Why I Quit My Job – and Why I Almost Didn’t

Several days ago I received a Tweet from a reader named Carolyn saying:

“I’m an ex-newspaper reporter in Atlanta who just found your (old travel) blog. Would love to ask advice if you don’t mind!”

Well, I’m a sucker for helping ex-newspaper reporters in Atlanta :-) (My regular readers will understand why!) So I emailed Carolyn and asked her to tell me more about herself. She replied:

“I’m 23 and have been craving a trip of my own for years. I’ve gone as far as planning it out, but I continue to let job/money get in my way. I was following (a journalism hashtag) on Twitter … and found you and started drooling over your blog. I’d love to hear your advice and tales!”

I wrote back:

“Since you’re a newspaper reporter, let’s do this in a fun way: Why don’t you interview me by email? Send me some questions, and — with your permission — I’ll post the answers on my blog.”

Carolyn sent me some great questions — plus permission to use her name — and she included a more detailed biographical sketch of herself. She says:

“I graduated from the University of Georgia in 2010 with majors in newspapers and English. I worked at a local newspaper for a year and covered the gubernatorial election, which was great, but then I faced some ethical issues with the management and decided to leave.

Now I work in the Honors Program at (the University of Georgia) as I decide what to do next, but it pays my bills, and I’m able to travel with the students — England, Ireland and South Korea in the spring!

What I’d truly like to do is figure out how to work for myself – or create passive income so I can work on my own projects without worrying about the bills.

Ding ding ding! Carolyn said the magic words. How can I not do everything in my power to help Carolyn live her biggest dreams?

And if that wasn’t enough, Carolyn ended the email on this note:

“Wrapping it up: I come from a poor family with zero business savvy, so I feel like I’m already starting out on the wrong foot from my mom’s bad financial habits. I’m teaching myself to change those now, and I’m confident that I can successfully earn passive income, but I know it’ll take time.

After bills, the paycheck doesn’t leave much for me at the end of each month, so it’s difficult to build on what little I can save, but I’m trying. I’m finding some great tips on your site.”

Wow. I want to give her a hug through the computer. Her head and heart are in the right place.

Carolyn, here are my answers to your questions. I hope they provide some guidance. And while I can’t speak for my readers, I’m pretty confident the whole Afford Anything community is cheering you on.

(Note: Carolyn’s questions are divided into 4 topics:

  • Newspapers
  • Travel
  • Launching Your Own Business
  • Passive Income

Read it all, or skip ahead to whichever topic you’re interested in.)

The First Topic: Newspapers

Q: What sparked your interest in journalism?

My sense of adventure. I wanted to be on the front lines of fires, floods and famines. I wanted to interview Presidents, sit in the courtroom for murder trials and — document history in the making.

Q: What caused the “ex” in ex-newspaper reporter for you?

Two weeks before I quit the newspaper, a suicidal bomber threatened to blow up Boulder (Colo.) Hospital’s emergency room with a detonator strapped to his wheelchair. A SWAT officer shot him in the chest after a 2-hour standoff.
why i quit my job
Sound exciting? In reality, I spent the day glued to my desk talking to public relations hacks on the phone: What time did the standoff start? Does the alleged bomber have a history of psychiatric treatment?

Snore. The questions became even worse the next day: “Will the hospital revamp its security procedures in light of Monday’s standoff?”

I know there’s a compelling human element to all these stories. The bomber’s family is trying make sense of what happened (and they’re sick of talking to reporters). There are frightened hostages in the hospital (whose identities can’t be revealed due to patient privacy laws.)

I want to tell those stories. But I couldn’t do it from behind a desk. I had to break free.

The Second Topic: Travel

Q: When did you begin planning your trip? What age were you when you left?

(Note to new readers: Carolyn’s referring to the two-and-a-half years I spent traveling across the Middle East, Asia and Australia.)

I started planning it 5 years before it happened. Sorry — that’s probably not the answer you want to hear!

I was 19 and I had just returned from a study abroad trip to Japan (paid in full by a scholarship). My time in Japan had bitten me with the travel bug, so I set a goal to travel for 2 years without a job or any responsibilities. By the time I was 24, I was ready to launch that dream. (I should add that I was a baby — barely 21 — when I graduated from college and started working my first ‘real’ job.)

Setting a clear goal was important. If I had been willing to work while traveling, I could’ve joined the Peace Corps or taken a job teaching English overseas.

But I had a clear vision of being able to travel freely, without responsibilities tying me down. And for the next 5 years, most of my financial decisions revolved around this vision.

