Broke, Unemployed, and Living With My Parents

I moved in with my parents when I was 27.

The football wallpaper in my bedroom was gone, and the bed was bigger. But it was still the room I slept in for the first 18 years of my life.

While most of my friends were married and starting high-salary jobs after years of graduate education, I was broke, unemployed, and single in a humdrum job market.

My options were few. That’s the way it felt, at least.

I had just traveled in Asia and Latin America for 14 months, then drove 8,000 miles around the U.S. and Canada for three months with a vegetarian friend I met in Thailand.

Traveling in my 20s was epic, and I was a better person for it.

But traveling wiped out my savings and hurt my career.

I moved in with my parents because I was strapped for cash and needed a job.

Two Questions

When my trip came up in conversation with friends and family soon after I returned home, everyone asked the same two questions.

1. What was your favorite place to travel?
2. What are you going to do next?

That first question was complex. I had just traveled to 20 or so countries and probably saw a dozen or more UN World Heritage Sites. I met interesting people from around globe every day.

None of them wanted to talk about my hometown sports teams.

I discovered river caves, waterfalls, ancient ruins, bizarre statues, the best cities in the world, and small towns barely on the map.

I swam with pink river dolphins, endured 22-hour bus rides, made shady currency deals, was robbed at machete point, and explored SE Asia helmetless without the constraints of time or money. 

It was an eventful year. But pick one favorite place to visit?

After babbling through different answers so many times, I realized nobody really cared what I said. They were only interested in the next question.

What are you going to do next?

You’d think after a year-and-a-half of exploring and journaling, I’d have had that figured out — all that free time to come up with my next big idea.

No. I avoided thinking about what was next.

I planned to move in with my parents to find a job in my hometown, which wasn’t really a plan.

Relative Adversity

My resume had a two-year gap. The job market was still sour from the events of 2001. I was overqualified for poorly paying positions that I couldn’t land.

Interviewing sucked, and my only suit was too baggy.

Potential employers didn’t understand why I’d voluntarily choose unemployment.

My pre-travel work experience was OK, but it was mostly irrelevant and not all that impressive to employers in my hometown.

Prospects seemed slim.

Dinner conversation is difficult when you’re unemployed and living with your parents.

Mom: How was your day?

Me: Not very good.

Mom: Did you find a job?

Me: No.

Mom: Any prospects? I’m sure something is out there.

Me: Not today. That one recruiter never called back. I turned down that telemarketing gig. 

Dad: You can’t be too picky.

Me: Yeah, well, the hour-long drive doesn’t seem worth it. Can you pass the broccoli?

Mom: Are you sure you don’t want any chicken?

Me: I’m not really eating meat right now, Mom.

Dad: You’re not getting enough protein. 

For the record, my parents were extremely accommodating during this period. I’ve always had the luxury of premium-grade family support.

The privilege of good parents was, in part, is why I went home. It was the low-cost path to get back on my feet.

Cheap was my primary language at this point.

The 18-month travel high was over, and I struggled to transition into the daily grind of a full-time job and career.

Twenty years later, I worked my way back out.

March on Washington

The stint at my parent’s house lasted about eight months. I spent the time hanging out with old friends and earning money doing temp work.

Short-term spreadsheet and data entry temp jobs were fairly easy to come by. One telemarketing gig was the worst job ever and the only job I’ve ever quit.

I earned $8-$14 an hour and kept my expenses low. My only fixed costs were a $221 car payment and a steady bar tab.

Job searching is exhausting. A recruiter would call one day with what seemed like the perfect job. So I’d rush to update my resume, and they’d vanish and never call again.

Or I’d come across a posting that fit my background and spend a few hours crafting the perfect cover letter. Then, the company wouldn’t get back to me, and I found out later that 500 applicants had applied.

One employer contacted me during the first week I posted my resume online. The small company had a position opening in the Washington D.C. area. I lived there after college and would consider returning since I was trying to search with an open mind.

But the job description was unclear, and the hiring company seemed unreliable. I’d hear from them for a couple of days, then not again for months.

