On Monday, I launched February’s low-cost, high-impact Deep Dives. Within days, 15 of the 22 slots were booked. (As of today, there are still 6 left if you’d like to try one.)

The first sessions happened on Thursday. And I loved running them. They feel like a cross between a great product review, an interview, and a coaching conversation—deep listening, structured facilitation, and then serving as a tour guide through the different paths each challenge presents. It’s been a long time since I left a workday feeling this energised. These sessions have been a strong reminder that I’m on the right path.

They’ve also been a great way to learn what people want to work through. 60 minutes is plenty of time when there’s a clear outcome in mind. And if there isn’t, shaping that together at the start increases the quality of takeaways and actions an individual is able to leave the session with.

Refining My Positioning

Through these Deep Dives and ongoing initial calls, I’ve been reflecting on who I’m best set up to serve and how I position myself to meet those needs. Previously, I thought of my work in a binary way—coaching for individuals OR advising for companies. But I’m realising that these lines are often blurry. In reality, both individuals and teams want elements of both.

I’m now exploring a more team-oriented positioning, focused on the outcomes I drive rather than strict role definitions. This means blending leadership coaching with strategic advisory work in a way that adapts as an organisation and its leaders evolve.

I’m also sharpening my view of the companies and leaders I’m the strongest fit for: growth-stage product companies that have found strong product-market fit and are now scaling product lines and teams. It’s not easy. But I’ve spent a lot of time at this inflection point and love the challenges it brings.

Three Learnings From the Process

• Granola is an excellent tool for writing strong follow-ups, but nothing replaces leading with my own synthesis and top 2–3 key takeaways.

• Two weeks’ notice seems to be the sweet spot for announcing and booking these sessions. Thursday, Feb 13th was the first to fully book, within 24 hours of opening on Feb 3rd.

• Good sleep, exercise, and nutrition are essential to sustaining a full day of deep conversations. A helpful reminder to pace myself to ensure the best outcomes for every session.

Emotional Themes From the Week

I asked ChatGPT to pull 10 emotional themes from my journals throughout the week: Excitement, Self-Doubt, Clarity, Gratitude, Tension, Validation, Frustration, Empowerment, Satisfaction, and Confidence. That pretty much sums it up.

Until next time ✌️

No matter how many times I’ve done this, I’m always surprised by how quickly you learn once your ideas are in front of real people. It’s not always conscious feedback—it’s in the context of inbound call bookings or the questions those calls spark. And these questions are gold. They’ve already given me a deeper understanding of my target audience for each offering and the common themes and challenges they face.

Most validating of all has been the number of inbound requests that perfectly match the challenges, people, and organisations I’ve dreamed of working with. Whether or not these become long-term partnerships, I’m increasingly confident the audience and their challenges are real. And I’m genuinely excited about the prospect of working on them together.

Beyond the steady flow of calls and deep-dive sessions, the rest of my week was filled with writing—a craft I’ve grown to love. Not just for my initial Substack posts, but to explore the big topics that have been swirling in my head for months: leadership lessons from my time at Monzo, the impact of AI on leading design teams, and the evolving role of ‘design managers’ in today’s layoff-prone, profit-driven business climate.

Lastly, Monday mornings feel like the most natural time to write these notes. The weekend serves as a natural pause—a chance to reflect, shifting from practical tasks to broader reflection. Not because I spend weekends writing—quite the opposite. Time away from the laptop helps me refine my thinking.

And with that, I’m just happy to be here. I’m glad you are too.

Until next time!

I wrapped up a lightweight visual identity centred around a lovely modern 70s-inspired typeface called Nutgame and experimented with Framer for the first time to build a simple website. Wow. It’s like Dreamweaver took a Time Machine into the future. I totally see why it’s so popular—it’s powerful, intuitive, and makes web design feel easy. Until I needed to tweak that one thing, which would take a single line of code in CSS that I no longer have access to. I digress...

The website content is nearly complete. I’m lucky to have wonderful friends who wrote glowing testimonials, and a friend’s video walkthrough helped me see my copy through the lens of the 99% of people who won’t read every word. A great reminder: less is more, and authenticity beats ‘professional’ wording that’s easier to gloss over.

Pricing was mostly locked in, but a trusted coaching pal gave me a fresh perspective, reinforcing what my gut was already telling me. It also helped me to consider a new tier for more established leaders dealing with greater complexity in their organisations. This insight aligned with feedback from an initial call earlier this week—where I learned my rates were ‘significantly less’ than this lovely potential client’s previous coach. Noted.

I’ve been wrestling a little with what to call myself. ‘Coach’ is broad and context-dependent, while ‘Advisor’ feels more directly aligned with my recent full-time role. But I’ve realised a single label matters less than making my approach clear: I aim to be a strong partner to leaders who care about great design. That clarity matters more than the title.

Oh, and I tried using ChatGPT to write these week notes. I fed it a bullet point outline and my journal entries from the week—it was… okay. But week notes like this thrive on vulnerability and authenticity, which ChatGPT struggled to distill. So I scrapped it and wrote everything here from scratch. A fun experiment, at least.

Right now, everything is theoretical. The conversations I’ve had are promising, and I feel conviction in my path, but until I launch, I won’t know how the world will respond. I hope next week goes smoothly, but I’m embracing the idea that uncertainty is the price of entry for forging an independent path aligned with my values.

I can’t wait to see what happens.

Until next time!