Advice on travel & adventures.

How should you approach booking travel/accommodation when life circumstances might change?

Focus on controlling the controllables — book affordable accommodation in advance when prices are low, even if upcoming life changes (like a new baby) make timing feel uncertain.

What's a sound long-term investing strategy for beginners?

Rather than trying to time the market or bet on single companies, invest for the long term in index funds (such as one tracking top NASDAQ companies), following Warren Buffett's approach.

What's the key lesson for a long remote road trip like driving to the Twelve Apostles?

Plan out exactly where you'll refuel in advance rather than assuming a petrol station will appear — remote stretches can go much longer than expected without services.

How do you avoid overweight carry-on luggage fees at the airport?

If your carry-on bag has heavy equipment like camera gear, take it out and hold it while the bag is weighed, then put it back into the bag once you've cleared the weight check.

How do you get a young child to accept limited music choices on a long car trip?

Prime the child beforehand with a believable reason (e.g., the car was serviced and music options are limited) and offer a simple binary choice, such as 'Daddy's music or nothing,' so they feel in control while you still manage the actual music played.

How can a family create a music playlist that works for everyone on a road trip?

Hold a dedicated 'playlist organising' session where each family member shares their favorite tracks and the child picks favorites from each parent's selection, blending everyone's music into one rotating playlist.

What should you do if you find someone's lost wallet with cash in it?

Track down the owner using identifying information (like a licence) rather than keeping the cash, and if they try to reward you, you can initially decline before accepting — don't let others who didn't help claim a cut.

How can you make the most of networking at a conference?

Lean into the mindset of being in 'your world' at a conference — actively seek out people you know or want to meet rather than hanging back, since everyone there is open to the same kind of connecting.

How can you find cheaper international flights when corporate travel agents quote high prices?

Josh and Naysan found that going directly through sites like Skyscanner, or using a browser without tracked cookies, and splitting a trip into multiple separate flights (rather than booking through a travel agent) got them a much cheaper fare than the quoted $5,500.

How can you negotiate a free stay at a holiday rental in exchange for content?

Offer to produce a shout-out plus a mix of photos and video; if you can't film or edit well, lean on friends/partners who can, and consider turning it into a structured piece (e.g., a real-estate style video, a sit-down interview, or a highlights reel) rather than vague 'content.'

What should you do if you discover an Airbnb booking isn't the private space you expected?

If sharing with the host feels too uncomfortable, it's reasonable to cut your losses, explain the misunderstanding, and leave rather than stay somewhere you don't feel comfortable, even if it means forfeiting money already paid.

How do you know if your writing is good?

George Martin argues that a hallmark of good writing is being able to read it out loud naturally; if it doesn't read well aloud, it suggests a forced or 'poser' writing style.

Soggy pie vs soggy sausage roll — which do you choose?

Tommy's stated rule (recounted from his blog) is that a soggy sausage roll beats a soggy pie if you have to choose between the two.

Is it a good idea to dip into your superannuation early during a financial crisis?

Avoid withdrawing early superannuation if possible — pulling out even $20,000 early can cost around $120,000 in lost growth by retirement, and the early-access scheme was really designed for sole traders who rarely contribute to super anyway.

How should you handle hygiene and reduce infection risk when coming home during a pandemic?

Scott Tweedie describes a strict at-home routine: removing shoes and a layer of clothing right at the front door, then using disinfectant wipes on everything touched outside (phone, EarPods, bank card) before fully entering the apartment, treating it like a personal quarantine checkpoint.

How do you negotiate a job move overseas while still under contract with your current employer?

Tweedie suggests playing it cool in negotiations (not appearing desperate), working through visa requirements with an immigration lawyer early, securing a reasonable get-out clause from your current contract, and keeping the move confidential from industry outlets until the new employer is ready to announce it themselves.

How do you manage your social energy while travelling long-term?

Recognise that energy flows both ways — sometimes you need to give energy to others and sometimes you need to withdraw and let your own energy be replenished; it's okay to go days without talking to anyone if that's what you need, and pushing yourself out when you shouldn't isn't good for anyone.

How do you keep a travel/reality show from being exploitative or offensive toward other cultures?

Choose subjects who are already passionate about and having fun with their own unique pursuits, enter into their world and share their enthusiasm rather than mock differences, and aim to highlight what's universally fun rather than what's culturally divisive.

Should a growing business self-manage its web hosting?

Don't let a non-specialist run system updates on self-managed hosting; find a provider (ideally local) that can be reached immediately when something breaks, rather than relying on overseas support.

Is it okay to pull kids out of school for a family trip?

According to a book Derek read, it doesn't matter if you take kids out of school before year 7 (primary school) for travel, as they'll likely learn more life skills travelling with parents than they would in class.

