How I Career Transitioned and Started Thriving Professionally

Wisdom to Make a New Career Happen

Whitney Easton
· 7 min read
Photo by NeONBRAND on Unsplash

For most of my 20s, I worked in social work and education as a teacher and counselor in the public school system. I worked for nonprofits, public schools, and charter school organizations in a variety of capacities. I was young, zealous, and committed to changing the world one child at a time. It was (and is) a noble effort. But, climbing my way to my 30s, I was burnt out, broke, and exhausted.

Here’s a PSA: there isn’t a lot of money working in public schools. Now, my idealistic younger self would tell you that it wasn’t about the money. But, my 32-year-old self would like to say: I live in California. It’s an expensive state, rents are high, and I have a life, dogs, and medical bills to pay. It was hard to imagine another decade spent grinding away in schools.

In 2016, I made a career transition and turned down a full time job as a school based counselor. I said “Yes!” to the Universe and a full time job offer as a copywriter and social media strategist. For the last three years, I’ve been copywriting professionally, curating social media content, providing creative direction to brands, and working with clients on social media strategy.

How did I manage to get a full time job offer in the digital space with a resume as a school counselor? I’m so glad you asked.


I’ll break down how I career transitioned at 28-years-old and am now thriving professionally today.

🖋 Start Doing What You Want to be Doing Right Now

My writing career launched with a blog post I wrote for Elephant Journal for free and no pay. I had an idea one morning: I should write something. I loved their publication and so I submitted. It was accepted! I was willing to start writing for free and they were a great platform for that. Plus, an editor took time to work with me and get my piece up to Internet standards.

I didn’t study communications, marketing, or writing professionally. But, I did write a ton in undergraduate and graduate school and I knew that I loved to write. I was in graduate school at the time for psychology preparing to be a full time Marriage and Family Therapist.

That first blog post I wrote for Elephant Journal would land me my first paid gig writing professionally. This takes me to my next point.

💁🏻‍♀️ Start Networking

Most of my jobs started through connections in my life. This will help you immensely in a career transition as sending a resume blindly with no experience to a company and having success may be an unlikely way to start.

I was a client at a holistic wellness startup in Venice, California. I was there weekly for bodywork sessions. I’m inherently a social being and conversationalist. One day I was in for session and told one of their employees I wrote a blog for Elephant Journal, a well known wellness publication.

The founder of the company overheard the conversation and asked if he could read my piece. Next thing I knew he said to me: “Hey Whitney, can you write content for us?” They needed someone to start writing their social media posts and their blog. I didn’t hesitate to say: “Yes!” And so began my paid writing career. It started as freelance and they loved my work. They kept adding more to my plate and then I wrote their website; next thing I knew I had a full time job offer and walked away from social work completely.

It happened quickly and it may sound out of reach. But remember this started with a simple blog post.

👩🏻‍💻 Be Clear About What You Can Do

This is key: know your strengths, as well as your limitations. Try things out, take risks, and be willing to fail. As a woman, I am the queen of undervaluing and underestimating myself. I still struggle with feeling like I am actually a ‘writer’ or qualified to be doing this. It can feel as if I need three New York Times bestsellers before I can officially say: “Hey, I’m Whitney and I am a Professional Writer.”

I can write and I know this. I cannot, however, edit videos. Video production drives me nuts and while I’ve done it, I’d rather not do it professionally. I’d rather oversee creative direction and leave the splicing and dicing to a seasoned video editor. I will not be taking video editing classes because this is not my strength. I am, however, proud of some of the videos I’ve overseen creatively. It’s taken trial and error over the years to hone my skills and to get clear about what I can and cannot do. This is a part of the journey.

I also enjoy coaching people, so I’ve started social media consulting and coaching with smaller businesses and individuals. It’s so much fun! I’m a people person and so I leverage that, too. I didn’t throw my past career out the window entirely; I draw on my strengths in a new way, today.

📱 Embrace Social Media

Hate it or love it, social media is a necessary part of any career landscape right now. Recently, I stepped down from a two year position with a well known and beloved baby brand. I was working in house as the Social Media Manager (a job I landed as a result of, yes, networking!). I left for a variety of reasons. In my heart, I wanted to focus on my writing career more exclusively and so I launched my own writing business.

I’ve made this announcement quite publicly via social media and I’ve been clear about what I’m looking for. You never know who will see your posts and I’ve had to get comfortable with marketing myself on social media. The Internet can be a magical place when you put the right intentions behind it. This week, I landed a free three month subscription to an absolutely beautiful new coworking space in Hollywood. A friend saw my posts about freelance writing and connected me. I can’t wait to start writing there and to bring my pup along to help me network.

🤓 Immerse Yourself

I’ve read hundreds, if not thousands, of articles about how to career transition at any age. Reading them, I realized I needed to be on Medium and so I started writing here. One resource that served me immensely was Career Contessa. They help women with professional development, specifically, and have excellent blogs and tips on career transitions. Bossbabe is another great resource for career transitions and growing professionally, also targeted at women. I devoured them all!

As a young career driven woman, seeking out resources that were friendly to millennials helped normalize my experience. It was a hard decision to walk away from the career I was working so hard to get a degree in, but I’m so glad I found the courage. Diving deep into the depths of Google is where I found a lot of solace, encouragement, and inspiration.

✨ Be Patient and Believe It Can Happen

I was lucky. Things happened fast for me, but I’m a true believer than when we are on our paths we can’t be stopped. When I was at the wellness startup in Venice years ago, just getting started as a freelancer, I had the opportunity to speak frequently with a higher up at a Vancouver based branding company. I took full advantage of my calls with him and asked him many questions. Their CEO saw a spark in me. He told me he saw potential. He believed in me and planted a seed that I could change careers and do this. He was right and I did. I’ve never looked back.

What started as a side hustle and a whim became my full time hustle. I utilized my experience and background in psychology by also writing about mental health, psychology, and relationships and hope to continue growing as a writer in this arena.

🙏🏼 Embrace Rejection As Part of the Journey

I don’t suggest you out and quit your day job until you have some experience under your belt, but I do suggest you believe in yourself and start taking steps today towards the life you want to be living. Let me also be clear: I have faced plenty of rejection along my path. That is the only certainty in any career transition.

As I transition once more from the comfort of my steady corporate life to the freelance world, I am stepping out in faith that this is my path. I’m embracing and celebrating my rejections and my successes. It’s not always easy, but it can be so rewarding to find the courage within to change course and to thrive.


Whitney Easton is a writer, content creator, and social media consultant & strategist. She’s lived through some things in her years on this place called Earth and lived to tell the tale. She is passionate about living a joyful life no matter what life throws at you. She is a creative soul at heart bubbling with ideas, vision, and stories. You can connect with her on her website or on Instagram. 👩🏻‍💻

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Whitney Easton

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I write about living a joyful life with chronic illness. Poet-in-the-making. Lover of nature.

The Startup

Medium's largest active publication, followed by +514K people. Follow to join our community.

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