The Mentorship Deficit

Seek a Mentor Early

My biggest career regret was waiting too long to find a mentor. I was too shy to ask senior colleagues for help, so I learned everything slowly. Once someone finally showed me the ropes, my skills took off. If you are new to the workplace, just ask for help. You will build confidence and get good at your job so much faster.

Matthew Reeves, CEO & Co-founder, Together Software

The data validates this urgency. Research from the National Bureau of Economic Research shows that mentorship significantly enhances career outcomes, with mentees being promoted five times more often than those without mentors. Perhaps more striking: mentees advance their careers 18 months faster on average, a compelling return on the investment of seeking guidance early.

Moving Beyond the Academic Mindset

Probe Why and Solve Problems

The single biggest regret I see from new grads is staying quiet and working in a total vacuum. They treat their first job like a series of homework assignments. They’ll spend days obsessing over a technical task, trying to make it perfect, without ever stopping to ask how it actually helps the company or the customer.

In my years building engineering teams, the graduates who struggle the most are the ones waiting for a perfect manual. They don’t dig into the “why” behind a project. That lack of curiosity is a killer. It leads to a ton of wasted effort on things that don’t matter and kills any chance of showing they can think strategically. NACE research shows this trend all the time—new hires are technically solid, but they’re often missing that “career and self-development” muscle you need to actually navigate a professional environment.

The real shift happens when you stop being an “order taker” and start acting like a problem solver. The regret usually sets in a year or two down the line. They look up and see their peers—the ones who weren’t afraid to ask the “dumb” questions early on—moving into leadership roles while they’re still stuck doing basic execution.

It’s easy to feel like you need to have every answer on day one, but your first job is actually the only time in your life where you’re expected to ask everything. Don’t let the fear of looking inexperienced stop you from learning how the business actually makes money. That’s the stuff that actually gets you ahead.

Amit Agrawal, Founder & COO, Developers.dev

The Self-Advocacy Gap

Document Wins and Advocate Yourself

One of the most common regrets fresh graduates have is assuming that doing good work automatically leads to recognition and promotions. What they later realize is that it’s important to keep track of your own accomplishments and know your worth. The regret isn’t that they worked hard; the regret is that they assumed someone else was going to give them credit for it. Once fresh graduates figure that out, they tend to gain much more confidence and take charge of their career trajectory without waiting for permission.

Aliyyah Camp, Founder & CEO, Aliyyah Media Group

Say Yes Then Set Boundaries

The power of saying yes to each and every opportunity that arises, even though doing so is knowingly risking the exposure of not knowing exactly what comes next, or how to deliver. That’s the absolute upside of being a fresh graduate – when will you ever again get the opportunity to boldly go forth and learn as you go. In my many decades of experience with seeing talent growth, I know first hand that those fresh graduates who boldly say ‘the answer is yes, what is the question?’ are the ones likely to see the most meteoric rise in their professional career. What I always see with those individuals too is the space to say yes, and then set the boundaries, so it’s not the case of saying yes to things to which they should have said no.

Mac Schimm, Founder, Cape Consulting

If you’re working hard but not getting feedback, coaching, or a chance to build new skills, burnout shows up fast.

Recognizing When to Move

Leave Comfort When Progress Stalls

A big mistake I see fresh grads regret is staying too long in a first job that feels “safe,” even when the learning has stalled. It’s easy to tell yourself you should just keep your head down and be grateful, but that mindset can quietly trap you.

One simple signal is whether you can actually make things better. If you’re being told what to do and how to do it, with no real ability to influence decisions, you’ll eventually feel stuck.

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Another sign is when the role becomes constant pressure with little mentorship. If you’re working hard but not getting feedback, coaching, or a chance to build new skills, burnout shows up fast.

My advice is to do a quick check-in with yourself every few months. Ask, “Am I still learning, do I have support, and do my ideas matter here?” If the answer keeps being “no,” it’s a good time to move toward a team where growth is part of the job. You’re not being disloyal by choosing your development. You’re being responsible for your future.

Steve Bernat, Founder | Chief Executive Officer, RallyUp

Pick Growth over Prestige

One mistake I hear fresh grads regret over and over is optimizing for the job title instead of the learning curve. They chase the shiny role, then realize six months in they’re not building real skills or getting meaningful reps. The people who grow fastest usually took roles where they could touch more things, ask dumb questions, and see how decisions actually get made. Early in your career, progress beats prestige every time. You can always change titles later, but you can’t get back wasted learning time.

Justin Belmont, Founder & CEO, Prose

Speaking Up and Speaking Out

Tell Your Manager What You Want

Here’s the thing about your first job. At Google, I missed out on a project I really wanted because I never said anything. I just assumed I was supposed to do my assigned work and wait. That was a mistake. Tell your manager what excites you. It’s often the only way to get the work you actually want instead of just the work you’re given.