How can you find genuine connection with interesting people while travelling?

Tommy suggests that connecting with people outside their normal habits and routines opens them up more, which is part of why meeting guests on a trip like this produces more meaningful interactions than usual.

What's a practical travel packing tip for liquids like cologne?

Make sure bottles with press-down tops have a cap/lid on them and ziplock them in a bag to avoid leaks while flying.

How should you word an awkward request to an Airbnb host about appliance usage?

Frame it around a practical need (e.g., 'we've got dirty clothes from being out and about, are we okay to use the dryer and washing machine each night?') rather than asking if there's a limit, which can come across as presumptuous.

Is it okay to want solo time while travelling with friends?

Tommy suggests that even while travelling as a group, it can be valuable to occasionally go off by yourself—for a meal, a walk, or just to be in your own head with music—without it being an antisocial gesture.

What should schools teach that they currently don't?

Will Connolly suggests schools should teach deeper connection with others and yourself, remove the pressure of marks/scores, and let students explore and find their passion rather than breeding ego through competition.

When is it okay to drink before a long flight?

Don't drink the night before and arrive hungover—that's not 'a drink before a flight.' Instead, drink in moderation once you're actually on the long-haul flight, and sort out a vegetarian meal through your airline status in advance if needed.

Is it okay to recline your airplane seat?

Avoid reclining your seat on short flights (under about 90 minutes); check if there's anyone seated behind you before reclining on longer flights as a courtesy.

How should you book seats when flying with someone else?

Tommy recommends booking two aisle seats across the row rather than seats directly next to each other, so you get breathing room but can still talk and have better banter with cart staff.

Should a daily podcast launch a separate weekly spinoff show?

Ash advises against it, saying a 'weekly' version under a similar name would muddy the branding of an established daily show, and recommends either dropping 'talk show' from the new name or keeping the two clearly separate.

Is private health or life insurance worth having if you don't have kids?

Citing the Barefoot Investor, Josh suggests not bothering with certain insurance if you don't have kids and don't earn over a certain threshold, noting that without dependents the personal value is low.

How do you get a disposable/film camera through airport security?

Josh advises declaring a film camera to TSA officers rather than letting it go through the X-ray scanner, since the X-ray can damage film.

How do you overcome imposter syndrome when pursuing big opportunities early in a project?

Josh argues that feeling undeserving of big opportunities (like interviewing Seth Godin with a tiny audience) is common imposter syndrome, and that you have just as much right to pursue those opportunities as anyone else — the key is putting yourself out there regardless of where you currently stand.

How can you plan an affordable long-term trip or travel budget?

Tommy recommends using sites like Nomad List to compare cost of living, safety, internet quality and other livability factors across cities, and Star Alliance's multi-city tools to price out round-the-world itineraries, plus tracking a spreadsheet of city-by-city costs while traveling.

How should parents handle a child who overspends like this?

Trevor Long says you can't let a kid rack up a bill like this without consequences — docking pocket money or restricting car use so they actually learn from it.

What should you do if you're unsure whether hotel minibar or room service items are free?

Always check the pricing list before consuming anything in a hotel room — if your card isn't the one attached to the booking, question whether items are actually complimentary rather than assuming they are.

What's the key lesson from the hotel minibar mishap?

Read the minibar price list before using anything in it.

What should you do if you get a phone call while your car is being serviced?

Be wary of mid-service phone calls proposing extra paid fixes (like wheel alignment or air-con mould repair); consider declining add-ons that weren't part of the original fixed-price service and pick the car up at the agreed time instead of engaging with upsell calls.

How do you avoid the touristy/bogan Bali experience?

Avoid Kuta and Legian; stay in Seminyak or Canggu for restaurants and then move to a secluded resort further south for part of the trip.

How do you grow through travel if you're naturally a homebody?

Deliberately put yourself into uncomfortable situations (like travelling alone without knowing the language) because you know it will be good for you, even if it doesn't sound appealing beforehand.

What should you check before booking a basic camping pod on Airbnb?

Confirm in advance whether the listing includes linen, pillows, sleeping bags, or power, since this pod only had two thin plastic-coated mattresses and explicitly listed no power or linen.

How do you make a connection with someone you've just met turn into something real?

Act on the small, seemingly silly impulse to reconnect - find any excuse (like a found hat) to make that first follow-up contact, because it can lead to a lasting relationship.

How can you carry the confidence you feel while travelling into your everyday life?

Josh suggests identifying one thing you'd do if on holiday—like getting up to take photos of the sunset or talking to strangers—and trying to actually do that same thing at home, rather than only feeling free when abroad.

