The Weekly
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The Weekly No. 37

The Weekly No. 37

Q/A Session - Answers, Part 1

Greg Bellinger
March 21, 2025

On the mind.

We're back in Bend after spending three weeks on Kauai!

Two weeks ago, I shared a blank form for people to submit questions. I’m splitting this into two parts, so I’ll be replying to more questions next week. If you still have a question, feel free to submit one — click here!

Check out the first batch of replies below…

“When you’re in the middle of a heavy workout, I want to know what you are thinking in your mind to motivate yourself through that workout at that time.

For example, when I’m lifting weights, sometimes I’ll pretend in my mind like I’m in a prison yard and all the prisoners are watching me work out so it’s really important that I hit all my reps with good form.

How about Greg?

Hope you’re doing well, brother.”

This one was hilarious! Mainly just thinking about how this person gets through a tough workout. I like his response. Let’s just put ourselves in the mindset of someone in jail. Everyone is watching you. Everyone knows everyone. Staying hard and having perfect form can be life or death in jail.

For me, every time I work out and need that extra push, I always think of my family—my wife and our kids. I do it for them. Those last couple of pull-ups, curl reps, or that final mile. It’s not that their lives actually depend on it, but the strength I’m mustering is for them. I picture them, and in that moment, it feels like something truly depends on me pushing through for them.

“Which part of your daily or weekly routine do you look forward to most?”

Since we just got back from Kauai, my routine is definitely off!

Before our trip and on the personal side, I really looked forward to my early morning sauna and cold plunge sessions. The energy I get from waking up that way is unmatched. On the business side, I’m currently excited about my time blocks dedicated to the new service company we’re launching this year. Starting something from the ground up and taking those first steps is where I truly thrive!

“What is your favorite part of the day and why?”

Similar question to the one above but looking at it from a different angle, my favorite part of each day is getting on calls with our team. I genuinely enjoy it. Problem-solving together, connecting, and just being in the mix. Since I work remotely by myself, I think that adds to it, but honestly, I just like back-to-back calls. The energy of other people keeps me going!

“What was your biggest pivotal moment starting WRG?”

More recently, a pivotal moment for me was stepping back and getting out of the weeds. Since pulling away from the day-to-day, I’ve seen a much stronger, more self-sufficient team. I believe that, in the future, when I look back, stepping into a true CEO role will stand out as the real turning point in building a successful culture and scalable business.

Another major early on pivotal moment was proving the business model—something that actually happened even before Abhilash and I co-founded the company. The model was validated when I started working with creative studios/individuals and realized that most were not technical and needed development support. Once I recognized the opportunity (and loved doing it), we went all in. I remember when we first started cold calling agencies to offer support and started gaining traction. There was a clear need, and our focus became building a reliable, strong company culture to support the web creatives of the world.

“I've read most of your newsletters, and I see that you spend a good amount of time with kids. How do you think unlocking childhood creativity contributes to innovation and problem-solving at the leadership level? Also, how do you foster a culture that helps employees retain and rediscover their creativity - especially in traditionally structured roles like finance, coding, or engineering?”

This is a very thoughtful, multi-layered question! I do spend a lot of time with our kids. Keep in mind, most of my photos are going to be of them, not of me staring at a computer or jamming remotely with our team so working and creating with our team is a big part of my life, of course.

First thought—hands down, I’m a significantly better person to work with since having kids. I have more empathy, I’m more understanding, and I genuinely look at the world a little differently now.

Something I talk about, and what I never want to lose, is the inner child in me.
Too often, our society tries to put a wall around us and straighten out some of the best traits of being a child. Sadly, our society does a really good job at this too! As we grow up, our inner-child traits start to get shunned. But I think people would be a lot happier if they had the freedom to be a kid all the way through life. To hold onto traits like:

Staying curious.
Asking questions to learn. Like asking the same question 10 times.
To do things that just feel right in your gut.
Laughing at stupid or silly things.
Being playful, even believing in magic.
Being fearless about being wrong.
Being honest with emotions. Kids cry when they’re sad, dance when they’re happy, and say what they feel.
This is a big one: not being worried about being judged. Just being authentically you.

Honestly, as I reflect on the list above, I see things I can improve on as a dad—to help preserve these traits in our kids.

My goal is for them to retain that inner child, to feel a sense of purpose, but also to understand how to work within the world we live in. I want them to know how to navigate the “system,” without losing themselves in the process.

When it comes to our culture at work, we’ve got a list of values we aim for, and some of them directly connect to that inner child energy: Having fun. Always learning with a growth mindset. Thinking outside the box. Not being just an order taker.

As for the last part of your question—Society is what it is. I’m not here to fight against it. I’m here to work within it and make an impact on the people around me. There are tasks every day that aren’t the most exciting and I have them too. Spreadsheets, tough conversations, repetitive tasks, etc. That’s just part of it. I do think there’s a lot of creativity in coding/engineering (a role you mentioned), but even then, you’ll still have to push through the less glamorous pieces to get to the big picture. My point is that those task are in every role. Just like true happiness doesn’t exist 100% of the time, neither does being in a constant state of creativity.

You really got me reflecting with this one. Thank you!