Turn your summer job into a full-time career

When Ryan Leonard needed a career change, he knew just where to go.

From 2016, the 24-year-old had spent his summers working at the Preakness Hills Country Club in Wayne, NJ, while getting his business management degree at Manhattanville College.

“It was a really good first job that kept me busy throughout the summer,” said Leonard. “I had fun and I liked the environment.”

Leonard started there as a food expediter, earning an hourly wage plus overtime, and in subsequent summers advanced to a pool pavilion manager role. After graduating in 2020, he eyed a career in finance, eventually scoring a commission-based insurance job at a Fortune 500 company.

“I was making 200 cold calls a day trying to nail a new client. It was very difficult, 11- to 12-hour days behind a desk staring at a computer screen,” said Leonard. “I was unhappy.”

Leonard quit in March 2021 and took time to regroup. He’d kept in touch with the Preakness Hills clubhouse manager and chef — and, that August, the staffer reached out to him, seeking temporary help.

“I was like, ‘I’ll be in next week,’ ” said Leonard.

After working for the remainder of the season, Leonard texted the clubhouse manager to express his interest in full-time opportunities. A few weeks later, he received an offer and began working as the assistant clubhouse manager in March.

“Being at the country club is like family to me. It’s very easy to work here and [I] enjoy it,” said Leonard, who isn’t complaining about occasional 14-hour days when evening events are held. “I like working where golf, tennis, activities and sports are involved. I get my cardiovascular fitness in, so that’s a plus. Being outside — it’s stuff you can’t beat. I have a desk here. I sit behind it for an hour — I’m not glued to it.”

Whether you’re scooping ice cream in the Hamptons or lifeguarding at the Jersey Shore, seasonal gigs offer opportunities to build relationships and gain new skills, creating a one-two punch for a solid career foundation.

Keeping the door open after the sun sets on each summer job, just like Leonard did, is crucial. “The occasional email or text to check in and say hi is always a great way to stay top of mind, especially in the event a potential job opportunity arises,” said Jeanniey Walden, chief innovation officer at on-demand pay technology platform DailyPay in the Financial District. “However, don’t be afraid to offer a coffee or lunch date. Nothing beats the in-person touch to keep a relationship vibrant.”

Whether you’re earning extra money, in between gigs or simply rebooting your career, “summer jobs are a great way to learn skills that will carry throughout your life,” said Erin Lau, manager of HR services at human resources consulting firm Insperity in Midtown. “Many summer jobs help teach invaluable customer service skills. There are very few jobs in someone’s career where they will not have to interact with people. Additionally, summer jobs expose employees to jobs and positions they never knew existed.”

Career discovery was key for Ashley Boutin, 34, of Newington, Conn. Working in the mental health field for more than five years had taken its toll, so she took a seasonal job as a summer director at Skyhawks Sports Academy. Boutin figured she had nothing to lose. “I knew that it was worth the jump — even if nothing came of it, it was a stepping stone,” she said.

That leap of faith paid off.

“It was one of my favorite summer jobs. I got to teach sports to children and nothing gets better than that.”

As Boutin worked at several different camp locations throughout the state, especially making an effort to work at more distant ones, she consistently communicated with her boss and expressed interest in a full-time job that she knew was opening. Before it was even posted, the corporate office contacted her.

Boutin said, “They wanted to offer me an interview because they heard positive things about me. It was a perfect opportunity to get my foot in the door and prove myself.”

Last September, she started full-time as Skyhawks’ area manager for Connecticut, managing 350 summer camps and 300 clinics and programs throughout the year.

Talking to her boss was a smart strategy, said Lau, since conversations for full-time jobs should begin by approaching your manager.

“The manager may not make the final decision, but they will be consulted on job performance,” she said.

When communicating to your boss, highlight what you’ve learned and express interest in working there long-term. If you are pursuing work in other departments within the organization, the same rule applies.

“It’s always best to speak with the current manager first,” said Lau. “Most managers are happy to help their team members develop and grow within the organization, so it should be a simple, organic conversation.”

Bear in mind that you can also negotiate pay by discussing how you’ve positively impacted the organization. “Strategically articulate your skills and contributions in detail to showcase why you are deserving of higher compensation,” said Walden.