5 Month Travel Plan

Last week I announced that I left my job of 11.5 years in pursuit of some long-term travel. Right now, I see this as a six month journey. However, that could easily change to shorter or longer depending on a million things, because…life.

I am a meticulous planner; I love travel planning and I think it’s half the fun of travel. For this trip, though, I’m trying to leave as much open as possible. I want the option of lingering in a town I like, working with tourism boards or jumping on a press trip, changing my route to avoid weather or rerouting to see something new. There are a few spots on my itinerary that require advance planning but for the most part, what follows is a very loose agenda of where I’ll be spending the next five months!


I worked until the 3rd of August, moved my belongings into a storage unit and I’m now on a bucket list hiking trip in Switzerland.

Switzerland Haute Route

After two weeks of wandering the Alps, I fly back to Chicago, with a 24-hour layover in Reykjavik! Upon landing back in the States, I’ll spend a few days with family and friends, tidying up any loose ends in Illinois and then hit the road. My first stop will be Olathe, Kansas. I will then head west to Colorado, where I’ll end the month of August.

9.19.09 - the historical village of Twin Lakes


In September, I’ll spend a bit more time in Colorado, and then boogie on over to Utah. The Salt Lake City area is high on my list for a home base if and when I’m ready to stop moving. I’ve been there twice for quick job interview visits, so I want to spend some quality time here and get a feel for what it might be like to live here. From SLC, I will head up to Oregon for a bit. Despite living in Washington for 3 years, I’ve spent very little time in Oregon. I want to visit Bend and Crater Lake, then I am booked on a 4-day whitewater rafting trip on the Rogue River with OARS. After this, I will head to Lake Tahoe, another first for me, and then swing through Southern Utah, one of my favorite regions in the U.S.

9/12 - Bryce


I will kick off October at the North Rim of the Grand Canyon, followed by a trip to Page, AZ for as long as is needed to see all the amazing sandstone features I can. Then it will be time to make my way to New Mexico, where I’ll be meeting up with my favorite ladies for a girl’s weekend in Santa Fe. We’ll start at the Albuquerque Balloon Festival and then travel to Santa Fe for a few days of girl-time. Once the girls have gone home, I will spend the rest of the month bouncing back and forth between New Mexico and Arizona. Places like Taos, Sedona, Flagstaff, Silver City and Ojo Caliente are all on my wish-list.

9/9 - cow pie formation in Sedona


As winter approaches the high country, I will make my way back to a spot that captured my heart many years ago – the Big Bend region of West Texas. I won’t be able to do a ton inside the National park with Bailey, but will explore by car as well as the areas outside the park. I missed out on a lot my first trip because I was sick, so I’ll revisit places like Marfa and Ft Davis. For the rest of the month, I plan to explore Tucson. Tucson is another place that I’ve considered for relocation as I love the desert and there is high elevation nearby to escape the heat. A couple of weeks should give me a sense of whether I might want to come back and settle in.

3.1.09 - Sonoran Desert Museum


Detouring from the road trip, I will begin December in Maui. I got a timeshare pitch/offer that I couldn’t refuse, so I will likely head to San Diego from Arizona and jump a flight to Maui from there. Once I return from Maui, I will make my way down the west coast as far as I can. I would love to spend the whole month in Baja Sur, but will need to iron out the details of driving through Mexico and what my comfort level is with that. I’m told it’s mostly safe, and the danger is in the road hazards more than anything else. I’ve also found online forums of snowbird gringos who drive down and organize caravans. If I decide I’m not comfortable doing that, I’ll kick back in Ensenada for the month, as it’s just a short drive from San Diego.


This is where my plans fizzle out…I have no idea what I’ll do when the new year arrives. If I’m having fun, and not yet broke, I’ll keep going. I would love to spend the whole winter in Baja, eating $1 tacos and drinking Corona to my heart’s content. (My ultimate dream? Winters in Baja, summers in Alaska, with a long, leisurely drive in between) I would love to squeeze in an international trip as well, possibly South America or Central America. Or, I may be heading back to civilization and looking for stable employment again.

