Everything I’ve Learned After Working For 23 Different Companies


I started working when I was fourteen. Since I wasn’t eighteen yet, I wasn’t allowed to work forty hours a week at any one place. That, however, did not stop me from working well over forty hours over the course of 4 different jobs, all at the same time.

From my first job at a deli and becoming Santa’s helper to banking and corporate marketing, I’ve worked in 23 different places.

Working with such a large variety of environments and people is not without its difficulties. I’ve learned a lot about how companies and how people work. I am a pro at creating a resume and at acing an interview. But more than anything, work has taught me so much about life. Things that I use every day, beyond the boundaries of a cubicle.

Work has made me a better me. Here are the 10 most important things I’ve learned from working for 23 companies.

Social skills

To say that I was socially awkward is the understatement of the last century. I didn’t have any close friendships growing up and I had no real idea how to interact with people. I was learning what it meant to be introverted and I wasn’t comfortable in my own skin. Talking to others used to be a major challenge but having to handle customers daily, helped me develop socially in a big way.


I was not a confident person. If something went well and it was because of me, I was afraid that they would later down the line discover that it hadn’t actually gone well. Working made me feel better about myself. I wasn’t another kid in a classroom or someone’s daughter, I was a worker. There were quantifiable expectations of workers and I realized that I learned quickly. I learned that I could be good at stuff.

Leave your problems outside

Things in my personal life weren’t great, but I still had to show up to work with a smile on my face and perform a job. I couldn’t bring my problems to work with me. I learned to leave my problems at home and do what had to be done during work hours. This did wonders for me because I realized that I couldn’t do anything about my issues while I was at work and that more than just distracting myself, I was choosing to focus on the things I could do.

How I think about money

Everything I made went directly towards bills. I was in charge of managing our funds and budgeting how much was being spent on what. My idea of what was expensive could be directly attributed to how much money I was making. I wouldn’t think of a new pair of jeans in terms of dollars, I would think about it in terms of how many hours I would have to work to afford it, and then ask myself if it was worth it. I still do this today and it makes for really good financial perspective.

Not to take it personally

Sometimes people would be mean or rude or (insert negative adjective here). At first, I would wonder if I had done something wrong and I would feel bad and be extra careful around that person next time I saw them. Then I realized that people had their own issues that had nothing to do with me. Sure, maybe someone was angry because we didn’t have the exact thing they wanted or something was running late, but in those situations, it’s still not about me. All I can do is be kind and keep moving.

Define friendship

Workplaces are weird. Working in a mall was even weirder. Everyone called everyone else their friend. In my mind, these people didn’t really know me, they had no idea what I was dealing with outside my job, and we were definitely not friends. It made me uncomfortable and led me to really think about what friendship means to me, ultimately causing me to create a 5 tiered system of friends. Everyone at the mall was level 1: People you only see at work, you are nice to each other.


I had to manage my schedule between different jobs, making sure I was on time, bringing the right things to work, on top of juggling school, and learning that sometimes you just have to do things you don’t like. There was no sense in crying about it (although at first, I did) because that wasn’t going to change what had to be done. I still have this mindset today when it comes to doing the things you have to do. Doing them now almost always guarantees that you’ll save yourself a headache later.


People would talk to my mom about me as if I wasn’t just standing right there. They would tell her that I was so focused and responsible because I was working. They only saw this serious, unhappy side of me. In truth, I didn’t even know if that was who I really was. I knew what I enjoyed but I did not feel comfortable enough to express my likes outside of myself. Being at work and seeing that everyone was so different, I realized that it didn’t matter who I was. I could be into what I was into and that had no effect on my work.

Create boundaries

Over the course of years, I can not tell you how many managers have tried to pressure workers into working for free. Working during a break, punching out for lunch but continue working, do this work before punching in. At first, I would say yes because I wanted to be helpful and I wanted to be favored by the people above me. With time I learned to say no. I learned that I and my time and my work are valuable and that ultimately if they didn’t have enough time to complete something, I didn’t have to take it on as my problem.


I saw lots of unsavory people doing many unsavory things. I saw a man stealing the deposit from a store’s open drawer. I saw a woman stuff clothes into her jacket before she went to get her bag checked. I learned that I was uncomfortable just letting these things happen and that my integrity meant more to me than the discomfort of speaking up. In smaller stores, you are often left alone and I felt best when I would do the right thing, even when nobody was watching.

Having so many jobs and having to work so much, probably isn’t what I would have chosen for myself.

As a teenager, I had wanted to play basketball and join the debate team. But putting my family first was more important and working was a necessity.

Regardless of the reasons why the truth is that I wouldn’t change any part of my life. Not even the bad parts.

While, yes, I was unhappy then and there was so much I was going through, there’s also so much I’ve gained from those experiences. Lessons that you can’t pay someone else to teach you. I can appreciate that now.

Were it not for my past of working so much I would most likely not be working as a freelancer today. I would not have been so tired of regular work and I wouldn’t have spent so many years thinking about what my dream job would actually be.

When you’re young, you don’t have a lot of say in what your life is like. As you grow and as the years pass, you can use your past as an excuse to not be your best self or you can choose to focus on the lessons your experiences have afforded you.

Working for so many different companies is something that I have allowed to positively define me. I love where I’m at now and I’m grateful.

Where are you on your journey?