Doing the thing that scared me most career-wise — taking on a project that I wasn’t 100 percent sure about — led me to where I am today: writing, editing, and working with awesome people.
When you’re a professional writer, people assume that if words are involved with their project, you can handle it. I had previously done copywriting for two issues of a literary magazine and taught and tutored writing for over four years. Between all of my previous experience, I felt confident enough with the fundamentals of copywriting to start working full-time with clients.
My very first “gig” was revising copy for a company that needed help with editing customer-facing product descriptions to make them sound snappier, more alive. Easy-peasy. But that same day, the project manager handed me another project: I had to come up with a brilliant tagline for a business-to-business (B2B) advertisement, with a deadline of that same day. My first thought: What the hell is a B2B ad?
Well, that was something I had to learn — and fast.
I think back to that moment and see how naïve past Julia was to take on a project that she knew almost nothing about, but I’m also grateful for that naivety. Once I finished that task, I kept pursuing more projects that scared me, and I grew more and more confident in myself.
Entrepreneurs probably know this feeling really well, because in order to grow your business, you’ll need to take some risks and learn as you go. It’s not irresponsible to try things that you haven’t done before to see if they’ll have a positive impact on your business.
While I had a project that was presented to me, perhaps you’re wrestling with an idea for a project that scares you, like that ebook you’ve been wanting to write, or bidding on a project you haven’t done before. With enough research and preparation (and a little bit of confidence), you’ll find that these projects really aren’t as scary as they seem.
Whether it’s for yourself, your business, or your client, there are many benefits of taking on a project that scares you — you’ll develop long-term confidence for future projects, and learn a lot more about yourself or a different industry as you go.
Here are some strategies for conquering the fear of taking risks as a professional writer or entrepreneur.
When I first made the decision to be a full-time professional writer (re: full-time freelancer), I was scared of what was to come. How was I going to find clients? What would I do if I didn’t know exactly how to do what the client asked? How could I promise delivery on a project that I had never done before?
These kinds of thoughts were based on the biggest fear of all: What if I fail?
If you think about it, fear of failing is at the root of most of our anxieties and fears, especially related to running a business or keeping yourself afloat as a professional writer. A little bit of this fear doesn’t hurt — if anything, it keeps us pushing through those late-night writing sessions or hours of planning for an upcoming project. But when fear of failing prevents you from growing, it starts to become an issue.
I had to recognize that my fear of doing something new in my career was based on being afraid of failing. But in order to overcome that fear, I had to risk failing. Sounds like a conundrum, right?
If I had let the fear of failing take over, then I never would’ve grown as a writer, an entrepreneur, or even as a person. I would’ve stayed stuck in my little comfortable (albeit unhappy) bubble that was my career as a teacher, complaining about my job every single day.
Succumbing to fear of taking the risk of changing your business or doing something new can end up making that ultimate fear of failure into a reality, which is exactly what you were trying to avoid in the first place.
So next time you’re nervous to take on a project, consider why you’re scared. Are you worried you don’t have the expertise to complete the project? Or maybe you do have the expertise, but you just haven’t done that specific task before? Chances are, you’ll discover it’s due to not wanting to fail.
But to conquer this fear, the best thing to do is to consider that everyone else has had to take on projects that they didn’t 100 percent know how to do — they just didn’t admit their fear to others. So just know that you’re not alone in this fear, and the best way to overcome it is to say, “Yes, I’ll do it!”
I’ve personally never been shy about asking questions (just ask any of the writers that I work with as an editor). But I do recognize that it’s easy to feel insecure if you think you’re asking a lot of questions — you might worry that it sounds like you’ve already failed when you show that you don’t know what you’re doing.
If you’ve never done something before, though, how will you know where to start if you don’t ask questions? You’ll basically be trying to read your client’s mind, or you’ll jump into a project and quickly feel like you’re in over your head. And this doesn’t just go for novices — even if you have years of experience in a field, there’s never harm in asking questions to clarify the expectations of a project.
When I began the copywriting project on B2B ads, I started from the very beginning: Who’s your target audience, more specifically? What do you want them to get out of your ad? What’s the goal?
Even though I wasn’t completely sure how to execute the ad itself, I knew that the best place to start was understanding how the client wanted the ad to function. This context helped me figure out the appropriate language for communicating with that audience, which made me feel more confident in completing the project.
