Side Hustling Your Way to Financial Success

The side hustle. The side gig. A Part-time job. Whatever name people give it, the same result follows. More and more, people are looking for ways to boost their income, improve their lifestyle, and achieve their dreams.

Defining the Side Hustle

Side hustle essentially means anything outside of your normal job a person does to earn extra cash. The term “side hustle” may be relatively new but the concept has been around forever. People have always been looking for ways to make a little extra side cash.

In the old days, people took something they had an overabundance of or an in-demand skill they could leverage to make extra money. People rented out extra rooms, sold extra produce, and even sewed dresses on the side to earn extra cash.

Today thanks to the growth of the internet, there are so many more choices than people had in the past that is easy to find a side hustle that is right for you.

There are a lot of benefits and a few drawbacks to consider when investigating side hustles.

The Financial Benefits

The advantages for doing a side hustle are numerous.

Financially Rewarding

First off, side hustles can be very financially rewarding. Let me explain.

Here’s an example. Let’s assume a person makes $60,000 a year. Take out about 30% for taxes and they are left with a salary of about $42,000. If a person saves 25% of this for retirement, they are investing $10,500 a year. Assuming a target rate of return of about 7% rate, it will take about 30 years to become a millionaire. In other words, if you start this at age 22, you’ll be a millionaire by age 52.

Now add in a side hustle. Let’s assume the side hustle generates an extra $800 per month (not unrealistic since I could get a retail store part-time job at $11/hour and work an extra 20 hours / week). This extra side money when invested at 7% now allows a person to become a millionaire in just 22 years! To put this in perspective, if you start the side hustle at age 22, you’ll become a millionaire by age 44!

This is just scratching the surface on what a side hustle can do.

Side hustles can even be more financially rewarding than the example listed above. It’s not unrealistic to earn $20K, $30K, or more from a side hustle depending on the skills that are leveraged. But that’s not all……

Pays Down Debt Faster

The money generated from a side hustle can be used to pay down debt faster. I used our side hustle money to payoff my girls’ medical bills.  The extra money could also be used to also payoff consumer debt (i.e. credit cards), student loans, and even the mortgage. Imagine being debt-free in almost ½ the time it would have taken by investing time each week into a side hustle!

Can Lead to Financial Independence Faster

Having a side hustle can also lead to financial independence. The definition of financial independence I will use is this: the passive income generated equals or exceeds my expenses.

Let’s assume the side hustle was a landscaping business that generated $35K per year in gross income. Let’s assume a 30% tax rate so you bring home roughly $24,500 per year. You invest this money every year starting at age 22 to what you already invest from your day job listed above ($10,500 / year). In about 16 years (age 38), you are now a millionaire!

Guess what you are now financially independent! Here’s why: Assuming you spend the remainder of your day job salary, your annual expenses are $31,000 per year. Withdrawing just 1% of your $1M portfolio at age 38 plus the income from the landscaping business now allows you to quit your day job!

Well what if you wanted to sell your business too and travel the world? Let’s look at it. Assume I sold the business for $250K (7 times gross income), my portfolio is now $1.25M. Using the popular 4% withdrawal rate means that I can withdraw $50K / year. Even taking out taxes at 30% means my take home pay annually is $35,000! My expenses are covered plus extra money left over. All this by age 38! Woo hoo! 😊

I don’t know about you but to me, choices are a GOOD thing! 😊

Develop Career Competitive Advantages

Side hustle can even provide a competitive advantage for your career. Let’s say there are skills that a person’s management says needs “refinement” (i.e. leadership, soft skills, technical skills, empathy, active listening, etc.), what better way to practice and improve those skills than through a side hustle?

A side hustle will challenge you to learn new skills. You’ll be exposed to learn different types of knowledge and different ways of thinking.  A side hustle can help you become unique in your main career since you’ll bring those new skills and perspectives to your core work role.

While it is important to enact these skills during your day job, it is not the place to practice… it is the place to PERFORM. Trying new things while working a side hustle can lead to experimentation. A person can figure out what works for them and what doesn’t then take those lessons and apply them to their day job.

