Weighing risk vs. reward when it comes to quitting your 9-to-5

More creatives and developers are migrating away from traditional forms of employment – what’s stopping you?

The concept of the path of least resistance has been buried in my mind from an early age. I think it stems from soldering together one of those FM radio kits with my dad.

I didn’t understand the magic of circuitry then, (and still don’t) but the basic concept is that electricity will always follow the path of least resistance.

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As humans, we’re wired to do the same. All of us do it on a fundamental level: we weigh the balance of risk and reward. Depending on our fabric, some of us lean towards risk (with potential high reward) and some of us lean towards stability (but losing a potential upside).

I’ve been fortunate enough to be surrounded by many creative, driven people that are looking for ways to kick the status quo. So I’ve seen a particular trend of people starting their own thing, and I think it’s a trend that’s growing every year.

Employers are beginning to realize that their employees are making decisions based upon this fundamental risk/reward rubric every day. For every benefit afforded by steady 9-to-5 employment, there’s tradeoffs.

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The benefits of being an employee (stable paycheck) are challenged with some serious sacrifices (lower overall income, inflexibility, and lack of independence).

The most productive and innovative employees will eventually inevitably leave for either greater compensation at another company, or for the greater risk/reward of alternative income.

So what’s stopping you from going out on your own?

What’s often overlooked by employers is that the risk-seeking type of employee – the one most likely to leave your company for greener pastures – is probably woven from the same fabric as the person who started the company in the first place.

Employees most likely to create new products, start new departments, develop new initiatives, and show strong leadership are suddenly the ones most likely to leave completely.

If you’re anything like me, you’ve probably felt that you can do a much better job by taking the reins yourself.

This narrative plays along with my personal experience. After college I had a series of 9-to-5 jobs that, while valuable, only served to prove to myself that I was a terrible employee.

This kicked off almost five years of freelancing, and then eventually co-founding an advertising consulting firm.

The path wasn’t always easy. And, like most unique things, there’s no central school for starting your own business. Even if you have skilled mentors, there are some things you just have to learn the hard way.

For the first few of those years as a freelancer, I learned that you had to wake up early and work all day. I learned that sometimes clients wouldn’t pay.

I learned that sometimes you can’t afford all the gear you want. And perhaps more than anything, I learned that perhaps the most glamorous niches to work in aren’t the most lucrative.

After a couple years of moderately successful and extremely stressful freelancing, I can identify the one “big break” I had. In my work producing media for nonprofits, I landed the opportunity of flying to Liberia during the Ebola outbreak.

I spent my birthday in a hazmat suit walking through an Ebola unit with a camera. Upon returning home, I endured 21 days of quarantine in my apartment, and then suddenly realized I had an audience.

I published a book about my travels, and after a few more years I’d hit 40 countries and consulted for dozens of large NGOs.

Today, my job is significantly more boring, but oddly even more inspiring to myself. After a couple years of extensive travel, I saw that there was an opportunity in marketing consulting and strategy, so my partner and I started Discosloth earlier this year.

We don’t have an employer who provides health insurance, 401(k)s, vacation days, or any other benefits. But if you’re sewn from a particular fabric of risk/reward, you don’t need that stuff.

You suddenly have greater control over your income, your work, your clients, and your lifestyle as a whole. As long as I have internet and a laptop, I can work. Why do I need two weeks of paid vacation?

And this isn’t just me: there are dozens of people I know who have left otherwise stable careers. It’s interesting to pull apart the threads and ask why this shift is taking place.

I think the most obvious answer is a financial one: it’s becoming much easier to make more money on your own rather than working for someone else.

We’re seeing an exponential increase in decentralization. For better or worse, the old way of cubicles, time cards, and thirty-year single-company careers is dying out. Workers are learning that, perhaps, their money doesn’t have to be tied to their time.

In my experience, those on the edge of this innovation are able to take the most advantage of it. Thankfully for creative folks like you and I, that means a strong grasp of tech and a certain level of communication savvy.

So what’s stopping you from releasing yourself from the bonds of the cubicle?

There are a few common reasons that people give me.

First, is that you simply don’t want to. And that’s fine. If you’re comfortable, and don’t have any major complaints about your position, that is amazing. Stick with it!

Second, is that you don’t know how to. But here’s the rub: no one knows how to. That’s why it’s such a huge step. There is no school for this. The closest you’ll get is listening to peers who have done it.

Third, is that you can’t go without a stable paycheck. And I’ll be honest: if you’re living paycheck to paycheck I don’t recommend the freelance life. I think you need six months to a year of living expenses saved before you step out into the void.

But many have done it with absolutely nothing in the bank. Sometimes being hungry helps!

Those who’ve left the nine-to-five don’t want to work 45 hours a week just to feed the beast: they’d rather work 60 hours a week for themselves.

Those who’ve left the nine-to-five don’t need a manager or a middleman between them and their work. Because of that risk/reward rubric, we’re no longer afraid of being laid off or offshored.

With the independence gained by losing the 9-to-5, freelancers and small business owners gain increased flexibility, higher income, greater independence, and the astonishing ability to build anything, anywhere – all thanks to the decentralization of communication.

So when you’re asking yourself why you’re still at your desk job, think about the upsides of working for yourself. It’s easier than ever, and there’s less excuses than ever!

Let me know your thoughts in the comments.

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About Gil Gildner

Gil Gildner is co-founder of Discosloth, a digital advertising company that creates innovative PPC campaigns for businesses. He has traveled to over 40 countries and is fueled by a mixture of coffee and Pabst Blue Ribbon.


  1. What a great and motivating article! But how to know you got what it takes to become a freelancer?


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