Flying Solo Newsletter
To:peggy@sterlingcooper.com
From:hello@keirwhitaker.com
Subject:✈️ Flying Solo #05 — July 02, 2025

#05Subscribe

Hello!

It's that time of the year when the man who accidentally finds himself with nothing but black clothes in his wardrobe has regret.

Yes, I'm English and I'm talking about the weather — but man, it's been hot. If only I had an AI agent to lower my body temperature. I'm sure it won't be long.

In other news, I am pleased to announce that I have achieved a 0.03% list growth since my last email. I remain positive despite ChatGPT telling me these are ridiculously poor numbers, even by my standards. That said, I did get a few replies to my delighters "article", which seemed to resonate. If I get a few more, I'll collate and share.

Anyway, here's what's coming your way this edition!


In Issue #05

  • Marketing as a Soloist
  • Craft+Work updates
  • 3 links from The Vault

Marketing as a Soloist

A quote from Emily Jeffrey-Barrett, founder and creative director at Among Equals, in a recent interview on Creative Boom, really stuck with me:

Is there anything harder than promoting yourself? I still struggle with it. I know I should post more on LinkedIn, but there's that voice saying, "Who cares?". I know I should share more opinions, but then I think, "Does the industry really need another lukewarm take on AI?" But I'm pushing myself. I wish I'd seen more women represented when I started out, so I try. I find it far easier to promote Among Equals than myself – championing the work, the team, and our clients.

I couldn’t agree more. She goes on to say:

But I'm also the biggest extrovert on the planet. I love being around people, speaking at events, doing podcasts, judging (work, not people). So I'm doing more of that. I just try to make sure what I say is useful – no one needs more noise.

While I would never describe myself as the "biggest extrovert on the planet", I do relate to a lot of what she says.

I am on LinkedIn, but I find the rhythm of posting regularly and in the "right" format difficult to maintain. It feels like you have to follow a certain template to get "engagement" and accompany every post with a contemplative selfie in a trendy hotel lobby. Kind of like this guy (image courtesy of ChatGPT)!

Maybe I should embrace it. But if not LinkedIn, then what? How do we share our work and expertise and show up online without burning out or feeling fake?

As someone running a solo business, I often feel like I’m not doing enough to promote what I do. There’s no company name to hide behind, and using “we” when it’s just me feels disingenuous. I can come up with loads of good ideas for clients (their words, not mine), yet I still find it hard to talk about myself online — even though I have plenty to say in person.

So yes, self-promotion still feels awkward — even after all these years. But here’s something I often remind my clients (and need to remind myself of, too) — a lot of what we’re already doing is marketing.

Thoughtfully replying to emails. Sharing a client win. Updating our websites. Speaking at an event. Guesting on a podcast. Offering a clear opinion in a meeting. It all builds a picture. It all counts. Maybe it’s time we gave ourselves a bit of credit.

Let me know how you're feeling about your marketing. And if you need a hand, cough, cough, hit reply and let's talk — I promise I'm way better working for you than I am for me!

This post was originally published on LinkedIn on Tuesday, 29th April 2025 … (I jest, of course)


Craft+Work 2025 — Updates

As you may know, I run a small event series called Craft+Work. It's for sololists, founders and leaders working in the Shopify Partner ecosystem and is focused on building businesses in the ecosystem. There are currently two events planned for 2025 in London and Toronto.

My goal with these events is simple — to break even and make it worthwhile for everyone who shows up. If you've ever run an event, you'll know it's part number-crunching, part crafting something meaningful. I'd love to spend more time on the latter — designing a day that's valuable, inspiring, and enjoyable and less time stressing over ticket sales.

With that in mind, if you're planning to join us, grabbing your ticket early really helps. It takes the pressure off and lets me focus on making the event the best it can be. Thanks in advance — it means a lot!

OK, here are some updates:

  • London is almost half full, with 24 of the 50 tickets sold
  • I am delighted that Mantle is back supporting us in 2025 as our Presenting Patron
  • Joining us as Global Patrons are long-time supporters, The Support Heroes, Sufio and Zapiet
  • I'm close to finalising the four invited guest presenters for London and have a few almost confirmed for Toronto
  • Spreading the word and reaching new people is, as always, challenging, but I've been buoyed by previous attendees sharing it with friends and colleagues, and I'm already seeing new names on the list.

I'll be sharing more updates on LinkedIn over the next few weeks. If we aren't connected, then please feel free to send me a request, and I'll click the button.


From the Vault

The Vault now contains 103 (and counting) links to tools, articles, resources, and events. Here are three recent choice cuts:

  • Creator Day — Looking forward to this one in 2026. I've even managed to convince Craig to come along, despite it being just about as far south as you can get from Lancashire!
  • Value-Based Pricing is a Lie — A very interesting take by Alex M H Smith.
  • When an Employee Wants Partnership — A great LinkedIn post by David C. Baker on how to handle the scenario of an employee asking for equity.

So, I nearly made it through this email without mentioning my trip to Toronto for TechTonic and Editions.

I've always enjoyed visiting Canada, and this time was no different. It was a real pleasure to reconnect with old friends and colleagues, and finally meet a few folks who've only ever existed as tiny squares on my screen.

I won't bore you with another hot take — LinkedIn has more than enough of those. Needless to say, the Shopify ecosystem feels strong, though there's definitely a cautious curiosity around how AI might shape things (for better and worse) in the months and years ahead.

I'd love to hear how you're using AI in your day-to-day. Hit reply and let me know.

Thanks for reading,
Keir


This is Flying Solo issue #05 by Keir Whitaker. Why not connect on LinkedIn and follow me on Bluesky? Subscribe for future updates.