How to Take On A Second Job

(Originally published December 3, 2022)

So for years now, I have done a lot of various different types of work in my personal life. The extra work I do helps to finance some of my ideas, projects, investments, and concepts. This work has helped to create this blog and given me something else to start investing in, as if there weren't enough options already.

In my own life, I've held more than one job at a time for the majority of the last decade. When I was younger, it was out of necessity; now, it is risk management. During these tough economic times, plenty of people are trying to think of ways to make more money. Maybe you'd like to change your career entirely. Maybe you just want to be able to have something on the side that would help you pay for presents for your kids. Whatever your financial goals are, you've likely heard time and time again that you can only cut expenses for so long before having a real impact on your quality of life. The "easiest" thing to do is to generate more income - this is in quotes because it STILL IS NOT EASY.

Now, what I do is a bit excessive. My friends make fun of me and ask me: "how many jobs do you have again? Why not just get one job that pays better?"

This is totally fair and I will admit that my day job doesn't pay amazing. What it does do, however, is give me a great work-life balance. This balance has allowed me the time to work on additional means of income outside of work. Sure, some of them might not make money this second. Maybe they'll never make money. Some of them, however, do make additional money. In fact, I just had to make my very first quarterly estimated tax payment this year because I needed to avoid having a huge tax burden come next April, as well as avoid paying fees and penalties for not being up to date on things.

It may not seem like it, but this is actually a good problem to have. Now the majority of it comes from maintaining a second job, but there are other things that I do that factor into my taxes. This isn't really supposed to be a self-portrait though, so let's move on.

I've worked a lot of day jobs, part time jobs, and structured employment. Those experiences have given me a diverse background - highly recommend reading the book "Range" by David Epstein for anyone looking to explore the distinguishing factors between generalists and specialists in a professional setting. Through this experience, I have found ways to expand outside of my immediate work experience.

I want to share some of this experience in branching out. Hopefully it can help someone to find a way to further support themselves or their loved ones. Maybe it will help someone to move out of their job into an area of work they find more fulfilling.

I started working multiple jobs when I was young, but if you're just now thinking of taking on extra work for the first time, here are some of my tips:

First, pick something that you really enjoy. Do you have any hobbies that you really like? Any certain aspect of your job that you find particularly interesting? What is something you have a good understanding of from some amount of passion? Working more than one job when you're used to 40 hours a week is going to take some adjustment, but it will be easier if you enjoy whatever it is that you're doing.

Second, determine how long you need some extra money for and how soon you need to start earning it. Could you pick up some seasonal work or part time work for a short period of time? It's always a nice thought to start your own side hustle, but realistically, this takes more time than people realize and isn't going to provide you a boost to your income in the short term, which is especially important if you need extra money quickly.

You'll want to examine both local options to your area for extra work, as well as check online. I personally have had some good luck finding extra work in sales, writing, freelance work and consultation work. However, I'm always curious and looking for new ways to add income to my bank account. I've worked multiple jobs in seasonal industries and temporary positions. Before and even during my time as a corporate employee in an office, I worked a multitude of part time jobs that included being a secret shopper, a caddie at a golf course, a delivery driver, a tutor, a business consultant, and many others. At no point did any of these jobs provide me with enough money that I could've done them as stand alone opportunities, but there are a lot more opportunities than people realize to try to use some extra time that they have to make extra money and help boost their income to better balance their finances.

I hope that this helps to motivate someone to start diving into alternative ways to add some income on the side and help get through some rocky times ahead. I would be happy to write more on this topic if there is a need and always am happy to help use the experience I've had finding work in various ways to assist others in their search.