Building a Sustainable Side Hustle

My experience building a profitable side business.

Have you ever built a fire in a hurry? The kind you light quickly — then scramble to keep going. The kind of fire that keeps fading and thick branches never catch. These types of fires never seem to last long.

These fires are a lot like certain side hustles. The type of business started with a lot of enthusiasm — maybe after selling a few products or completing a couple of gigs. Unfortunately, these side hustles tend to die out quickly.

There is no shortage of viral success stories showcasing side hustles going extremely well, seemingly overnight. My experience is completely different. For 15 years I overlapped a full-time job with a side business. If my side hustle were a fire, it didn't even catch flame for a few years. However, years later, I was able to leave my full time job. And the fire continues to burn hot.

This post is a reflection on how I built a sustainable side business. A reflection on my mindset, my priorities, and the rewards. Like a nice fire you can enjoy for hours, it took time to create.

First, I had to gather some fire wood

I am a professional transportation engineer. My full time job was focused on finding innovative solutions to transportation problems. I started my job for the State of Ohio in 2005 . I enjoyed the work, the people, and the pay.

My side hustle started a couple years later, in 2007. I have been building websites since high school. So, I started?building websites for friends, family, and local churches.

Initially, these projects did not make any money. But these projects had other benefits.?Each project introduced a new?learning opportunity. These opportunities provided skills I would later use for a long term, sustainable business.

Then I needed to collect different types of firewood

Different types of wood are needed for a long-lasting fire. You need different sizes and eventually a fire hot enough to burn thick logs. Much like twigs and branches are not enough for a serious fire, technical skills are not enough to run a sustainable side hustle. Without any customers, project management, or communication skills I was not making any money.

Over the next couple of years, I developed web apps to solve problems I encountered. Here is one example: As a transportation engineer, I often worked with maps. However, location information was usually provided in one format and most online mapping tools wanted a different format. So I created my own solution. Then I published it to the Chrome Webstore and other people started using it.

I repeated this process for many web apps and mobile apps. The process went something like this:

• Build products that solve a problem I was facing
• Learn new skills with each project
• Ship the end result for others to use

Different types of firewood were being collected. The "shipping a product" and "sharing it with others" type.

Eventually I started laying out the fire wood

Once the firewood is collected, it is time to start setting up the fire. You know, flammable stuff on the bottom, kindling above, bigger pieces stacked nicely — I like the "lincoln log" approach — and thick logs on standby.

A lot of building a side business is fairly non-sexy. And I had plenty of non-sexy experiences over the years. Like getting up at 5AM every day to work on my side projects. Like staying up until 2AM some nights figuring out Xcode. Like slowly giving up sports to spend more time on my client projects. Like obsessing over mobile apps so much that my friends were annoyed. Like leaving a few hours late for vacation to finish an app update.

You get the idea. You often hear entrepreneurs talk about the grind. About putting the time in. In my experience, this is real. There is no shortcut. You have to trust the process and put in the hours.

Years later, I lit the kindling on fire

Okay, time to bring out the matches. When you have taken the time to set up a fire properly, lighting it is painless.

At some point I had to start working with paying clients. Showcasing my previous work landed me a couple for-profit projects. I still remember receiving my first check from a client!

But I still did not look through my business with profit as the primary goal. Remember, I was only just lighting the fire. I had to keep a close eye on the flame to ensure the best chance of a long-lasting fire. I wanted to make sure my paying clients felt like I was a good investment.

Trying to squeeze more money from my earliest clients would have been a mistake. Each opportunity could have been perceived one of two ways: make more money or continue to learn. Here are a few examples of opportunities I was faced with during these early years:

Client Question: Could we make this website look more appealing?

Potential Answer: If you pay me $200 more.

Answer to Client: Yes.

Self-Talk: I can use this as an opportunity to learn more about UI/UX design.

Client Question: Could we add a new feature on this site?

Potential Answer: That was not in our original agreement.

Better Answer: Yes.

Self-Talk: I can use this as an opportunity to learn a few new skills.

Client Question: How can our staff update the information on this page?

Potential Answer: You can't. For a small monthly maintenance fee I can keep the content updated for you.

Better Answer: I can install a content management system. Then I can create a simple tutorial video for your staff to follow.

Self-Talk: I better learn how to do those things.

I used each opportunity as a learning experience. Trying to squeeze a little more money from my initial clients was not the best way to position myself as a professional. As my skills continued to grow, I was able to attract better clients. The patience eventually paid off.

I first earned money from my side business in 2009.?Although calling it a business was a bit of a stretch. In all of 2009 my business earned me... wait for it...

$1,240

Not much, but hey, it was more than $0. For the next few years I did not get much better at earning money from my business. However, I never stopped working at it. I made a few?websites for clients. I had a few apps making money from the App Store. I kept learning new technical skills. I kept improving my soft skills. And I continued to build the habit of putting in the time.

Looking back, I was creating the building blocks for a more successful future. The fire was started. It was easier to envision what the fire could look like in the future.

Then I had to keep it burning

Once a fire reaches a certain point it is much easier to keep it going. But, you still have to keep an eye on it, move it around from time to time, and continue to feed it.

As I continued to grow my skill-set, I realized something. People were not only interested in me as a developer. They were also trusting me as a consultant. A lot of my early clients did not know exactly what they wanted. I had to pry beneath the surface and help them identify exactly what they were interested in. I was learning a lot more than technical skills.

Then the large firewood started burning

The flame was spreading and the temperature was rising. It was only a matter of time before the logs caught fire.

When a good opportunity came my way —?see the second half of this blog post — I was able to seize it. That opportunity in late 2015 was a turning point. My business started earning enough over the next couple of years for me to start dreaming about working for myself full-time.

When the thick logs are burning it becomes much easier to keep a fire going. The hot coals at the base make it much easier.

At this point, I had to change my mindset. It was finally earning a serious profit and I no longer needed to say yes to every opportunity. During these years, there were a lot of decisions that, in hindsight, make a lot of sense. However, in the midst of these decisions they were difficult to make.

Potential Decision: Dropping a $50 /month maintenance client.

My initial reaction: This is easy money each month. The client (a friend) will be offended.

Eventual results: Landed my first $75 /hr client.

Potential Decision: Spending $300 in Google Adwords.

My initial reaction: Ads are weird. Probably a waste of money.

Eventual results: Landed a $7,000 client.

Potential Decision: Turning down a $30,000 project.

My initial reaction:?Take the project — this is a lot of money!

Eventual results: Well, I will never know for sure. But, there were a lot of red flags in the scope and schedule. Experience taught me to stay away from these projects.

So, more than 10 years in, I switched my default answer for every new request to no. I became selective which projects to accept and which clients to partner with.

Finally sitting down to enjoy the heat

Getting a fire going, especially the right way, is a good feeling. At some point the fire takes care of itself and we can get out of the way.

In 2022 — after 15 years of overlapping my full time job with a side hustle — I finally made the jump and left my full-time job. I am incredibly grateful for how well self-employment is going these first 15 months. This experience has provided me with more control of my schedule, more financial freedom, and more unique challenges to pursue.

Once a fire is burning nice and hot, enjoy it! Savor the heat on a cool night. Enjoy the conversations around it. And make sure to get off your butt from time to time and throw in a log. This fire didn't build itself.?