Q: Did you have any hesitations about leaving? When/how did you finally decide, “OK, I’m doing this”?

Yes, absolutely. I’m from an Asian immigrant family with an ethos of “work, work, work.” It was hard for me to “un-do” that conditioning and become intentionally jobless.was it hard to quit your job and travel?

Climbing to the next rung on the career ladder inspired me to leap off that ladder. When I was a reporter, I offered a letter of resignation. My boss countered with a promotion and a $10,000 raise.

I gave into temptation and stayed on staff for another 8 months. Then I spotted an opening for an editor position at a wine magazine. The job sounded perfect — travel to vineyards across the world! Sip wine and edit a magazine! I applied, and out of 100 candidates, I made it into the running for the final 2 candidates.

I realized that if I accepted this job, I’d never leave. I’d never see my vision come true — a vision of traveling without responsibility, of seeing where the world would take me. At best, I’d get to occasionally take a business trip to Italy, where I’d have a nice dinner, gather a few quotes, snap some photos, and fly home after 4 days. That wasn’t the type of travel I wanted. But it would be “okay enough” — satisfactory enough — to keep me in the job.

That became the catalyst. I had to get out now, or I never would.

The Third Topic: Launching a Biz

Q: When you returned from the trip, how did you adjust to a settled life and decide what to do next?

During the two years I traveled, my friends kept asking me the same question: How can you afford this?

It was actually fascinating to watch their assumptions. Many people try to “let themselves off the hook” by pointing fingers.

people assume someone must be richThe most common assumption I heard was what I call the “Someone Else Must Be Rich” theory. My friends assumed my family was rich. My family assumed my boyfriend was rich. And on and on. Everyone pointed to someone they’d never met and declared, “That person is rich and he/she/they are footing the bill!”

There were other theories, too. Some people assumed I went into massive credit-card debt to fund the trip. One close friend from college thought I made a killing in the stock market during the height of the 2006 – 2008 bubble.

I don’t care what people assume about me. That’s their problem, not mine. But I do find it sad that people — people I love — disempower themselves by deciding that their dreams are out-of-reach.

So I decided to start a blog that encourages and inspires. Originally I was going to create a travel blog, but then I thought — there are SO many dreams out there. Why not encourage everyone, no matter what their dream is?

As for the first part of your question — “How did you adjust to a settled life?” — I never settle. I still travel frequently, and when I’m at home, I’m motivated everyday by a higher purpose — helping others through this blog.

Q: Was it difficult to set up your first venture? Does one escalate into another?

“Difficult” in what sense? Is it a lot of work? Yes. It’s a ton of work. Early mornings, late nights, lunch at my desk. Do I love every second of it? Yes. Not to get too spiritual, but I feel like this is a higher calling. This is my creation and my contribution to the world.weaving a web in your business

And yes, one venture definitely leads to another — though I wouldn’t say it “escalates” so much as it “connects.” I’m not escalating, or climbing, a corporate ladder anymore. I’m weaving a web.

So my blog leads to writing and speaking opportunities. And my writing and speaking leads people — like you — to my blog. And on it goes.

The Fourth Topic: Passive Income

Q: What is the best way for a person to generate passive income when starting from scratch?

The two most common roads are dividend investing and real estate. Dividend investing means investing in companies that pay big dividends. The idea is that you hold on to the stock and simply live off the dividends.

For example, if you had $1 million invested in dividend stocks that paid a 4% yield, you could live on $40,000 without selling off any of that stock. Or — more realistically, if you’re just starting out — if you have $10,000 invested, you could collect $400 a year, enough to pay your car insurance. If you have $1,000 invested, you can collect $40 a year and treat yourself to a birthday dinner. (Of course, if you want to reach $1 million, you’re better off re-investing that $40 dividend).earn passive income through real estate

The other method — which I prefer — is real estate. Frankly, I like this method because I understand it better, and to paraphrase Warren Buffet, you should only invest in stuff you understand. Don’t be afraid to shrug your shoulders and say, “Um, I just don’t get it — and so I’m not going to invest in it.”

The key to passive income through real estate is to buy the right property. Find a property in which the water + trash + insurance + taxes + mortgage + maintenance + 1 month per year of vacancy = less than the rental income. In some cities, like Manhattan or San Francisco, this is nearly impossible to find. In other cities, like Atlanta and Cincinnati, these properties are everywhere. I own a 3-unit building in Midtown, Atlanta, that matches this description.

