Getting the most out of time off

Time off is the only time my hours are mine. The rest of the year work owns them, and the roles I’d grieve losing — father, husband, the guy doing magic and balloons — get whatever is left over. A good break is when those roles eat first. But time off is a skill, and I’m not naturally good at it: left alone I vegetate, grind a to-do list, or sneak back to work. I’ve written up every break since 2020 so I’d stop re-learning the same lessons. This post is the distillation.

When you sacrifice identity for consumption, you end up with neither.

That’s the whole trap in one sentence — vegetating feels like rest, but it quietly starves the roles that make you you.

The flip side is just as reliable: if you plan to have a good time, you will. When I decide up front that I’m going to enjoy something, and set up the conditions for it, I almost always do. Enjoyment isn’t luck; it’s mostly the people I’m with and the memories I build, which are the two ingredients Brooks keeps coming back to in the appendix. Planning is how I get both into a trip before it starts.

Time off — off from what?

Everybody talks about time off. Nobody ever says time on — the missing half of the pair. But it’s hiding in plain sight: time on is when work owns your hours and you’re time poor; time off is when you get them back and you’re time rich.

Like being “money rich”, being time rich can solve lots of problems, but it comes with the same traps:

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The phases of time off

A common question is whether to take two short vacations or one long one. I don’t have an opinion on that, but I’ve learned my time off goes through a few phases, and I suspect each has a fixed time component. If I understand the phases, I can get more out of the break:

  1. Vegetation — getting over being tired.
  2. TODO list — crossing off the small things I’ve been putting off.
  3. Freedom — savoring the ability to do nothing.
  4. Personal development — realizing there are important-not-urgent things I can do at my own pace.

The phases get more pronounced with extended time off. For what happens when you take a full year off at 50, see the gap year paradox and my wrestling with the decision.

Vegetation

Work is stressful, it follows me home, and it takes several days to “drain”. Vegetation is that draining. It used to take me a solid week — these days I can do it in about a day. I guess I’m getting better at work-life balance.

Vegetating comes in three flavors: ignoring my responsibilities and task list, ignoring my habits and discipline, and ignoring my friends and family. Only the first one is actually fair.

Ignoring the task list — I deserve it. Ignoring habits feels deserved too, but that’s the resistance lying to me: habits are time-negative (barely) and energy-positive, so skipping them means less energy and feeling worse, a double whammy. Ignoring family is the least clear-cut; they want to enjoy themselves and I also need alone time, so the move is a fair balance, with expectations set and honored.

I want to skip Future me recommends
Tasks and responsibilities Ignore ‘em, you deserve it
Habits, exercise, and discipline Do them, you’ll have more energy to enjoy your vacation
Friends and family Seek balance, set expectations, and honor them

So, on behalf of future me: time-box it. Acknowledge I deserve to vegetate, take a day or two guilt-free, keep the habits, and at the end of the limit start fighting the resistance.

TODO list

Time is scarce, things to be done are infinite, and they pile up when time is limited. Once my work stress drains I get a burst of energy, and I apply it to the to-do list. This is very satisfying — I feel energized and productive.

The trap is getting stuck here, either grinding the list forever or avoiding it entirely, so I never make it to the later phases. Staycations are the worst for this: it’s easy to oscillate between vegetating, grinding the list, and ruminating on work. One way out: play tourist in my own city, off my Seattle list.

Freedom

With the list handled, there’s a stretch of guilt-free nothing. It’s different from vegetating — vegetating is being too tired to choose, freedom is choosing nothing. It’s short, and it’s worth noticing while it’s happening.

Personal Development (PD)

When I’m recharged and enough is off the list, I’m ready to build a better me. PD can be personal, like becoming a better writer or training for a marathon, or professional, like building a skill my career needs.

PD is essentially working from home, but for my future self, so it needs the same family expectations working from home does: a dedicated space, getting out of the house, a calendar they can see. And even though getting to do what I love is awesome, I still want to love my family. Time off is extra energy to spend on them, so spend it.

What to do about it

Strategize against the resistance

Fight the resistance by making addictions harder. For me, that means uninstalling TikTok.

And by making positive habits easier: writing a time-off list before the trip (every trip post below starts with one), remembering what my good habits are and how much better I feel when I do them, then running a habit app to make sure I do them.

