How to make a successful career change, from someone who’s been there


A career change can be a carefully plotted move, or it might be something you make up as you go along. Jen Maseda found her passion after an unexpected change in circumstance forced her to shift her focus. Here, she shares her secrets to career change success.

Jen Maseda is full of energy and a joie de vivre that you find in entrepreneurs who truly believe in what they’re doing.

In less than a year, she managed to create a conference which included world-class speakers, business leaders, a networking reception, an exhibitor’s hall, and a center for coaching and resume reviews for its hundreds of attendees.

And she did it all without spending a dime.

It might seem like this was all a part of Jen’s long-term career plan, but it came about unexpectedly.

Jen Maseda Headshot
MetroWest President & CEO Jen Maseda

With a college degree in exercise physiology, part of Jen’s early career was preparing members of the United States Coast Guard for their missions.

That background in exercise physiology gave Jen a base to “prepare people who want to be healthy,” but Jen wanted to dig deeper than that. She also wanted to know, “what are the influences within the community that are distracting people from being their healthiest self?” That question drove her to earn her Master’s in Public Health from Harvard University.

From there, Jen briefly worked for the local school system before working for a community organization for 12 years.  She worked her way up the ranks, eventually landing the roles of Senior Vice President and then Chief Philanthropy Officer. But after being dismissed from that role, she set out to find a new career path.

Take time to think about your next move

Like most people, Jen immediately began looking for a new job. But eventually, a friend told her that she just needed to breathe, take a step back, and refocus on what she really wanted.

Jen says looking at the bigger picture was crucial. “I stopped looking for a job and started instead to just listen to myself about what I wanted to do and what I was truly passionate about.”

From there, Jen gained some perspective on what had happened.

“Honestly,” Jen says, “It was great that I was pushed out of that job, because I probably never would have left on my own. You get so invested and work so hard that sometimes you can’t see the forest for the trees anymore.”

“They did me a huge favor because I finally saw my life again,” she explains. “I finally saw my schedule. I finally saw the person I was. And I could see all of this without any outside influences or distractions for the first time.”

Jen gave herself a year to figure out what she was going to do. She didn’t necessarily have to have a job in place by then, but she needed to have a plan and know what her next steps were going to be by the end of that year.

If you’re figuring out your next career step, it’s important to use this time to take stock of your life and what you want. With a little breathing room, you can find an array of career possibilities that you may have not considered before.

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Use your network

Before diving back into the working world, Jen spent some time focusing on what matters most to her. “I had the best summer ever with my kids,” she says. “We went to museums and water parks and everything we always said we wanted to do but that we were often too busy for.”

Jen also made sure that she kept “poking around” (as she called it) and talking to people to help give her a sense of what her goals and plan should be.

Jen joined a number of boards to keep her busy. She also took on a number of projects with these organizations to help them with outcome development, as most were nonprofit and could benefit from Jen’s expertise.

Jen knew she could benefit from trying new things, as they could guide her in figuring out her path.

If you’re looking for a new job, reach out to your networks and see where you could lend a helping hand. You might be the perfect person to help them launch their new venture, or you could be put in touch with someone who is looking for your expertise.

Create your own opportunities

In December of 2016, around 6 months after she’d been let go, a friend called Jen the night before the Massachusetts Conference for Women in Boston. She told Jen that someone at her company had dropped out and asked if Jen wanted their ticket. Jen jumped at the chance to attend the sold-out conference.

At the event, Jen felt a spark of inspiration. She turned to her friend and said, “We need to do this on a more local level and we need to do this fast.”

The conference showed there was a market for women-only events, but Jen wanted to create something with a more practical focus. And with that, the idea for the MetroWest Conference for Women was born.

“Women need a place where you can share your dreams and where you are well supported. That’s what we are creating with this conference.”

“It all just kind of came together really quickly. And it wasn’t until I was driving home that I realized, there’s talking about this and then there’s doing it. And I’m really doing this.”

