How to Start a Side Hustle and Be Your Own Boss


Many of the business owners we work with started their businesses as a side hustle and eventually left their job to be their own boss.

Many of these business owners started this later in life. Not everyone who owns a business had a marvelous idea and just started it right after they got out of high school and became a success.

Owning your own business is a dream that many have, but most people don’t even know where to start. According to Mark Cuban, the first place to start is ”knowing what you love and what you are good at”. Not everything we love we are good at and not everything we are good at we love.

If you are one of those people with a passion that you love and that you are good at and you wish could turn into a thriving business here are some tips for you.

Tip 1: Believe in your passion even if others don’t.

The first step is believing in your passion even if others don’t believe in it. There will always be people who will be naysayers and most of the time those people don’t understand or have no business giving you an opinion.

However, there are times when people don’t believe in your idea and want to protect you from wasting your time, but we will address that next.

Some of the most successful ideas and people in the world were given rejection letter after rejection letter and were told their ideas were not good.

Examples of successful people whose ideas were not supported at first.

Henry Ford

When Henry Ford was an American industrialist and business magnate who had the idea of creating a motor vehicle for everyone and epically failed 2 times and had little support.

With the support of Thomas Edison and others, he finally launched the Ford Motor Company on June 16, 1903. Ford showcased a newly designed car on the ice of Lake St. Clair, driving 1 mile (1.6 km) in 39.4 seconds and setting a new land speed record at 91.3 miles per hour (146.9 kilometers per hour).
The Model T debuted on October 1, 1908. Here we are today, years later and the Ford Motor Company is one of the most successful companies in the USA.

Stephen King

King is an American author of horror, supernatural fiction, suspense, science fiction, and fantasy. He grew up in a challenging environment and was considered to be very poor.

His father left him when he was a kid and never returned after “going out for cigarettes”. Writing has been a passion since he was a kid which continued into adulthood.

As an adult, he struggled with addiction and depression, but his wife was there supporting him along the way – even though he was rejected by 30 publishers and told that no one would read his books. In 1974 he got a deal to publish his first novel, Carrie.

Today, we all know this novel was wildly successful as well as many of his other classic novels.

Walt Disney

Imagine being the Walt Disney we know today and being told that he “lacked imagination and had no good ideas”. We would think that is crazy, but that happened to Disney while he worked for a newspaper in 1919.

Later, Disney started a cartoon business in 1920, but it failed, so he moved to Los Angeles to pursue other ventures. He then created Oswald the Lucky Rabbit, which was the first incarnation of what would become the household name – Mickey Mouse.

Initially, he was told that a big mouse like Mickey would scare women but he did it anyway. Mickey Mouse was rejected over 300 times. Disney is now a household name for all generations and who does not love Disney World and DisneyLand?

Tip 2: Make sure your ideas are fairly sound..

As we mentioned above, sometimes there are people in your life that might say your ideas are not good for a good reason. They care and want to protect you.

However, this is your journey and it is good to listen to what everyone says around you, pay attention, do your own research, and make your own decisions.

Take some time and ask yourself some important questions about your passion and be real about it. Going after something we love comes with risk, but we like to encourage calculated risks.

Here are some questions you can ask yourself:
  • Is there a need for what I have to offer?
  • Why do I want to go after this passion?
  • What is driving my desire to follow this passion?
  • Do others make money doing the thing I was to pursue?
  • How much money would I need to invest to get started?
  • Who can I get to help support my idea?
  • Is there a support system I can lean into?
  • Is there a local business office I can reach out to that could help?
  • Will I need a website?
  • What else would I need to get going?

It is important when asking yourself these questions and evaluating the feedback you have received by people around you that the decision that you make to either take a step back now or move forward is done from a place of vulnerability and honesty.

A great idea might not be a good business. A strange and unique idea, might be an awesome business. There are so many variables to consider, but take some time to really consider everything. Don’t overthink – but dig in and evaluate “all the things”.

Tip 3: Find the people who will support your idea even if it is lofty.

In the case of Henry Ford, the support of Thomas Edison was very helpful, as well as Steven King’s wife having his back.

A great place to start is not alone. Finding someone who can be a cheerleader or just someone you can talk to about your ideas, concerns, challenges, and ideas is beyond helpful.

If it is not a family or friend, it could be a therapist or even a local small business office that gives free advice to small businesses. Many cities have them. 

Going alone at anything is hard, but even if you can’t find the support you need, you can still do it. Many people have had to go at it alone, just know that we are here believing in you even if no one else does.

Tip 4: Be realistic about the time you can dedicate.

We live life to have fun and enjoy life. Taking on a side hustle is a lot of work and can take quite a bit of time, but if you have the time and energy – do it!

It is important to be healthy in life and not overwork or to do a side hustle that exhausts you and affects your main income stream.

Take some time and figure out the days, times and how much energy you have to dedicate. Make sure you have time to play and recharge.

Take it from an older (kinda older) workaholic who loves what they do. It does not matter how much you love your side hustle or your current job, if you overwork, you will eventually pay for it.

It can also affect your relationships, so take some time to figure out the details of what you can dedicate. Balancing life, work and passion is important.

Tip 5: Offer your service for free for a limited time.

As a person who believes you should always pay people for their time, this is something to consider if you are unable to find clients who want to pay right away.

Many people doing side hustles or freelance work offer their services for free to a limited number of people in exchange for a Google Review, feedback and referrals.

If you want to move in this direction, dedicate a small number of people you are willing to do this for. A good number is around 5. Reach out to your network, post on social media (if you have a tight knit group of people) and say:

I am __________________, I am starting a business doing __________________. Let me know if you or anyone you know might like to try my service for free in exchange for a review, feedback and referrals if you love what I do.

