How Doing One “Scary Thing” Each Week Led Me to My Dream Job


When I landed my first job after graduating from college, I liked the role, the company, and the comfortability, but it wasn’t my dream job of being a professional writer. I knew I had two choices: I could either stay on the path I started, or I could push myself toward pursuing my dream career. I took a chance on the latter and started working as a freelance writer on nights and weekends.

It was exhausting at times, so to stay motivated and keep making progress (while balancing a very busy workload at my day job), I challenged myself to do one scary thing a week that could potentially propel my dream career forward—like showing up unannounced at my old internship office with a bag of treats. Was it scary to stop by out of the blue? Yes, but getting in front of them helped me land them as one of my first freelance clients. After a year of doing things just that like, I landed a job that was a much closer fit to what I was looking for and was able to more easily build my freelance business on the side. And eventually, I was able to quit that to pursue my dream career full-time as a writer.

Looking back at the scary things I did each week didn’t always lead to a new opportunity or some sort of progress. More often than not, nothing happened at all, if I’m being honest. But when putting myself out there worked, it really worked. Getting out of my comfort zone and doing these scary things for the sake of my dream allowed me to make immense career progress, so I’m here to share a few of the things I did to inspire you to do the same if you’re feeling stuck in your current position or career.

I started a side hustle

There has been a lot of negative talk about side hustles in recent years, and while I agree that overworking isn’t ideal, having a side hustle doesn’t mean you can’t have a work-life balance or push through it temporarily for the sake of your dreams. There were some late nights that I didn’t love when I balanced my full-time job and freelancer work, but more often than not, my side hustle filled me with energy, fulfilled me creatively, and helped me advance my career while earning a lot of extra income.

The key to making a side hustle a positive thing instead of something that drains you is to not plan on it being a part of your life forever. It’s OK if you use a side hustle to help you gain the experience you need to transition to a new industry and then drop it once you find the right job. For example, if you haven’t held an official position as a graphic designer but taught yourself the ins and outs of Adobe at home, you can start a side hustle as a graphic designer. Once you build up a great portfolio, you can apply for full-time design roles. Similarly, you can work a side hustle to help you afford to move to a new city where there are more career opportunities.

While you can’t accomplish all of that in one week, you can officially start your side hustle in one week (or even in a day) and can then set weekly goals to help you keep making progress toward your dream. Especially if you’re trying to take a scary leap into a new industry or pursue working for yourself, taking that first step into developing new skills, improving your resume and portfolio, and making new connections through a side hustle can help propel you forward.

I attended networking events alone

Building your professional network is a great way to open doors. You never know when you will meet someone who will help you land your next big role, give you career-changing advice, or connect you to a new client! Networking events are a great outlet for this, but the key to getting the most out of them is attending them alone. Networking events can be very intimidating, and they can feel easier to attend when you can find a friend or colleague to tag along with you; however, if you only attend events where you’ll have a plus one, you may miss out on a lot of good networking opportunities. For example, when you’re not caught up in a conversation with a colleague or a friend, you’re forced to strike up a conversation with someone you’ve never met, and that connection could make all the difference in your career trajectory.

To find events to attend, do a quick search online for networking events in your industry and in your area (for example: “Graphic Design Networking Events in Chicago, Illinois”). If you’re a business owner, look to your local chamber of commerce. My last tip? Don’t go home early. Make sure to stick around for every coffee chat and cocktail hour to meet as many people, and form as many connections as you can.

I bragged a little

When I first quit my job to start freelancing full-time, I spread the word quietly to a few of my clients and colleagues. I feared that if I posted about this change on LinkedIn and didn’t succeed I would be embarrassed down the road, so it took me six months (!!) to share the news with my professional network. Within five minutes of sharing this update on LinkedIn, someone I didn’t know commented and said they didn’t realize I started freelancing and wanted to offer me work. That one scary LinkedIn announcement led to five figures worth of work, and it only took 60 seconds of effort and bravery to land that gig.