Andrew Yan, Co-Founder and CEO, AthenaHQ

Experiment with New Tools Independently

Most new grads I know wish they’d played around with more tools outside of class. I stuck to my job description at first, but things change so fast now with AI and all the no-code apps. At Roy Digital, the people who just try stuff without being told are the ones who get noticed. My advice is simple: don’t wait for permission. Just experiment, learn fast, and show you’re curious. That’s what actually gets you ahead.

Hrishikesh Roy, CEO, Roy Digital

This counsel arrives at a pivotal moment. The Cengage report reveals that 48% of recent graduates feel unprepared to even apply for entry-level positions, with 56% citing job-specific skills as their biggest gap. The willingness to self-educate on emerging tools can help bridge this preparedness divide.

Industry Immersion and Role Alignment

Pursue Sector Exposure Now

Not having real experience in the job market, especially in the sector.

This is something I have always observed in friends who are older than me, classmates from similar cohorts, and people who graduated the year before. There is a mismatch between job expectations and the reality they encounter. Even those who do have work experience—usually through small jobs in hospitality or small retail—often assume that many of the problems they faced in those low-skilled jobs will completely disappear once they find a role as recent graduates.

Another myth, also created by a lack of experience in the sector, is the belief that studying is over, or at least that the period of intense studying has ended. In many professions, the opposite is true. Now is when you need to study in order not to fall behind, while adapting to the reality of a new work environment. Even worse, some people expect the company to take them by the hand and guide their professional career, when in reality they must take control of their own path and decide which skills or programs to study in order to grow.

For all these reasons, I believe that having contact with people who are ahead of us—sometimes even a whole generation ahead—can help us better understand this reality. And if we also take the opportunity to do internships as close as possible to the kind of work we would like to do, it will give us valuable perspective and allow us to develop more realistic expectations.

This results in a lower baseline that impacts future raises and talks for years to come, leaving money on the table.

Jose Garcia, Economista 3909 – Marketing 447, Economista Jose Garcia

Raise a Mismatch to Switch Teams

I see new hires take jobs that aren’t quite right, hoping it’ll just click. We had a new grad who was struggling with all the writing. She was an analytics person, really. Once she spoke up and switched teams, her work completely changed. If a new role feels off from the start, be honest about it. That one conversation makes a huge difference.

Vincent Collado, Marketing Director, Braff Law Car Accident Personal Injury Lawyers

The Compensation Conversation

Negotiate Your First Offer

Most recent graduates take their first job offer exactly as offered because they feel grateful just to be hired. This results in a lower baseline that impacts future raises and talks for years to come, leaving money on the table. A starting salary grows over the course of a job, so a small shortfall at the beginning can add up to a big loss later on.

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People often don’t want to negotiate at first because they’re afraid of looking greedy or losing the offer. However, companies expect some flexibility in the numbers they give you. Even a small increase adds up over time. Before you receive an offer, study market prices, practice your negotiating language, and make a confident yet courteous inquiry. The worst case scenario is typically a straightforward “no,” which still leaves you in the same position you were in before asking.

Phoebe Mendez, Marketing Manager, Online Alarm Kur

The financial stakes are substantial. Only 45% of workers negotiate their starting salary, yet 78% who do receive a better offer, according to recent surveys. Your first salary sets a baseline that compounds throughout your career—each raise, each new position typically builds from that initial number. For those who accept without negotiation, the cumulative cost over a career can reach hundreds of thousands of dollars.

Building Professional Networks

Meet Folks and Lend Help

I’ve seen new guys in construction make the same mistake. They keep their heads down and focus on their own tasks, then miss out on everything. They don’t get the good advice from the crew next door or hear about the better projects. A quick chat, offering a hand, that’s what people notice. Just introduce yourself and ask a few questions. It makes the whole day run better.

Joseph Melara, Chief Operating Officer, Truly Tough Contractors

The Communication Imperative

Use Your Voice on Day One

From my experience watching fresh graduates step into their first jobs, the one career mistake they regret the most is staying silent instead of asking questions early.

Many freshers believe they need to prove themselves by figuring everything out alone. They stay quiet in meetings, hesitate to ask for clarity, and pretend they understand things they do not. This usually comes from fear of looking inexperienced. Ironically, it slows their growth and increases stress.

I have seen graduates struggle for months because they did not ask simple questions in the first few weeks. Small confusion turns into repeated mistakes. Confidence drops. They start doubting themselves, even though the problem was never capability. It was communication.

Later, when they feel more comfortable, they often say the same thing. “I wish I had spoken up earlier.” By that time, habits are already formed and expectations are set.

What they learn too late is that the first job is not about perfection. It is about learning fast. Managers expect questions from freshers. Asking early shows responsibility, not weakness. It helps build trust and saves time for everyone.

The biggest regret comes from realizing that silence did not protect them. It only delayed their growth. Fresh graduates who speak up early, ask for feedback and clarify expectations settle faster and build confidence sooner.

If there is one lesson here, it is simple. Your first job is not a test. It is a training ground. Use your voice early. It is one of the most valuable tools you have.

Safdar Khurshid, Full Stack SEO Specialist, BestMobileLaptop.com

Fresh graduates who work on their people skills along with their technical abilities are more likely to experience faster career growth.

