I recently accepted a junior role at a startup and was excited when they invited me to attend a company-wide event at their overseas HQ during my first week. The trip is about a week long, and I thought it would be a great opportunity to meet my new colleagues. However, I ran into some issues with the travel arrangements. Two weeks before my start date, I reached out to the HR manager to discuss flight options, specifically a direct flight that was available for a reasonable fare. Unfortunately, after several follow-ups, I didn't hear back for eight days, and when she finally booked my flight, it was for a much longer journey with a long layover. I felt this was unreasonable, so I requested a change. The HR manager then went out of the office the next day, leaving me unable to get any clarification. I tried contacting another HR manager and the event coordinator, but they also didn't respond. Now, with my flight scheduled for tomorrow, I'm stuck with the long itinerary they booked. I had thought about asking if I could fly out a few days early to explore the city at my own expense, but I didn't want to seem like I was taking advantage of the situation. Now, I regret not asking because I’m facing this long flight anyway. I’m also considering whether it would be reasonable to ask about changing my return flight to a shorter option, but it would cost $300 and only offer a slight improvement. I’m worried about coming across as demanding, especially since this will be my fourth request. I’m feeling really frustrated with how this has been handled, and it’s added a lot of stress before I even start my new job.