What I’ve Learned After One Year of Freelance

Learned After One Year of Freelance

From something fitted to something grey

One year ago, I drove home for my last hour and 45-minute rush hour commute, wearing something fitted and professional. Today I’m wearing grey ribbed sweatpants, a sports bra, an off the shoulder beige sweater and my hair is in a ‘day 4 of not washing’ ponytail. I can’t narrow down the exact day I went from dressing like I have my life together to dressing in a rotation of leggings and sweatpants but I can say that I have four different pairs of grey sweatpants. They’re each special and unique in their own way.

Making this major life change was something Julian and I had thought about for years beforehand, amidst project deadlines and having babies. Somehow it made total sense and no sense at the same time. But it was happening, and I was thrilled. The journey from corporate professional to permanently working from home freelancer has been terrifying, exciting, uncertain, ambiguous, and…cozy. Let’s just say, i’m loving the sweatpant life. Full disclosure, I get dressed and look like a human woman when I leave the house but there is about a five minute window between when I come home and then take off my bra shortly after. I’ve clearly embraced the freelance life. Yet, I wouldn’t go so far as to say it has embraced me.

That first week

That first week of career transitioning, I was home and attempting to write while my son was napping, I sat down with my notebook and two lists. One was a list of brands that I dreamed to collaborate with for this blog and another was a list of digital publications I thought about writing for the past ten years. Casual. I remember the first pitch I sent. Looking back, I can see myself typing and thinking, “this is it. I’m finally doing what I have wanted to do my entire life.” Fast forward two weeks later…silence. After not hearing back for an additional two weeks, I sent a polite follow-up email. Silence. Indefinite silence.

Spending hours crafting the perfect email, only to hear a deafening silence immediately and long after, is a feeling of rejection that lingers with you for quite some time. I refreshed my email a few times, thinking maybe the new emails were simply not loading. Nope, still nothing. “Maybe something is wrong with my internet?” I thought to myself in desperation. It’s perhaps the most cruel form of rejection because so much is left unsaid. Literally everything.

Learned After One Year of Freelance

They’re just not that into you

With a swift “we’re not interested,” at least you can move on with your life. With silence comes ambiguity and the lingering hope that you could still get a reply at any moment. “Maybe they’re just busy,” I reasoned with myself in an obvious state of delusion. Editors are obviously very busy people. And so in the back of your mind, there is always a chance. Call it optimism or self-trickery. It’s being back in high school again when you’ve told the guy you like that you’re into him and waiting anxiously for a response. I thought I was past that point of my life but clearly some lingering emotions remain.

Although, if you think through the “exchange” clearly, someone who is interested will reply to you in less than a month, whether in romantic or professional affairs. Sometimes, they’re just not that into you. That’s a difficult concept to accept but one that I’ve grown okay with. It was my first lesson regarding the freelance life – success is not immediate. And so I kept grinding, kept emailing and let’s face it, kept wondering if I had made a terrible mistake. With little to no signs of better days to come, the negative self-talk started to play a major role in my mind. I had never felt so vulnerable in my life as I continuously pitched brands and media companies and obsessively refreshed my email.

A small win

Months later, there was hope. A publication I had been pitching for years replied that they were interested in an article idea I sent over. When I say months later, I mean months of weekly pitching and follow-up emails. I read that email four times just to make sure I wasn’t dreaming. Miraculously, it was all real. That small win was all I needed to keep going. This brings me to the second lesson of freelance I quickly learned-keep hustling.

One year of freelance later (and change), I’m so happy I believed in myself enough to take a chance on myself and keep moving forward. I’m not where I want to be, but I think I’m on my way. I wanted to share a few things I learned throughout my trials and tribulations in freelance writing and blog content creation. It hasn’t been easy and there is still so much I know I have left to learn but I can confidently say that I’m happy I made the move. Below, the learnings I plan on taking into year two.

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What I’ve Learned After One Year of Freelance

• You will feel rejection in your core and more than once. In fact, so many times. It will hurt. You will think it’s a sign that you’re not meant to do this or that you made a mistake. You will obviously take it personally. Once you’re done with your initial reaction, move on. Realize that it’s not personal, it really is just business. Persist.

• Sometimes rejection is an indicator that this is not your time. Maybe you have things you need to work on. Failure can be the catalyst that gets you to where you need to be. One of my biggest takeaways has been to not let failure define me or make me lose confidence in myself. Failure has made me resilient and taught me to work harder and do better. Previously, another rejection email would make me look inward and criticize every part of my being. Now, it makes me think about what I need to improve upon for next time.

• Realize that the skills you gained in your previous job will be applicable to your new career. For example, sending analytics to a client after a project is complete, communicating with professional and typo-free emails, or creating a great resume and cover letter. Think about what made you successful in your previous role and bring it with you. Don’t let yourself forget that you bring a unique perspective and narrative to your work that no one else has.

• You will work harder than you’ve ever worked in your life-1. because you have to and 2. because you need to prove to yourself that you can do this.

• Stay in your lane. You may catch yourself comparing yourself to those that are further along in their path. Don’t. You’re on your own path. Stay focused.

• Professional ghosting is a thing and it can drive you crazy. For how to manage it, these tips are a must.

