Tips for Leaving Your Job to Start a Creative Career

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Have you ever caught yourself staring longingly at a beautiful logo or elegantly simple website wishing you’d made the decision to become a designer or photographer back in school, but feel like you’re too late to move into the creative world? If you didn’t go through a traditional creative education, becoming a successful creative can feel like a near-impossible task. But never fear! With the incredible wealth of resources available today, moving into a creative career is more accessible than ever, no matter how difficult it may seem.

Image from Getty | Credit: Jules_Kitano

We asked a few of the creative career mentors at RookieUp about their transitions from jobs outside the creative industry to creative careers they love, as well as their tips for planning the move to your creative dream job!

  • Danielle Eastberg was a systems engineer at Lockheed Martin before becoming a Visual UX Designer at Audible.
  • Christian Rudman worked in retail before picking up photography and eventually starting his own photography studio.
  • Caryle Cunniff was a professional Irish Dancer until she left and became a Senior UX Designer at Amazon.

Choose a skill and dive in head first

Pick a skillset and immerse yourself in it completely, whenever you have free time. If you prefer to teach yourself create a list of online courses, articles, books, and blogs written by the top experts in your field and dive in, practicing as you go. If you prefer a teacher-led environment with 1-on-1 learning, consider a bootcamp at a school like General Assembly or even a condensed 1-year design school degree.

Danielle says: I was filling up my nights and weekends learning Photoshop and web design, taking weekend workshops and teaching myself online. I read a book called The Artist’s Way by Julia Cameron and that changed my whole world! I set up a plan to save money and within a year I left my job and went back to school at the Fashion Institute of Design and Merchandising in LA. They had a really neat fast-track program (1 year full-time).

Carlye says: I was fortunate enough to take a 3-month intensive UX Design Bootcamp program with General Assembly. This type of learning environment allowed me to completely focus on learning the new skills I needed, and forced me to jump into the new career – even if that leap scared me.

Surround yourself with experienced creatives in your field

No matter what you’re trying to learn, the best way to improve quickly is by surrounding yourself with people who have been honing their skills for years. Being able to watch experts practice their craft and in turn give you feedback on your work is crucial for getting better.

Christian says: I accompanied other photographers whose work was markedly better than my own on their shoots– helping them and learning while watching them shoot and networking by rubbing shoulders with the people they worked with. Relationships are always the most valuable aspect of anyone’s life and it’s no different in the creative world.

Danielle says: Be around other designers! Having teachers and mentors who know what to look for and know what feedback to give you are incredible when you are starting out. You also start learning how to have a “design eye” and everything can become inspiration. From Pinterest to the way the leaves are scattered in the park…it all becomes input for your next project.

Build a portfolio of work (it doesn’t have to be client work)

When you’re ready to find your first client, having work to show them is crucial. As a new creative, you likely won’t have any client work to show, so don’t be afraid to fill your portfolio with projects you’ve been working on throughout your creative education!

Danielle says: Of course a portfolio is great, but I want to emphasize that it doesn’t have to be work from a specific company or client. Concept work (any project you make up and explore on your own) is great to show your skills and have discussion points of your interests. I’d rather see someone with critical design skills than someone with a long client list. You can start wherever you are!

Expand your creative vocabulary and become a better communicator

Spend time becoming intimately familiar with the vocabulary of your new field. Being able to effortlessly communicate with peers and potential clients can make the difference between a missed opportunity and a new long-term client. The best way to do this is to focus on building relationships with peers in your field and totally immersing yourself in the creative world.

Danielle says: The most helpful thing for me was to build a design vocabulary so that I could speak intelligently during interviews. Companies will often give you a work sample and ask you what to improve– you need to practice a lot to be able to see and give those pointers on the spot.

Carlye says: I think we tend to underemphasize the importance of “soft-skills,” especially for people making career transitions. Yes, you need to have a portfolio, and real-world experience will certainly help, but I think more important is your ability to translate your former job skills into your new field. You can learn Photoshop and interaction design, but those skills are worthless if you are a poor communicator or can’t work with ambiguity. Have a clear idea of what you’ll bring to a team and leverage those, alongside your new skills, when making the switch.

Find a mentor

Having someone you can turn to with questions, concerns, frustrations, and requests for feedback is crucial for improving as a new creative. Whether you have a mentor that you see everyday or someone you chat with just once a month, it’s important to find someone who knows what your goals are and can help you achieve them.

Christian says: Having a mentor was greatly instrumental in my career. I had someone who didn’t teach me a ton about techniques, as I had already learned a considerable amount before I came to him, but he taught me about storytelling. Storytelling is such an integral part of creativity, and I wouldn’t have the ability to draw out a story from a concept and work alongside a full creative team if it hadn’t been for this time spent learning from a master storyteller and leader.

Carlye says: My instructors at General Assembly both served as amazing mentors for me during the process. I literally came to class the first day, surrounded by people who were switching from careers in Product Management or Visual Design – I couldn’t even draw a rectangle in Photoshop, so it seemed like they were all miles ahead of me. My instructors were incredibly encouraging. That constant belief that I was going to be fine did wonders for my motivation.

Jump, and the net will appear.

Danielle says: My favorite quote from The Artist’s Way is “Jump, and the net will appear.” Changing careers can be scary and it’s not always a linear path to happiness, but things do have a way of working out. The resources are there for you if you want them. Why not answer those “what ifs” and find out what you’re made of?

Carlye says: I struggled with the idea that I was not ready to be a designer throughout the process of making a career switch. I still struggle with that imposter syndrome at times, even in the position I’m in now. Design, by definition, is problem-solving, so every time I’m given a new problem I panic a little bit. But it always gets solved, that’s what is so fun about design. That panic is part of the process, so when you’re learning, try and embrace it.

So what are you waiting for? Go out there and make your creative dreams a reality. Build a portfolio, meet other creatives, immerse yourself in your new field, and launch your new career! If you want to chat with a creative mentor as you start your process, chat with any of the design mentors at RookieUp. And if you want to follow a proven framework during your job hunt, answer two questions to get a personalized action plan sent directly to your inbox!


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