We’re taught that “bragging” about ourselves is distasteful, but don’t stay quiet about your accomplishments! If you earned a new degree, an industry award, or a major new contract at work, let people know. You want your professional network to know how impressive you are and what you can bring to the table. Similarly, don’t be shy when spreading the word about what you want to achieve. Making your dream public is a great career manifestation tool that can garner strong results.

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I made investments

The old adage is true. Sometimes it takes money to make money. Spending money when there is no guarantee it will lead to success or end up back in your wallet is scary, but the year I started investing in my career, I doubled my income. Now, I don’t think you should throw money at every online course, career coach, advanced degree, or software that promises to make all of your dreams come true. However, if you do your research and find a tool or resource that can help you learn a valuable new skill, improve your business operations, or enhance the quality of your professional brand, making room in your budget for that investment can be well worth it.

For example, if you have always wanted to learn photography so that you can pursue it on the side and make extra income, investing in a course that teaches you the ins and outs of lighting, shooting, posing, and editing is a strong investment that you can pay back after your first few gigs! Similarly, if you are a business owner and stuck in the weeds of running payroll, investing in someone who can do it for you can open your schedule up to work on things that will move the needle in your business.

I asked for help

Asking for help can be uncomfortable and intimidating. It’s common to not want to admit that you need it (even though we could all use it!), and it’s also common to fear that someone will say no. But do you know what is scarier than both of those things? Letting your dreams slip by due to staying quiet.

Need an introduction to help open a door? Want to know exactly what your boss expects from you to earn a promotion or raise? Want to know more about a different industry through an informational interview? Ask! You may not always get the answer you’re looking for or at the exact time you need it, but you gain nothing by staying quiet.

Be thoughtful and polite when asking for what you need, and someone will usually be happy to help you. Don’t stop yourself from asking for the help you need out of fear. Plus, sending a nice thank you note or a gift card after someone helps you or does you a favor can go a long way in them wanting to help you out again.

I was bold

Sometimes, you need to do something so outlandish or unexpected that you never think will work. Why? Taking big chances can lead to big rewards. For example, I once attended a local panel where the founder of one of my favorite jewelry brands was speaking. I didn’t get a chance to ask a question during the panel, so I guessed her email address, explained that I was at the event, and asked a follow-up question.

Before I sent the email, I updated my signature to emphasize my work as a fashion copywriter instead of a more vague freelance writer title. I knew it was a long shot, but I wanted her to know who I was and what I did without asking for a job. The next thing I knew, I was in their office studying their new fine jewelry collection. It was a small yet bold move that I thought would go nowhere, but I was happily proved otherwise.

So go ahead and be bold. Move to a new city where there are better career opportunities, even if you don’t know anyone there. Reach out to brands you dream about creating content for on social media. Even if you feel shy or embarrassed, pack those feelings away and do it!

I reached for the stars

Just this year, I published a story with one of the magazines I dreamed about writing for as a teenager via their online publication. This meant sending a cold pitch to an editor at a heritage publication which, in my experience, often results in a lot of radio silence, but this time, it didn’t. I got a response and wrote for this prestigious publication. Dreaming big and pushing past the fear of failing led to one of my favorite stories to date. I share this to say that you truly never know what can happen if you don’t try. The saying, “If we aim at a moon, we may hit a star,” has truth to it even though it’s cheesy. Maybe you won’t get exactly what you set out for, maybe you will, maybe you’ll land somewhere close, or maybe you’ll land somewhere better.

Apply for a job where you don’t match all of the requirements on the job posting. Hit send on your application for that impressive fellowship. Dreaming big is a scary act in and of itself, but you won’t know if you can achieve those dreams until you try. You might end up surprising yourself.

Final thoughts

One of the biggest takeaways I had after doing a scary thing each week for a year was how not scary these things started to seem. Attending a weekend conference alone in Palm Springs didn’t seem like such a big deal after going to smaller networking events all year. Sending cold emails pitching new clients started to simply become part of my routine.

Everything got easier, and instead of having to push for progress every week, my career began to automate itself. Happy clients sent referrals to new clients, brands reached out to me directly about wanting to work together, and other writers asked to pick my brain. Picture pushing yourself to do scary things like building muscle. Over time, you’ll realize just how strong you are.



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