What Having 21 Jobs in 25 Years Feels Like

What Having 21 Jobs in 25 Years Feels Like

The path to your dream job isn't always the clearest one.

Awesome AJ

To preface the answer to this question — it’s not irresponsible or unstable.

There is much understated value to come from experiencing different working environments.

However, let’s address the fundamental question:

Why would anyone need to work 21 jobs in any time frame?

I’m 25 years old right now, but I started working at the humble age of 12. My father was an entrepreneur from the west side of Chicago, so work ethic and independence was highly valued by him and instilled very early in my life. The only reason I needed money at the time was to pay for a monthly, local outing at the neighborhood skating rink. My father would have me come into his office, file paperwork, and enter invoices into the computer.

Working continued for me when a classmate of mine told me about how she worked at a small, family owned restaurant down the street from our homes. I was 15 then.

From there, when I was 18, I worked a summer job right at the local pool right before leaving for college, as well as worked on my college’s campus for a little bit. A semester later I swapped schools to save money, came home, and worked various jobs in customer service. Within the last two years of my college career, I worked as a server along with working four different internships in the marketing field.

At the end of the day, the ability to take care of my expenses was the overarching reason for needing to work multiple jobs. It was exhausting, to say the least, but so essential in helping me get through college, pay bills, and break my introverted personality out of its shell.

What do you gain from working multiple jobs?

People Skills

Present day, I have the blessing of working in the field I studied: marketing. I'm also blessed to work in what I believe is my dream line of work: brand management. However, if it wasn’t for the skills I gained from working in customer service alone, such as the ability to take direction, the ability to strike up and hold a conversation, and the ability to access people’s needs, I wouldn’t be any good at what I do now. My career requires me to work under and with others, it requires me to mesh with the culture, and it requires me to create and distribute assets that relate to applicable target markets — those skills allow me to accomplish these things.


Working many jobs and in many environments allows you to figure out which job type and environment work best for your skill set. Essentially, the sooner you can find out what works for you, whether it’s an open versus closed floorplan, client-facing or internal work, or a micromanaged versus self-lead environment, the quicker you can get to the job of your dream. In order to attain the job of your dreams, you need to master that field of work, regardless of how many tries or jobs it requires for you to get there. It’s not about the path to get there — it’s about reaching the end goal.


The path to your dream job will also require you to have the right people to meet, walk through, and grow with you during the process. Worst case scenario, having two to three people who can serve as solid professional references will help you greatly in making the next career move. However, knowing multiple people from your field and beyond is also important in helping you learn more as a professional and an individual.

How to ignore the stigma

Hands down, there’s going to be assumptions that people — employers in particular — are going to make about those who have multiple jobs under their belt, especially from older generations.

However, here’s what you should keep in mind:


If the company you work for is a start-up, or is in debt, you may not make the money you’d like — let alone, deserve. And your goal, first and foremost, should be to have financially stable in whatever job you’re in. Don’t get caught up in perks like unlimited days off and the company keg and yet struggle paying bills and saving every month.


Being successful in your role requires growth in multiple aspects. Whether it’s growth in learning/mastering your role/field or being promoted into higher roles, you have to continue growing in whatever way necessary to truly add value to your field. If your company doesn’t support/provide learning opportunities or does not have many opportunities for growth within the company, if that’s something you desire, you should explore other job options.


This speaks to the intrinsic value your company can provide you. Does your job mesh well with your personal life? Does it allow you to work from home when you need to? Does it give you a reasonable amount of off days? Does it require you to work beyond business hours? Your work life shouldn’t be your whole life; it should complement your life. Commonly said, you should work a job that you enjoy so you don’t feel like you’re working, and having a job that is flexible enough to respect the demands and desires of your personal life are essential to being able to enjoy your job.

Multiple jobs allow you to access to growth and experiences that you may not have received from one or few jobs. Of course, once you find the best match for your skill set, STAY and HOLD TIGHT to that employer. Know that there is little to no value in taking the easier route if it doesn’t allow you to maximize your skill set. Be sure, in every experience, to take notes on the lessons and new abilities you’ve gained from each role, and execute them accordingly in your new role, and especially in your dream job.

Your dream job is out there, despite where you come from and how long it may take you to get there. Remember to keep your eyes on the prize and never become complacent.

Best of Luck,


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This article has not been reviewed by Odyssey HQ and solely reflects the ideas and opinions of the creator.
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