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Strengths + Abilities




Lessons from my first year freelancing

I’ll be honest — the first few months were bleak. I didn’t have any projects lined up when I made the leap to freelance, so I spent months playing video games and started questioning everything. I contacted everyone I knew, eventually landed a project, and began figuring out how to make it all work.

From that first project, I experimented with different approaches and eventually found a rhythm. Now a year later, I have had the opportunity to work with some incredible people at GoogleAirbnbLonely PlanetFeedlyUnsplashSegmentFantasyMetaLabElephant and several others.

So while it’s still fresh on my mind, I’ve documented the lessons learned from my first year in the wild. Some of this will be familiar to fellow freelancers, hopefully some will be useful to others considering the switch themselves.

1. Relationships are everything

They’ve helped by allowing me to learn from others, plug into a community, and work on exciting projects.

Learn from others

I’ve worked with some very talented people. The work ethos I witnessed simultaneously filled me with admiration and frustration. Admiration: when I saw solutions implemented that I wouldn’t think to do myself. Frustration: every time one of these solutions was implemented, I felt like I was falling behind and losing touch with the ever-moving cutting edge of product design and development.

Yet I used that frustration to dig back in as a freelancer and hone my design chops, while continuing to learn from those same people. Countless conversations provided the insight necessary to operate at a high level from the get go. Now whenever I get stuck on a problem, someone who has been through the same thing is just a phone call away.

Don’t be afraid to lean on others for their advice or opinions.

Plug into a community

One of the best things about full-time employment is that you are surrounded with individuals who share a common goal. It’s fun to bring together a diverse set of people and accomplish something big together.

When I went freelance, a lot of that went away. A team of friends and a common goal was replaced with my dog and a desk at home. While it was novel and exciting at first, the experience quickly lost its luster. Life and work started blending together and things started getting weird.

I rented a desk at a co-work space, and I’ve enjoyed the separation between my home and work life. I like my house more. I like my work more. And most importantly, I am again surrounded with smart and talented people that are doing their own interesting work every day.

Surround yourself with good people to stay productive and enthusiastic about showing up every day.

Work on exciting projects

In addition to all of the valuable advice and support I’ve received from friends and colleagues; I’ve also received 100% of my work from them too. That’s why it’s incredibly important to show up every day and do your absolute best. Help the people around you. Strive for excellence. Be nice.

The goodwill you give to others comes back to you down the road.

2. Every day is an opportunity to grow

Earlier in my career, I worked on so many questionable projects. I’ve done everything from clipart business cards for gas station attendants to a website that sold chemicals that you inject into your body to become tanned. Yes, really.

But regardless of the subject matter, I have always tried to lean into the work and make it something more. The reason is simple: every project is an opportunity to learn something. And while I don’t take on projects that are as questionable anymore, I still encounter challenging situations that take on a variety of different forms.

Doing great work and getting through challenges with grace makes you stronger. Keep that at the front of mind and you’ll grow every day.

3. Communication is a differentiator

I feel like there’s a common preconception about freelancers: they sleep in, never take showers, don’t leave the house, flake out, and don’t work well with others. Isn’t that why they work alone? So it’s extra important as a freelancer to exude professionalism and meet clients where they are — use the apps they use for communication, understand and speak the language of their organization, and own the problem with them.

This approach is important, starting from the very first conversation you have with a prospective client. If you’re going for new business and it’s between you and another freelancer, and both of you have good work, what determines who wins? Good communication is what sets people apart.

And the benefits don’t stop after the business is won. You cut down on countless hours of work and rework if you are able to more effectively communicate the thought process behind the work. People want to believe that you know what you’re doing, you just need to make sure you’re giving enough cues that show this is the case.

Regular and clear communication is fundamental to developing trust in any working relationship.

4. Work can be done anywhere (with good Wifi)

A while back I moved to San Francisco solely for the purpose of working on big, complex products in technology. So my biggest fear when moving from San Francisco to Nashville was that I was also saying goodbye to the work that came with the geography.

But that hasn’t been my experience so far. Tools like Slack, Hangouts, and Dropbox make it easy to share ideas and work with people anywhere in the world. If it’s needed, I can also hop on a plane and get anywhere pretty quickly. And because this is still such a new industry, there is a limited supply of skilled practitioners that are able to meet the demand of all the companies that are transitioning to technology. All of this means that there is a never-ending flow of challenging work and fun problems to solve.

As long as you show up and are able to solve problems effectively, the work is there.

5. Defining a goal is important

I’m sad to say that in my entire first year of freelancing I never sat down and wrote down the goals of what I was hoping to accomplish. I just took most of the work that came my way, and somehow have still been able to make ends meet. But that approach hasn’t allowed me to grow with intentionality. So, yesterday, I sat down and wrote my vision, values, methods, obstacles, and key metrics I would track to determine whether or not I was working toward my goals.

Without this important step, you run the risk of floating from project to project not anchored to a larger vision. Just the exercise of writing down the key methods you’d like to achieve each year, does something to you mentally that drives action. It’s a meta-checklist that you subconsciously start working through whether you know it or not.

When you look back at it several months down the road, you’ll find that you’ve been working towards your goals with more intentionality than you may have realized. It’s worth the investment of a day.

Leaving the comfort of a full-time job and a team of people can be scary. But it doesn’t have to be. Tools are launching every day that are making the prospect of working remotely easier. Platforms (just like this one) connect like-minded people and their different experiences, and provide everyone a better sense of community.

As we all learn and share, our collective experience matures and evolves the profession and makes it slightly less daunting than it was yesterday. And as more and more people make the move to independent work and consulting, we’ll find new ways to connect to each other and to projects that may dramatically change the ways work gets done.

Just remember to always bring your best.




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