A great example is a side hustle I used to work in retail sales. I received feedback from my day job management that my soft skills needed some refinement and it was impacting my leadership. Luckily, my management gave me some great examples of things that were occurring at work. I took this feedback and applied them at my side hustle. One thing about management skills… these are transferable. 😊

I studied and emulated how my side hustle management treated both the employees and customers especially under time of duress. I took these lessons learned, practiced them at my side hustle, and when I felt ready, applied to my day job. I recently did an informal survey of key personnel that I worked with and found out that my soft skills have improved remarkably in a short period of time.

Grow and Diversify Network

Lastly, a side hustle is a great way to grow and diversify your network. Creating a side hustle will lead to learning self- promotion. You’ll meet people that might not otherwise cross your path in your normal line of business. Some of these new contacts made through your side hustle may even prove beneficial to your day job. Additionally, you might find your social circle widening when meeting others who share or appreciate your passion.

The Psychological Benefits

Mental Rejuvenation

One great psychological benefit of working a side hustle is mental rejuvenation. A side hustle can provide a welcome change of pace from the doldrums of a career. It can be refreshing to use a different part of your brain and to develop different skills that are not normally used.

Creative Outlet

A side hustle can also be a great creative outlet. For example, if your career is technical oriented (i.e. writing code, engineering, etc.), having a creative outlet for a side hustle (i.e. photography, writing, painting, etc.) will develop new skills that are transferrable to your day job.

Expands Core Identity

A lot of people tend to define themselves by their chosen career. Having a side hustle expands that core identity and puts their identity in a different perspective. For example, a side hustle might involve giving back to the community in ways not possible in your career.

Safety Net

A side hustle can be a psychological safety net for trying out a new career. Starting a side business allows a person to try it out to see if they like it, to experiment, and to develop a customer base. It minimizes risk since income is still coming in from the career.

Pressure is off since if something isn’t going well at your day job and you manage to get your side hustle to progress, you’ll feel like a success. Positivity and success in one aspect of your life will carry over into other aspects as well. This success will also make it easier to cope with your work-related frustrations, disappointments and setbacks.

A good way to view a side hustle is a “hobby with benefits” 😊. If you can do something that is rejuvenating, rewarding, uses other parts of your brain, expands your identity, AND can make some side cash to boot…. Why Not?

The Drawbacks


Putting an extra 10-20+ ours/week into a side hustle reduces the amount of downtime available. While a side hustle can be both fun and lucrative, there is a temptation to have the side hustle consume the available time a person has. Past times that do not earn income can seem unproductive and have no practical purpose in your life. Do not discount the need for breaks from demanding aspects of one’s life.

Some types of side hustles require an upfront time and/or financial commitment. Some side hustles may require months or even years of effort before a substantial revenue stream starts to occur.  With any new endeavor, be sure to ask yourself if the work you will put in is worth it. For example, if you need income to start immediately to pay down debt, this may influence the type of side hustle you pursue.

An example is what I experienced when I pursued a side hustle a few years back. Friends were encouraging me to pursue a consulting side hustle since this could be a very lucrative endeavor. After much thought, I decided to pursue other opportunities because my family’s needs came first.

I was worried how much of a time commitment consulting would be, how it would impact my time with my wife & children, and how much additional stress it would add in my life (trust me, I had plenty of stress already from all the kids’ medical issues, I didn’t need any more). Looking back, I’m glad I made the choices I did. While I earned a lot less that I had hoped for, I also had time with my family that I would not have traded anything for.

Can Add Additional Stress and Complexity

Relationships with family, friends, and loved ones have the potential to be neglected since the activities your partner wants to do may not seem productive towards your goals and may seem like a waste of time since this takes away time of your side hustle.

Ensure priorities are setup and maintained appropriately. Remember there is a strong probability that one of the reasons you are working so hard is to have the freedom to spend time with the people you care about. Don’t neglect these relationships in the short-term in order to get the long-term benefits.

Balance is one’s life is needed in order to not only manage the additional stress a person is under but also maintain your sanity.  Keep your priorities in order and take care of the people who have been taking care of you. The question you need to ask yourself is, “Is it REALLY worth the sacrifices if all this work alienates the people you care about?”

Can Feel Like a Job

Another potential drawback is that after awhile all the time, energy, and work that is poured into a side hustle can make it seem like drudgery, like work, like a job not a hobby with benefits. Remember the reason why this side hustle was chosen and what made this fun in the 1st place. Learn to enjoy the journey along the way to financial independence.  