So…that’s my plan! Some parts of it feel super rushed. Winter comes early in the mountains and I’ll be racing the clock in September and October. I’m surprised that in a 4-month road trip covering only seven states, I’m still not going to see everything I want. With a plan to camp most nights, I don’t want to move every night, and I’ll supplement with hotels as needed. In anticipation of this trip, I traded in my American Airlines credit card for a International Hotels Group card – this way, every penny I spend will earn points towards stays at Holiday Inn Express, which I have found to be the most convenient dog-friendly option when traveling.

As much as I want to leave up to chance, I would love to hear what your favorite spots are along this route! Especially hikes, campsites, diners, bakeries, taco stands, swimming holes and pet-friendly hotels. Let me have it!


trips out west

Share This:
Facebooktwittergoogle_plusredditpinterestmailby feather

Career Break at 40…OK, 41!

“Don’t be afraid to give up the good to go for the great.” – John D. Rockefeller

I’ve been collecting travel quotes for about 18 months now…waiting for this moment. Counting down months, then weeks, now days! I knew it would go fast, and here I am!

Yesterday, I left a pretty darn good job and a wonderful company where I spent the last 11.5 years. Today, I pack what’s left of my belongings and move them into a small storage unit near my sister’s house in the Chicago suburbs. Tomorrow, I move into my mom’s house. Wait, what?!

Ok, not really, but it will be my mailing address. What’s up, Moline?!

taking a career break at 40

Overcoming Debt

As a Gen-X’er, we are really the first generation to be mostly reliant on self-funded retirement. Pensions are nearly non-existent and my peers and I often joke about working until we die. (We also grew up during the 80’s peak of conspicuous consumption, spending our entire teenage paychecks on Benetton rugbies and Guess jeans. Who didn’t lust after Jake Ryan and his Porsche?!) So I surfed the credit card waves through my 20’s and 30’s, buying things I couldn’t afford and didn’t need. Thankfully, I eventually came around to my senses and started to reverse that trend! Unlike many others in my generation, I’ve been lucky on the employment front. I’ve never suffered a layoff and have never been fired, which means I’ve been working since 1990, with never more than a two-week break between jobs. Even when I moved across the country. Twice. Call it a mid-life crisis, but I’m just past 40 and I’m ready for some time off!

Saving Up for a Career Break

Ok, full disclosure here: I was in the right place at the right time and had some nice stock options that made this career break possible. I only had to wait 4 years for them to vest, haha! I used to hear of people taking a career break, or a gap year, and used to make all kinds of assumptions about how they did it. Honestly, had I not spent so much on dumb stuff, I could have done this much sooner. (If I had $1 for every Clinique “free gift” I got…oh, God!) So, it’s not impossible, it’s actually quite achievable, but I wanted to be honest about how I’m doing it. I also have sold a lot of belongings, curtailed my travel in the last year and reduced my expenses greatly, while at the same time trying to enjoy my last year in Chicago.

Of course, the smart move would be to continue investing and put this money towards my retirement, but frankly I’m tired of waiting for retirement. It might never happen. I’d rather travel now while I’m healthy and work forever if I have to. If you pull into a diner in Tucson in 2045 and see me waiting tables, don’t be surprised!

career break at 40

Image from 365travelquotes.com

What’s Next?

After a brief trip to Switzerland, I will be traveling the Western US through the end of the year. The ultimate goal is to find a new hometown, and it will certainly be in a drier climate than the Midwest! I may try my hand at remote work, or I may decide to return to the comfort of life in a large corporation. There are certainly benefits and drawbacks to both, which I will debate endlessly in my head while I’m out hiking for the next 5 months! It’s surreal to think that I have no idea where I’ll be at this time next year. For someone who is used to meticulously planning out my 4 weeks of PTO every year, sometimes a year in advance, it’s an interesting, but unsettling feeling. I don’t know how it’s all going to work, living in my car. I’ll probably stop at every Target between here and the Pacific Ocean, or I’ll be dumping more things at Goodwill along the way!

taking a career break at 40

Sign up for email updates!

Want to know where I go next? Subscribe to my email list in the upper right – I’ll send weekly posts of my travels, as well as a monthly recap for as long as I’m traveling full time! Stay tuned next Friday for more details on my travel plans for the rest of the year!

road trip quote

Share This:
Facebooktwittergoogle_plusredditpinterestmailby feather