• There are no 1:1 meetings or check-ins to make sure everyone is on the same page. You set your own exceptions and milestones.

• Learn something new daily. Whether it’s reading a book, taking a tutorial, or watching a YouTube video, learn something to advance your career. A few years ago, I didn’t know a thing about Search Engine Optimization (SEO) or Photoshop. I realized that I had this knowledge gap and started taking steps to learn more. If you’re looking for a great book on SEO, I recommend this one.

• Reaching out to other freelance writers is a wonderful thing and feeds your soul. There’s something about connecting with others that are going through a similar path that makes everything better.

• In many ways, you’ll need to reprogram how you work. Going from a structured corporate job to freelance was…different. Gone were the days when my boss gave me an assignment, I completed it on time and received feedback accordingly. Working for yourself comes with a sense of creative freedom and risk that takes time to get comfortable with.

• Don’t sit around and wait for dream clients to contact you. Set a goal of sending at least five pitches per week. Being proactive will help advance your progress.

• You may find yourself, as I did, refreshing your email constantly. Think about all the things you could be doing instead to advance your career. Set an hour each day for checking email and spend the rest of the day avoiding it (unless it’s urgent). When I’m waiting anxiously to hear back from a brand or publication, the only thing I can do on my end is move forward. That means continuing to pitch other companies, refining my resume, updating my LinkedIn profile, and doing anything else necessary to be productive. Anything but refreshing my email incessantly.

• At the end of the week and month, evaluate what went well and what you can improve upon. Create your own personal development plan so you’re always getting better.

• Treat your freelance writing like it’s your business, because it is. It’s not something you do for fun, it’s not a hobby and you deserve to be compensated for your experience and skills.

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• The negative self-talk will bring you down. You may be kind to everyone in your life but downright mean to yourself. In the words of my four-year-old daughter, be kind.

• Give yourself the freedom to create. You can’t create something out of nothing when your phone is lighting up every few minutes and you’re checking notifications.

• Talk it out. I can’t tell you how many times I have talked to Julian with raw emotions and endless tears about how I think I’m failing and how I thought I would be further along at this point. It helps to get the words out so you can cry it out and then get back to work.

• That steady biweekly paycheck you depended upon will be missed. So missed. You’ll need to hustle for every client and every job. This hunger will motivate you and amplify your work ethic.

• You will need to protect and prioritize your time. There is no clocking in and out. No one is watching you or keeping tabs. You could watch the latest series on Netflix or you could finish editing a blog post. It’s up to you but know that the results will speak for themselves.

• You will need to value yourself and not accept any less than you think you should based on your experience and skill set. As a pharmacist, when I negotiated my salary in the past, I have stood firm with what I thought was appropriate based on my qualifications. Yet, I wasn’t applying these same principles to my work as a freelance writer. I now make it a point to stand up for my earnings as a writer and blogger. I have certainly lost work as a result and brands have gone with other bloggers but I can honestly say I have no regrets. Creating quality work requires fair compensation. Be willing to walk away.

• Fear will overcome every part of your being. Putting your whole self out there for the entire world to read your personal thoughts is a scary thing. The fear will manifest itself in subtle ways and take over your thoughts. Fear that you’re a terrible writer, fear that you made a mistake, fear that you will be laughed at. Don’t let the fear overcome you. It’s temporary.

• You will learn more about yourself than you’ve ever known. You will feel lost. I felt lost. I realized quickly when I left my job that much of my self-worth was derived from my work. And when I didn’t have steady full-time work, I felt like I lost my purpose. I learned to differentiate my work self from my whole self. My work is important but there is more to me than my career.

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“Following your passion”

There are so many times when quitting your job and “following your passion” is glorified in the media. It’s hard to even recognize it because of the subtle messages we get in books and movies (and blogs). All signs point to leaving your stable corporate job to “follow your dreams.” Once you do, it feels like you should be seeing results immediately after you quit. And if you don’t see immediate success? Does that mean you’re a failure? Or is failure an inevitable part of a long journey ahead?

For a long time, I thought that if I did x, y and z, then I would achieve my goals. In pharmacy school, success came if you studied hard and put in the work. As many people can relate, the road to good grades is more of a linear path. The world of freelance is open ended and consistently vacillating. Things take time. When I heard Maxie McCoy speak at the Penn Women’s Conference this year, she put it perfectly-“Give yourself the patience and courtesy of understanding that success is not immediate.”

I’m not sure where I’ll be in a few years or if things will come together. I do know that I won’t have any regrets when it comes to my career. I’m giving myself the chance to pursue a path that has been running on loop in my mind since the fourth grade. I owe it to the little girl sitting in her room, surrounded by magazines scattered around the floor. I owe it to my daughter and my son, who one day may want to pursue something that doesn’t really make sense but will need to find it within themselves to push forward.

The freelance life

The freelance life is exhilarating, terrifying, intoxicating and it seems like I question myself on a daily basis. Nevertheless, I can’t tell you how excited I am to continue, despite the uncertainty and rejection. Going from what you know to what you’re slowly figuring out teaches you a lot about yourself. Truthfully, it’s certainly not helping my nail-biting habit. After one year of freelance writing, I do know one thing. None of this is easy, but nothing worth pursuing ever is.


Location: Lokal Hotel in Fishtown // Photography: Alex Ashman

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