The First Job Comes With a Paycheck—and a Lot of Unspoken Rules

“I thought my paycheck would be my annual salary, divided by twelve, divided by two,” Michael Martinez said.

It was the kind of arithmetic people do when they are trying to reassure themselves. A number on an offer letter, a clean division, a clean landing. Martinez, who works in wealth management, had done it too. “And boy, was I wrong,” he added.

On January 15 at Guttman Community College, a week before the semester began, that simple calculation opened the door to a much bigger conversation. The City Tutors launched its 2026 Connector Series with First Jobs, First Paychecks, sponsored by Landing Point, with CUNY EDGE helping anchor the day on campus. Learners arrived from across the City Tutors network—from different schools and partner organizations—carrying the same question in different forms: how do you step into work with your footing under you.

The opening segment lasted about fifteen minutes, but it set the tone. Martinez began with the document people are expected to understand quickly and quietly: the offer letter. He described it as something that looks like it was written by “what seems like 25 different attorneys,” then offered advice that sounded less like finance and more like permission. Print it. Highlight it. Write questions in the margins. Go back to HR with questions. “The more questions you ask,” he told the group, “the better off you’ll be.”

He walked through what sits between salary and take-home pay: taxes, health insurance, retirement contributions. He admitted he had made the classic first-job mistake—stopping at the salary figure and assuming the rest would be simple. It was not.

Once the first question came, others followed.

Rebeca, interviewing for a nonprofit role, asked about a 403(b). Martinez explained that it works like a 401(k), just offered by nonprofits. Chrissy, already hired, said her employer offered a plan but no match. Should she still contribute or open something on her own? Martinez encouraged her to start small, protect her cash flow, and build an emergency fund before locking money into accounts that can be costly to access early.

Then the questions shifted from paperwork to leverage.

Navid asked how to negotiate salary without losing an offer. Martinez recommended research, a reasonable counter, and restraint. Make the ask, he said, then stop talking. Let the employer respond.

Shariya asked why someone would open a Roth IRA if a job already offers a 401(k). Martinez explained the difference in plain terms: taxes now versus taxes later. What you pay early shapes what you keep later.

A mentor named Stacey joined from Zoom with the clarity of hindsight. She said she wished she had put more into Roth accounts earlier because time compounds faster than people expect. Martinez shared a simple comparison: one person saves $500 a month starting at 25; another saves $1,000 starting at 45. At 65, the early saver has $1.3 million. The later saver has $528,000. The point was not trivia. It was about control, while the numbers are still small enough to manage.

But the event was never just about finance. It was about first jobs, the stress that comes with them, and the private rules people are expected to know without being taught.

When the panel began, the room widened. Anuj moderated a conversation with professionals whose work rarely sits next to each other on the same stage. Ellen, a senior advisor in real estate and credit investing who has led large financial teams across global markets. Jan, a drug development executive who runs a biotech company focused on new therapeutics. Shubham, a data practitioner whose career has moved through data engineering, consulting, and large-scale analytics. Jimmy, a data engineering leader who shared that he had been promoted that morning at a startup a short walk from campus.

Jimmy told the group he wanted people to stop “walking around like a resume” and start turning skills into “signals” that tell an employer: I’m ready to work.

Asked what advice she would give someone starting out, Ellen offered something that sounded like relief to the room. A first job is not a final verdict. Do your research. Do not become a difficult candidate. If you sense you are being underpaid, one approach is to ask for a check-in after six months, once you have built evidence and relationships.

The conversation moved to a question that haunts early decisions: big company or startup.

Jan offered the sharpest distinction. In a startup, she said, nobody can hide. Your work touches the whole company. That can be a powerful learning environment, and it can be punishing. Big companies tend to have built-in training and formal programs. Startups expect you to teach yourself.

As the event moved toward its final stretch, the day took on the shape City Tutors aims for when these gatherings work. Learners spoke in their own language about what they actually heard and what they planned to do with it.

Andre said the message that stuck was blunt: networking matters. Blind applications waste time and energy. He described a goal he planned to act on immediately—five new connections a week, every week, until something changes.

Justin framed his takeaway as a line he could reuse. Your resume gets you the interview, he said. Your skills get you the job.

Christopher said hearing others speak helped him let go of the idea that he was late. Feeling late does not mean you are late. People move on different clocks. Being present matters more than comparison.

Mervin talked about money without pretending confidence. Learning the difference between pre-tax and post-tax felt like a switch flipping. Understanding fundamentals changed how he thought about control.

Christion said her takeaway was about networks as ecosystems—not just direct connections, but the connections of connections. Ask who you know, and who they know, and use the resources already around you.

Akkeem said he was leaving with a question he wanted to answer clearly for himself: what do I bring that is different? A mentor responded immediately. Walk into interviews knowing you are offering something too. When an employer asks if you have questions, silence is a missed opportunity.

After the panel, the event broke into smaller conversations. Some learners joined virtual breakout rooms. Others stayed for in-person speed networking, where mentors rotated from group to group. The fields were wide—healthcare, law, finance, analysis, technology, nonprofit. Learners stayed in place. Mentors came to them. No one had to force an introduction or compete for attention.

By the end of the afternoon, learners left with clearer language and a few concrete questions they could carry into the next moment: an email to HR, a salary conversation, a first team meeting, a networking ask.

For some, that was the start. They will keep coming back—for more Connector Series events, for 1:1 mentoring sessions, for more exposure to the people and pathways they are trying to reach.

For others, it was enough. One strong session at the right time. One set of introductions. One afternoon that made the first job feel more legible.

Either way, the work had begun. The City Tutors’ Intro to Corporate Work and Financial Education series will run throughout the year, building on the same idea that carried the day at Guttman: fewer guesses, more access, and the confidence that comes from hearing the rules out loud.