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A full-time job vs. the bucket list: Making more time to travel

Updated: Jun 14, 2019

Social media is full of travel photos and yolo captions that tend to be more annoying than inspirational, especially when most of us only get 2-3 weeks off a year to chip away at that bucket list. But the reality is life is short and opportunities come and go, so there is no time like the present to make some decisions before something out of your control chooses for you. Much to our collective dismay, no one else is going to clear our schedules—so it may take a little creativity, patience and planning (and sometimes guts) to make it happen for ourselves.

Below are a few ideas for how you might be able to carve more time out of your 9-to-5 to travel.

Negotiate more paid vacation time

Whether it's an annual review or you're accepting a new job, there is always the option to negotiate extra paid time off in addition to, or in lieu of, a higher starting salary, a raise or a cash bonus. In fact, it's often easier for HR to concede to more PTO than a higher wage, because wages are a budget thing and time off is more of a policy thing. Know your worth and do some quick math so you have a number in mind. This is not an time to shortchange yourself, so don't just go in planning to accept an offer that "sounds" good. Calculate your daily wages and know what exchange you're comfortable with before starting the conversation.

Groom a backfill on your team

Sometimes you have the PTO, but no one to cover you while you're out. This is the worst. Talk to your boss about cross-training team members and assembling a plan for how to readily transition work to and from each other. Maybe it's about improving project and process visibility (i.e., statuses), a one-time training session, a pre-made process guide for your role, or maybe working with HR to identify a pool of freelance candidates who are often available for short contracts.

Make long weekends work harder

I used to think 3-day weekends were made for extra lounging, but now it's like an inviting challenge to see how much travel I can squeeze in. All it takes is a little planning, potentially a bit more budget (if it's a holiday weekend), and a willingness to vacation hard. If you can get an extra half day off from your boss, even better.

We flew to Vancouver from LA and spent 3 full days hiking in Whistler over Labor Day weekend. The trick for us was to fly out of LAX (by our work) and return on Tuesday morning to drive straight into the office. We parked our car at the airport and left a change of work clothes in the trunk. We were only an hour late to the office (gave the boss a heads up of course), and spent every second of that weekend on vacation. If you can handle being a little (or a lotta) tired on the first day back, then it's an good tradeoff.

If you do fly somewhere, I would advise you limit your destination to 3.5 hours away, and cap any subsequent drive to 1.5 hours so you aren't spending so much time in transit.

These cities are great for 3-day exploits:

Portland - tons of things to do, plus endless trails within an hour of the city

Banff - only 1.5 hours drive from Calgary! This one's pushing it, but oh so worth it

Los Angeles - endless options: desert, mountains, beach, or all 3

Seattle / Vancouver - the Cascades and Olympic National Park, plus Squamish and Whistler in British Columbia

Daytrips are always a good idea

And if you only have the standard two-day weekend, day trips are a classic favorite. An overnighter a couple hours away can be all you need to satisfy the travel bug for a bit. The options obviously depend on your location, but regardless of where you go, there's a few things you can do to maximize the quality of your time away.

1 or 2 nights?

Personally, I like to leave on a Friday night only if we have to be up early (i.e., sunrise photos) on Saturday or have a full day of activities. It just saves you the cost of Friday night's lodging if you don't have to be there first thing Saturday. Plus, you're not really getting your money's worth rolling in at 8 or 10pm Friday. If you just want access to their amenities (i.e., pool) Saturday before check-in, just stow your bag at reception.

Don't be too ambitious.

Don't plan to drive too much, and don't overpack your itinerary. Spending a precious weekend driving all day is not relaxing or memorable, and rushing around to see a list of things sucks too. I rarely go more than 4 hours one way, unless it's for a specific objective like photography (in which case it's not so much about leisure anyway). I've found 2 hours is the sweet spot.

Have a plan.

