When are you taking your next vacation?

When are you taking your next vacation?

It’s the middle of December, 2014 and I am finally on the way to my first week off for the year. Sitting on the plane now, I reflect back on what it took to prepare for this trip. Obviously, all the hard work during the year, but here is what I did.

Yuri frequently points out to me that I complicate my life by over thinking and over planning. “It’s just my nature.” I respond to him that: “Our brains are wired differently!”‚Ķ.and he nods with a smile. Men vs. Women?! Men are from Mars, Women are from Venus! Well maybe. Do you agree?Mauna Lani  Big Island, HI

Mauna Lani, Big Island, HI ~ December 2014

I came to realize, whatever your approach to life is, these critical steps have to be addressed

1. Packing

Now this is were Yuri and I will never agree. Yes, I need more clothes and shoes, and jewelry and make up! I think you get it:)

Let’s start:

-What kind of trip are you taking? Beach vacation, exploring and sightseeing, a cruise, a little bit of each?

-Check the weather.

РHow long is your trip? Think an outfit per day. I always bring two extra, in case the weather prediction is off. (Well, let me be honest … in case I change my mind:)

-Think comfortable shoes. Don’t forget a pair of dressy shoes for a special night out. Yes, men you too! Can’t wear Toms all the time!

2. Closing the loop at work & home


-I feel that the most productive day at work is the last day before your vacation starts.

-Wrap all the outstanding projects, or extend your deadlines.

– READ and answer all emails.

-Are you bringing your computer with you?

– Will you be responding to emails?

– Is your vacation responder on?

– Who is your point of contact in case of work related emergency?


-Do you need a home sitter?

-Who’s watching your pets?

-Newspapers and mail suspended on hold

3. What you gonna do when you get there?

I know that you’ve already planned your trip.

– Are there any last minute items that you need finalize?

-Hotel, flight and car reservations confirmed?

-Travel documents in place? Visa and/or passport?

-Some trips I don’t plan much ahead of time. Just get there and figure out on the spot. Other trips, makes sense to think through and pre-book excursions or other activities ahead of time. It saves money:)

4. Money

Last, but not least!

This time around, I actually prepared well in advance.

-We paid for flight, hotel and car ahead of time.

Remember, Fixed Expenses?

-The only expenses left are food and entertainment. Variable Expenses.

Now, just like in the everyday life, come up with a budget. I know vacation is about relaxing and having fun. But you will agree with me that when vacation is over, you don’t want to be stuck with a huge, unplanned bill to pay.

-Figure out how much you will spend per day. Do you need $200, $300 or $500 per day for variable expenses (food, entertainment, excursions)

– If you use a credit card, know your limit! Use your daily budget as guideline.

-I prefer to have estimated budget amount already allocated in my checking account. Only use credit card in emergency, or not at all.

I know that I may have forgotten something, but my most critical items are taken care off. Now it’s time to relax and have fun!

Anna Sergunina
Anna Sergunina

I'm Anna Sergunina, CFP®, President & CEO at MainStreet Financial Planning, Inc. My passion lies in serving others through financial planning, helping clients achieve their dreams like buying a home, saving for education, or retiring early. With over two decades in the industry and a CFP designation since 2009, I'm dedicated to excellence and continuous growth. Beyond work, I cherish moments with my son Liam, prioritize self-care, and engage in content creation for my Money Boss Parent Podcast and Money Library blog.

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