MetroWest Logo
MetroWest Conference For Women logo

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As President, CEO and Founder of the MetroWest Conference for Women, Jen built on that vision and created a successful inaugural conference which brought together more than 500 women from throughout the Framingham, Massachusetts area in September 2017.

Her advice to anyone in a similar predicament is to “be open to opportunities.” It’s all about being flexible and understanding that “if a moment presents itself, you should be open to it... Don’t limit yourself from thinking something is possible.”

Surround yourself with the right people

Any challenge is made easier with the right people behind you. Because Jen envisioned a conference that empowered local women, it was important to assemble a team led by women.

She created a list of requirements for her team: they had to support the principles of the conference, bring a network of individuals that would strengthen their brand and audience—and be pleasant to work with.

“I didn’t want to work with people who were going to make this harder than it had to be,” Jen says.

“Women need a place where you can share your dreams and where you are well supported. That’s what we are creating with this conference.”

In her previous role, Jen had been instrumental in women’s leadership within the region. She had built a network of business, community and personal contacts, so she reached out to these women to assemble her new team.

“As a female executive, you often feel as though women better understand your struggles and what you’re going through to rise to the top of an organization.”

Jen says her team gave her a newfound satisfaction in her work. “I chose the 28 people for the board because they would be flexible and a joy to work with. I was tired of working in an environment that was painful.”

“Every time we get together, we work hard but we also laugh and have a good time.”

MetroWest team
The team behind MetroWest

Jen suggests anyone who’s looking to embark on a new project should surround themselves with people who have the right attitude. “Have people who are going to be honest and supportive. But also not merely yes men or constant naysayers,” she says.

“You have to be selective because when you share an idea with someone who is supportive and honest, you have a very different outcome than if you share it with someone who is going to rip you apart and not work to build you back up.”

A network can come in many guises: from workmates and mentors to family and friends. When you’re embarking on a career change, speaking to a wide range of people can help you gain perspective. If you’re not sure where to start, seek out groups or organisations in your community that will give you the ability to connect and learn from others.

Reach out for resources

After setting up the board, Jen assembled a team of volunteers to help run the conference and began approaching sponsors to help with costs. Jen wanted to ensure the conference fee wasn’t out of reach for guests. The team kept the fee low by reaching out to companies and speakers for a helping hand.

“Staples is donating printing for all of the marketing collateral, all of the speakers are coming for free, and all of the flowers and decor are being donated. Plus, we personally made the effort to make this affordable to women attending. Usually an event like this costs $250 - $600 for the day, but we’re only charging $50.”

IG MetroWest
Instagram post shared by MetroWest

Jen says Canva was instrumental in their marketing strategy, allowing her to create polished social media graphics and flyers.

“We literally could not have done what we’ve done or done it as successfully without Canva.”

“I use it every day for every piece of marketing collateral that I’ve created. It’s the easiest platform I’ve ever used, and I can say that because I’ve been in marketing a long time.”

Jen says she learnt a lot about design simply by looking through Canva’s templates—and suggests that anybody else creating their own marketing materials should do the same.

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“I looked through all of them not because I might use them, but to look at how they are designed and to see what font combinations work best together. The number of possibilities for both designs and fonts can be overwhelming, so I use the templates to give me an idea of what works together.”

Make sure you consider all available resources you might have at your disposal. Whether you’re looking to build marketing material, or just need a second set of eyes for that resume you created, using the resources and people available can make your life easier and help you reach your goals.

Take a chance

Whether you’re looking to create your own business, or seeking a new job, it’s easy to get weighed down by all of the options—and the obstacles. Jen says it’s worth taking a risk.

“Just believe that you can. I know that may sound easier said than done, but you have to tell yourself you can do it and then go and do it,” she says.

“Get out of your own way and believe that you can do something. You don’t need to wait to be 100% ready to try.”