My most popular post, If I Had a Million Dollars, I’d Go Into Debt, outlined both these strategies. And next week I’ll share my story of trying to buy a few more properties — which I’m in the midst of doing right now.

There’s a third strategy, as well, and that’s creating a business that becomes so successful that it produces passive income. This requires a ton of work, and I’d recommend you only try this IF your goal is growing a business. If you’re motivated by money — rather than by pure love for the work — you’ll probably burn out.

Q: When your friends (and blog readers) ask for advice about passive income, what do you find is the biggest mistake they’re making?

Expecting it to happen quickly. It won’t. It takes a long, long time. I started working towards passive income one year ago, and I got two lucky breaks that put me ahead of the game (I’ll go into detail about those lucky breaks on Monday, Oct 17., when I describe my current attempts to buy more real estate).

Despite those lucky breaks, I reasonably estimate it will take me 25 years to earn enough passive income to support me. I’m 27 now — turning 28 on Wednesday (happy birthday to me!) — so I expect to be living on passive income by the time I’m 53. If I got ambitious, I’d set a goal for 50. If I got super-ambitious, my goal would be 45.

Carolyn, if your goal is to travel within the next 5 years and you’re starting from scratch, your best bet is to save for your trip, enjoy it, and launch your passive income journey when you get back. Of course, you could also choose to live and work overseas and start your passive income journey from a hammock in Bali.

And I’d like to give a huge thanks to my friend and mentor Len Penzo for running a guest post from me, 4 Surprising Truths You Must Learn Before You Can Be Rich. Check out his blog — he’s a fantastic writer.

Photos courtesy Barock Schloss and Inju.


  1. says

    Making career decisions is scary! I changed my career 7 times. The only time I was scared was when I started my various businesses. The internet has made starting a business easier and inexpensive to start a business and best of all it can be started part time.

  2. says

    I love posts like these. :) I didn’t realize you had planned your trip for that long. I’m a big planner myself. Right now I’m thinking to make a career change in 3-5 years to drop my day job to work primarily online with a side job or two. I have a lot I want to learn before then and I get a lot of satisfaction out of my day job too which is great and is helping me save for my lifestyle shift. -Sydney

  3. says

    I also have the travel bug, and traveled for three months last summer. I saved up frequent flyer miles (over several years) to make my international ticket extra cheap. Staying with friends also helped make it affordable.

  4. says

    Yes… Paula, I literally was about to e-mail you with a similar request. Carolyn and I are in similar stages of life (23, living in the south, just our of college) and have similar goals and dreams (to travel, be self-employed, etc.)and similar problems (current stable job, fear of instability, failure). So this was just the perfect post for me to see today. THANK YOU!

    I’m still figuring out what to do and how to do it, but your blog is certainly helpful in that journey. To get a little Freddie Mercury on you- I want to break free!

    • says

      @Maggie — That’s awesome!! I’m so glad this is helping so many people! Feel free to pose more questions. I want to bring this all into a public forum and create a community where people are inspired to break free!

  5. says

    This is off topic – You can/should delete this comment if you want

    What is wrong with that guy holding the newspaper in the water? His foot is rotting or something. Did you notice that?

    • says

      @Brad — I did notice that! It was a little weird, and I considered cropping it out, but cropping out his foot would cut off too much of the photo. And I thought the photo was hilarious, so I wanted to use it. I can only assume his foot is covered in seaweed?? At least I hope that’s the case!

  6. says

    OK, so I had to go back and look at the foot. I sure hope he stepped in some muck or something or else that right foot is going to fall right off, and the left foot is starting to get infected too!

    I would love to invest in real estate, but I am just nervous. I live in Metro Detroit, and things are so volatile here that not sure it would be the right thing to do now. However, prices such are enticing.

    I will have to give this more thought as I would love me some more passive income.

    • says

      @Kris — I have no idea what I would do if I lived in Detroit. That city seems to defy all the rules. I hear stories of houses selling for $1, and I don’t know what to make of it. I guess I’d have to live there — or at least make an extended visit — to figure it out!

  7. says

    Hi, Paula. I found your blog through a comment you left on Erica.biz. This post addresses a lot of assumptions that I, too, have encountered from other people. I have taken several road trips around the U.S., a couple trips abroad, and the longest I’ve worked a “steady” job was for about 9 months (with a month off for a trip to Europe). Everyone asks how I can afford to travel. I ask how they can afford to stay in one place for so long. In my experience, lots of travel comes with less possessions to update or maintain, and less steady bills. No rent, no utilities, and you aren’t constantly updating your wardrobe or accessories because there’s no point! I took a two month U.S. road trip in 2009 and spent less on the entire thing than I would have for one month living in an apartment.