How to find out if a side hustle is right for you

Below is a list of questions you can ask yourself to determine not only if a side hustle is right for you but what type of side hustle may fit your unique situation:

  • What are you looking to get out of a side hustle?
  • Why do you want to pursue a side hustle?
  • What is the long-term objective you want to achieve?
  • Does it incorporate skills you already have?
  • Is there a career or job you have always wanted to try?
  • Is there a skill you wanted to learn but afraid to try?
  • Are there skills for your current career that need refinement but cannot find the place to practice and master?
  • Are the things you’re good at marketable and can generate revenue?
  • Do you want more responsibility than you currently have in your career?
  • Can you treat the side hustle as a hobby with benefits or more like a job?
  • How to set priorities so your family is not left behind in the dust:
    • Do you need flexibility to be there for your family?
    • Do you want the big payday or a steady paycheck?
    • How many hours can you commit without jeopardizing “family time”?
    • Are you able to take on additional stress, complexity, and deadlines?

Ideas to Investigate

Online services

If you are looking for a freelancing gig, Upwork or Fiverr might be right for you. These sites allow freelancers and prospective clients to meet and negotiate a gig. To be successful at this, a person needs to understand what their services are worth on the open market in order to negotiate a fair price.  Among the types of jobs posted on these sites are:

  • IT / Internet-Based Services
  • Web Design
  • Creative Writing
  • Marketing / Advertising
  • Publishing
  • Graphic Artists
  • Photography
  • And Much more!

Creative Hobbies

Are you a good writer? Have a knack for cooking or photography? Try leveraging a hobby into a money-making endeavor. You’d be surprised what people want and will pay for. My suggestion is to make a list of things you enjoy and things you do to decompress. For example, if you enjoy yoga and are good at it, a side hustle might be teaching a yoga class. You do it anyways so why not get paid for it? Find ways to minimize time spent and maximize pleasure.

Retail services

Need a steady paycheck? Enjoy talking to and helping people? Check out a retail services gig. Hours are flexible, work is steady, and even builds leadership skills if hired for a supervisor / manager position. If you just want to clock in, have some fun, and go home, jobs like that exist too.


From discussions with some of my friends, consulting can be a very lucrative field to investigate. Some of the keys to consulting is to understand what expertise you have that other people might need, what is the market for that expertise, and how much people are willing to pay. There is a lot of upfront work needed to get you name out there and build a reputation. There could also be long hours and added stress since you’ll have deadlines you have to meet. The bright side is it could lead to a significant income to the point where it may lead you to quit your day job and become your own boss! 😊

Leverage Your Skills

Another way to create a side hustle is leveraging the skills you already have. For example, I know accountants that do personal taxes on the side to earn extra cash. I know electricians who fix wiring in homes on the weekends for extra cash. If you’re a teacher, there are several online forums, when you can teach students in other countries and in remote areas of the U.S. Sometimes the key to financial success is leveraging what you already do for a living in a different way.

Leverage the Things You Already Own

One the easiest things to do to get started with a side hustle is to leverage what is already owned. For example, if you have a house with a spare room then rent it out. A friend of mine earned enough money renting out 2 rooms in his house to pay off his mortgage is less than 10 years!

Another example is becoming an Uber or Lyft driver and use your vehicle to chauffer people around.

Another popular thing to do is sell items on eBay or Etsy.

If you own something, there is probably a creative way to turn it into a side hustle.


If you’re in need of earning some extra cash to pay down debt, save for a child’s college education, or expedite your way to financial independence investigate taking on a side hustle.

Like any new business venture, consider how to maximize revenue while minimizing expenses. A side hustle can be both financially and psychologically rewarding. Ensure to weigh the pro’s and con’s to see if a side hustle is right for you. It can be a huge impact to generating income as well as potentially test the viability of a new business venture or phenomenal new career.

A side hustle should enhance your life, not detract from it. Don’t let it interfere with the family and enjoying life. Be wary of pitfalls that can deter your success or risk financial security.

Done right, it can change your life. Done wrong, it can add more stress and complexity to an already hectic life. My experiences have been fruitful, and I hope yours are too!

Live the Life You Love, Want, and Deserve! 😊