The Squiggly Path: How I Navigated 6 Career Changes (And How You Can Too)

My career path is more of a squiggly line than a straight one.

These are just some of the roles I’ve had since graduating with a BA in Media Studies 10 years ago:

1. Donor Data Entry for a Children's Charity

2. Marketing Manager for a Theatre Company

3. Guest Experience (essentially working a ticket desk) at the Museum of Modern Art

4. Community Engagement for a Jewish healthcare charity

5. Wellbeing Advisor at Save the Children

6. Led the Workplace Bereavement Programme for a national Hospice Charity

Each time I made a career change, I had a plan and sought advice from people with more experience. Now, ironically, I’m the one people ask for advice on breaking into new fields.

Here are the key lessons I share with anyone looking to switch careers or break into a new industry:

1. Start small: volunteer wherever you can.

When I first shifted from Marketing to Community Engagement, I needed two things:

1. A way to test if I’d actually enjoy the work before making a big leap.

2. A way to build experience and credibility without already having a job in the field.

For me, that meant volunteering. I found a great weekly opportunity through New York Cares, working with a local community group. It gave me hands-on experience, confirmed that I enjoyed the work, and helped me develop relevant skills. The project’s Team Leader even became a job reference. I was open about my career goals, and she was happy to answer my questions which gave me a lot of reassurance about taking the next step.

2. Talk to people who already do the job.

I reached out to a handful of people on LinkedIn who had roles I would love to do. I sent them a message asking for 15-20 minutes to ask them about their daily tasks, what skills mattered most, and what advice they’d give someone new to the field. Most were super gracious and actually really enjoyed reflecting on their career path. Their insights helped me figure out which skills to focus on and how to position myself in my resume. Sometimes these conversations can even lead to job referrals or interviews.

3. Study job listings to identify essential skills.

When I realized I wanted to make another pivot to work in Learning & Development, I noticed I lacked some key skills, particularly around software experience. I went through job postings to see which ones came up repeatedly and then took advantage of free trials and created mock projects to practice. This not only helped me learn and not feel inexperienced but it also gave me examples to showcase in interviews. It was a great way to show hiring manager initiative even though I didn’t have direct experience yet.

4. Recognize and use your transferable skills.

Your past experiences are more valuable than you think. For example, in Arts Marketing, I worked with the press a lot. When I moved to the nonprofit world, that experience helped me secure free media coverage, something that was critical to our fundraising efforts. Take a bit of time to list the skills you’ve gained in different jobs. You’ll be surprised how much applies to new industries.

5. Keep learning and networking.

These days, there’s so much free knowledge online. I love listening to podcasts and watching YouTube videos to build my skills. People give away so much great advice for free. Following industry leaders on LinkedIn is also a great way to learn what’s trending, what they’re reading or what events are worth attending. If you do reach out to someone for a connection or a job, it’s also so much better to be able to show genuine interest in their work instead of just asking for a favor. People appreciate thoughtful connections and they’ll notice that you’ve made an effort rather than just click ‘connect’.

The bottom line: You don’t have to figure it out alone.

Career changes aren’t always easy, but they’re worth it. The effort you put in will pay off when you land a job that you truly enjoy and excel at. There are plenty of people who’ve been in your shoes and are happy to help.