The Great Freelancing Advice I Never Took

Because I started freelancing at age 15, I would often struggle with what I would do after I graduated from college. I could start my own business and freelance full time, or I could get a “real” job. At one point, while I was in the throws of this existential crisis, my dad and I went to dinner with a family friend who happened to be starting his own business. This friend, who was close to my dad’s age with two kids of his own, offered me some advice. I, being the headstrong early 20-something male, promptly disregarded it. It wasn’t until I was towards the end of my 20s that I realized it was some of the best freelancing advice I never took.

“Get a Full Time Job”

So what was this sage advice? He said when deciding whether I should start my own business or get a full time job right after college, I should get the full time job. His advice made perfect sense, though my Millennial ears wouldn’t hear it: A full time job would afford me the chance to see how industry professionals worked. I would see real-world code and learn tricks of the trade through on-the-job training. Though he didn’t put it this way, it was really the next phase of my education. And it would be the most valuable because it was outside of the academic bubble.

He said I would also make new connections; I could network with coworkers, bosses, and clients to cultivate relationships. Then, and only then, should I go off and start my own business.

A Millennial Long Problem*

Here’s the problem, and my fatal flaw. I thought I already knew how things worked. I mean, I had been freelancing for like 7 years! I was getting my Master’s Degree, I was already good at networking (that part was true) and school already taught me everything I needed to know. Plus I was really good at teaching myself!

People love to bust on Millennials. I hear things like, “Millennials think they know everything,” that we don’t want to work, and that instead of climbing the corporate ladder, we feel we should just go to the top of it. We, as Millennials, want to skip right to the end.

I don’t know how true that is. Maybe it’s more common in my generation. We do seem to complain a lot. I would like to think it’s common of all young people and not just my generation, but I haven’t been around long enough to make that call. I will admit this though: in the moment when I decided to ignore that advice, given to me by someone more than twice my age who’s been there before and was there again now, I was the stereotypical Millennial.

My False Perspective

The problem isn’t that I ignored everyone who ever gave me advice. I’d like to think I was usually pretty open to it, even in my early 20s. The problem is that I had a false perspective. I thought the stuff I knew was as good as the stuff our friend knew because I was already doing what I wanted to and was modestly successful. It wasn’t until I actually got a full time job that I saw how right he was.

So as you might have guessed, I went right from school to starting my own business. I actually tried it from 2 angles, and one was a complete disaster (more on that later). The other was pretty good…for a while. However, problems started to emerge, partially due to my lack of experience. I just wouldn’t realized it until later.

Stuck in a Silo

The biggest problem – and a problem many freelancers face – is that I was stuck in a silo. The freelance community wasn’t as strong then as it is now, and the WordPress community is currently stronger than it’s ever been. So, everything I was doing I was trying to figure out on my own without trusted sources to guide me and tell me if I was doing something right.

Sure, I could bounce ideas off of friends and even some other freelancers, but it’s a little different when you have someone else as vested in a project as you are (or someone who’s just really vested in you as an individual). The bottom line is I wasn’t growing as fast as I should have been, and my business suffered for it.

Diversity in Projects and Problems

I always thought that going after the same type of project was a great idea. I’d get really good at solving the problems that type of project (let’s say construction websites) presented, and I could churn out websites faster. I’d have a nice niche market.

Now I’m not saying this is an issue for everyone, but during the ages I freelanced full time (23-26), it was really important for me to choose projects that would grow my skills, not stagnate them. I didn’t really know or think that.

Working Backwards

When I finally did accept a full time job at my alma mater, The University of Scranton, it was like night and day. My coworkers were knowledgable in their fields and solved a diverse range of problems. I learned a lot from them, especially in my first year. That really encouraged me to learn more on my own – I finally knew I didn’t know. At my current job, it’s like that but tenfold.

I love my current job and plan to stay there for a long time (more on that later too), but I know exactly what that family friend meant. I am much more equipped now to go off on my own than I was at 23. I do feel like I’m working backwards though. I sometimes wonder if I would appreciate everything I have now if I hadn’t freelanced full time right after school.

The moral of this story isn’t, Work for someone else before working for yourself, though that might have worked better for me personally, had I pursued a full time freelance career. The moral is this: keep an ear out for good advice, especially from people who care about you and have an interest in your success. At the core of a successful freelance career is good relationships. Cultivate them as much as possible.

*See what I did there?