Pros And Cons Of The Side Hustle

Ask many established software developers and you’ll discover something interesting. A lot of us are doing things on the side that aren’t considered traditional hobbies. Many of these things might eventually be used to make a living or improve our careers. What is it about tech and the people in it that drives this trend and what benefits and problems can you expect if you take up a side hustle? We’re about to help you answer that question for you.

Whether it is producing content such as podcasts, blogs, and videos, consulting, or building applications for personal use or for sale, or even creating other content like music and books, there is a lot to be gained by hustling on the side, a lot of which is much more difficult to get in a regular job. This can often be puzzling to those who work with developers, as nothing seems to motivate us to give it up. Let’s talk about why that is.

“Side activities that are a little bit more than a hobby but a little bit less than a job.”

There isn’t a good, widespread agreement on what side hustle means. It is intended to make money. If you aren’t trying to make money, it’s a hobby. They don’t always succeed. It’s more of a business venture than not. This differs from training, in that you have to contend with finding a market. This differs from investing, for the same reason. It stops being a side hustle once it becomes a full-time job.

Taking on a side project can help build your career and your skills, provided you do it in an intelligent fashion. If you are considering starting a side project of your own, an early awareness of the upsides and downsides can save you a ton of pain and frustration. Careful investment in a side hustle can help you make more money and can put you ahead of many other developers.

Episode Breakdown


11:50 Opportunity to play with new tech.

If your day job is doing ASP.NET WebForms, you can do .NET core and angular on the side. This is a great way to build up skills that you know you’ll eventually need. It’s also an opportunity to try new things that may change the way you look at your existing work.

13:11 Ability to make your own mistakes rather than mitigating others’ mistakes.

“It wears on you after a while because I know the perfect decision but can’t.”

Technical debt is a serious drain on motivation. When you aren’t having to fight tech debt or general structural issues, it can remind you of how you felt when you first got into coding. This can either help improve your attitude going back into the office or can spur you towards changing jobs, either of which is good.

15:15 Possible extra income.

Don’t count on this if you are building an app, but it works out for a lot of things. The extra money may not be enough to pay all the bills, but even a little can make it easier to save for various goals. If you are making money on the side from your work, you can also write off some expenses. This also makes it easier to justify the time you are spending, both to yourself and to others. Don’t discount this; it gets more helpful over time.

18:45 Better networking in areas in which you are interested.

If you are doing something interesting in a particular space, you’ll begin interacting with people in that space. Those people can help you. If you stick with it for a while, you will have established a strong body of work in a particular specialty that can help you get a job in it if you choose. You really never know where your contacts lead when you are networking without desperation. A side project is a great excuse to do this.

20:20 Ability to cross-train in a variety of areas other than just software development.

“When we started podcasting, neither one of us knew anything about audio equipment and editing.”

If you are building your own thing, you’ll get to learn about sales, webhosting, marketing, design, and all other kinds of stuff. The upside on this is hard to predict.

23:25 Being challenged when much of your day job is writing boring code.

A lot of us spend a lot of our day writing glue code between things other people have written. It can get old quickly. It’s easy to do this for too long and stagnate your career. A new project gives you the opportunity to break out of stagnation and can give you ways to approach things that are useful in your day job. Never underestimate the value of avoiding complacency.

26:50 Can help protect you from burnout if you do it right.

This is a space that you control. Others can mess up their space, but not yours. It’s also relatively consequence free if you decide not to work on a side project, or quit it entirely. You can outsource some of the stuff you don’t like doing if you have cash. You can even sometimes design the project in such a way that you can avoid the things you don’t like about your job.


29:22 You may waste a lot of time.

“I’ve had one side project or another since 2004.”

Many developers have had one side project or another throughout their careers. Most of them don’t make any money. It would be easy to look at these as incredible wastes of time. They can cost hundreds to thousands of dollars in lost time and resources.

32:55 Your boss may not approve of it.

Many employers don’t want you to have side work. They have to watch and make sure you aren’t misusing resources or violating your employment contract. It can also interfere with the regular course of business when you have a hard cutoff on the time you leave because of side work. If you are competent, they may be worried about you leaving.

35:10 Could be a distraction to your day job.

Don’t be the developer who drags in to the 9:00 meeting exhausted from staying up working on a side hustle. Don’t take phone calls or emails related to your side hustle on the clock. Don’t bring it up in conversation with coworkers. You might be disciplined, but they may not be and you’ll be seen as the source of trouble. Be careful about media consumption on the clock if it could be even peripherally related to your side hustle.

40:00 Will take time away from other things that need attention.

“I was fit, we used to work out a few times a week then I went to med school and gained like 60 – 70lbs.”

If you sleep 8 hours and work 8 hours, you only have 8 hours left in the day, not including transit, meals, etc. You have to be careful how you spend it. It’s not just family, but friendships can feel the strain when you have a side project that is taking up too much time. Most of this comes from picking ideas that are either too ambitious or timelines that are too ambitious. This can also impact your other hobbies and your fitness. It’s a good way to get in big trouble. Don’t cut into your sleep to provide time to your side hustle. It just makes you dumb in the long run.

45:05 People may resent your project because it becomes a target for their frustrations.

Even if you are careful about how often you mention a side hustle, be prepared for any mistake you make to be blamed on it. You need to go to a lot of extra effort on the things that aren’t side hustles to avoid this. That may mean extra hours of work. Understand that most people, when comfortable, don’t understand why you aren’t.

47:05 Is a really easy way to get burned if you do it wrong.

Don’t do more of the same thing you do all day. Don’t do more work than you can actually afford to do. Don’t allow cross contamination of emotion between work and your side hustle. Ever. In either direction. Even if it is positive.

Tips and Tricks

Limit your scope. Nothing is worse than trying something too big, getting most of the way, then quitting. Limited Resume-Driven Development is ok here. Learning while doing this is a good way to hedge your bets. Start with a market and work backward. You don’t want to build something that no one wants. Pick something that interests you. Money eventually doesn’t motivate you enough. Come up with a mechanism for taking notes about where you are and plans. This fits around the rest of your life, so it will be getting interrupted frequently.

IoTease: Product



“Our mission is to make the whole procedure of venipuncture automated to reduce error and decrease venipuncture times.”

This is a really fascinating use of robotics and IoT in the medical industry. It’s a robot that uses ultrasound and near infrared imaging to map the veins in a person’s arm. It then selects the best spot to insert the needle. Now this obviously doesn’t have the touch of a good nurse or doctor but will help with patients that are chronically ill and have to have lots of venipunctures or have deep or hard to find veins. While this isn’t for the average IoTeaser check out the website and read the story about how two students designed this to help with medical research and patient care.

Tricks of the Trade

Embrace the oblique. Hey, diddle diddle, straight up the middle is not always an effective way to move forward due to resistance. Instead, pick ways to move forward without charging straight into resistance.

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