Financial Case Study: Jeremy Jones, Living the Dream (and Other Websites)

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Jeremy Jones started his first travel blog called Living the Dream in 2008 to chronicle a long-term trip he was going to take in 2010-2011. That trip came and went. He took another one with his now wife, Angie, in 2013-2014, and since then he morphed the website to a general travel blog focusing on adventure travel, food and beverage, and off-the-beaten-track destinations. It has featured 74 countries on five continents so far. 

In 2015 Jeremy and Angie moved back to Pittsburgh, PA, to work day jobs and started a local blog for the city called Discover the Burgh which rapidly grew in popularity as one of the top resources for all things to see, do, and eat in the city with over 1,000 unique experiences featured (and counting). 

In 2018 these two sites grew large enough that Jeremy could quit his day job and pursue the websites full-time. In 2020, he expanded his blogging portfolio by adding a wine blog, The Grape Pursuit, and a weekly blogging newsletter called This Week in Blogging!

Holy moly. I’m tired just writing about all these websites. I don’t know how he manages them all. Read on to learn more about Jeremy’s career and lifestyle progression from part-time blogging to managing four websites full-time! 

(See also: Tips for Transitioning to Full-Time Blogging)

Financial Case Studies

How long have you been living/working on the road, and where have you traveled to? 

I’ve been blogging full-time since 2018 and pursuing blogging as a part-time business since starting in 2008 (I would say I probably started taking it seriously in 2014, however). I’ve been on two long-term trips where I tried to pursue travel writing full-time, but the blog never grew large enough to sustain itself before we ran out of money so we had to return home and pursue outside employment. 

That brought us back to Pittsburgh, where we were living prior to traveling, and we started the local blog that was the spark that was needed to move the business forward. 

Now that I do this full-time, I still am based in Pittsburgh, but I travel roughly 100 days a year; 3-4 weeks with my wife (who still works a day job) and the rest on solo trips either regionally (often driving distance) or internationally. 

We like to travel hack a lot with points, and my wife’s day job requires her to travel a lot too, so we end up splurging on points-based trips here or there. In 2020 before the pandemic hit we spent two weeks in the Maldives almost entirely on points (excluding food and experiences, of course)!

Please describe what you do for income.

I am all about passive income. I really hate working on sponsored campaigns and being beholden to deliverables, so virtually all of my income comes from display advertising and affiliate sales. This is a lot more predictable and is all based on my traffic levels, so my work revolves around publishing new content and increasing traffic wherever possible.

How many hours per week do you work on average?

0-100? Haha. Just kidding. It is hard to define this one because my two blogs have essentially turned my interests into work. Is going out to a restaurant to review work? Technically yes. Is drinking a bottle of wine work? Also yes. If we ignore this and talk about just the back-end tasks of running a blog (writing, social media, etc) I’d probably estimate 30-50 hours a week.

How much money do you make? 

Before COVID (so, 2019), I grossed about $85,000 for the year on around 250-350k monthly page views. But because I am so heavy into display advertising (>75% of my income) it was heavily dependent on seasonal trends. Q1 could possibly be sub $5k but Q4 could exceed $10k, for example. 

In 2020 my travel blog income tanked as no one was traveling, but the local blog held on fairly well as people were sticking fairly close to home. I feel fortunate to still have made about $65,000 in 2020 despite all the uncertainty going on.

I’ve been writing more and more for affiliate focused content in recent years to increase that income stream too. In travel, the sales funnel is so large that readers may check out our content for inspiration (where we get ad displays), but it may be a year or two before they actually book a trip and we naturally do not get any credit for that even if we helped contribute to that sale. So I’m working on shifting my content style to help provide more content closer to the time of purchase to increase my income on this front and, pre-COVID at least, it seemed to be working. For 2020 with everyone sticking closer to home, Airbnb’s new affiliate program was a lifesaver. I’ve been pushing about $1,000/month on that alone – during a pandemic no less! [Unfortunately, since writing this case study, AirBnB has discontinued their affiliate program.]

Travel-Blog-Income-Report Jeremy Jones

Do you make enough money to support your lifestyle?

Before I quit my day job I used my blogging income to pay off all our debts outside of a mortgage – student loans, car payments, etc. This cut down my required monthly spending substantially, which reduced the amount of money I needed to earn to have the same quality of life. Once I met that with my blogging income alone, it was off to the races and I quit my day job (with a pay cut). It only took a year for me to get my income back up to what my day job income was alone thanks to all the extra time I had to work. 

That being said, my wife still works her day job. I cannot discount the peace of mind that brings, even if I am still responsible for my half of the bills as usual. (Also, hooray health insurance!)

Any extra money I have either goes into a 401k, mutual fund for individual stocks, or investing into continuing education. I recently completed the WSET Level 2 wine course for my new wine blog and am starting Level 3 in a few weeks. My intention is to move on to the two-year+ Diploma track which could open up more work opportunities later on but costs a pretty penny to complete. 

What do you like most about your career and lifestyle?

There were two things I hated about working a corporate job: making worthless CEOs money and having to get up early. I don’t have to do either of those now, and I enjoy it immensely. I may not be helping bring in multi-million dollar contracts like I did in my former day job, but at least I’m seeing all the profit from my work now as opposed to, well, a pittance from it.

What are some of the challenges you have with this career and lifestyle?

Working for yourself inherently means stability is out the window. COVID was a great example of this where many bloggers saw their incomes decrease 30%, 50%, or more overnight through no fault of their own. 

When you work for a major multi-national company, you may be a cog that helps the machine move forward, slowly but predictably. But things move fast when owning your own business so you always have to be at the top of your game and work for growth at all costs. 

It is also a lot harder to manage a work-life balance as well, especially when you are blogging about all your biggest hobbies! When we go out to dinner, there will be photos. When we open a bottle of wine, photos. When we travel, photos. I’m not allowed to start any more blogs based on hobbies because of this (I’m ok with it).

What is your vision for the future of your lifestyle on the road? 

I’m in a unique scenario in that I have a home base, a mortgage, a dog, etc. A lot of that requires me to spend a fair bit of time in Pittsburgh. I don’t envision changing this at all any time soon, but I have toyed with the idea of selling our local blog at some point in the future just to not be tied to any given location. But that is a ways off as I have no desire to leave Pittsburgh any time soon. I’ll take traveling ~100 days a year for now. It’s a nice balance and was more or less my goal when I started this endeavor anyway!

See Also: Being a Digital Nomad vs. Having a Home Base

Jeremy Jones and his wife in the desert Living the Dream RTW

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