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Smart Side-Hustling

On priorities and the subtle art of doing one thing at a time

I discovered the side-hustler’s dilemma back in middle school shortly after we’d all survived Y2K.

The year was 2001. My friends and I killed time playing Nintendo 64, waiting for the impending release of Diablo II for PC. My parents had recently upgraded the family computer to a next-gen beast with an Intel Pentium 4 processor. I was thrilled despite the lack of any alternative to the sloth-like dial-up internet service available in Rural Ohio where I grew up.

And there was music. Lots of it.

Right around the dawn of the new millennium, music went through a rapid evolutionary period characterized by an explosion of new artists, genres, and sub-genres. This was, for example, the heyday of pop-punk rock, and Blink 182’s Enema of the State album spent more time in my portable CD player than I’d like to admit.

Napster and the ability to burn custom playlists to CDs heralded mass exposure to new and different kinds of music over the internet, and how consumers acquired music was changing. But not everyone had the equipment or the know-how to burn their own custom CDs.

Being the visionary entrepreneurial seventh grader that I was (yuk yuk), I saw lots of opportunity in the space. I bought a bunch of writable CDs and downloaded Nero Burning ROM and Napster. I was all set to start taking orders from my middle-school classmates for custom CDs. In other words, I had my first side hustle.

The orders lined up. For ten bucks, I made people custom CDs. They told me what they wanted on their playlist, I burned the CD and delivered it to them at school. I soon found myself arriving home from school and rushing to start the downloads for the songs people wanted. This was, after all, a time when downloading a song over dial-up internet took hours.

It didn’t take long before I became more interested in making money with my CD-burning side hustle than focusing on my primary responsibility, which was school. I’d push homework to the periphery and prioritize customers’ orders. My internet bandwidth was reserved for downloading songs. Research for school stuff could wait.

But, of course, the school stuff couldn’t wait. I soon found myself under-performing on both fronts. My school work suffered and more customers complained I was taking too long to deliver. My side hustle shortly fizzled out as at-home CD burning became more widespread and easy.

Although I didn’t realize it at the time, my little venture in seventh grade gave me my first exposure to the side-hustler’s dilemma: It’s really hard to do more than one thing at a time.

Fast forward to today, and I know a lot more about the perils of trying to run side-hustles and secondary projects. I’ve done it for most of my adult life to varying degrees. It’s an art form, really. And it can be a slippery slope. Juggling priorities to keep multiple efforts moving forward isn’t a skill they teach you in school, but anybody who has started a business outside their regular employment or taken on freelance projects to make some extra money knows exactly how critical it is.

The challenge is that side hustles often inspire more passion than do primary jobs. Especially initially. Side hustles are usually born out of ideas inspired by exploration of interests or elucidation of good opportunities. My first instinct is often to throw myself completely into a new venture. But, of course, I can’t do that.

Reining in my passion and prioritizing so as not to compromise my primary commitments is something I’ve been learning about since my early foray into an entrepreneurial side hustle in middle school. What I’ve learned over the years is that the concept of “multitasking” is misguided.

No matter what any productivity guru tells you, you can only do one thing at a time if you want to do anything right. It’s of course possible to switch between projects, but all you should ever be doing at once is mono-tasking. I believe failure to recognize the shortcomings of multitasking is what causes a lot of side hustles to fall apart.

Let me explain. If you’re sitting at work at your primary job thinking about your side hustle, you’re half-assing it on both fronts. Likewise, if you’re constantly interrupting your side-hustle to address issues related to your primary commitments, that’s bad too.

What’s been essential for me is maintaining a priority list. But the list has to be dynamic and malleable. Mine adjusts constantly throughout the day. But whatever is at the top of my list gets my undivided attention. Sometimes a given task only stays on top of the list for a short time, but while it’s there, I’m focused.

Ihave met a lot of people who’ve failed to make progress because they have more than one top priority. This is where the fallacy of multi-tasking swoops in to convince these people they can divide their attention and do more than one thing properly.

Prioritizing one thing at a time helps build patience, too. Sometimes I don’t have any time during the day to dedicate to projects that are important to me. That makes it seem like those projects aren’t progressing as quickly as I’d like them to. But I’ve learned that I have to be okay with that.

Sometimes I can’t shift some things that are important to me to the top of my priority list for days at a time. I have a wife, a couple kids, a dog, and a house. That means life happens. A lot. When I have to be a dad or take care of a problem with the house, that shifts to the top of my priority list. I have no choice.

For a long time, not working on my side hustles for even a day bothered me. But now I’ve learned to shift my sense of accomplishment to align with my priority list. If I’ve progressed on whatever is on top of my priority list at any given time, then I’m satisfied.

