The Messy Reality of a Massive Career Pivot
What relocating to London taught me about the skills you actually need to start over
Hi Everyone! I’m writing this from a cafe in London, three weeks after I landed in the UK as an expat.
The LinkedIn version of this story is a sleek, curated adventure featuring global supply chain strategies and walking past centuries-old architecture, but it’s also been exhausting.
The reality of the last three weeks has been acting as the crisis project manager for a transatlantic deployment, including liquidating our vehicles, donating almost all of our stuff, and navigating a new city on foot. It’s the mind-numbing administrative friction of establishing life, lugging suitcases, and trying to setup services while explaining for the hundredth time why you don’t have a local bank account, phone number, or address.
Everyone loves the romance of a massive career jump. Very few people talk about the hidden cost: the absolute destruction of your established baseline.
Whether you are moving across an ocean, jumping to a new company, or taking on a massive promotion, surviving it requires building three muscles they don’t teach you in school.
1. Choosing Discomfort
Taking a risk is mostly about having the stomach to disrupt a perfectly comfortable life. Everyone wants the shiny opportunity, few are willing to endure the pain of intentionally fragmenting your life.
When we moved our family from Seattle to Austin years ago, I built the initial muscle for career transitions. That said, crossing the Atlantic is an entirely different weight class of risk. You are actively choosing to trade your immediate competence for massive friction. You go from knowing exactly how your life operates to not even knowing how to execute a basic grocery run without a car.
The skill of taking a risk is not about being fearless. It’s about becoming comfortable with temporary chaos in exchange for a long-term vision. It was a joy to see how much our family grew in Austin and, even though it wasn’t always easy, it challenged us to define life on our own terms and build new relationships. It also allowed me to catapult to a senior leadership role at work and provided the visibility I needed to get on the radar for this role in London.
If you’re truly happy, then you should enjoy your life. But if anything internally is pulling on you to take that risk, it may be a sign to do it and embrace the inevitable friction.
2. Relentless Execution
Once the romance of the risk fades, you are left with the physical and mental reality of execution.
During the day, I advise supply chain leaders on how enterprise AI and digital transformation are reshaping the global workforce. In the evening, I am finalizing lease agreements, coordinating upcoming move-in logistics, and preparing for the next day.
Execution during a pivot is entirely unglamorous. It requires applying a rigorous, operational mindset to basic survival. Relentless execution means staring at a mountain of administrative friction, organizing household logistics, and knocking it out before performing at work. Much like the supply chains I study, operations is the invisible backbone of every successful transition.
If you want a great career (and life), then you must be willing to do uncomfortable things, consistently. Whether it’s your health, career, school, or relationships, it’s critical to recognize that doing hard things leads to an easy life, while always doing the easy thing leads to a hard life. You just have to keep executing on the right stuff over a long period of time.
3. Refilling your Cup
If you only execute, you eventually break. When you are the one driving a massive transition, you are the primary asset and you can’t optimize every single hour of the day.
Last weekend, I had a million things I could have, and arguably should have, been doing to get our lives organized. Instead, I bought a spread of picky bits from M&S, sat on the couch, and watched Friends for a couple hours. It was the exact grounded nostalgia I needed and it’s part of a strategic reset that allowed me to wake up the next day and actually show up well for my family and my team.
Refilling the cup is also about human connection (even for us introverts!). Recently, I was walking around Covent Garden and turned onto a street completely packed with football supporters cheering during a World Cup match. It reminded me that saying yes to a pub invitation isn’t just about “networking.” Building relationships is the foundation of long-term success, but more importantly, enjoying good company and cheering alongside strangers is just incredibly good for the soul.
What Risk Aren’t You Taking?
Taking a massive career leap is exhilarating. It absolutely leads to adventures you never thought possible, but the most valuable takeaway from this entire transition hasn’t been a new technical framework or an AI insight.
It’s the realization that in a highly volatile world, the ultimate life advantage is the skill of starting over. Take some time to consider what risk you have been putting off and commit to taking the first step towards it. I’d love to hear what it is and if there’s any way I can be cheering for you.
P.S. — I work with a small number of readers one-on-one to help them apply these frameworks to their own career. If you are at a moment where you need more than a newsletter, book one off or ongoing sessions here.
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