20something Hustle: The Ins And Outs Of Being An Independent Contractor

Chris Castillo
Chris is the founder of Empowered Achievers, a development junkie, and an unwavering believer that work doesn't need to be painful. She come from the corporate advertising world, so she know a thing or two about the pressure of a 9 to 5 (or 6, or 7). She started Empowered Achievers in order to help women to develop their perfectly designed career "puzzle piece" to fit into a fulfilling life. When she's not working, you can find her enjoying the trails in the Rocky Mountains.


I’ve been working on building out my business in professional development and coaching since this past fall, and I finally took the big leap a few months back to pursue it full time. I stayed on as a contractor at my old company, while building my business in the meantime. It has been a terrifying yet exciting process, and I’ve learned a lot over these past few months. If you’re considering moving from a full-time employee to a contractor, whether it’s working on your side-hustle or just to have more flexibility in your schedule, read on for some insight into life on the other side!

Communication is key

Contractors don’t work in the same way as full-timers, so plan your work accordingly. Since I transitioned while staying at the company I was working with, the shift in dynamics was noticeable. You can no longer just dabble on every idea that comes up. Since you are being paid hourly, you need to establish a relationship with your boss to understand what they need from you and respect his or her time. The best way to ensure success is to communicate authentically and often. Personally, I have a document I work on every week to lay out my workload and estimated hours, notifying my boss if things change in real time and I need additional hours.


Timeblocking is your best friend

In this vein, consolidating time has been a lifesaver. Not only does it help for timekeeping purposes, but it also helps me to be more productive. As a contractor, it is easy to be working on projects as they come up, but that doesn’t set me up for success. Since I have my own business to build, my mind would be elsewhere if I was working as a contractor for a few odd hours a day. I try to consolidate my hours so that when I’m contracting, I am fully dedicated to the company and all of my logged hours, and when I’m off, I can spend my time devoted to my own business. It takes a great deal of diligence, but has been a valuable lesson.


Plan time for socialization

Working as a contractor makes you more of a lone wolf, especially if you are remote. If you have a need for social interaction, be sure to plan accordingly. Personally, since I work from home and on my own much more, I’ve been attending business networking groups. You can find the groups that are more your style to get your social fix for the day.


Flexibility is awesome

Going for a hike in the morning is an amazing way to start the day. Seriously. This aspect of contracting has met the hype. Take advantage of it.


If you’re building out your own business, don’t burn yourself out in pursuit of greatness.

This is my last piece of advice, but arguably the most important if you’re leaving your 9 to 5 to turn a passion project into a full time role. When you turn your passion into a business, it’s natural to want to work all hours of the day. I know because I learned this lesson the hard way when I first started working on my business. I stayed up late hours because I was OK with that lack of balance and it didn’t bother me that I wasn’t practicing what I preach. I loved the work I was doing to help people in their careers! After some time going full-speed, though, I realized I was exhausted and losing motivation. I’m not saying dedication is a bad thing, but it’s important to carve out time to rejuvenate, whether that be a workout class you’ve been wanting to try or time with loved ones. If we really want our businesses to be sustainable, we need to create them in a way that sets us up for success, and running yourself ragged until you get burned out and take a 2 week break is the surest way to fail.


Enjoy the ride

Whatever caused you to move to contracting, this is a big time of change in your life. Enjoy the lessons you learn along the way and be patient with yourself.

Now go forth, and contract to your heart’s content! Maybe you’ll even turn that side-hustle into a fulfilling career in the meantime.