Making Time Off Work for You

Welcome to one of the regularly occurring expensive times of the year: summer vacation season kicked off by gay christmas aka Pride Month which features events which could also easily drain one’s bank account. The pride month question I’ve long struggled with is: how to get to enjoy the fun and vibes when I have to work it around work? This year it all feels more complex, as wrestling with the realities of a horrific US-funded war and an election season that’s only going to get more intense as time goes on also opens the question: how to participate in protest if it might mean missing work?

Getting to take a vacation or have paid time off is a luxury that should be commonplace. But, funding these can create struggle. Read on to learn about access to paid time off, how people fund vacations and “planned unplanned” time off, and to hear my story of how I’ve make a lot of travel work for me at the wildly different income levels of my life.


Many people in the US don’t have paid time off. The Urban Institute did a study in 2021, learning that working full time for an employer and having a college degree correlated to an 80% likelihood of having access to any kind of paid time off – but part-time workers and Hispanic and Latinx workers are least likely to have paid time off [PTO], and the impacts of not having PTO are felt most acutely by people doing care work outside of their paid jobs.

Focusing on paid vacation time, the Center for American Progress found that “79 percent of all private sector employees have access, while 40 percent of part-time employees and(43 percent of the lowest 10 percent of earners … have access” [using 2023 BLS data]. In 2024, the National Partnership for Women and Families [NPWF] found that23 percent of the [US] workforce lacks access to even a single day of paid vacation.” 

The NPWF also found that the benefits of vacation could have outsize impact for workers who also have family caregiving responsibilities – often women – and those who have higher likelihoods of heart disease and strokes: health issues that more often impact Black women. They also found that Black and Latinx workers feel less able to take PTO, even if they do have access to it. Finally, only 45% of LGBTQ+ people [source, 2022 data] have access to paid leave that’s inclusive of LGBTQ+ families, (which correlates to types of professional jobs which, of course, correlate to certain class, gender, and race demographics).  

Access to certain types of jobs can increase the likelihood of having paid time off for vacations or care work – but what about for people who work for themselves? When you work for yourself, it can be hard to incorporate ways to cover your life expenses during times you’re not working, but increasing rates/prices, or adding in work time so you have more money and therefore have reserve savings to pay for these things makes a huge difference in your quality of life, reduced stress about what’ll happen if you need time off, and can increase your overall resilience.

My self-employed clients and friends fund time off in ways which boil down to:

  • working extra days or gigs to have cash on hand to cover costs during unpaid time
  • regularly putting “PTO” savings away,
  • and/or working while traveling [aka the digital nomad promise, which is not, technically, time off].

Finally – if you have one of the many jobs that does not give you paid time off, you’re surely aware that the ways to fund time away are saving ahead and reducing the costs you leave behind, like subletting your room/home. Which leads us to discuss…


Whether you have a job that gives you paid vacation or have to fund your life during time off yourself, there’s still the matter of the additional cost of the vacation itself. 

Are you flying somewhere? Driving – gas and tolls add up. Staying at a hotel or BnB? Need to buy any special gear or new ‘fits? Food on the road or once you’re there? Special experiences you want to have? It doesn’t have to be pricey to travel, but boy can it be!

Where does the money come from? I see people do a few things:

  • One of the simplest ways if you have consistent income is to annualize and save regularly: if you look over the next six months and expect to spend $2500 travelling and for holidays, save $425 a month in a separate account, and take that money out to pay for airline tickets and travel related costs as they arise.
  • Some people like to put “extra” money to one-off costs [like travel], so sometimes I see people put their tax refund, or – if you’re paid every other week – putting the extra 2 checks a year to travel, or working a specific gig or project that funds vacations. 

There are ways to decrease the amount of money you need and make travel more affordable, like:

  • Stay with friends instead of a hotel
  • Use credit card points or miles for air travel
  • Get brought in to teach or perform, and get travel and lodging paid for
  • Look for deals on last minute tickets or buy waaayyy ahead of time


Sometimes, you gotta make a political statement that might result in arrest and future court dates. Those of us who are self-employed or who have values-aligned jobs can usually give clients or colleagues a heads up that we might be out of the office on a certain day with no further explanation, but people with jobs that require showing-up-or-else, have a harder time accessing time off flexibly and usually coordinate action around existing days off. Generally organizers are sensitive to the fact that we live in capitalism and therefore unpaid time is not accessible to a lot of people, nor is the cost of legal representation, and work with people to address these ahead of time. If you need to cover getting paid for a day off, community support and or savings are what most people look to.


I love travel and adventure and basically require looking forward to it, to get through the grindy parts of life. Especially as a former over-worker and recovering overachiever, I make myself take at least one week off – really off, no computer time allowed – every few months.

Now that I have fancy jobs and bougie job money, to make travel a reality, I:

  • Negotiate PTO when I take dayjobs or choose jobs where I have control over my PTO
  • Keep money in business reserves so I can pay myself even when I take a few weeks break from working
  • Tactically, I annualize my savings: $300/month for bigger travel over the year, have a smaller, flexible monthly budget line of $100 for random day-long or overnight getaways since I live somewhere jawdroppingly beautiful I like to go see, and put $150 a month towards end of year holidays [so I can buy my mom a plane ticket and everyone’s presents!]. 
  • I also use one credit card for most monthly purchases and pay it off every month, so I accrue credit card miles which I used recently to pay for my flight and half the hotel costs on a trip with my bb, which meant the cash I needed for the trip was only half of what it would have been otherwise

Back when I lived on $30k a year, my travel money looked more like:

  • Having jobs that were flexible about me travelling, and sometimes had PTO
  • Subletting my room in NYC if I was going to be gone a while
  • Saving $150/month
  • Traveling by getting brought in to talk, perform, teach – and then staying with friends or extending the trip to enjoy the location a bit more
  • Living short term places I wanted to visit, by working from somewhere and subletting for awhile, so as to enjoy the place and the people there a bit more without having to rush around


Not to yuck any yums here but … as climate change and the true cost of carbon usage awareness grows, the carbon footprint of all our travel is not trivial. You can, of course, do less air travel and choose train, bike, or other local traveling options. You can carbon offset your air travel [looking at you, Taylor Swift]. You can drive an EV instead of a gasoline-powered car on your trip. There’s no clear and easy answer besides the one you come to.

Whether you have PTO or self-fund time off and travel, how do you travel and make it work??