How to turn your side gig into a profitable business

"Hello. I'm, um, here for my payment?"

I walked into a cold, minimalist office, nervous. It was one of my first gigs as a freelancer: I'd written a press release for a local art gallery, and they didn't have much to say about it. The owner sat behind her desk, silent. She took out her checkbook, wrote down a paltry number, then handed it to me without even making eye contact. I expressed my gratitude and sprinted out of the gallery.

I was devastated. I wanted to launch a writing career, and my writing was so bad it actually left someone speechless.

This was my first failure as a freelancer, and it was a significant turning point that set me on the course for earning a living as a writer.

It seemed pointless to keep trying my hand at writing, but I really, really wanted to do it. It didn't even matter if I sucked. Every time I failed, I decided to keep moving forward, even if that meant failing again. I came to terms with the fact that I might not be very good, but if I wanted to do what I enjoyed, that meant not only moving on from failure but also embracing it and learning to get better. I had no idea how to start freelancing, but I figured it out as I went along (in fact, I'm still figuring it out).

Learning to embrace failure was one of the most important lessons I learned, though. Beyond that, here are some specific actions I took to turn my side gig into an actual business. This is by no means a blueprint that will work for everyone, but it's what worked for me.

Embrace the Power of Networking

If you're anything like me, the phrase "it's not what you know, it's who you know" makes your skin crawl. I don't care who you know, if you don't have skills, it will be difficult to make progress.

That said, your network is an invaluable resource. For years, I tried to deny this, because I hated asking for things and I thought I could get by with hard work alone. You definitely CAN get by with hard work alone, but finding the right person to network with is like taking ten steps forward so you can showcase your hard work on a bigger, better platform.

My first dose of networking was with a former coworker who left the job to become editor of a major lifestyle website. She was a hard-working, intelligent woman, and even before her move, I always looked up to her, and we kept in touch after she quit.

Networking in Action

When I started taking my freelancing seriously, I did what a lot of freelancers do: I sent out tons of pitches to magazines and websites in the hopes that one of them would allow me the honor of writing for them. Then, I thought about my former coworker. On a limb, I emailed her. It went something like this:

Hey Lisa!
Hope you've been well. I've been focused on my freelance writing lately. Do you have any advice for an aspiring writer? Of course, if you're ever in need of a guest post, I'm happy to send something your way and would appreciate the opportunity. Hope to talk soon!

Months later, she was looking for new writers, and remembering my email, she offered me an ongoing, paid gig.

Reaching out to her took all of five minutes, after I spent hours pitching other editors to no avail. She wouldn't have offered me the gig if she didn't trust my work, but it goes to show you just how powerful networking can be. If you don't really have a network, here are some tips for cultivating one:

• Email other professionals who are doing what you want to do. Ask them for advice.
• Attend meetup groups, workshops, and events with like-minded people.
• Simply tell your friends and acquaintances about your goals. You never know how they might be able to help you.

Networking, like friendship, is a two-way street. You don't network to get something out of someone. You network to build a community of like-minded professionals so you can offer your own help and insight, too. My old writing teacher said it best: "it's not about using someone; it's about making progress and moving ahead together."

Learn When to Say Yes (and No)

One of the most important lessons I learned when I first started freelancing? Say yes.

And one of the most important lessons I learned shortly after? Say no.

When I first started, I said yes to everything. An investment firm wanted me to write press releases for their studies. I said yes. Lifehacker asked me to launch a personal finance blog. I said yes. Friends asked me to work on a web series with them. I said yes.

There are lots of reasons it's important to say yes. You open yourself up to new opportunity. You learn new things. You enjoy work you didn't even know existed.

After a while, though, your plate becomes overwhelmingly full. You have to turn down other work, because if you say "yes" one more time, you'll never get any sleep. You start to resent projects or gigs you don't really enjoy because they feel more like obligations now.

The "Three Question Method"

As a freelancer, you have to learn to balance this line. You have to learn to say yes to new opportunities and say no to obligations. Sometimes it's straightforward. Other times, the line between opportunity and obligation is blurry. I use the "Three Question Method" for standing on the right side of the line. An old neighbor suggested it for deciding on freelancing gigs you're unsure about. Ask yourself the following three questions, and if you can answer YES to two of the three, you have an opportunity on your hands. If you can only answer YES to one, it's most likely an obligation:

1. Will I enjoy this?
2. Does it pay well?
3. Will I learn something?

I've written about this method in more detail over at Young Adult Money, so be sure to check out the full post here.

Don't Be Afraid to Negotiate

As a beginner freelancer (and even when I started my first "real" job out of college), my Dad would always tell me, "Ask for more money. Value your work."

I scoffed because he didn't understand how freelancing worked. You were lucky to get any job at all, much less one that allowed you to negotiate your rate. But this was a harmful perspective that cost me a lot over the years. A recent study from Temple University found that a worker who negotiates just $5,000 more in their starting salary earns $600,000 over the course of their career. Sure, there are a lot of variables that can affect these numbers, but it's staggering to see just how much the math compounds over time.

Not long ago, I vowed to start asking clients for more, just to see if it was possible. I asked my current clients for pay increases that I thought were ridiculous. When new clients offered gigs, I forced myself to ask for more money. I knew none of them wouldn't bite, but I wanted to challenge myself. Something funny happened, though. Every single client said YES to my new rate. In a month, I nearly doubled my income as a freelancer. I was thrilled. I was grateful. I was empowered.

However, because it was also SO EASY, I realized just how much I'd been devaluing myself. My fear of speaking up and asking for more has likely cost me tens of thousands of dollars over time.

Later, I started with a new client and asked for a higher rate than they were offering, and they said no. I was rejected. You'd think that would be discouraging, but it actually had the opposite effect: it was hugely liberating and motivating. First, it showed me that the worst that can happen is a client says no. Assuming you negotiate appropriately, they're not going to be offended and rescind the job altogether. They're just going to say no. But more importantly, this made me feel like I was being paid as much as possible, and that's a great feeling. I was doing a better job of valuing my work.

Take Risks

Finally, one of the most important lessons I've learned in working for myself is to embrace calculated risk. By all means, you want to calculate risks responsibly, but they can be hugely profitable or rewarding. When I started Brokepedia a couple of years ago, I risked wasting my time, dignity, and a little bit of money on a site that could quite possibly fail. It ended up doing okay, though. I garnered a steady monthly audience with an income stream of about $1,000 a month, and occasionally, I was interviewed by radio outlets and blogs. I could have done better, but I don't regret taking the risk.

Recently I risked my work reputation by saying no to a client who asked me to do extra work for the same rate. I was scared, but I knew accepting the work would mean my overall performance would suffer, and that wouldn't be good for either of us. I risked what they might think of me (or worse, getting fired) in order to keep producing quality and protect my time. They didn't fire me, and they didn't seem to think less of me. In fact, I think they understood and respected my decision.

When you weigh your options and outcomes and know what you're getting into, risks often pay off. Hell, even when you fail, risks pay off. Failure helps you learn, grow, and do it better next time. From my experience, risks are key in turning a steady business into one that flourishes.

When I first started freelancing, it was just a couple of jobs I did in my spare time. They didn't pay much, and it seemed damn near impossible to get to the point where I'd refer to freelancing as my "business." Not long ago, I was faced with the decision to find full-time work or pursue freelancing as a full-time career. I was scared, but I chose the latter. I had a lot of luck, too, but without learning these valuable lessons, I wouldn't have been able to harness that luck and make the most of it.

The post How I Turned My Side Gig Into a Profitable Business appeared first on The Wild Wong.

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