The company’s customer needed a very specific software skill that was listed on the bottom of my resume. The competency was so rare that no one in the immediate D.C. area had it.

Not that it was anything super-specialized. Nobody had the skill because so few organizations needed the software.

The customer was unreliable, too. Multiple approvals and funding requests needed to settle before they could bring me on. The wait was frustrating, but the software was so uncommon that it made the job seem real and legitimate. The job took seven months to materialize.

After months of uncertainty and bad temp gigs, the call finally came through. The company offered me $19,000 above my pre-travel salary to move to D.C. and become a technology specialist for a large government agency. 

The offer was bittersweet because it meant leaving my hometown again. This time, probably for good.

Eight months of spending time with old friends watching the same old sports teams at the same old bars made me realize that if I stayed, I was done exploring.

Even though I knew D.C., moving for the job was a big leap. Most of my friends there had left. I moved into a house with two guys I barely knew in an entirely new neighborhood. But it led to a whole new group of friends. It was a fresh start.

I was 28 at this point. Still broke. Still single. But not for long.

Letting go of the unemployed and living with my parents label gave me vigor. Moving was still overwhelming, but in hindsight, it opened up massive opportunities.

D.C. is far more connected to the world than my hometown. This allowed me to volunteer with organizations with ties to places I visited, helping to keep the backpacker mentality in me alive.

My new friends included former Peace Corps volunteers and others with similar overseas experiences. D.C. was a better fit.

The Path of Least Resistance to Financial Independence

Somehow, I remained employed by the same guy who called me back in the Fall of 2002 for 14 years. His company nearly collapsed after the dot-com bust, but it wasn’t dead. I became his second employee and recruited an old colleague to be the third.

But the owner wasn’t forthcoming with these details at the time. 

At our peak, we had nearly 50 employees. I didn’t think to ask for equity until several years into the job, and I never got it. 

Despite my loyalty, the company was always a mediocre employer. As the company grew from nothing, the owner never invested enough into the company or his employees.

Profit margins were thin, benefits were average or below, and we always lacked a long-term strategy.

Almost everyone is replaceable, but I convinced my boss that I was not. Because of this, I received a salary and sales commissions beyond my worth in the open employment market.

For this reason, I considered my job to be the path of least resistance to financial independence. But as a one-income family of five for many years, the sub-par benefits eventually motivated me to look elsewhere.

Here is the Moral of the Story

When I moved home with my parents, opportunities were everywhere. I just wasn’t looking in the right places.

The day I moved in with my parents was more opportunity-filled than just about any other day in my life. I had a free roof, free food, reliable internet, a car, friends and family, and a paid-for college education, and I lived in a country made of opportunity.

It was the perfect time to take big risks. I could have started a business, worked for startups, or worked multiple side hustles to find my way into a career path that excited me.

My time was unlimited, and expenses were minuscule. Nobody relied on me for anything. I was completely free to do whatever I wanted even though I was broke. 

But I chose what I perceived to be the easy path — to find a boring job and settle into a typical career path.

Not having a plan was my fault. Maybe I lacked ambition or knowledge. But being relatively young with my life in front of me was a golden opportunity.

Young people have a way of feeling suppressed or lacking opportunities because they’re young. But it’s the complete opposite. Youth is unrestricted freedom and opportunity. It doesn’t fall into your lap. You have to go get it. All too often, people age before they realize it.

Everything turned out well for me. I’m not living with my parents anymore. I met the right partner. We married, started a family, and we’ve built wealth together. We’re on the path to retirement when we’ll explore the world full-time again.

The two-year gap is still proudly displayed on my resume. No mention of travel or spreadsheet temp work. Just “Non-working period”. No one reads that far down anymore.

Read More: The Retire Before Dad Story

This article was originally published on February 8th, 2017, and slightly modified in May 2024. 

Photo Credit: Ryan McGuire via Gratisography

Craig Stephens

Craig is a former IT professional who left his 19-year career to be a full-time finance writer. A DIY investor since 1995, he started Retire Before Dad in 2013 as a creative outlet to share his investment portfolios. Craig studied Finance at Michigan State University and lives in Northern Virginia with his wife and three children. Read more.