Thoughts on Freelancing

Freelancing. Consulting. Contracting. Whatever you call it, I’m doing it and it’s going pretty well. However, I realize now that as much as I thought I could do this “on my own” about 10 years ago, it’s pretty lucky that I didn’t. I’m not quite talking “two roads diverged in a wood”-level stuff here, but I am thinking about my 25-year-old self’s inherent immaturity and myopic view of what she did and what she wanted to do. Off and on, for 10 years, I fantasized about starting my own thing; trying it for myself, but it was never the right time. And I tend to feel like things work out as they should, when they should, but it’s hard to remind yourself of that when you’re stuck in the middle of it all.

So here are the things I grossly underestimated back when I was whining about having to work for someone other than myself, day in and day out. Also: apologies to all of the people to who I may at one point have whined; I’m better now.

Thing 1 – Freelancing is Hard

There is a whole bunch of stuff that goes into any given week keeping oneself busy (it’s partly the reason that this is my first post since August: eek). My 25-year-old self imagined her weeks as an idyllic time, half of it spent furiously coding websites in her pajamas, the other portion sipping coffee in a Starbucks while furiously coding websites. This was the thing that I loved to do at the time so of course my fairyland ideal revolved around this. However…this is not how I spend my weeks.

My weeks are at least one-third to one-half meetings. Meetings to see what the next project is. Meetings to check in on the reaction to the last deliverable. Meetings to discuss what someone else needs to do. Meetings to discuss strategy and timing and interoffice politics…MEETINGS. The rest of the time is, absolutely, spent doing something that I enjoy, but the work is much more multifaceted than that one little thing that got me into tech in the first place. More on that in a sec.

Thing 2 – Networking Maketh the Money

I don’t know where 25-year-old me thought she was going to get all her clients. Beating the streets and passing out business cards? Cold-calling? I think she imagined that she would be shopping at some local business and strike up a conversation:

“Oh, you need a website? Well, you’re in luck ’cause I make those!”
“Hello, sir. Did you know that your business name domain is available?”
“Your website is a single page with a rotating ‘EMAIL’ animated .GIF…but it could be so much more!”

Truth is, many of these clients I am working with now are people that I have worked with in the past. I’m hired, as much as half the time, based on existing rapport. That took time to develop and is certainly not something 25-year-old me had working for her: I had had a few jobs, but my previous connections weren’t movers and shakers who knew other movers and shakers who could pass me business. Furthermore, we had just moved to new city and state about which I knew zero. It would not have gone well.

Thing 3 – Street Cred Matters

Via; thanks, Audrey. Photography by Cindy Palmano
Via; thanks, Audrey.
Photography by Cindy Palmano

Back in 2005, I had spent a sizable portion of my nights and weekends for the previous six or seven years working on a fan site for one Tori Amos and this was, mainly, the bulk of my experience to tout. The other portion of it had been spent working on websites for my alma mater in their online education division for a few years. So my portfolio wasn’t really comprised of sexy stuff, or if it was sexy or innovative, people didn’t understand the whole Tori thing and failed to see the value.

Most interviews went something like this:
“Who is this person?”
“Tori Amos.”
“Ah…” the interviewer would said, gaze shifting from the image of my website printed on a sheet of the more expensive paper from Kinkos—depicting a red-haired woman kneeling on a dirty mattress in a field, integrated nicely into the layout of the site’s masthead with some fancy overlayed gradient effects and, if I might add, very nice typography—to the red-haired woman sitting in the chair across the desk.
“You mean you weren’t paid to do this?”
“Well, it’s more of a fan thing so…”

So now, 10 years on, I’ve worked on things that people actually relate to or on brands that people have heard of. Without that credibility I wouldn’t have gotten very far, and, knowing me, might have given up and tried to pursue something entirely different.

Thing 4 – Unknown Unknowns

Ten years ago, I was a web designer full-stop. I was self-taught full-stop. Because in the 1990s, when I went to college, my school (and most schools, I reckon) didn’t really offer courses in User Experience-oriented education. It was my dream to build websites (from scratch, not with Dreamweaver or any of that other crap, scoff scoff) that were beautifully designed and fun to use. I didn’t even realize there were whole other jobs that contributed to get a website over the side: I genuinely believed that it was about being indispensable and being a “one-stop shop” of a person. Designer, Front-end Programmer, Back-end Developer, Project Manager, and Accounts Receivable.

Furthermore, my view of the industry was myopic (in spite of the fact that no one had iPads and their ilk in mind at the time; I certainly did not) and I needed more experience to become a worthwhile investment to a company (as an aside, I also needed to understand that being a “worthwhile investment” wasn’t a personal affront and was, instead, good business). I didn’t know what I didn’t know.

Lastly, but perhaps most importantly, I needed realize that there were lots of means to that end of creating a digital experience that felt perfect. I needed to have opportunities to wear lots of hats. I needed to learn how to involve others in my projects and to ask for help. I needed to learn to defend my ideas with grace and to give way to better ideas without getting more than a little petulant.

In short, I needed to grow the hell up.

All this is to say that I really, really love being a consultant. I love having a flexible schedule and a wide variety of clients; I love the challenge of keeping myself busy busy busy. But the 25-year-old me would have caved under this kind of pressure. She wouldn’t be thriving. I can say that because I am me, of course; I couldn’t say that for anyone else. Though she might not have liked it, she needed to suffer in big and small ways so that I can, now, appreciate my current situation.

I am grateful and happy and challenged, day in and day out. But without going through the gauntlet of all those years, I wouldn’t have any ruler by which to measure this happiness.

Leave a Comment

Your email address will not be published. Required fields are marked *