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#86 - Navigating Your First Career Change with Luca Milletti

Jan 21, 2025

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For anyone that's considering leaving their job, in the process of searching for a new job, in the application or interview process, or anywhere in between, this episode is for you.

This week on Guyset, my friend Luca Milletti is here to talk about leaving his first job after two and a half years and the process of finding a new one.

You’ll hear about why he decided to leave, how long the process took to find a new job, how many interviews he went through, how many rejections he faced, how he dealt with that rejection (and advice for you on rejection) the conversation he had with his boss, how he told his coworkers, and so much more.

In this episode, Luca and share actionable things you can do in your own job search, where and how to start, advice for applications, interviews, cover letters, standing up for yourself in the workplace, the difference between being confident in your work and self-absorbed, and how he’s feeling about starting his new job. We also both share our experiences with imposter syndrome and hear his perspective about living on his own for the first time.

The Complete Guide to Leaving Your First Job: Real Advice from a Guy Who Did It

Based on an interview with Luca Maletti, who just completed his transition from first job to second job after 2.5 years

Leaving your first job out of college is one of the biggest career decisions you'll make in your twenties. It's terrifying, exhausting, and often takes way longer than you expect. But if you're feeling stuck, undervalued, or simply not growing anymore, it might be time to make the leap.

In this comprehensive guide, we'll walk through the entire process based on a real conversation with someone who just went through it – from recognizing when it's time to leave, to navigating 20+ interviews, to successfully landing a new role.

When You Know It's Time to Leave Your First Job

The Warning Signs

You've stopped learning and growing. After about a year and a half in his analytics consulting role, Luca realized he wasn't gaining new skills at the pace he wanted. "I felt stuck from a technical perspective," he explains.

You feel pigeonholed. Being trapped in the same type of projects or clients without opportunity to explore other areas of the business is a major red flag.

Promotion timelines keep getting pushed back. When your company's "up or out" promotion structure starts taking an extra 6 months to a year due to economic conditions, it's a sign the growth you're seeking isn't coming anytime soon.

The money isn't following your performance. In consulting specifically, everyone at your level makes the same salary regardless of performance. The only way to earn more is through promotion – so if that's not happening, your earning potential is stagnant.

The Real Catalyst Moment

For Luca, it wasn't one dramatic incident but a combination of factors: working long hours, not enjoying the work as much, feeling disconnected from the office environment, and being stuck on similar projects repeatedly.

The breaking point: A conversation with his parents during a visit home where they simply said, "Maybe take a look somewhere else."

The Job Search Reality: What No One Tells You

It Takes Way Longer Than You Think

The timeline: Luca interviewed for nearly a year, averaging about one interview process per month. He went through 20+ interviews across 8-10 different companies before landing his new role.

The process: Most companies follow a similar structure:

Initial recruiter phone call
Hiring manager interview (slightly more technical)
Technical interviews with hands-on exercises
Final presentation rounds, often meeting executives

Rejection Is Brutal (But Normal)

The harsh reality: Of his first five interview processes, Luca was rejected in the final round of all of them. "You go through the whole process, meet the executives, do the presentation, and then they say you're great but they found someone with 3-5 years experience in your exact role."

How to handle rejection:

Take breaks between processes to reset mentally
Reflect on what you could improve, but don't beat yourself up
Remember that rejection often comes down to factors outside your control
Use each interview as practice for the next one

The Application Strategy That Actually Works

Quality over quantity: While Luca applied to 100+ positions, his advice is to be more strategic than he was.

Create multiple targeted resumes: Instead of one generic resume, create 2-3 versions tailored to different role categories you're targeting.

Use ChatGPT for cover letters: Create template cover letters for each role category, then use AI to customize them for specific job postings.

Go directly to company websites: Some of his best opportunities came from finding roles on company websites that weren't posted on LinkedIn or Indeed.

Having "The Conversation" with Your Boss

When You Get a Competing Offer

The setup: After receiving his first job offer, Luca used it as leverage to have a promotion conversation with his career advisor.

What he said: "I feel as though I have been in this position for X period of time, I'm unhappy with where I'm at and I want to be progressing. This other role is giving me the opportunity of doing that with higher pay. I want to know your thoughts on getting promoted in the next month and whether you can help me move off the engagement I'm on."

Critical timing: He strategically had this conversation during the same week that promotion decisions were being made.

The Golden Rules for This Conversation

Have an actual offer in hand – never bluff
Be prepared for them to say no and potentially view you as having "one foot out the door"
Focus on your own experience rather than deflecting blame onto others
Be specific about what you want and when you want it

The Interview Process: What Actually Matters

Preparation Is Everything

Go beyond the bare minimum: It's not enough to just look good and sound competent. In today's job market, you need to show how your presentation or technical work prepares you for the actual role.

Know yourself deeply: Be ready for curveball questions like "If I were to fire you in a year, what would it be for?" Practice articulating your genuine weaknesses without deflecting.

Research the company thoroughly: Understand not just what they do, but their culture, recent news, and how your skills specifically apply to their challenges.

Standing Out in a Competitive Market

Be proactive, not just reactive: Don't just respond to what they ask – anticipate their needs and show initiative.

Demonstrate self-awareness: Be honest about areas where you've struggled and what you've learned from those experiences.

Ask thoughtful questions: Show you've done your homework and are genuinely interested in the role beyond just getting any job.