Solicit Blunt Feedback Fast

My biggest mistake starting out was waiting for feedback. Don’t be like me. Everything changed when a colleague finally told me my ad copy sounded like a robot. Our team started getting honest with each other and stopped making the same dumb mistakes. If you’re new, just ask your manager what you’re doing wrong. It’s the fastest way to actually get better.

Jon Kowieski, Lead, Growth Marketing, Brex

Establishing a feedback culture early proves transformative for career development. Research shows that consistent feedback helps professionals identify strengths and weaknesses, develop critical skills, and cultivate a growth mindset—viewing challenges as learning opportunities rather than threats. Those who actively seek constructive criticism in their first months build resilience and adaptability that serves them throughout their careers.

The Skills Balance

Balance Tech Mastery with People Strengths

The most common career mistake fresh graduates make is believing that technical skills alone will guarantee success. While technical expertise can help you get your foot in the door, sustainable career growth depends on developing important soft skills. Many newcomers focus only on their core competencies without realizing that communication abilities and emotional intelligence often determine career advancement more than technical skills.

In my years of mentoring young professionals, I have seen many talented individuals struggle because they ignored relationship-building and teamwork. Fresh graduates who work on their people skills along with their technical abilities are more likely to experience faster career growth. Remember, in professional settings, how you communicate your ideas can be just as important as the quality of those ideas. It is essential to balance your development in both areas.

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Sahil Kakkar, CEO / Founder, RankWatch

The evidence supports this dual-track approach. Research from TalentSmart found that 90% of top performers have high emotional intelligence. While technical skills remain essential for initial hiring, teams led by emotionally intelligent leaders consistently demonstrate higher performance, elevated morale, and reduced turnover. In today’s workplace, the combination of technical excellence and interpersonal mastery increasingly separates those who advance from those who plateau.

Setting Clear Expectations

Clarify Success Metrics Upfront

The error that comes out the most frequently during the first year is taking up a job but having no idea how one can be judged successful. Most of the graduates are concerned with title, brand name, or wage and believe that they will know expectations after time. Instead, they get into the context in which performance expectations remain unclear, feedback is not uniform and development is reliant on unspoken rules. That is why progress is slow; not because there is no effort put into it, but because there is no direction.

Remorse normally comes in about month six. There is a job being done, but it is not clear what the outputs are that are actually important. Reviews become subjective and promotions go down. Conversely, graduates that initially inquired about metrics, the right to make decisions, and what good performers do differently are more likely to move on to greater heights even in less glamorous positions.

The lesson is practical. Students must be aware of how the success will be determined within the first ninety days and first year before they agree to take an offer. Once they start, they are supposed to rearrange those expectations with their manager, in writing. Careers are hastened when work is coupled with observable results. Even good performers are unable to gain momentum when expectations remain unspoken.

Maegan Damugo, Marketing coordinator, Platinum Consulting Services

Speak Up with Bold Ideas

I see a lot of new hires hold back because they don’t want to rock the boat. So we started these informal meetings where anyone can suggest something. Now people are more engaged and we’re trying more things, even when some don’t work out. So don’t be shy. Your take might be exactly what we haven’t heard yet.

Ben Hathaway, CEO, Wedding Rings UK

understanding the Reality

Request a Typical Tuesday Walkthrough

Look, most new grads I know wish they’d pushed for details on the day-to-day before saying yes to a job. They get excited, sign on, and suddenly they’re burned out doing work they didn’t sign up for. My advice? Ask them to walk you through a typical Tuesday. It saves you from a rude awakening on week one.

Edward Piazza, President, Titan Funding

The Path Forward

The convergence of these eighteen perspectives reveals a fundamental truth about early career success: technical preparation, while necessary, proves insufficient. The graduates who thrive are those who approach their first role not as a destination but as an intensive learning laboratory—one where curiosity trumps caution, where asking questions matters more than appearing knowledgeable, and where building relationships and advocating for oneself prove as crucial as mastering job-specific skills.

In a job market where three-quarters of employers are hiring the same number or fewer entry-level workers than in previous years, the margin for error has narrowed. Yet the strategies that separate early career success from stagnation remain remarkably consistent: seek guidance proactively, communicate expectations clearly, document accomplishments systematically, and recognize when a role has stopped serving your development.

The Path Forward The convergence of these eighteen perspectives reveals a fundamental truth about early career success: technical preparation, while necessary, proves insufficient.

These lessons carry particular weight because they come not from those dispensing theoretical advice, but from leaders who have lived these regrets firsthand and watched countless others repeat them. Their counsel is not about perfection in those first months, but about intention—approaching your first professional role with eyes open to both its opportunities and its pitfalls.

For those entering the workforce now or still finding their footing in early roles, the message is clear: the mistakes that haunt careers are rarely the technical errors made in week one. They are the questions left unasked, the mentors never approached, the boundaries never set, and the voice never used. Your first job will teach you something regardless of what you do. The only question is whether you’ll shape that education or let it shape you.