Reflections on 24 years from freelancer through building one of the first Shopify studios in the world through burnout and back to soloist

I’m giving a talk tomorrow at a small event in New York City for founders of mostly small firms working with and around brands on Shopify.

My talk is meant to be a candid look at my 24-year journey from freelancer in New Zealand to building one of the first Shopify studios in the world to growth through my move to NYC, to hitting burnout, selling half my agency, downsizing, and ultimately returning to soloist.

My talk will almost certainly touch on the key milestones of this journey, the serendipitous moments, the struggles, the epiphanies and learnings (that often come years after the experience), the ups, and downs.

I’ve been struggling to write down my 24 years of experiences—let alone to condense them into under 20 minutes. But, I’ve been giving my journey considerable thought these past weeks as I prepare for my talk.

I’ve been reflecting on how I started my “career” as a 20-year-old in my first (and only) year of university. How I stumbled across a Student Job Search ad for a website designer, downloaded a demo of Dreamweaver, and somehow got the job.

I’ve been reflecting on how I was paid $150 per website, how the firm that I worked for charged $750, and how I quickly realized that if I worked for myself, I could keep the $600 difference for myself.

I’ve been reflecting on how much harder it was than I’d expected going out on my own. How I spent the next year literally walking the streets of Christchurch visiting florist, night clubs, bike shops… asking if they needed business cards or brochures or websites or logos.

I’ve been reflecting on my first hire 6 years in. How busy I was; but how, in hindsight, busy often doesn’t equate to productive. How expanding the team increases overheads and management needs significantly but not necessarily income or profitability.

I’ve been reflecting on how hiring people who were good at skills I had was probably a mistake. Few were ever as passionate as me, I was good at my craft, I needed to direct and manage them, and I needed to find enough work to keep them productive. The management became the work.

I’ve been reflecting on how someone told me that I should work on the business; not in the business and that I should focus on the “$1,000 an hour” things no one else can do. And how this actually spun me off in the wrong direction.

I’ve been reflecting on how in hindsight, I’m actually really good at the work; I’m not so strong at running the business. How I should have surrounded myself with leaders who could enable me to do what I was best at and help me avoid being distracted by things I wasn’t.

I’ve been reflecting on my relentless drive to build a people-first organization. And how misguided that was. How loyalty and longevity in a team can paralyze growth, fulfillment, good work, and profitability. How healthy attrition is good for everyone.

I’ve been reflecting on profitability. On how our core values can’t ultimately come first but, instead, it needs to be profit-first, core-values-second-equal. How we can’t run a business that achieves our dreams and goals if we’re not sustainably profitable.

I’ve been reflecting on trying to keep everyone productive and fulfilled and happy at work and how big a toll that took on my own mental health and wellbeing and the growth potential of my company.

I’ve been reflecting on how, if we’re not careful, we don’t own our companies but our companies own us.

I’ve been reflecting on how the process became the work. How we were doing increasingly bigger projects but the quality and value wasn’t increasing; we were simply keeping more people busy for longer.

I’ve been reflecting a lot on who we serve. How it’s easy to think we serve our clients but that collectively we are working together with our clients to serve their customers, which is only partly true.

I’ve been reflecting on how, in reality, we can’t serve the people we want to help most if we don’t serve ourselves—and our families and those who depend on us. How who we serve, help, support, and provide for are intertwined. But, how crucial it is to understand the priorities.

I’ve been reflecting on how often we actually already know what we need to do, what direction we need to take, and what decisions we need to make—we just need to find the courage and clarity to make them. Easier said than done.

I’ve been reflecting on how fortunate I am to be able to do what I love and love what I do for work. But that this can make the work/life balance blurry and that it’s important not to underestimate the headspace cost of doing what we love for work.

I’ve been reflecting on how ultimately none of this matters—how good we are at our craft, who we can serve and help, the processes we develop, or the results—if we can’t master sales and marketing and storytelling.

I’ve also been reflecting on how far out of my comfort zone I am giving public talks and how this is why I said, “yes” 😳 Because the only way to get better at and more comfortable with public speaking is to do it more often, right? 🤪

Wish me luck!

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jamie@example.com
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