Choosing Between Multiple Offers

What Actually Matters

When Luca finally received three job offers, his decision factors were:

Company reputation and name recognition: Especially in tech, working for a company known for hiring top talent can significantly impact your career trajectory.

Growth opportunities: Look for roles that will teach you skills you actually want to develop.

Company size and culture: Luca specifically wanted to move from a 100,000+ employee company to something under 10,000 for a more intimate, impactful experience.

Compensation: While important, this wasn't his primary deciding factor once he reached his salary goals.

Breaking the News: Telling Coworkers You're Leaving

The Awkward Reality

"My biggest weakness is telling people tough news," Luca admits. The conversation is inherently awkward, especially with colleagues you're close to.

A Script That Works

For close coworkers: "Hey, you know I've been in a bad place with the work I've been doing. I haven't been getting promoted, and I put in my two weeks last Friday. Next week is going to be my last week. I'm doing a quick happy hour – I'd love to see you there and say my goodbyes."

The key: Be honest about your situation without oversharing or complaining extensively about the company.

Managing Imposter Syndrome in Your New Role

It's Normal to Feel Like a Fraud

Even after successfully landing a new job, Luca admits: "I feel like I actually have imposter syndrome now. I'm really worried that I'm gonna show up and not know if my experience at a big consulting firm is going to translate."

Strategies for the First Few Months

Ask questions without shame: It's better to ask seemingly obvious questions than to pretend you understand and fail later.

Remember you were hired for a reason: They chose you out of many candidates – trust their judgment.

Focus on learning, not proving: Your first 90 days should be about absorbing information, not demonstrating how much you already know.

The Biggest Mistakes to Avoid

In Your Current Job

Not building internal sponsorship: The biggest regret? Not cultivating relationships with senior people who could advocate for promotions and raises.

Being too humble: If you don't advocate for yourself and your work, literally no one else will.

Staying too long hoping things will change: Sometimes the structure of the company simply won't allow for the growth you want.

In Your Job Search

Applying without intention: Don't just blast out applications. Be strategic about the roles and companies you target.

Settling for the first offer out of desperation: Even after months of searching, don't jump at the first opportunity if it doesn't actually solve your original problems.

Not preparing adequately for each interview: Each interview should feel tailored to that specific company and role.

The Financial Reality of Job Transitions

What to Expect Salary-Wise

For context, here's what Luca shared about consulting compensation:

Entry level: Mid-80s to 95k total compensation Second year: Around 105k Post-promotion: 40% jump to 130-150k range

The key insight: In many large firms, everyone at your level makes the same salary regardless of performance. Promotion is the only path to meaningful salary increases.

Living Solo During a Career Transition

The Additional Challenge

Luca was simultaneously navigating living alone for the first time while job searching – a combination that can amplify stress and isolation.

Essential Survival Tips

Make your living space conducive to productivity: Keep your apartment clean, make your bed, and create boundaries between work and personal space.

Force yourself to leave the house: If you work from home and live alone, it's easy to become isolated. Make morning walks or gym sessions non-negotiable.

Invest in accountability systems: Join classes, sports leagues, or activities that require showing up – especially important when you don't have roommates for natural social interaction.

The Mindset Shift That Changes Everything

From Desperation to Selectivity

The transformation happens when you go from "please, anyone take me" to "I have value and I'm going to find the right fit." This shift typically comes after:

Getting through your first few interview processes
Receiving your first offer (even if you turn it down)
Realizing you have transferable skills that companies want

Building Confidence Through the Process

Each rejection teaches you something: Whether it's interview skills, presentation abilities, or simply resilience.

You get better with practice: By his final interviews, Luca was significantly more prepared and confident than in his early attempts.

The market validates your worth: Multiple companies wanting to interview you proves you have valuable skills.

Practical Next Steps

If You're Considering Leaving

Audit your current situation honestly: Are you learning? Growing? Being compensated fairly?
Identify what you want next: Don't just run from something – run toward something specific
Start building internal sponsorship: Begin cultivating relationships with senior colleagues who can advocate for you
Update your resume while everything is fresh: Don't wait until you're actively job hunting

If You're Ready to Start Searching

Create 2-3 targeted resumes for different role categories
Research companies, not just job postings: Find companies you'd want to work for, then look for appropriate roles
Prepare for a marathon, not a sprint: Budget 6-12 months for the process
Practice interviewing before you interview: Do mock interviews with friends or career counselors

If You're in the Interview Process

Prepare specific examples: Have detailed stories ready about challenges you've overcome, conflicts you've resolved, and successes you've achieved
Research each company thoroughly: Understand their business, recent news, and culture
Ask thoughtful questions: Show genuine interest beyond just landing any job
Follow up professionally: Thank you emails and thoughtful follow-up questions demonstrate continued interest

The Bottom Line

Leaving your first job is scary, but staying somewhere that's not serving your growth is scarier. The process will likely take longer than you expect, involve more rejection than you'd like, and challenge your confidence in ways you didn't anticipate.

But here's what every guy who's been through this process knows: it's worth it. The skills you gain during the job search, the confidence you build by advocating for yourself, and the career growth you unlock by making the move far outweigh the temporary discomfort of the transition.

Remember: you're not just changing jobs – you're building the foundation for the career you actually want. Take the time to do it right.

Ready to hear more career transition stories and advice?

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