The next challenge of an old freelancer

Writing this down is an attempt at making sense of the myriad of thoughts and ideas swirling in my head. Turning them into a blogpost might help giving them some substance and clarity. Hell, I might even come up with ideas for a new course to set myself on.

Currently

I started working on the web as a copywriter in 1998. Today, I teach a handful of front-end related courses at school and freelance the rest of the time, designing and building content-centric websites for clients and agencies.

I design, write HTML, CSS and DOM related Javascript, know a few CMS like the back of my hand and use modern tools like Gulp, Sass and deployments on a daily basis. I also happen to have degrees in Philosophy and Communication. Oddly enough, I enjoy writing proposals, specifications, and talking with clients to find out how the web can help improve their businesses.

However, I don't feel comfortable carrying on like this for three main reasons:

• I would like to be involved with web projects at a more strategic level. How does that website fit with the overall communication strategy of the organization ? How will the web presence we are building evolve over time?
• I feel I am most valuable when I work with clients on the long term. So far though, most of my freelance gigs have been relatively short-term engagements (one to three months) where I have been tasked with the conception and implementation of a website.
• I miss working with a team, sharing ideas, rubbing shoulders, etc. Twitter, Slack and a solid network of friends in the field can only go so far.

Possible roads ahead

I have been thinking about this and looked at the career paths of others in the industry for inspiration. I would definitely like to continue working in the web world that I discovered nearly 20 years ago and have loved ever since.

Ideally, I would also like to carry on teaching the few courses I teach at school (HTML / CSS (Sass) / CMS), but maybe this is not compatible with my future career path.

Here are the three ideas I came up with so far:

Project Manager (web agency)

This kind of role would allow me to still be "in the trenches" but in another, less technically focused way. My experience as a front-ender might be a plus when working with a team: I would understand the problems or issues they are facing. That kind of role likely involves more thinking at the strategic level as well.

The main issues here might be the stress levels involved and the fact that I am not sure this can work as a part-time gig for an agency. I am planning on doing a few experiments in the coming months with a couple of companies I regularly work with to see if it could work.

Digital Communication Officer (internal team)

A lot of non profits, medium-sized businesses, etc. still need help in using social media or building their web presence and are bringing these competencies in house. Some of them might not need a full time position for that but could use the help of a freelancer part-time.

I would be less expensive than an employee and could even help design and develop part of their web presence, which possibly gives me an edge over someone with less "hands on" knowledge of the field. I could also put my communication background to good use.

Just to be clear, I don't rule out the possibility of becoming an employee again.

Join friends & start a business

I regularly work with a few friends: a back-end sysadmin and a couple of developers with a JS / Laravel focus (you should hire them, they're great). We could join forces and create a company of our own. My roles would be half design / front-end / CMS, half strategy and sales.

That's unlikely to be less stressful than the freelancer life but I will be diversifying and learning new skills. Obviously, I would stop working on my own and would have the perspective of gradually transitioning out of dev in a few years if I feel like it.

There, that old head of mine feels a bit tidier now. Let’s work on finding the next challenge before I turn 43!