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5 Surprising Jobs to Boost Your Entrepreneurship IQ

Updated on February 1st, 2022
Boost Your IQ

There is no magic class that can teach you everything you need to know to be an entrepreneur, and the only true way to test your skills as a small business owner is to dive in and give it a go. Whether you are looking to start a freelance side hustle or go all-in on a new startup idea, having the right skills is vital to success.

Some business skills can’t be learned at business school, but you may pick them up working odd jobs or through interesting life experiences. Here are some jobs that give you important business management skills. Some of them might surprise you!

Summer Camp Counselor

Working at a summer camp entails a lot more than you see in Wet Hot American Summer. In addition to antics with the rest of the staff, camp counselors have big responsibilities. Working at a camp, you are responsible for keeping young people alive and safe when surrounded by nature, bad influences, and members of the opposite sex.

Working as a camp counselor teaches leadership, management, decision making, mediation, and interpersonal skills that are all useful when running your own business. These skills actually come in handy in other parts of your career as well, including when working as a full-time employee.

I spent seven years on the staff of a Boy Scout Camp and my wife was a summer camp counselor for a summer camp for two seasons. Those skills have helped us run several businesses successfully including our flash mob company and my $10,000+ per month freelance writing business.

Big Box Retail

While the pay isn’t great and you have to deal with an occasional angry customer, working at a big box retail store instills more helpful skills you can apply to freelancing and other business models. Depending on where you work in the store, you can learn about inventory management, customer service, retail operations, front end checkout management, and more.

I worked at Target in high school and spent time working on the sales floor, as a cashier, and running the snack bar. While I didn’t have plans of a career in retail, learning how to handle upset customers, merchandising, and general operations management taught me a lot that I was able to apply when I was working a day job and as a solo entrepreneur.

Food Service

In between jobs, I decided I should be making money rather than being a deadbeat Millennial and got a job as a server at a local restaurant. I only spent three months as a server, but I learned a ton from that job. As a server, you have to be organized, make quick decisions, and know how to read and interact with different people regularly throughout the day.

Decision making and relationship skills are vital when running your own business, and knowing how to quickly prioritize and break down projects into smaller, bite sized tasks can keep you from getting overwhelmed and losing productivity to analysis paralysis.

I also learned how hard servers work in restaurants and started tipping better overall. Did you know that your server has to share tips with other workers at the restaurant? At the restaurant where I worked, the first 10% of our tips was shared with bartenders, bussers, and expos – the guys who get the plates ready to go out to the tables. Once I got a bad tip from people from a foreign country where tipping is not as common. I ended up losing money on the table as my tip out was higher than my tip!

Property Management

Problem tenants and problem clients have a lot in common. There are many symptoms of problem customers. Rudeness, unrealistic expectations, missed bill payments, and other nastiness is common in the world of property management and landlording. Knowing how to handle those while maintaining your long-term relationships is tricky, but possible.

The same goes with running a business. You may have some important clients or vendors you don’t love working with, but are key to your financial success. Knowing how to navigate those relationships during stressful situations is key to success in managing your own business.


Knowing how to effectively communicate, keep people’s attention, and make quick decisions are core skills in classrooms around the world. I dabbled in teaching at a local religious school and found exactly how tough it can be to juggle the competing demands of multiple students while keeping them engaged and interested in my agenda for the day.

As a business owner, you have an agenda as well. While teachers are not for profit and you are a business trying to earn money, much of the skillset overlaps. Startup CEOs pitch to investors, solo business owners sell to new clients, and freelancers are always thinking on their feet trying to come up with creative approaches to solving problems. Spending a day in a classroom, you’ll realize that teachers are essentially running a micro business every single day.

Apply Your Skills to Your Business

No matter your background, you are certain to have skills that apply to running a business. Even basic skills use learn as a student or a parent apply to business. If you are creative and work hard at it, you may find yourself behind the helm of a growing enterprise before you know it.

Eric Rosenberg

Eric Rosenberg

Eric Rosenberg is a personal finance expert. He received an MBA in Finance from the University of Denver in 2010. Since graduating he has been blogging about financial tips and tricks to help people understand money better. He is a debt master, insurance expert and currently writes for most of the top financial publications on the planet.

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