Ch-ch-ch-changes — From Freelancing to Joining a Team

After nearly seven years of running my own practice, I joined the Chromatic team as a Front-End Designer and Developer. This marks an exciting new chapter in my career, but like all major life events, it’s a challenging endeavor. In this post, I’ll explore some of my experiences in transitioning from running my own design and development practice to joining a distributed team.

But first, context…

Everybody’s career is different in its own way, but this is especially true of freelancers. I can only speak for my own experience, so a bit of background is in order.

Since about 2003, I have held several jobs as a designer both in Puerto Rico and the United States. These positions focused primarily on print and branding design, with a bit of wayfinding and exhibition work sprinkled in. In 2010, I decided to strike out on my own and start a freelance practice. I had the good fortune of maintaining a solid relationship with ex-employers, so the bulk of my initial work came from a few of them. Around that same time, I started working on front-end development and design, and by about 2014, my practice focused on digital work almost exclusively. Early last year, I transitioned to a partnership with a close colleague of mine with whom I had been collaborating for a couple of years.

By the end of last year, the 6+ years of courting clients and constant hustle had caught up with me. After re-evaluating my priorities, I realized I wanted to be more productive by focusing on getting work done instead of chasing work. So the job hunt began, and that’s how I ran across —and eventually had the good fortune to join— the team at Chromatic. The past few weeks have been a whirlwind; here are some of the most important lessons I’ve learned.

Time-tracking and accountability

In my experience, it’s easy to be too lax when tracking time as a freelancer. I learned the value of tracking time spent on client projects early on in my freelancing career (even with flat-rate projects), but getting in the habit of tracking internal time was always a struggle. I got a chance to improve on this during my brief partnership last year —one wants to do right by one’s business partner, so one aims to be accountable— but it was a bit hit and miss.

For a company like Chromatic —which not only has a ton of client work, but also encourages team members to write blog posts, contribute to open source software, give presentations at industry events, and educate ourselves continually— tracking internal time is vital to the health of the company. The balance between work that directly leads to getting paid and work that has other, less quantifiable benefits is a delicate one. Being a recent ex-freelancer, it can feel a bit daunting to track this internal time, especially if you are not used to doing so. And let’s face it: the independent spirit that once emboldened you to jump into the deep, cold freelance waters might even throw a little fit at the prospect of keeping such detailed tabs of everything you do. You’ll soon find, however, that it’s quite liberating.

Tracking internal time not only keeps us accountable to our fellow team members and bosses; it actually keeps us accountable to ourselves. It’s easy to develop an inaccurate notion of how much time and effort we spend on anything when we don’t keep track of it. During my freelance years, I often underestimated the time I spent on non-client work tasks, which led to the notion that I didn’t work hard enough on my business. That led to me working myself straight into burnout on more than one occasion. Accurate time-tracking helps me avoid this; it gives me a realistic sense of how I spend my time, making it easier to respect my own work/life boundaries.

Clients are new to you; and you’re new to them

Chromatic doesn’t shelter its team members from face time with clients. Having probably interfaced directly with multiple clients of your own gives you an awesome advantage as a potential candidate in a company like this. But it’s important to keep in mind that, once you start your new job, you no longer represent just yourself. It’s a good idea to take cues from your teammates. Get a sense of how (in)formally previous conversations have been with each client and gauge the tone of conversation.

I’ve partnered with a few larger web design or development shops in the past, and often times this called for meetings and email exchanges with their clients. This is not new to me at all, but I still find myself treading lightly at times in an effort to make my interactions with clients not come across as “an interaction with the new guy.” Alas, this still happened on one occasion. The topic might sound a bit silly to dwell on, but this can be even trickier to navigate if you haven’t experienced this kind of situation before.

Think about it from the client’s point of view. Their relationship with your new employer likely precedes you, they’re used to a certain kind of tone in their conversations with your company (some of them keep it loose and and easy-going; others might prefer a more formal tone), and their project probably involves some level of tacit knowledge. What’s more, they might have their own reservations or anxieties about getting assigned “the new crew member”. Being sensitive to this yourself, it’s easy to put those fears at ease by taking stock of the projects you’re assigned before you interact with clients. Review recent exchanges on GitHub issues or Slack channels, ask your coworkers to give you an intro to the project and the client. The more knowledgeable you come across and the more your interactions feel like conversations they’ve had in the past, the better clients will feel about working with you.