Begin with the end in mind

  • Read my eulogy, to remember what matters most.
  • Remember not to procrastinate.
  • Remember what actually makes me happy:
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Re-stack your roles

Reading the eulogy reminds you which roles matter; time off is the chance to actually re-stack them, because ordinary life quietly mis-sorts them. I sort mine into three honest tiers:

  • Non-negotiables — protect first, daily. The two foundational Healths: Physical, banked before the family wakes up, and Emotional — awareness and compassion, handled as it happens. Everything else is built on these.
  • Frequently starved — feed these. Father / Husband, and the Joy Giver — the balloon-and-magic guy from the eulogy. The roles I’d grieve losing, and the exact ones I let go hungry when work gets loud. Time off is their window; the jovial me comes roaring back the moment I stop starving him.
  • Over-invested — dial back. Technologist, and honestly everything else, parked way below where they run in a normal week. Not because the work doesn’t matter — because it’s the finished room, and I keep redecorating it instead of walking into the ones that aren’t.

Try one-on-one trips

Instead of traveling as the whole family, take separate trips with one person at a time — one with each kid, one with Tori. I’d felt guilt around this before, but when I tried it, it worked amazingly well:

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The pro is that you can really focus on what you and that person want. The cons are that it feels less efficient, and that someone always seems to be missing out — but missing out is really about fairness. So the keys are: spend time with each family member so it’s fair and everyone feels included, and don’t forget to take time for yourself.

Every trip since 2020

Each break gets its own post: the plan written before I leave, then what actually happened. Newest first.

The rules

These are the learnings from every trip above, deduplicated. The stories behind them are at the end of the section. I need to re-read these before and during every break.

Before you go

  • Pre-write what I want out of the trip. Begin with the end in mind, then check in and tune as I go. Don’t overdo the list — it’s a break.
  • Plan the last day to be the best one. Peak-end rule: the ending is most of what I’ll remember.
  • Wrap up work the week before so there’s no work baggage. Load up the back-at-work list and trust I’ll pick it up.
  • Visualize the fight with the resistance. If I don’t plan to keep my habits, I won’t. Decide now when I’ll check in on the plan.
  • Write a won’t-do list. Mine: don’t get sucked into programming.
  • Write up my psychic weight. Just naming it gets it under control.
  • Logistics are separate: see Travel logistics and the packing list.

Every other day check-in

  • Refresh — re-read these rules and the trip’s priority list.
  • Know your real riches — is anything more valuable than satisfaction and health? Probably not.
  • Pay yourself first, do the habits — they charge me up and give me the energy for everything else. Magic and the hot tub count.
  • Use my own evaluation criteria, and beware sunk cost — what “should be best” usually isn’t. Am I actually doing what I enjoy?
  • Hobbies are fine as charging up — before the family wakes, and tell them the plan so expectations are set. Tech and content time before the kids are up is totally fine.
  • Handle the to-dos and psychic weight early — done or scheduled, so they stop dragging me down.
  • Check the relationship-time vs self-time balance — family and relationships are precious; so is time alone, for me and for them.

Physical health

  • Get a gym pass wherever I’m staying — a membership is cheaper than day passes, and it anchors the day.
  • Morning movement daily — 10–20 minutes of mobility or strength. On drive days, 5–10 minute micro-sessions at rest stops.
  • Bring light gear — bands, foam roller, something to self-massage with, and kettlebells in the car. Enough for a short, high-value session.
  • Do extra stretches and cardio — energy positive, and it keeps me injury-free.

Diet

  • Nothing tastes as good as skinny feels — true for every metric: feeling great, looking great.
  • No booze — those days are over for me. It wrecks my sleep and I feel worse. Cold shower instead. Airports included.
  • Bring a couple of favorite low-calorie foods I can make in the room, and a travel scale — weighing in daily keeps me mindful.
  • Airports: power bars. Road trips: a cooler, filled with fruit and vegetables that move to the hotel fridge.
  • Meds that need a fridge: see the tirzepatide appendix.

Where to eat

  • Eating out isn’t worth it for me. Honestly it’s not that enjoyable, and past 45 my gut can’t handle the grease — restaurant food leaves me feeling worse, not better. I’d rather eat simple.
  • Book a place with a kitchen. Whenever I can, I get a room or Airbnb with a kitchen so I can cook plain, non-greasy food from the grocery store instead of eating out.
  • Shop the grocery store. Some of my best travel meals come straight out of a supermarket — there’s nothing wrong with a cucumber, some fruit, and a rotisserie chicken. Cheaper, healthier, and you skip the wait.
  • Skip the tourist areas. The food ringing the big sights is overpriced and mediocre. Walk a few blocks out, or eat where the locals do — the meal is better and so is the bill.
  • Skip the hotel breakfast — but the motel breakfast is fine. The family loves the hotel spread and it’s a great deal, but I never should: I can’t afford the calories, and the greasy abundance just leaves me feeling worse. The motel breakfast is a different animal — easy, cheap, great for the kids, and modest enough that my self-control holds. Details under Diet → Hotel breakfast.