And this doesn’t just pertain to situations where you’re working directly with a client. If you’re considering developing a new product for your business, try sending out an email survey or asking your current customers for suggestions on what they’d like to see as a new product.
Asking questions may show that you aren’t an expert in a certain subject matter, but that’s okay — you’ll find yourself seeking information from people who will help you create a better end product.
This may seem like the obvious alternative to asking questions, but really, doing your background research and asking questions should go hand in hand.
Start by reading up on the type of project you’re hoping to dive into, and see how others have approached or started a similar project. People love to share their experiences with tackling certain projects or submitting articles to competitive columns. Read up on these, and hopefully it’ll help shape how you can also approach these projects.
You can also try to find samples of particular projects you’re trying to accomplish, though depending on how niche the project is, this can be a little difficult. Having something to reference and compare against when you’re working on your own project can be incredibly helpful.
When trying to create a B2B ad, I went home and researched what various B2B ads looked like in that industry. It helped me understand what my client was expecting me to accomplish and also gave me ideas for developing creative language for the ad.
This research-style approach applies across multiple industries, and it doesn’t have to be boring! If you’re looking to write a motivational ebook, read motivational writers and listen to their TED Talks. If you want to become better at writing as preparation for other projects, learn from the Greeks or other master writers. If you’re hoping to become a social media whiz, follow people who are doing it well on Twitter or Instagram (or both).
If it’s possible, the most direct approach to doing research on your project is to ask your client for samples of past projects of a similar style. This is a great way to figure out what you don’t know about the project, along with giving yourself a chance to find out what they want you to improve on when you’re tackling the project yourself. See, I told you questions and research can go hand in hand!
Sometimes, when you’re in the thick of things — and you’re debating whether or not to take on a new and scary project — it’s hard to remember the goals you set that relate back to the big picture of your business. You’re wrapped up in the moment, making it difficult to remember that, at the end of the day, you want to grow your business and grow as a person.
Taking the time to remember your bigger goals helps put the smaller details (i.e., individual projects) into perspective. Sure, it’s stressful in the moment to tackle something when you’re worried about failing. But by reminding yourself that you’re doing this for the sake of growing, and to achieve your bigger goal to learn more or develop as an entrepreneur, it helps the stress of the moment feel like it’s worth it in the long run … because from that stress, you’ll have learned so many new things!
My goal was to change my career and become a full-time writer. Well, the first step to doing that was trying something I hadn’t done before, and putting myself out there with the risk that it may not work out smoothly.
It wasn’t the smoothest transition ever — I still had to juggle my day job while taking on my first clients — but I’m now happily at the point where I’m balancing multiple clients, all from taking on that very first project where I didn’t entirely know what I was doing.
Keep your bigger goals at the forefront of your decisions by writing them down on a piece of paper and posting it somewhere you’ll see on a regular basis, whether it’s in your daily planner or on the wall of your office. You could also find a mentor or a writing coach who will help encourage you along the way.
Growth almost always comes from taking risks, especially in the business world. Smart risk takers who do their research, ask questions, and make calculated but risky decisions are the ones who often succeed the most in the entrepreneurial world.
There are multiple benefits of taking on projects that scare you, whether it’s a personal writing project that intimidates you, working on a client project where you have zero background experience, or having projects that feel so ginormous, they’ll never come to fruition.
The biggest benefit of all? You’ll discover that, by successfully completing a new and scary project, you’ll have the confidence for future projects. And you’ll probably learn a lot more about yourself, as well as a new subject in your industry.
Start by recognizing that it’s the fear of failure that’s keeping you from tackling something brand new, then consider how you can make the project more approachable by asking questions and doing your research.
When you have big goals to succeed — whether as an entrepreneur or a professional writer — you’ll have to learn to take risks and cannonball into the murky waters of a scary project. But you’re not alone — every entrepreneur before you has had to make that same leap off the diving board.
Come on in, the water’s fine.
Julia Hess graduated from California State University, Fullerton with a Master of Arts degree in English. She has worked as a college writing tutor and instructor, a contractor at a major tech company, and a freelance editor and writer. An avid podcast listener, Julia provides editorial feedback, consultation, and detailed show notes for CYC’s podcast, Writers Rough Drafts.