    Like you, I choose to minimize my spending in areas that don’t appeal to me, and that naturally helps me save money. I have chosen a slightly different path than you, in that I am currently in the Peace Corps, living in Armenia. But during the two years I am here, I am working on ways to earn passive income so I can travel freely later on.

    I feel like in many ways, we have the same type of mindset when it comes to money and travel, so thanks for this blog; I will be checking back. (And happy birthday!)

    • says

      @Ev — Precisely! I can tell that you totally “get it,” and I love the part of your comment where you say: “Everyone asks how I can afford to travel. I ask how they can afford to stay in one place for so long.”

      I’ve had that same experience. When I traveled, I never felt the urge to spend money on nice clothes or to get my hair cut at a nice salon. We never ate at nice restaurants and we almost never drank beer (especially traveling in Muslim countries). Now — well, let’s take today as an example — my roommate is at a salon right now, getting highlights in her hair, and when she comes back, we’re going to a sports bar to watch the Michigan-Michigan State game. Just IMAGINE how much today will cost her: at least $100 for her hair, $20 for a burger at the sports bar, $10+ for beer = at least $130, assuming she doesn’t do anything after the game. When I was traveling, $130 could last me for 4-6 days of all living expenses, including “rent.”

      Cheers for serving in the Peace Corps. My sisters grew up in Nepal and one of their high school teachers was a Peace Corps volunteer. My family is in that unique place of being a proud “recipient” of Peace Corps service :-)

  8. says

    That’s very inspiring. I would love to travel more, but I feel like it’s too late now that we have a kid. We’ll probably wait until he’s off on his own before we do more back packing trips. Or maybe we can all go when he’s a bit older.

  9. says

    @Paula – I’m really enjoying your blog.

    One thing I would also recommend to Carolyn is to look into freelancing. I’m assuming she’s a decent writer given her profession, so she could consider applying for small freelance gigs (elance.com). Once she builds a reputation on there, she could “travel” to places like Nicaragua, Ecuador, Argentina, and even places like Italy and France. You can live quite nicely for under $500 in Nicaragua, and most of the country is quite safe (safer than NYC or LA, anyways).

    • says

      @Brave New Life — I’ve never used elance myself, so I can’t make recommendations about it one way or another. One frequent criticism I’ve heard is that the pay rate is low. Again, I haven’t used it myself, so I don’t know what a freelance writer could expect to earn, per hour, on average.

      I do, however, know that 2 things: 1) cost of living in other countries is low, so you can comfortably get by on $500 – $800 a month or less, BUT 2) in many places, the internet is incredibly slow, so working online is a major headache. If I were to work online from overseas, I’d definitely have a state-of-the-art 4G card or whatever other technology I needed that would ensure that I’m not dependent on a wireless network or on a shared cybercafe connection.

      • says

        Gonna have to agree with you on the challenge of working online from overseas. I had a certain amount of internet trouble even in Oslo — not exactly a place that comes to mind when you think of unreliable internet.

        • says

          @Eavan — I wouldn’t have suspected Oslo as a spot with internet trouble … but I guess wifi problems are worldwide! It’s gotten better in the past few years, especially with the invention of 4G.

  10. says

    This a very inspiring post! I have the same mindset and same goals as you and Carolyn here (though I am not 23, more close to 30). The best time to invest was 10 years ago and the second best time is now. It’s better late than never.

    • says

      @That Thing Call Money — Carolyn’s the super young one here … I’m 28 and my boyfriend, who traveled with me, is 32. We just bought our first investment property, and in comparison to our friends, we’re starting young!

      My parents were nearly in their 40’s when they moved to the U.S., went to grad school and got their “first jobs” // launched their careers. So it’s certainly never too late!

  11. says

    I hope to invest in real estate at some point. My family has always used real estate to move ahead, and I completely understand the ins and out of sweat equity!

  12. says

    I am officially addicted to your website. This is such an amazing post, and I thoroughly enjoyed all the advice you gave about travel, investing for passive income, and pursuing your dreams. I feel like I want to join the Peace Corps now and see what the world has for me.

    • says

      @Matt — Aw, thank you!! :-) And if you want to join the Peace Corps — go for it! I’m a huge supporter of the Peace Corps. I worked for their Denver office for two years as a representative/recruiter.

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