How to Get a Paid 4-Week Vacation



I’ve just returned from my first month-long vacation.


Now I want to do it again.


As Ferris Bueller once said, “If you have the means, I highly recommend it.”


Most people never take more than a two-week vacation and many people struggle to get away for even that long.


Of course, a vacation doesn’t require travel, but if there’s a way to get out and see the world, why not do it?


Now that I’ve figured out how to extend vacations, I’m teaching others how to arrange similar adventures.


By the way, I did not totally unplug from work on this trip. I did three phone calls and checked email regularly. I also got some writing done, but I enjoy work, so these activities didn’t seem like tasks at all.


Four ways to get an extended vacation

Here are four strategies to get you out and about for the long breaks you deserve:


1. Arrange an ongoing revenue stream.

Every situation is different, but people who are authors and speakers can create recurring revenue by creating an inventory of products that can be purchased online.


Recently, I created an online course titled, Present Like a Pro, a six-week intensive that covers every aspect of the speaking trade. It’s a transformational course that teaches my clients how to generate income from speaking.


People can sign up for the class at anytime and the self-study nature of the course means that services can be rendered even when I’m on vacation. Sure enough, someone signed up for the class while I was on the super-long vacation.


2. Eliminate the boss.

No, not like that.


The boss almost always denies requests for 4-week vacations. Long “vacays” are not the standard at most companies and if the boss says you can disappear for a month, she has to give others permission, too. #NotLikely


Being self-employed means that you are the boss and being in charge makes it a lot easier to get away for longer periods of time.


3. Tap your network.

Being gone from home or work for a long time requires a certain level of resourcefulness.


Your personal network can help provide everything from home stays to hotel discounts and even complimentary hotel rooms.


I used email, social media, my website and phone calls to inform my network that I was planning a long trip to Florida. This resulted in many invitations, as well as interesting conversations about the trip’s possibilities.


4. Offer your talents during the trip.

Again, being a professional speaker can come in very handy when traveling.

I’ve done “stand-up meetings” for hotel teams in return for special considerations.

I also speaks at service clubs while traveling, which helps me build a bigger network and seed plans for the next time I return to town.


Trip itinerary for my first 4-week vacation



My epic vacation began on December 20, 2018 and ended on January 18, 2019.


Rene Pothetes and I visited:

– Greenville, South Carolina

– Tampa, Florida

– St. Petersburg, Florida

– Sarasota, Florida

– Fort Myers, Florida (including Sanibel and Captiva Island)

– Naples, Florida

– Nashville, Tennessee


The trip included museum visits, lots of fun restaurants, four home stays, a day of boating, some hotel nights, some shopping, a movie day, a Segway tour and other assorted activities.

We visited with a high school chum that I hadn’t seen for 40 years, slept ocean side and ate alligator.

Neither Rene or I got sick or injured during the trip, although we were involved in a minor fender-bender when a lady rear-ended our vehicle at a red light.

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