10.7.2014

Seven Months of Freelancing

Today finds me realizing several things. The first is how difficult actually keeping up with a personal blog and writing meaningful content can be. I had great plans for this little corner of the internet, and so far it's collected mostly cobwebs (apologies). A second bit of realization is the fact that I've been freelancing for seven months, and I've been able to do some awesome work in that time with some very talented folks (thank you).


I wish I had kept a better Captain's Log during this time in my life, where I scientifically documented every failed project, every tiny victory, and in turn made someone else's journey easier or meaningful. That hasn't happened nearly as much as I'd like. At any rate, I'd like to share seven things I've learned and appreciated over these seven months.

1. Feast and Famine isn't a fairy tale.

There are a few things you'll hear about any line of work or pasttime. These adages are generally met with an eyeroll, or worse, completely ignored. I heard "There's going to be busy and slow periods, so make sure you plan accordingly" so many times before I began freelancing that I thought I knew it all by heart, and then it actually happened. There's something exhilerating about earning buckets of cash in a short period of time, and there's also something terrifying knowing that you probably aren't going to see that kind of dough for another couple months.

I went through several high and low periods, and I'm happy to say our family has weathered the storms. We also have had our share of "That project should be sending a check any day now" moments, but that's to be expected. What I will say is that I wish I had done a better job planning that from the get go.

2. Challenge yourself to not repeat "what works"

As a freelancer, you'll most likely be working from home or from coffeeshops or co-working spaces in your city. If you're like me, not having a team around you can present the temptation to repeat certain conventions or design "tricks" that you've used on other projects to get the job done. There isn't anything objectively wrong with this, but it's certainly not going to make you better at your craft.

To combat this, I have a variety of friends and connections who I've been able to send work to and get real, quality feedback. Doing this ensures you're not just crapping out the same work you did for the last project, and also keeps you accountable to a creative community at large. I highly recommend having this type of system in place if you're a freelancer.

3. Take a break!

When I first started freelancing, I heard many responses along the lines of "Wow, good for you. If I worked from home I'd never get anything done." While that's true for some people, I quickly realized that I have the opposite problem: I work way too much. Implementing a schedule from the beginning and sticking to it helped me focus my energy and take time to spend it with my family. Coffee and lunch breaks with my wife and daughter (no coffee for Evelyn, don't worry) helped keep me sane and was also good for my output.

If you're just starting freelancing and you don't have a plan to combat the "just ten more minutes" bug, get a plan in place now. Keeping to a schedule will help you prevent burnout, be more productive, and hopefully keep your important relationships happy and healthy.

4. Get off your butt.

If I had things my way, I'd eat a pizza and a bag of cheetos every day, washed down with a six pack of my favorite micro-brew. However, doing so would be absolutely hazardous to my overall health and wellness, so I like to keep some semblance of physical fitness present in my life. Running in the morning is good, even when it sucks, because it keeps me healthy and helps me prepare for the day. Walking to places instead of driving is also good. If you're into the idea of a standing desk, go with that. If not, make sure you're getting up and about throughout the day. Just because you don't need to go into an office doesn't mean you don't need to take care of yourself.

5. Know thyself.

When I started freelancing I tried a variety of projects. Some were with clients on the east coast, other were with some awesome remote teams! I quickly found out that working with a remote team or a client I'd never met in person didn't work very well with my personality and style. My output wasn't as good as what it should have been, communication can get weird, and I generally wasn't as happy with the work. Realizing this helped me focus my energies on things that I was excited about and better at, and it's led to some fun projects with really great folks.

Finding the type of work that best suits you is not selfish. It will actually help you become a better designer and freelancer when you're in roles and relationships that foster good work and communication. I don't say this for you to make excuses or be irresponsible; it's more about honing in on what really makes you tick as a freelancer so you can better partner with folks around you.

6. Making things is great.

Since I spent time figuring out what really gets me going, I had a huge revelation: doing product design is awesome! Last year I thought up a concept for a Windows Phone app on a flight to Chicago, and pitched it to some friends who were app developers. The past year has found me pouring tons of time and energy into Maestro, the actual email app that came out of it. We got a bit of funding to make this a reality and I'm now working with a very talented team to get this thing done.

I've done a lot of marketing websites in the past three+ years, and I've realized that I'm getting a bit burnt out on them. That's why I've found product design so refreshing: There's something extremely satisfying about doing something from start to finish and taking care of all the details in between. It's a truly cohesive design "project" and there's always something new to learn and accomplish.

7. I miss being on a team (Put me in, Coach!).

About a month ago, I realized that there was something freelance life was lacking. Sure, I've been able to do some great work for some awesome companies like AMC, Intel, Bose, Nuru International, and Spotify, but I've largely created on my own. I have an awesome little home office that I love the crap out of, but I'm still making stuff by my lonesome. For those of you who know me, you'll know I'm a very extroverted person who loves solving problems with others (an ENFP, if you're into that sort of thing), and the solo life is actually pretty draining for me.

I had a heart-to-heart with my wife who confirmed that in me, and that got me thinking about what my future held. I began to keep an eye out for teams that might need someone like me, and started paying a bit more attention to the world outside my home office and twitter feed. This led to some conversations and introductions to some truly talented and incredible people.

All this to say, today I'm proud to announce that I'm joining the design team at Opal and I'm very excited for what the future holds. They're a truly talented bunch, and I'm proud to be signing on with such a dynamic team.

This was a big decision, and one I didn't make lightly. I'll still be putting my blood, sweat, and tears into Maestro and posting stuff on Dribbble. If you want to chat more or have any questions, as always get in touch.