Tips for Starting Your Second Job

These days it’s common to change jobs after a year or two. In fact, a lot of people would comment and be surprised when I told them I worked for the same company for five years. It took me a while to leave my first job after college because it was great.

The first company I worked for was small so they were nimble with employees. I had various roles in operations from behind the scenes to in front of customers. I was able to dictate for the most part my career path at this company. It was exciting, being able to plan out how I would run a team and then be given the opportunity to execute it. I was also lucky enough to relocate a few times during my tenure.

However, after a few years at the company, I realized I wanted to be a product manager and knew this company wouldn’t have a PM position available given my background in operations. A few months ago, I started as a PM at another job, and here are some tips I have for starting your second job:

1. Different doesn’t mean better or worse. It just means different.

The first and my current company are in the same industry, so I thought I would have an easy time picking everything up. I didn’t account for the differences in culture. Each company has different processes, and that doesn’t mean one is better than the other.

For example, each company used the management software Jira differently. I tried to replicate a Jira process from my first company at my current company. It didn’t work since each company was using a different version of Jira. I was disheartened and felt like the current company wasn’t using Jira to the fullest. However, I soon realized that my use case was unique to me. Only I needed to create a list of Jira tickets that needed to be constantly replicated. As the result, the use case of uploading tickets to Jira via CSV wasn’t useful for my coworkers.

2. Talk to people and get to know your coworkers.

I started my new job during quarantine so I wasn’t able to meet my coworkers in person. I didn’t realize how much I missed the deep relationships I had with my coworkers from my first company until a month into the new job. I longed for knowing what to expect when I got on a call or how to troubleshoot a bug.

It wasn’t until I hopped on a call with a different team and bonded with a few folks on winter in NYC that I felt connected with my coworkers. After that interaction, I occasionally reach out to coworkers about relevant news like the first NYC snow of the season. I’ve lived in a few major cities and found that to be a great starting point to connect with my coworkers.

I also reached out to other folks who onboarded around the same time I did. I found it comforting to share my concerns with people who were going through the same thing as me. We were able to bond over the experience and share our learnings.

One of the new hires gave me the recommendation of writing out the problem statement whenever the request is unclear. I applied it to learning a new workflow, and it helped immensely to understand what the issue is before understanding how the workflow fixed the issue.

3. Starting a new job is a transition, and it takes time.

I hate being uncomfortable. It’s why I tend to avoid new things unless I feel very safe. Starting the new job was uncomfortable since I didn’t know where to go or who to turn to when I ran into an issue. I had my manager, but I didn’t want to bombard him with questions. I was hired since he had a full plate, and from personal experience, I know it can be difficult to train someone when you have so much to do.

In the moment, I didn’t allow myself to breathe and take this as a learning opportunity. Whenever one learns something new, one is going to make a lot of mistakes and will need help from others. I learned to take time to understand requests before proposing next steps to my manager. For instance, when someone reaches out about a bug, I try to guess what is causing the bug and ask my manger to verify my hypothesis. It shows I’ve thought about the issue and encourages my manager to be more forthcoming with assisting me.


Since I am a perfectionist, I have a hard time letting myself fail, but I have found that failing fast means I can learn faster. Being open to different approaches, getting to know my coworkers, and giving myself more time has made the transition to the new job so much better. It has also been a huge relief to my mental health to remove all of the high standards and expectations I put on myself.

Let me known down below if you have any recommendations on how to adapt to a new job.



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Lilly Chan

Lilly Chan

Hey! I’m a 20-something year old who loves discussing self improvement. I’ve worked in operations and product at tech companies.