Let’s say it’s Saturday afternoon and the kitchen sink starts leaking. I’d planned to write or catch up on some pending work for a new business I’m launching. But the sink gets bumped to the top of my priority list out of necessity. This used to piss me off. But it doesn’t anymore. I now call it a good day if I spent my time on whatever was at the top of my priority list all day.

The great thing about having a dynamic priority list and always focusing on priority one is that it’s easy not to waste time. If you always make an effort to assess what you’ve got going on and place something worthwhile at the top of your priority list, it’s quick and easy to identify what you should be doing with any spare time you have.

It’s easy to slip into meaningless wastefulness in spare time if you don’t have a priority list to remind you what’s important. Time has the potential to magically add value to your life. But it can also slip away without contributing anything to you other than increasing your chronological age. A priority list makes it much more efficient to squeeze the value out of your time.

Does all this mean I work all the time? Not at all. Because work per se isn’t always at the top of my priority list. Aside from family, I do place my own mental health at the top of the priority list periodically and relax, read, exercise, or educate myself on something I’m interested in. But this is what I call conscious idleness. I’ve chosen to be idle and grant myself leisure time because I believe doing so will help me accomplish my long term goals. Burn out is obviously counterproductive, and I’ve been there. It sucks.

My goal is to never let myself become bored. Boredom means your mind is active and ready to engage in something but you’re failing to employ your mental energy toward something productive. Any time I feel a twinge of boredom, I consult my priority list and jump into whatever is at the top.

Even when I’m having a hard time getting motivated to go after my top priority, it’s always worth it to pick myself up and dive in because there’s satisfaction waiting at the end of the day when I’ve progressed on my top pending priority. On the other hand, I’m bound to be frustrated with myself and discontent at the end of the day if I neglect my priority list and let my time slip away without extracting its value.

The thing about a side hustle is that it’s necessarily going to progress more slowly than your primary work. A side hustle can only grown when it’s at the top of your priority list. And that can’t be all time time. And that’s okay.

Long-term goals should always provide guide rails for your priority list, but you should never confuse your daily priority list with your list of long-term goals. I’ve been guilty of this confusion myself, and it never fails to create frustration. Long-term goals don’t necessarily need to be ranked in priority order, they just need to be worthy causes.

For instance, some of my long-term goals include 1) raise kids that will say I was a good dad when they’re adults themselves, 2) build a business that contributes value to society, 3) publish a book people enjoy reading, 4) help other people grow personally and professionally, 5) provide a comfortable and joyful life for my family, 6) become financially independent, 7) maintain good physical and mental health.

Just with those seven long-term goals I’ve listed above, I could build a daily priority list hundreds of items long. But I don’t need to. As long as I make sure that I always have something as my top priority that justifiably moves me toward any one of my long-term goals, that’s a worthwhile top priority at any time.

Your side hustle should align with as many of your long-term goals as possible. The more long-term goals your side-hustle aligns with, the easier it will be to transition your side hustle from a strategy to make a few extra bucks here and there into an ongoing stream of value for your life.

I don’t write down a priority list every day and adjust it throughout the day. I keep my daily priority list mentally. But it’s not a bad idea to write down your long-term goals. Then, whenever you’re adjusting your immediate priority list, always double check to make sure whatever is at the top of your list aligns with at least one of your long-term goals, preferably more.

Back when I was burning CDs for my middle school classmates, I had no sense of long-term goals. I only knew that each ten-dollar bill a kid handed me in exchange for a CD was satisfying as hell.

This is as far as many people get in their side hustles. Sadly, this is also almost a guaranteed recipe for burnout, inefficiency in life overall, and failure. Indeed, I didn’t even make it to the end of that school year before my grades and my side hustle slipped off.

Humans have a troublesome tendency toward instant gratification. This is a major obstacle that must be overcome if you want to build a successful side hustle. The daily priority list strategy I’ve outlined here is a great way to go about squashing this barrier. It’s not too difficult to train yourself to get that little dopamine hit you need by working on your daily top priority when whatever is on top of your list is meaningful.

Had I known in middle school how to prioritize like I do now, who knows how far I’d have been able to grow my little side hustle. But I do know that my side-hustle game is stronger now than it’s ever been, which is really quite amazing considering that I have far more responsibilities than I’ve ever had before this point in my life. I am living proof that the prioritization strategy I’ve described here works.

So go on. Get after it. Set your priorities, and progress every day. One day you’ll look around and realize you’ve accomplished all those long-term goals. And you will have done it one top priority at a time.

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