The messy middle

Keir Whitaker is a business consultant and coach who supports agencies and app companies in the Shopify ecosystem. Before starting his consultancy in 2019, he spent seven years at Shopify. “It was an amazing run, but I knew it was time for a change and wanted to start my own business focused on helping founders and companies I’d met during that time.”

His initial offers focused on marketing, copywriting, and events. Over time, he also started working with solo agency founders who were looking for someone to support them in their own development as well as their business. “Thanks to my being around the block a few times myself, I apparently had a lot to offer!”

He hosts an intimate event series called Craft+Work, which brings together self-employed folks to share their experiences and learn from each other.

It’s all about conversations, openness, and helping each other through the ups and downs of doing our own thing.

Coming to London on May 31 (bought my ticket!) and NYC and Toronto later this year.

I was going to suggest postponing our chat as I thought he’d be too busy, but he got back to me, “in the spirit of done is better than perfect.” There have been a few unexpected hiccups, but he seems very chilled about it. As our mutual business coach Ellen Donnelly would say, “Stay Calm and Authority On.”

I like how he’s found a way to combine consulting, coaching, and events to keep things interesting. Read on for his best advice and tips for dealing with the messy middle (years!) when you feel like you’re constantly experimenting and questioning everything (more on that in the video chat).

Thanks Keir, and apologies for calling Shopify Spotify – all these tech companies sound the same 😉

Nika ✨

What are you struggling with right now?

Upping my own marketing game. Last year, I started questioning my business, what I was doing, who I was doing it for and even if I should change tack entirely. It’s hard to market with confidence if you’re not sure what you’re offering is right. As a result, I kind of hibernated, and things slowed down.

Thankfully, something clicked earlier in the year, and I’m now in a rebuilding phase and feeling more confident about moving forward. The struggle now is to put the plan into action and build consistency, which has been the hardest part.

What are you most excited about?

Growing my event series Craft+Work and working on attracting a few more 1-1 coaching and advisory clients, as well as serving my existing ones.

After questioning every aspect of my business last year, I have found a renewed interest in my work and feel more positive than in a long while – which is exciting.

How did the coaching thing happen? Did you train as a coach?

It was a small agency owner based in NYC. We’d met previously, and when he knew I was leaving, he wondered if there was a way to work together. I came up with an amazing proposal (says I) and added a throwaway line: “And we can meet each week for an hour to chart progress.” He came back to me and said, “Can we just do that?” That’s how it began. I started attracting more clients over time.

I’ve had coaching myself over the years and found it very beneficial. I’ve always enjoyed working 1-1, so I’ve gained much experience supporting people’s development. Last year, I did a five-day course focused on Executive Coaching, which was great.

I meant to follow up with an essay to get the formal credit, but my mother-in-law got diagnosed with cancer, so my motivation was at a low, and the writing bit didn’t seem worth it at the time. Maybe I’ll finish it one day, but I’m okay with not getting the certificate.

I also read a lot about coaching and am part of a mastermind of other coaches where we share experiences, tools and techniques.

How do you stay on top of industry trends?

With difficulty. I’ve always been interested in all aspects of business. As a result, I often find myself going down rabbit holes of learning, which distracts me from focusing on developing core skills or staying up on trends directly related to the services I offer. That said, being a “generalist” has paid dividends over the years, so it’s not all bad.

When not in a rabbit hole, I enjoy reading the wide variety of marketing, coaching, e-commerce, and culture-related newsletters I subscribe to.

I also have a group of colleagues and friends who act as my unofficial advisory board. They are great for intel, advice, and updates on what’s happening in our industry.

How are you getting yourself out there and selling your services?

I try to attend as many relevant events as I can. Over the years, I’ve been fortunate to meet many interesting people who have become friends and clients at conferences and workshops.

I also host my own events, which means I have a good excuse to reach out to people I don’t yet know and ask them if they’d like to participate or attend. Even if both answers are no, it often leads to a good conversation and has led to work.

Outside of events, I try to engage on LinkedIn. It’s something I want to improve at, as it often feels like an afterthought and is not part of my daily schedule.

How do you define success? Balance ambition and contentment?

I consider myself pretty driven but less by money and more about working to create a life where I can take time out to travel, spend time with family and friends, and stay relatively stress-free. It’s not always easy to achieve, but that’s my goal. Overall, I’m pretty content, but my family might disagree!

What’s the best piece of advice you’ve been given?

It’s tough to narrow it down, but if you’ll permit me three they would be:

Early in my career, a mentor said, “Focus on getting really good at what you do, and the money will come.”
Business is all about relationships, so take time to invest in building and maintaining them.
The ability to listen well is a competitive advantage.

How do you take care of your health and prevent burnout?

I’d love to tell you I have a well-thought-out regime, but I don’t. I used to travel so much that finding time to exercise proved difficult, but a few years ago, I started playing tennis with a friend. We’ve been very consistent (lockdowns and injuries aside) in getting on the court since. It helps my mental health and blows out the cobwebs from sitting in front of a screen all day.

I enjoy a good walk, eat well, and try to stick to one coffee daily. If getting older has taught me anything, some form of regular exercise and general moderation in most things pays dividends – possibly dull, but true.

Where do you live, and what do you love about it?

I live in Bath, in the West Country. After years of living in London, it was quite a change, but I can’t imagine being anywhere else now (at least while my children are still at school).

Once you get over the fact that every building is the same colour, you appreciate the city and all it offers. There are great pubs and restaurants, beautiful parks, and it’s only a short drive to the coast. Plus, it’s only 1 hr 20 to London by train, and Bristol Airport is a gateway to Europe.

Can you recommend any resources for entrepreneurs?

The Acquired Podcast. I’m going to recommend a podcast where episodes frequently top three hours but hear me out. Oh, and don’t be fooled by the title – it’s not a startup bro fest focused on flipping tech companies.

Instead, each episode covers the back story of great companies, discusses what makes them successful, and explains how we can apply those lessons in our businesses. Yes, there are tech companies in there, but as a child of the 80s, it’s fascinating to learn about Atari, Sega, and Apple. The episodes on Costco, Walmart, and Hermes are equally fascinating.

What help or support have you had that’s helped you get where you are today?

(from Nicola Washington @ Too Much Social).

I couldn’t do what I do without spending the last 12 years in the Shopify/e-commerce ecosystem. I couldn’t have done that without the support of my wife, who was often left literally holding the babies when I had to travel. Don’t worry – I did my share upon returning 🙂

I’ve also been fortunate to work with several amazing people who believed in me and gave me opportunities that changed the direction of my career. Many became friends and mentors and still guide me today.

Finally, I’d say the belief that there’s always more to learn and people to learn from keeps me going.

Where can readers find you?

Everything is on or available via keirwhitaker.com

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