Here Are 10 Reasons Why You Should Start a 5-To-9 (Even If You’re Happy With Your 9-To-5)

Declan Wilson
Photo by Garrhet Sampson | Unsplash

By now you’ve almost certainly heard the buzz words: side hustle, recurring revenue, solo-preneur. You either find them inspiring or are sick and tired of them.

I get it. Sometimes it’s just more comfortable to lean back in your ergonomically-designed office chair and hide away in your cubicle.

That is until your cubicle is taken away from you, for good.

Take my friend

Todd, for example, who recently lost his job. Todd writes:

“I never intended for my side hustle to become my main gig. But when I got pushed out of my comfortable cubicle, I found myself wishing I had prepared a little differently.”

I’m all for people having traditional 9-to-5 jobs. They provide a secure means for most people. They have benefits. And they’re a great way to build skills and tap into a well-established industry.

But what happens when it’s taken away? Are you prepared?

Fearmongering aside, I’ve been preaching about the benefits of running a 5-to-9 outside of your 9-to-5 for some time now. It’s not just a strategy but a mentality. And the mentality is this:

There is time spent aimlessly and there is time spent creating value.

Or as Todd says, “Take it from a guy who just lost it all — you can never do too much to secure your own future.”

If that’s not enough for you, here are my top ten reasons you should start your 5-to-9…

1. You learn something new

You’re going to learn something when you start a 5-to-9. I can personally guarantee that fact.

A 5-to-9 isn’t a hobby. It’s not paint by numbers or dabbling in your garden. For a 5-to-9 to work you need to bring a variety of skills to the table. Skills such as marketing, design, writing, time management, accounting. I could keep going.

You won’t have many of these skills when starting out. That’s okay. You’ll slowly acquire them as you face new obstacles.

As your skills grow, your 5-to-9 grows. As your 5-to-9 grows, your skills grow. It’s a perpetual loop of learning.

2. You create better habits

For someone to have a traditional 9-to-5 job — as well as other life’s responsibilities — and run a small business on the side, they’re going to need to be stringent on how they spend their time.

Starting a 5-to-9 creates better habits, because it has to.

Not only are you juggling multiple facets of your life, but you also have to squeeze in additional dedicated and focused work into your schedule.

You create better habits to work more efficiently. You create better habits to be more productive. You create better habits so that the little free time that you do have is spent recharging for the next bout.

A 5-to-9 is your habit growing incubator.

3. You find a healthy distraction

I get bored easily. It’s probably why my career is a hodgepodge of 5-to-9s and side projects. I can’t focus on just one thing, I end up getting tired of it and moving on.

When I used to work in a corporate office, I wrote on the side. I had to. Showing up every day at that cubicle was a bore. Working on my side hustle gave me something to look forward to.

It was an exciting distraction from the drabness of punching your time card and waiting for the clock to strike 5.

A 5-to-9 is something you want to do, not something you have to do. Therefore, it’s bound to be a little fun.

4. You meet interesting people

I met Todd online. It’s not that weird to say anymore, because it happens all the time.

I wouldn’t have met Todd, now one of my closest friends, if it weren’t for both of us working on our 5-to-9.

Besides my small group of childhood and college friends, everyone I hold near and dear I’ve met in some way or another through my 5-to-9s.

I’m sure your 9-to-5 co-workers are nice. Mine were. But there are other interesting people out there. And when you find people who are just as passionate and motivated as you are about your 5-to-9, you’ll build an inseparable bond that all of us humans are looking for.

When Todd and I speak to each other, it’s not generic pleasantries, it’s much deeper. We talk about our hopes and our fears. We strip away the superficial because we both know we are in this together.

A 5-to-9 gets you out Kansas and into Oz.

5. You experience flow state

Flow is a state of consciousness. It’s a state where creativity thrives off of the effortless control of our abilities. When you achieve flow, time warps, self-consciousness evaporates, and challenge and skill perfectly balance.

You’ve probably experienced flow before. Have you ever sat down to approach a task and by the time you looked up, hours had passed? That warped sense of time is flow.

“The best moments in our lives are not the passive, receptive, relaxing times… The best moments usually occur if a person’s body or mind is stretched to its limits in a voluntary effort to accomplish something difficult and worthwhile.” -Mihaly Csikszentmihalyi

Difficult and worthwhile, two perfect words to describe a 5-to-9. Working on your 5-to-9 is the epitome of facing a challenge that hones your skills but doesn’t overwhelm you.

Achieving flow state is a good feeling and it’s what makes your efforts towards your 5-to-9 feel worth it.

6. You feel more in control

We live in an entropic universe, which means everything is geared towards disorder and chaos. Even our innate survival instinct tells us the more control we have the greater chance of survival we’ll experience.

However, humans have a unique capability of creating a sense of order and control over our lives. Psychologists call it our locus of control.

Those who have a strong internal locus of control see outcomes as direct results of their actions. In other words, they feel as if their actions matter and have an effect on their lives.

Those who have a strong external locus of control feel the opposite — that their actions are almost meaningless and have no effect on their lives.

A 5-to-9 strengthens your internal locus of control.

7. You flex your creativity

If you’ve never thought of yourself as a creative person, stop right there. No matter how technical or straight-forward your 5-to-9 may seem, it needs a dash of creativity to make it your own.

Creativity isn’t a magical process, nor is it reserved for a select few. Creativity is a process.

In other words, it’s a skill that can be learned and your 5-to-9 is an opportunity to grow those skills.

8. You fail faster

Failure is good. Learning to quit is also good.

These are two things 5-to-9s can teach you that college and traditional 9-to-5s cannot. When you work at a traditional 9-to-5, failure is to be avoided. You take fewer risks because there are metrics to hit and shareholders to please. Therefore, you learn very little.

When you operate a 5-to-9, time is precious. When something doesn’t work, you cut it out and move on. You learn to quit, assess, adapt, and grow from taking risks.

You have to fail fast because failing slowly is a waste of time and resources. Only a 5-to-9 will give you a learning experience such as this.

9. You make money

I purposely listed this one towards the bottom. Yes, making money should be one of the main reasons to start a 5-to-9 (if it isn’t, then you have a hobby, not a 5-to-9).

However, the excitement is fleeting. The first time you make money from your 5-to-9, it’s a good feeling. But like all things, it wears off and soon it’s not enough.

For me, it’s the idea that the words I write earn money to be used for vacations or presents for my kids or towards a new car that makes my efforts feel worth it. The dollar amount isn’t as rewarding as the extra security and freedom it brings.

So yes, go make money from your 5-to-9 but don’t chase dollars for dollars’ sake. Think about the bigger picture.

10. You make a career

It won’t happen to everyone, but for a few, a 5-to-9 is an opportunity to create a whole new career for one’s self.

I have a degree in industrial engineering. My first real job was as a supply chain analyst. Although those were valuable experiences in my life, I built my own career with a laptop and good wifi.

It’s difficult, but it’s not impossible. Starting a 5-to-9 gives you a chance to create the career you’ve always wanted. You just have to start.

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Stay-at-home dad. 9-to-5 escapee. Aldi aficionado.

Baltimore, MD

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