Lessons I Learned Becoming a Successful Freelancer


For many people, the idea of running their own business, or at least working for themselves has huge appeal. What could be better than making your own hours, answering only to yourself and doing something you love? It sounds awesome, right?

As someone who’s both a freelancer and an entrepreneur, I can tell you – it IS great. Making the leap was both the hardest and best thing I’ve ever done. In the process, I’ve learned a lot about how to leap successfully. I hope that by sharing it with you, you’ll avoid some of the mistakes I made.

Lesson 1: It’s WAY harder than you think.

At first it sounds simple, right? I’m great at x, so I’ll just do that and people will hire me to. WRONG. You’re amazing at x, that’s true. But NO ONE knows this. To overcome that gap you must SHOW people that you’re good at x. Prove it. Whether it’s an online portfolio, a demo piece of code…anything that proves you can do what you say you can.

Once you’ve got the proof, you must find people to show it to. This means sales and marketing! Networking, applying for freelance jobs…hitting the streets and getting your name out there. If you’ve never thought of yourself as a sales person, that changes starting now – you’re selling yourself and your skill set. And unless you’ve kept your day job, you’re not making any money yet! Which brings me to lesson two…

Lesson 2: It takes time. More time than you think.

The first time I tried going out on my own, I’d been laid off for the gazzillionth time and had had enough. I figured, what better way to prevent it from happening again than going out on my own. I had some savings and I figured it wouldn’t take long. Boy! Was I wrong. I chewed threw all my savings and had almost nothing to show for it. I wound up taking a bunch of temp jobs just to keep going. Be prepared for it to take at least a year before you start making much.

Lesson 3: Grit is essential.

Every day consists of slogging through potential clients, attempting to contact them, following up, and figuring out more ways to get your name out there – even once you’re established. You HAVE to complete these mundane tasks in order to do the thing you love – from your living room, in your pjs, on your time.

Lesson 4: You’ve got to have hustle.

Hustle goes along with grit. You’re going to be pulled in a million directions and keeping track of a thousand things. From client needs/wants, to potential clients, to billing – EVERYTHING is up to you. Clearly, organization is important, but hustle even more so. You have to stay on top of all of this while doing the actual work and seeking even more work. You’re going to FEEL like you don’t have time to do it all while actually finding the time to do it all.

Lesson 5: Find a service delivery that works for you.

Part of my entrepreneur work involves helping people. My heart’s always been called in that direction. I kept running into a wall, though. I WANT to help, but I’m not great with people…my boyfriend says I’m on “team animal.” What I finally discovered is that I CAN help without having to interact too much. Instead of taking on individual clients, I post online classes and co-host retreats.

Think about your biggest road block to doing the thing you love. Now, think about some alternate ways to provide the same service. Can you teach instead of doing? Can you do it instead of teach? Can you host online classes instead of teaching live? No matter how nutty it sounds, it might be worth trying.

Lesson 6: Taking risks is a MUST.

Let me be clear, there’s a huge difference between taking risks and gambling. Taking risks means you evaluate and then leap – not just leap. With the service delivery lesson, I took a risk to switch my marketing focus from individual clients to online classes. I took a risk to learn video editing software and I took a risk that people would want to see (and pay for) the classes I posted.

Working for yourself involves risks on a regular basis. It’s taking on a client you’re not sure you’re totally equipped for, but knowing you can learn the skills, switching your marketing focus, or a myriad of other things – you’ll be taking risks. Not all of them will pay off…and that’s where the lessons seven comes in.

Lesson 7: Redefine “failure.”

The first time I tried to go out on my own, it didn’t work out. Deep within me, though, I still knew I wanted to work for myself. It took me a long time to realize that I hadn’t “failed” the first time. I simply hadn’t found the way that works for me. What would have been a failure is if I’d stopped trying.

Lesson 8: Find your niche.

Let’s say you want to freelance doing graphic design. Great! That’s an in-demand skill at the moment. But it’s also quite broad. Do you want to do logos, large scale projects like billboards, business signs and car wrap designs, menus, something else? Figure out your niche. It doesn’t mean you can’t or won’t do work outside that, but it’s important to know your major focus. Here’s why…

Lesson 9: Know your target audience.

Knowing your audience helps determine your marketing plan. It tells you WHO you need to find so you can start to figure out WHERE. Your niche matters because it tells you who. Looking at the graphic design example, if you’re niche is large scale projects, you’re going to be focused on billboard owners/leasing companies, advertising agencies, and fleet owners. Whereas if your niche is logos, you’ll focus on business owners, start-ups and business card companies.

I could go on for DAYS sharing all the lessons I learned…but you’d get sick of listening to me. Instead, I’ll stop here for now and share some more another time. If you’re getting ready to take the leap – congrats!

#successfulfreelancer #SarahWoodard #entrepreneur

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