Culture, teamwork, and camaraderie

Freelancers are nothing if not a diverse bunch of folks. The circumstances and motivations driving someone’s decision to run their own practice are as varied as the people who navigate the self-employed waters. That said, there are some traits I’ve found to be fairly common amongst freelancers and other self-starters, and which can sometimes come into sharp relief when they become part of a team.

Anecdotally speaking, the majority of my contract work colleagues range from mildly introverted to outright misanthropic. Although it’s probably not true of most, many freelancers have something akin to a loner streak. For this type of person, interactions with other people can be emotionally draining. I know this because I naturally tend to range around the lighter end of the spectrum, with occasional periods of leave me alone or so help me I will cut you. And in my experience, running your own practice can sometimes encourage further isolation.

Many years of trial and error have taught me to carefully manage my people-time and my alone-time to allow myself the opportunity to recharge batteries in between interactions. I’ve honed this skill well enough that I’m able to manage a coworking space (with all the interactions implied in that pursuit) and not be an insufferable mess at the end of each week.

Joining Chromatic exposed me to the better part of a couple dozen people between team members and clients, all within a week. As I got onboarded onto our internal processes and projects, with a trip to NYC thrown in there for good measure, I found myself a little overwhelmed. This was due in part to the newness of it all (more on that later), but being in frequent contact with other people throughout the day certainly played a significant role. The fact this is a distributed team helps with this, but video and chat interactions are ultimately still human interactions and those require a lot of energy to someone like me.

Nothing beats setting time aside for yourself that you deliberately dedicate to the activities that help you recharge, but the support I’ve received from our company’s leadership has been invaluable. Our partners took the time to make sure that I was getting the support I needed, didn’t leave me to just figure things out on my own, and gauged how I was holding up throughout the process. They went out of their way to avoid me getting completely overwhelmed. It was all a bit to take in, but knowing they’re looking out for me was very encouraging. If you’re hiring, get invested in the onboarding of your new hires; a little bit of hand-holding goes a long way towards their success. (Metaphorically speaking. Don’t hold people’s actual hands. That’s creepy.)

For all my curmudgeonry, there’s something to be said about the camaraderie that springs from a team of creative problem-solvers working together. While freelancing, it’s easy to find yourself too close to a problem to see the right solution and no one around to bounce ideas off of. In the short time that I’ve been working with Chromatic, the value of regularly interfacing and collaborating with teammates has not only improved the way I work but also made me feel better at the end of each day. Working remotely strikes the right balance between forming part of a group of folks who interact both professionally and socially, and being left alone when I need it.

Finally, it’s important to note that transitioning from freelancer to team member means that your blind spots are covered. While it’s true that working closely with others means your work will be more closely scrutinized, it’s also true that this scrutiny removes the onus to think of everything and get it all just right every time. Running your own practice, you often find yourself the sole person responsible for an entire project, an undertaking that feels less daunting with experience but which never stops being a huge responsibility. Running with a team means that, while you should still put out your best work, you can lean on your teammates to get a second or third pair of eyes on something. The chances that some embarrassingly obvious mistake makes it to production are reduced immensely.

The biggest challenge of all: Everything. All at once.

If you’re contemplating making this transition at some point in your career, do yourself a favor and prepare for this: Everything is about to change. Shortly before a business trip on day 5 (!!) of my work at Chromatic, my wife noticed I was a bit under the weather and asked how I was feeling. My answer was:

Everything is new. Everything is different. Man, even this laptop is new. Where’s my old laptop? I want my old laptop!

(She had already commandeered my old laptop for a project, so that ship had sailed.)

Change is hard with a capital H, and the move from running your own practice to a more focused position within a larger team carries with it a significant lifestyle change. Be mindful of this, and do right by yourself by taking deliberate steps to ease your transition. Chances are you already gave the decision a lot of thought before seeking and accepting a full-time position, so trust your judgement and don’t let the stress of change discourage you.