, automatically.

    Imagine it.

    It’s Automattic.

    Now in 2024, I feel that vision could be quite different with the additional products Automattic now owns, and if anything, it could be even more compelling. I do acknowledge that this is just ‘one’ way someone could encounter all these products, and that they could well exist independently. To me though, there was something powerful about a product like this, if it could be pulled off of course!

  • A Conversation Around WooCommerce Blocks

    I recently joined Bob and his hew co-host Noëlle Steegs from Do The Woo to talk about our work on the WooCommerce Blocks.

    It was a great conversation with both of them, my colleague, Darren Ethier and Manos Psychogyiopoulos, Head of Product at SomewhereWarm. We covered our current work on the new Cart and Checkout blocks for WooCommerce, how we approaching working with our third party community and the challenges we face as we look to improve the checkout experience for our merchants and their customers.

    If you want to get the latest on our work on the WooCommerce Blocks have a listen below.

  • Just P2 it!

    I came across this tweet recently and it made me think how fortunate we are to have a product like P2 at Automattic.

    For the most part – you could replace any one of those things with a P2 post:

    Could this meeting be a P2?

    Could this zoom be a P2?

    Could this phone call be a P2?

    Could this email be a P2?

    Which from my experience normally is a much better solution as it results in more open communication and less reliance on people being in the same place, timezone etc.

    Obviously there are times when a meeting or zoom call are needed, but, if you have something like P2 – often it might well be the better option – as we say at Automattic – just P2 it!