Career Break at 40…OK, 41!

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“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

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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

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road trip quote

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21 thoughts on “Career Break at 40…OK, 41!

  1. You will be missed, but what an amazing adventure you are headed on! Can’t wait to see where your journey takes you!!

  2. Amazing! I’m still not the besf with my money but this gives me hope that I can get better, sort it out and maybe one day save enough for a short career break for travelling. Congrats, can’t wait to read about your adventures!

  3. I am so happy for you Leigh, living the dream. Wherever you decide to call home, they are a lucky community to have you. I’m thinking Colorado??

    • Thanks, Cheri! I don’t know, Colorado is getting a bit crowded (and pricy!) but we’ll see 🙂

  4. Honey, you don’t need a Target in CO. I’m bouncing off the walls for you!! Be safe, be smart and I’m looking forward to hearing about your adventures. Muah 💋

  5. Awesome adventures ahead for you, Leigh! Would love to continue reading about them, new quotes, insights and books you encounter. My first thought about your adventures is one of my favorite books, “The Alchemist.” Happy trails to you!

    • Thanks, Chang! I will have to check that book out; I will have lots of time for reading now!

  6. Can’t wait to hear all about your adventures! You are truly living your dream, and I admire your character in making it all happen. You have re-lit the passion and drive I once had at my fingertips. I look forward to reading more of your quotes; so inspiring.

  7. Only just very new to your site, but this sounds like an absolutely wonderful adventure! I have done the telecommuting/remote working and yes while there are definite benefits to doing this, it can be very hard to do to! Best of luck with the decision when it comes to that time.

  8. Nice to “meet” another Gen X travel blogger! Congrats on the escape! We’re looking at doing something very similar soonish. Looking forward to reading about your upcoming adventures!

  9. I love this and am taking it as motivation to “let go” of the comfort of a paycheck to live and help others. Travel makes me feel alive and I think it’s time to be able to get that feeling back!

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