Last week was the 9th week I have completed for a company in my adult corporate life.
I spent the first week of my professional career at a company called Great American Gaming, where I was hired as a Marketing Assistant in 2005 for $29,000 a year. I wasn't even their first choice; they had originally told me no and then called me back a week later when their first choice turned them down. Great American Gaming owned four small casinos in the greater Seattle area, and my job was to run the promotions, player rewards, and whatever other marketing was needed. One of my jobs was to create and set up new graphics for their LED signs out front of the casinos, and I had no experience and/or business doing this, but that's what you do when you're 23 and handed the keys to a new job.
The first week of my first sales leadership job was spent with my new team telling me everything that was wrong, why they all were underpaid and under-supported. Then I spent the next few weeks firing four of the six of them.
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My first week at Zillow, I spent it trying to figure out what the hell my team was selling, as I had entered a whole new industry selling a whole new product.
My first week in Dubai, I spent it trying to figure out where in the world I was and how I got there, as the shock of being in a new country was real.
My first week in my last role, I got stopped at the Canadian border because I said I was there for work. I learned they happily let you enter the country if you just say, "I have meetings."
The first week anywhere is full of new learnings, and it can cause you to second-guess everything. Thankfully, this past first week was fantastic and put me at ease about my new career path.
One of the strangest things about building a long career is that you can become incredibly experienced and still feel completely clueless the moment you start something new. You can know how to lead people, how to make decisions, how to navigate conflict, and how to get results, but none of that means you know the people, the politics, the product, or the culture of the place you just walked into.
That is what makes the first week so uncomfortable. You are carrying years of experience with you while simultaneously realizing that almost none of the context does. The confidence you built in the last environment does not automatically transfer to the new one, and for a few days or a few weeks, you are back to asking basic questions and trying to figure out what everyone else seems to already understand.
You should not confuse that discomfort with regret, just like you should not confuse uncertainty with being unqualified.
Experienced people hate that feeling because we get used to being the person with the answers. At some point in your career, people start coming to you for guidance, and you start to build an identity around being the person who knows what to do. Then you change companies, industries, roles, or countries, and suddenly you are the one asking where the bathroom is and what the hell half the acronyms mean.
The mistake is assuming that feeling new means you made the wrong decision. A transition is supposed to feel uncomfortable because you are leaving an environment where everything was familiar and entering one where almost nothing is. You should not confuse that discomfort with regret, just like you should not confuse uncertainty with being unqualified.
If you continue growing throughout your career, you are going to have more first weeks. You are going to walk into more rooms where you know less than everyone else. You are going to take jobs where you need to learn the business, the people, and the problems before you can become effective. That is not a sign that you have gone backward. It is usually evidence that you are still willing to put yourself in situations that require you to grow.
I hope I have a few more first weeks left in me. I hope I keep finding opportunities that force me to become a beginner again, ask stupid questions, learn something new, and occasionally wonder what the hell I got myself into. The alternative is reaching a point where everything feels familiar, comfortable, and predictable, and I am not sure that is the kind of career I ever want to build.