Emotional health

  • Pay yourself first — morning time to myself, early to bed, coffee shop time, gratefulness journal, meditation. It grounds me through the day and gives me the calm to figure out what’s essential.
  • Meditation travels — churches are perfect for it. No cushion needed. Old churches and cathedrals are some of the best rooms for sitting quietly: duck in, take a pew, be still. They’re built to slow you down; let them.
  • Have lots of slack (see Essential). Time with family is much more enjoyable when I’m not in a rush and success is just being with them. Same at the airport: hours early means delays don’t matter — I can write, meditate, do inner work.
  • Continuous learning — every mess-up is a learning opportunity. Learn what needs learning and move on.
  • Don’t berate mistakes. Caring is the emotional response, and it’s unavoidable; mattering is the objective difference the mistake makes, to whom, and over what time period. Most of my mistakes care a lot and matter not at all.
  • Don’t catastrophize. The “lost” credit card, laptop, and checked bag all turned up fine.
  • Stop panicking and think. There’s usually a fix.
  • Don’t fret micro-optimizations. The cycles I spend sequencing a day almost never change how it goes.
  • Remember the sublime states — loving kindness, compassion, altruistic joy, equanimity.

Identity health

  • Go to improv jams and dojos.
  • Do balloons for kids — they love them.
  • Do magic for folks. Find someone by himself to practice on; he won’t feel threatened.
  • Kettlebells are a blast — keep them in the car.

The stories behind the rules

  • Zero magic (Thanksgiving 2021). The one break I didn’t pre-write. I did what I wanted and got a tonne done, but got sucked into the tech and did zero magic — the thing that gives me the most energy. That’s where “if I don’t plan to keep my habits, I won’t” comes from.
  • The gym membership (FISM and Canada, 2022). A GoodLife membership was cheaper than day passes and let me do my top priorities daily. The last one I tried had a saltwater pool, a cold plunge, and massage chairs. Then the pool closed on my last day — grateful I’d had several days of it.
  • The sunglasses (same trip). Getting off the plane in Toronto it was blindingly bright. I opened my sunglasses case and found a second pair of regular glasses. OMG, this will be terrible. Meh — I spent 20 hours on the beach that weekend and it turns out I can squint. Then I remembered a friend was flying in and had him bring my sunglasses. Panic, then think.
  • The credit card and the bag (same trip). On the flight I realized I’d left behind the credit card the rental car was booked on, the one I needed for the insurance. Freaked out; it was totally fine. I also thought I’d lost my popcorn popper, balloon pump, and laptop — all in the extra pocket of my suitcase. Then my carry-on got force-checked and I was sure it was gone forever; it was right there, and while waiting for it I met a really cool person.
  • Belleville to Hamilton (same trip). I spent the drive working out what time I’d arrive and whether to do gym, work, my sister, or lunch first — lots of cycles micro-optimizing. It didn’t matter at all.
  • Ten hours of magic a day (same trip). At the conference I burned out on the thing I came for. Skipping the kinds of magic I like less, in favor of my other hobbies and seeing the city, was the right call — my own criteria, not the schedule’s.

Travel logistics

The packing master list lives at /packing — every trip is trimmed from it, so I won’t repeat it here. These are the non-packing learnings.

  • Flights: more legroom is usually worth paying for. Don’t take the seats in front of the emergency exit. Just get wifi for flights over 3 hours; don’t agonize. Nexus is well worth the hundred bucks.
  • Rental car: just get one if there’s lots of travel. Put the insurance on the credit card — and bring that card. Take 10 minutes to learn the car: wipers, locks, cruise control, fuel.
  • Leaving: pack the afternoon before so there’s no rush in the morning. Keep a leave list (Notion) so the recurring forgets get caught at the door, batteries charged. Leave for the airport 3 hours early; hanging at the airport is fine, and better than being late.
  • At the airport: Sudafed, earplugs, a bag with bands and a foam roller, and the balloon inflator for the kids waiting at the gate.
  • On the road: think through the daily routines and when I’ll do them — ad hoc doesn’t work. Re-pack the day bag so I’m not hauling stuff I won’t use. A fanny pack for keys and wallet so I’m not worrying about losing them. Book Friday and Saturday hotel nights ahead.
  • Forgot something? Buy it at Walmart or Target instead of suffering — it’s basically disposable. And check the extra pocket in my suitcase first.
  • Captive wifi portal won’t appear? Open http://captive.apple.com/hotspot-detect.html.

Road trips

  • Set an end-of-day stop that’s only 4 hours of driving, otherwise there’s not enough time to smell the roses.
  • Kettlebells and a club in the car, with 5–10 minute mobility sessions at each stop, every 2–3 hours.
  • Lots of audiobooks.
  • Cooler and the food plan from Diet, with a Walmart stop to fill it.
  • Pre-mount and configure the Insta360 before leaving — battery charged, card in, horizon lock — so it’s one-button ready for the cool stuff.

