Roommate Life Lessons: 3 Years of Living Together and What We Learned About Jobs, Relationships, and Adulting

A candid conversation about navigating your twenties, from brutal job searches to long-distance love

Listen to the full episode on Apple Podcasts, Spotify, or wherever you get your podcasts. Search for "Guyset Podcast" to hear Reid's complete story and our full roommate debrief.

Living with roommates in your twenties is basically a crash course in adulting. After three years of sharing a West Village apartment, my roommate Reid and I sat down to reflect on everything we've learned about work, relationships, and the art of not driving each other crazy.

The Reality of Job Searching in Your Mid-Twenties

Reid just wrapped up one of the most challenging job searches I've witnessed. Over three to four months, he interviewed at more than 10 companies, with each company putting him through 3-5 rounds of interviews. The math? Approximately 50 interviews total.

"I probably got rejection letters every single day for over two months," Reid shared. "Originally I thought it was me - I'm doing something wrong, I'm interviewing incorrectly."

Breaking Through Interview Anxiety

The constant rejection took a toll on Reid's confidence, affecting not just his interviews but his work performance. His solution? Working with an interview coach who gave him a game-changing analogy:

"She said that if you were a patient and you got a nurse either with shaky hands or steady hands, which would you want? Obviously you'd want the one with steady hands to inject you with a needle."

This perspective shift helped Reid realize that confidence matters more than having perfect answers. Even if you don't know something or they don't like your response, you need to deliver it with confidence.

The Robotic Interview Trap

After so many interviews, Reid fell into another common trap - sounding rehearsed. "I was being very robotic in my interview process. I had done it so many times that I had memorized what I wanted to say and it came out robotic."

His fix? Preparing less and making interviews more conversational. Instead of memorized responses, he focused on hitting key points while asking questions and engaging naturally with interviewers.

Maintaining a Six-Year Long-Distance Relationship

Perhaps even more impressive than Reid's job search persistence is his six-year long-distance relationship with his girlfriend Michelle. They've been separated by distance their entire relationship, from college through their current careers.

Practical Tips for Long-Distance Couples

Stay Connected Throughout the Day: Reid calls Michelle during walks, commutes, or anytime he's transitioning between activities. It's about making your partner part of your daily routine.

Netflix Party Sessions: Using browser extensions that sync up streaming, they watch shows together in real-time while chatting, creating shared experiences despite the distance.

Monthly Surprise Calendar: Reid creates a calendar each January with photos from the previous year, designating specific days as "gift days" throughout the year. These aren't expensive items - maybe a Chick-fil-A gift card or a massage voucher - but they give his girlfriend something to look forward to regularly.

Regular Visits: They see each other every two to three weeks, alternating who travels.

The key insight? "It's definitely two sides. Even if you try your best, if your partner isn't about the long-distance relationship, then it's not likely to succeed."

Roommate Survival Guide: What Actually Matters

After three years of living together (plus a summer internship), Reid and I have learned what separates good roommates from problematic ones. It's not about being best friends - it's about basic consideration and communication.

The Non-Negotiables

Clean Up After Yourself: This seems obvious but it's where most roommate conflicts start. If the trash is full, take it out. If dishes are dirty, wash them. If you use the last of the toilet paper, replace it.

Communicate About Guests: Always give your roommates a heads up when people are staying over. It doesn't matter if it's your brother crashing on the couch or a friend visiting - just communicate.

Handle Shared Spaces: Kitchen tables, bathrooms, living areas - clean them when you're done. Your roommates notice and appreciate it.

The Relationship Dynamic

Interestingly, Reid noted that our conflicts never involved each other: "Reed and Jordan do not fight. Sometimes it is Reed and Jordan versus Josh." The lesson? Sometimes having a mediator roommate helps maintain household harmony.

We also discovered that living together doesn't automatically mean hanging out together. There were weeks where we'd pass each other in the apartment but never have quality time. Making intentional time for roommate bonding - whether cooking together or watching shows - requires effort.

Career Advice from Someone Who's Been There

Reid's job search and early career experience offer valuable insights for other twentysomethings navigating similar transitions:

For Job Seekers

• Don't take rejection personally: Often you're competing against people with more experience

• Work on your confidence: Shaky delivery hurts more than imperfect answers

• Make interviews conversational: Engage with interviewers rather than reciting rehearsed responses

• Get outside perspective: Whether it's friends, family, or a professional coach

For New Employees

• Meet as many people as possible: Network within your company across different departments

• Learn the culture and systems: Understanding how things work is as important as doing good work

• Get your name out there: You never know who might help you in the future

For Salary Negotiation

Reid successfully negotiated his salary by researching market rates and presenting his unique value proposition. "I showed her what the market value for someone with my skill level is... I showed her the skill set, the unique skill set that they'd be adding and how much value I'd be bringing to the company."

The Challenge of Maintaining Friendships in Your Twenties

One area where both Reid and I struggle - and most guys in their twenties can relate - is staying in touch with friends who don't live nearby.

"I do not follow up or not as much as I should with people that aren't New York," Reid admitted. "I have a good friend in DC, Virginia area or Miami so I feel like... definitely make sure you're still in contact with your buddies that aren't in your surrounding vicinity."

The solution isn't complicated, but it requires intentionality. Instead of mindlessly scrolling through social media during breaks, use those moments to text or call a friend you haven't spoken to in a while.

Relationship Insights for First-Time Partners

Reid's six-year relationship is his first serious relationship, giving him a unique perspective on what works:

Get interested in your partner's interests: Reid learned about diamond painting and got into reality TV shows because Michelle enjoys them. This isn't about losing yourself - it's about showing you care about what matters to them.

Ask follow-up questions: When your partner shares gossip or news, dig deeper. Ask why, what happened next, how they felt about it. Reid learned this lesson when Michelle would ask questions about stories he shared, and he'd realize he hadn't gathered those details.

Make the effort during challenges: Long-distance relationships require missing some social events and making sacrifices. Reid missed parties and friend gatherings to visit Michelle, but only because he wanted to prioritize the relationship.

Moving Forward: Transitions in Your Mid-Twenties

As Reid prepares to move to Philadelphia and live with Michelle for the first time, he's experiencing what many people face in their mid-twenties: multiple major life changes happening simultaneously.

New job. New city. New living situation. It's overwhelming but also exciting.

His advice for others going through similar transitions? "Spend as much time as you can with your friends. You're never gonna have this time again because when we're getting older, we start getting married, having kids."

The Bottom Line

Your twenties are messy, and that's normal. Job searches are brutal. Long-distance relationships are hard. Living with friends tests those friendships. But with the right mindset and strategies, you can navigate these challenges successfully.

The key themes from Reid's experience:

• Persistence pays off, but don't let rejection destroy your confidence

• Relationships require intentional effort, especially when distance is involved

• Good roommates prioritize communication and consideration

• Maintaining friendships takes work as everyone gets busier

• Major life transitions are easier when you have strong support systems

Whether you're job hunting, navigating a relationship, dealing with roommate dynamics, or just trying to figure out this whole adulting thing, remember that everyone's figuring it out as they go. The people who seem to have it together? They're just better at rolling with the uncertainty.

🎧 Want to hear the full conversation? Listen to Reid's complete episode on the Guyset Podcast, available on Apple Podcasts, Spotify, and all major podcast platforms. Search "Guyset Podcast" or find us wherever you listen to podcasts for more insights on navigating your twenties.