Time is short, so be prepared. We made a trip out to Santa Barbara once and I had no idea what to do when we got there. I don't like wandering around aimlessly, so it was frustrating to be frantically Yelping and researching on the curbside. Bookmark a handful of eateries and points of interest in advance, so you have options around town wherever you end up. Make reservations for any activities in advance, and have an idea of travel times between things.

Take unpaid time off

Not the fan favorite, but an option every once in a great while. If you're PTO bankrupt, talk to work about just granting you a few days off. You may have already used up all your hours on another trip, or you just had few to start with. Either way, you haven't technically "earned" this time, so it may be a sensitive issue.

Freelance or contract work

That freelance life is a game changer. This is not an option for everyone, plus it has its downsides (private insurance, job instability) and a barrier to entry (experience, networking, demand). But the upside is total control over when you work, plus higher pay. The creative services and tech industries are the best example of where there's heaps of contractors who work weeks or months at a time, taking long breaks in between jobs.

According to this NPR article, there a trend of contract labor going on the rise so businesses can stay flexible amidst emerging and changing markets. They estimate half of the labor force will be contractors in 10 years.

This is how my husband and I travel as much as we do, and we'll keep it up until it doesn't suit our needs anymore. I'll write more about this later, but if in the meantime you have any questions on the transition or realities of the lifestyle, just send me a note.

Work travel

In the event you have the opportunity to travel for work, consider bolting on a few days of vacation afterwards. The company pays for a return ticket in either event, so you just add on the cost for the extra stay.

The holy grail of time off... a sabbatical This requires substantial planning and saving. The elusive sabbatical, an extended leave of absence for personal time off, is only observed in the wild on occasion. They generally last anywhere from a couple months to a year, and are unpaid. I am a huge believer that a well-planned break from work to travel can help kickstart new chapters in life. Whether its breathing new life into an existing career or fueling a new direction, it's a total reset. Not to mention the onslaught of life experience you can expect to gain. My husband and I have taken a few several-month-long breaks, and it's been the best investment of our lives.

This is a major life event, and there are a few specific issues to consider before you start planning.

First, decide if you want to return to your current job or plan to find a new one when you return. If you stay, your company is not legally required to hold your position beyond the terms of your accrued PTO/sick time. Therefore, it's more like a verbal agreement that you'll have a spot waiting at your return. And if you do, it's reasonable to assume you may lose seniority or other perks you'd accumulated. I left my advertising job in a high point in my career, when I was learning and growing the most, and when others around me were, too. Leaving meant giving up seniority in a competitive environment, but it also set me up to start freelancing (which I finally had the experience for).

Second, it's expensive! If you're traveling, you need funds to travel, plus savings to cover your overhead at home for however long you're out. Most people I've talked to take about a year to plan logistics and finances. For a really cursory estimate of basic costs, assume the cost of living per day between $50 to $200, depending on the country and your travel style, and that's your starting range. This is not including airfare and daily transit, plus emergency cash, insurance, entertainment, overhead expenses at home... there's a lot more to consider for a complete budget. Your daily costs could get as low as $30 a day backpacking in places like SE Asia, or well over $500 a day culture-ing it up in Paris or Amsterdam. We chose to reallocate what was a house down payment to periodic travel breaks over 2 years. I've also read others made the same life choice. So that should give you an idea for what kind of investment we're talking about.

Last, be prepared for a degree of change when you return. Professionally, you may feel different about your job after some extensive soul searching and want a change. Or maybe your office dynamic will evolve without you, and your role won't be what it was. Personally, your perspective on life priorities or friendships may shift. Maybe free time will become more important than money, or you will find yourself connecting more with different types of people because you're now a different type of you. Hobbies, values, goals and passions will spark and evolve, and it will be for the better. In any event, you're likely to return refreshed, impassioned and ready to take on new challenges, wherever they may be.

The PTO struggle is real. Just know you have options and where there's a will, there is usually a way (albeit by brute force at times). We aren't getting any younger, people!

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