Tip 6: Know Your fee and what you want to charge.

If you don’t know what to charge, do some Google searching about your industry. See what others charge and how long they have been doing it and adjust accordingly.

When you meet with the customer/client that you are offering free services to, have the fee you would charge so when you meet with your new prospect that you can let them know what you charge if they want to meet or work with you again.

At the end, invite them to return to you by offering them 20% off their next session/product/service as well as offering the same 20% off to any friend they might refer to you.

Make sure you thank them and let them know how helpful they are to you pursuing your passion.

Tip 7: Referrals are your golden ticket to more clients/customers.

In most businesses referrals are the way to build businesses. As a website design, SEO and marketing company, we work with numerous clients to help them not only market themselves, but build up sales, traffic and new customers/clients.

In this we tell everyone we work with that referral is the #1 source of quality client acquisition that can’t be matched with anything else.

If after you have offered your service free to a small handful of people and no one returns or refers to you then we always suggest another small round and if those don’t pan out either then it is important to ask yourself why.

Here are some questions to ask:
  • Did I ask for honest feedback?
  • Is my session/product/service good?
  • Is there anything I can change?
  • Did my clients/customers seem happy?
  • Did I remind people to refer to a friend?
  • What could I do better?
  • Do I want to give a couple more free opportunities?
  • Is it time to choose another passion and move on?

Tip 8: Validate your side hustle with a paying customer.

If things are going well and you get a couple of paying customers, then you know you are on the right track.

However, if you don’t like what we mentioned above and nothing panned out for you – you still are on the right track to finding out why and what to do next.

If you have moved into acquiring a few customers that will pay for what you are offering, then this is a great place of validation but also a great place to start asking yourself more questions.

Tip 9: Ask yourself lots of questions.

Yes, I know we ask a lot of questions. Keeping yourself on your toes and asking yourself questions can help you move forward and keep the ball in motion even if it feels slow or stuck.

  • Do I enjoy what I am doing and want to do it more?
  • Do people like the products/services that I offer?
  • Which ones do they like or gravitate to?
  • Am I charging too much / too little?
  • Is there anything I need to change based on feedback?

By asking yourself these questions and others that are more specific to your side hustle you can get a bigger picture on what is the next step to move forward.

Are you doing so well that you need to register yourself as a business? Did you notice that you are so tired that you need to cut down the time invested? Do you just love everything about it and are excited to keep moving forward?

It is all relative to your current experiences.

Examples of Side Hustles

If you want to start a side hustle but don’t know where to start but know you want to work for yourself here are some ideas for you to ponder.

Walk Dogs

Dog walking is not only fun if you love dogs, it is great exercise and can really help out the people who might not have the time to walk their dogs or the health to do so. Dog walking not only helps the dog but the people who have them.

Pet Sitting

If you love dogs, cats, birds and other animals – pet sitting might be for you. People like myself need good quality people that we can turn to watch our pets if we travel or need to go places. When people find a really good pet sitter, referrals are what most new jobs are acquired by. Become an awesome pet sitter and you will be flooded with work over time.

Deliver Groceries

I get a lot of value from being able to order groceries personally. I don’t do it all the time, but when I do it is so helpful for me. There are people who are sick, elderly or are just so busy with kids, school and life that bringing them groceries is life saving! Also, if you like diving, driving around your city playing the music you love is a great way to work. Plus, if you are an introvert, there is very little interaction with people.


If you are good at math or even music there is always someone looking for tutors. Tutors get to make their own schedule and you can do it between working. If it goes well, you could even move into teaching courses.

Teach Courses

Teaching courses online is a fun side hustle when you are teaching what you love. You can also teach courses in person as well.

Sell Handmade Goods

Do you love making jewelry, art or something else that people might like to buy. It is free to set up an Etsy store and you can even sell on Poshmark.

Online Surveys

We are mentioning this because you can make money doing this, it is minimal but something a little cash goes a long way so we felt it was important to mention it. You can use sites like Swagbucks or Toluna.

Sell & Flip Goods

Do you love shopping at the Goodwill or your local thrift store? Have you ever found something that you know you could resell? This is a great opportunity. You can resell the items on Facebook Marketplace, Craigslist, Ebay, Poshmark, or Amazon.

Sign Up To Upwork/Fiverr

 Do you have a skill you can sell, but don’t know where to start. Many people start on Upwork since it has a network of people already built that are looking for work. You will give back 20% back to the platform typically, but they are providing the leads for you – so it is worth it. Over time if you build up a clientele, you can move away from such a platform and do it on your own – even launch your own business.

Become A Virtual Assistant

Virtual Assistants are needed worldwide for a wide variety of tasks. You can be in control of your hours and choose who you want to work with and what kind of tasks you love doing.

We asked ChatGPT what tips they would give to start a side hustle.

If you don’t know what ChatGPT is, in layman’s terms, ChatGPT is a chatbot that will answer any question or tell you anything you wish once you type it into the input area (We will show you how to do this later). Learn more and test out ChatGPT.


It is a big jump, but also an exciting one to pursue the things we love. It is not easy and any entrepreneur, even successful ones will tell you that the work to be your own boss is often more work that having a boss.

However, being your own boss is exciting, powerful, it helps you make your own schedule and live a more free life. You only have to answer to the people you want to answer to (mostly).

Although it is not easy, anyone can do it if they believe in themselves and they are honest with the process along the way. Lofty dreams don’t work. Dreams with solid plans, constant evaluation and reevaluation, the ability to take constructive criticisms and get back up when you fall down is key.

Are you going to start a side hustle? We would love to know more – leave us a comment below. Need a website for your side hustle, get in touch!