Other thoughts

Optimize for energy, not time

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Can you have too much time off?

Research suggests there’s a sweet spot. From this study:

Many people living in modern society feel like they do not have enough time and are constantly searching for more. But is having limited discretionary time actually detrimental? And can there be downsides to having too much discretionary time? We find a negative quadratic relationship between discretionary time and subjective well-being. These results show that having too little time is indeed linked to lower subjective well-being caused by stress, having more time does not continually translate to greater subjective well-being.

Having an abundance of discretionary time is sometimes even linked to lower subjective well-being because of a lacking sense of productivity. In such cases, the negative effect of having too much discretionary time can be attenuated when people spend this time on productive activities.

That’s the case for productive activities during extended time off, which is exactly what the gap year approach is about: rather than endless leisure, intentional investment in health, relationships, and mastery. See the gap year paradox for the full framework.

Appendix: 9 Rules for a Happier Vacation (Arthur Brooks)

I struggle to take real time off, so this one hit home. Below is my distillation of Arthur Brooks’ Office Hours episode 9 Rules for a Happier Vacation — he frames it as “me-search,” a fellow workaholic figuring out how to actually do this. Full transcript in this gist.

  1. Discern your motive before you book anything. Most unhappy vacations come from a mismatch — you want to escape, but you booked something intense and stressful. A 2015 study of Danish tourists found six core motives: exploration, escape, relationship-deepening (family/friends), prestige, nature, and history/heritage. Know yours (you can have a few, ranked), then design around them. Almost regardless of motive, sharing the trip with people you love amplifies the payoff — we’re social animals.
  2. Savor the anticipation. One of the happiest parts of a vacation is looking forward to it; studies of Dutch and Chinese vacationers show happiness rises in the weeks before the trip. It’s dopamine — the “wanting” neuromodulator — so feed it deliberately: book early, study your destination, learn about what you’ll see. (Brooks studied opera scores with his son for months beforehand.) Just don’t over-inflate it into a fantasy of constant bliss, or you’ll be disappointed.
  3. Manage your expectations about how long the glow lasts. Your limbic system isn’t built to keep you permanently happy — a great vacation lifts mood and energy, but a 2010 Dutch study found the effect largely vanishes by the end of the first week back. The goal is great memories and real recovery, not a six-month life change.
  4. Break one big trip into smaller “vacationettes.” Fifteen long weekends beat one month in Borneo for most people — more frequent, smaller doses give a more durable afterglow, since the next break is always around the corner. (See Effects of Short Vacations, Stress and Health.)
  5. Take fewer pictures. Photographing a moment pulls you out of it — you’re mentally living in the future-past instead of the present, and estimates put the enjoyment hit at 15–20% during highly enjoyable activities. Brooks’ compromise: assign one person per day to take all the photos; everyone else is off duty.
  6. Don’t post. This is the prestige motive (social comparison) hijacking your trip — you start living the vacation for other people’s envy, which reliably makes you enjoy it less (Journal of Consumer Research, 2018). Posting for the explicit purpose of sharing is the worst case. At minimum, don’t post while you’re still there.
  7. Leave your work at home. “Just a little work” is a trap for workaholics: a Stress and Health finding shows work activities lower the positive effects of vacation 1, 3, and 10 days after returning — it kills the glow. If you need to busy your mind, read something generative you’re not paid to learn instead.
  8. Come home early. Don’t travel up to the last second — get back a few days before you have to return to work so you can ease in. That buffer becomes a mini second vacation. Brooks aims to be home before the weekend rather than landing Sunday night into a full work week. (“Living each day as if it were the first day of your honeymoon and the last day of your vacation.” — Tolstoy.)
  9. Brace yourself on return and manage your feelings. A successful vacation sharpens the contrast with ordinary life, so the day-to-day can feel flat or frustrating coming back — like a carrot after candy. It’s completely normal; expecting it defuses it. Brooks’ policy: don’t make significant life changes in the first week back. Not being surprised is how you keep your feelings from managing you.

Appendix: Traveling with tirzepatide (or any med that needs a fridge)

Tirzepatide — and plenty of other meds — wants to stay cold. Three things make travel painless:

  1. A TSA-approved travel cooler. Holds cold for a full travel day, so the airport-to-Airbnb gap is covered:
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  1. No fridge in the room? Ask the front desk. Most hotels will happily stash medication in a staff fridge — just ask. And don’t assume the minibar cabinet is cold enough; confirm it actually chills.

  2. Pack the whole trip’s supply. You almost certainly won’t get a refill on the road, so count out a dose for every week you’re gone (plus a spare) and make sure the cooler’s big enough to hold them all.