To:peggy@sterlingcooper.com
From:hello@keirwhitaker.com
Subject:Flying ✈️ Solo #07 — September 16, 2025
#07
Hello!
Somehow it's already mid-September. The summer break feels like a blur of half-finished to-do lists and the odd summer stroll, and now we're straight back into it. For me, that means pulling together the last details for Craft+Work London and Toronto — two days I'm really looking forward to.
Alongside that, I've pulled together a few updates, some ways I can support you this autumn, and my usual stash of links and recommendations.
Let's dig in!
In This Issue
- Craft+Work: London & Toronto
- First Officer: Coaching & Advisory
- From The Vault: Links, Tools & Distractions
Craft+Work: London & Toronto

If you're a soloist, founder, or leader in the Shopify Partner ecosystem, these are for you!
If you're new to Craft+Work, you can read all about it on the Story so Far page.
Get Your Tickets →
First Officer: Coaching & Advisory
First Officer is my ongoing, flexible, month-to-month coaching and advisory service that gives you steady support, perspective, and accountability — part strategist, part mentor, part co-pilot.
Most of my work focuses on things you could classify as marketing and business development (but not always). Here are five ways I can support you:
- Positioning and Messaging — Making sure you're crystal clear on what you/your company/your app do, who it's for, and why it matters.
- Marketing — Reviewing your current marketing efforts to spot what's working, what's missing, and where the gaps are.
- Content — Helping you come up with content ideas, reviewing what you've written, or building out a full content plan.
- Event Strategy — Whether you're hosting, sponsoring, or attending, I can help you plan your approach, maximise visibility, and make the most of every opportunity.
- Creative Direction — Need a fresh idea, a second opinion, or a gut check? I'm here for that too.
I've currently got a couple of First Officer slots available. If you'd like to learn more, let's book a call to chat.
Book a Call →
This time I've cast the net wide — a mix of articles, books, tools, and random finds worth a look.
BTW, you can find even more links to distract/interest you in The Vault (105 links and counting).
- Strategies for Thriving on Your Own — Loved this! So many good ideas for the soloists amongst us.
- How to Increase Your Surface Area for Luck — "You should just do things".
- Leader Blueprint — Introduced to me by an old Shopify colleague (thanks, Tiff), this is a simple but highly effective way to get to know your work colleagues better.
- Footers — Am I the only one obsessed with footers? Well, clearly not, as someone has gone to the trouble of creating a site full of them!
- TinyWow — Lots of PDF, video, image and other online tools all for free!
- Favicon Extractor — A neat little API that allows you to instantly check and download favicons from any website.
- Unreasonable Hospitality — Quite possibly my favourite "business" read of the last couple of years.
- Deck.Gallery — Simply put, "good deck well documented"!
- The People's Graphic Design Archive — Fill up the Nalgene, get comfy and get that mouse finger ready, as you'll be in it for the long haul once you start clicking around this site.
- For Starters — My favourite "new" email newsletter of 2025.
- "I am not a fan of the deliverable activity" — One for consultants! David C. Baker on how, in the early parts of an engagement, the only deliverable is good communication.
- Penco — A "pen company" (and more). Simply lovely stuff for your desk and beyond. Melamine mug, anyone?
- Presentation Tips — 15 things to remember when presenting. Also impressive use of line length for effect!
- So Many F*g Conferences — An interesting take, what's your take?
- Mopak Weekender Duffel Bag — I love a bag, it's kind of a problem. This duffel from Mopak is great — perfect for a couple of days away.
Right, that's enough rabbit holes for one issue. Do you have any premium (or not-so-premium) links of your own? Hit reply — I'd love to see them.
As always, thanks for reading,
Keir
PS: Even if you can't make Craft+Work: London, perhaps you can make the meetup the night before?
This is Flying Solo issue #07 by Keir Whitaker. Why not connect on LinkedIn and follow me on Bluesky? Subscribe for future updates.