I left my first job, here's why and how I navigated it. If you're considering leaving your job or feeling stuck in your current position, listen to this. 

How to Quit Your First Job: A Complete Guide for Your 20s

Originally shared on the Guyset podcast - a guy's guide to what should be talked about

Why I'm Sharing This Story

At 23, I left my first job after college - and I realized there's almost no guidance out there for guys our age on how to do this well. Everyone talks about staying at your first job for two years, but what happens when you get a better opportunity earlier? Or when you stop learning and growing?

I want to share exactly how I navigated leaving my first job, including the conversations, emails, and decision-making process that most people never talk about openly.

When It's Time to Consider Leaving

The Growth Factor

The main reason I considered leaving wasn't because I was unhappy - I actually loved going to work every day. The issue was that I felt I'd stopped learning and growing at the pace I had when I first started.

For several months, I found myself asking: "Am I developing new skills? Am I being challenged? Do I see a clear path forward?"

The Career Path Reality Check

I wrote myself a note that became pivotal in my decision: "Look up, do the people above you have a role you see yourself in? If not, do what you can in your role to get yourself somewhere else."

This was my lightbulb moment. I realized I didn't see myself wanting the positions of people above me, which meant I was in a pipeline leading somewhere I didn't want to go.

The Promotion Conversation That Changed Everything

At my one-year mark, I didn't receive a promotion or raise. This led me to have my first real workplace confrontation - asking to meet with my boss and their boss to discuss advancement opportunities.

How I Prepared

• Wrote down bullet points of my accomplishments

• Documented projects where I exceeded expectations

• Prepared specific examples of additional responsibilities I'd taken on

The Reality of the Conversation

Despite all my preparation, when you're actually in that room, it's just you and what comes out in the moment. Eye contact became difficult when I was nervous, and I could tell my anxiety was showing.

The conversations went better than expected, which is why I initially turned down the outside opportunity.

How the New Opportunity Came About

I wasn't actively job searching when I was contacted on LinkedIn. The initial call with the founder was essentially an interview where I had to prove I wasn't too young for the role.

Interview Preparation Tips

• Refreshed my entire resume (hadn't looked at it in over a year)

• Reviewed recent projects and accomplishments

• Practiced talking about my current role and responsibilities

• Prepared examples of how I'd helped other teams and projects

Why I Eventually Said Yes

The new company offered:

• A mentor figure who would be my direct supervisor

• Better salary and growth opportunities

• A role where I could continue learning and developing

How to Leave on Good Terms

This was my biggest concern - maintaining relationships with people I genuinely respected and cared about.

My Conversation Strategy

I prepared these bullet points for telling my boss:

• "I received a really exciting offer that I can't turn down"

• "I've been loving my work here and originally turned them down, but the offer became too good to pass up"

• "I want to give at least three weeks notice because working here has meant so much to me"

• "I want to make this transition as smooth as possible"

• "This feels like the next best step in my career"

The Actual Conversation

I didn't schedule a separate meeting (though I wish I had). Instead, I used an existing meeting with my boss. The conversation went much better than expected - probably because I was genuine about my reasons and appreciation for the experience.

Managing the Emotional Side

Telling Work Friends

This was harder than telling my boss. I cared about these people and was sad to leave them. My advice: if they're real friends, you'll stay friends. The job change doesn't end the relationship.

The List Strategy

I made lists of:

• People to tell before announcing (only a few trusted friends)

• People to tell immediately after telling my boss

• People to email once the announcement was made

The Farewell Email Template

Subject: Thank You!!

Hi team,

I can't believe today is my last day at [Company] after [X] years. As you may know by now, I'm joining [New Company]. While I'm sad to leave the incredible team here, I am really excited to see where my next adventure takes me.

Thank you for making the past few years so memorable. I will take the lessons I've learned here with me in all my future endeavors. I am truly grateful for the experiences I've had here with you.

Please don't be a stranger - let's stay in touch. Wishing you all the best at [Company] and beyond.

Best, [Your name] [Personal email, phone, LinkedIn]

Key Lessons Learned

Everyone's Always Looking

I discovered that most people are passively open to new opportunities, even when they're not actively job searching.

Timing Matters More Than Tenure

The "stay two years" rule is outdated. If you're not growing, learning, or see a future you want, it might be time to explore options.

First Jobs Are Learning Experiences

Your first job doesn't have to be perfect or forever. It's a chance to:

• Figure out what you like and don't like

• Build professional relationships

• Develop workplace skills

• Learn what kind of environment suits you

Maintain Your Network

The connections you make at your first job are valuable for life. Put effort into staying in touch with people who matter to you.

When You Should Consider Leaving

• You've stopped learning and growing significantly

• You don't see yourself in any of the roles above you

• You're not being challenged or developed

• Better opportunities arise that align with your goals

• You feel you've outgrown your current position

When You Should Stay

• You're still learning valuable skills regularly

• You have mentors who are investing in your development

• There's a clear advancement path you're excited about

• You're building important relationships and experiences

• The timing isn't right for a transition

Final Thoughts

Leaving your first job is emotionally complex because it represents the end of one chapter and the beginning of another. For me, it was about recognizing that while I was grateful for the experience and relationships, I needed to prioritize my continued growth and development.

The process taught me that career transitions don't have to burn bridges. With genuine appreciation, clear communication, and professional courtesy, you can leave on excellent terms while pursuing what's best for your future.

Remember: your career is a marathon, not a sprint. Make decisions based on where you want to be long-term, not just what's comfortable right now.

Josh shares more insights about career development, workplace navigation, and professional growth on the Guyset podcast. New episodes drop every Tuesday with practical advice for guys building their careers.

Considering a job change? Remember that there's no universal timeline for success. Trust your instincts about when it's time to move on, and always leave with grace and gratitude.

Thank you for listening to Guyset, the guys' guide to what should be talked about! Subscribe or follow the podcast, give this episode 5 stars, and leave a review. Send in your questions for next week's Guyset Toolkit #3! Click HERE to connect with Guyset on Instagram, HERE to connect with Guyset on TikTok, HERE to watch the full episode on YouTube, and HERE to check out Guyset.com.

You can reach me on Instagram DMs HERE or by email josh@guyset.com. See you next Tuesday!