Should you book the last flight of the day when flying between cities with airport curfews?

Avoid the last flights out before a curfew (e.g., Sydney to Melbourne), since those are the ones most likely to get delayed or cancelled, potentially stranding you overnight far from the airport.

What's the best way to pack for a trip?

Josh recommends packing the night before a trip to maximize sleep and avoid the high chance of 'fucking shit up' in the morning rush.

How can you reduce end-of-year stress about holiday plans?

Book a holiday or share house up to a year in advance so friends have a default place to gather, rather than scrambling each year to decide what to do for summer or New Year's.

What kind of travel is most transformational?

Josh suggests smaller, single-focused intentional trips may be more transformational than long trips where you're also working (editing, podcasting) and get absorbed into daily travel habits.

What should I pack for long-haul flights to stay comfortable?

Tommy recommends a toiletries bag kept accessible (not buried in checked or carry-on luggage) with eye drops to hydrate the eyes, painkillers, asthma medication (e.g. Ventolin) in case of emergency, a toothbrush, and a beanie to pull over the eyes for sleeping.

How should you manage money while travelling for a long period?

Set a budget on a weekly rather than daily scale so you have flexibility day-to-day; if you overspend one day (e.g. $280 on dinner), you'll have buffer to spend less elsewhere, rather than obsessing over every transaction.

How do you resolve arguments while travelling as a couple?

Deal with conflict immediately rather than letting it fester, since while travelling you don't have the usual escape of going to work or seeing friends to cool off separately.

How can you get good tickets to a Broadway show without spending a lot of money?

Arrive about an hour before the performance and enter the venue's ticket lottery; winners can buy some of the best seats in the house for around $36 cash, with ID required.

Does the quality of your camera gear matter when creating content?

Tommy argues it's not about the gear you use but what you do with it, noting he created a successful web series using only a basic point-and-shoot camera.

How can I avoid overpaying for a US ESTA visa application?

Don't click the paid ad listings that appear first when searching 'ESTA' online, as they charge inflated fees (up to $120); instead search something like 'ESTA scam' to find the legitimate ~$14 official site, or better, use the Smart Traveller website which links directly to the official visa page.

Should I worry about posting on social media while travelling on a specific visa type?

Be cautious about what you post on social media while travelling, since officials could use it as evidence against your stated visa purpose (e.g., posting about filming a documentary while on a tourist visa) if you're pulled aside for further questioning.

What should you do if you feel unexplainably stressed, even while on holiday?

Write a dot-point to-do list of everything on your mind; unaddressed tasks nag at you subconsciously even when you think you have no responsibilities, and getting them down on paper brings clarity.

How do you avoid feeling ripped off while travelling in cheaper countries?

Josh advises against fixating on small price differences (like paying $2 instead of $1 for a drink) since the absolute cost is still low in real terms; he suggests keeping perspective on what things actually cost rather than reacting emotionally to relative price jumps.

How can I compare the cost of living between travel destinations?

Use the website Nomad List to compare costs like coffee, a bottle of Coke, and monthly accommodation across different cities, which is useful for travelers zigzagging between expensive and cheap locations.

What's a good way to quickly learn a new city's history while traveling?

Take a free (tip-based) walking tour, typically 1.5 to 2.5 hours, to get steps in, see the city, and learn its history before tipping the guide at the end.

Where should I travel if I want an affordable, worthwhile European destination?

Consider Poland, particularly Krakow, for its low cost of living, good food and coffee, and the opportunity to visit Auschwitz for historical perspective.

How can you budget for restaurant meals while travelling in expensive parts of Europe?

Tommy advises sharing one meal and sticking to water or sparkling water rather than ordering drinks, warning that ordering a full meal each with drinks at scenic waterside restaurants can easily balloon the bill.

Should I get a group boat tour or a private boat tour when visiting Capri/Italy?

Get the smaller "private" boat tour with around 8 people rather than the big group boat with 25-30 people; it costs about €90-110 each but is worth it because you get lunch included and a much better experience.

How do I avoid having to socialize with strangers on a boat tour?

Pretend you're seasick (you don't even have to actually vomit, just look queasy) so people will leave you alone, or claim you don't speak English.

How can you manage bad wifi while travelling and still watch YouTube content?

Josh recommends subscribing to YouTube Premium and downloading videos while on good wifi so they can be watched offline later without using data on poor connections.

Should you trust that big infrastructure promises (like a train line) will actually happen on time?

Josh suggests not getting excited or making plans around announced infrastructure timelines (using the NBN as a cautionary example) until the project is actually complete.

How much bottled water should you buy when staying in a hotel short-term?

Don't buy more bottled water than you need just in case — buying excess water that gets left behind or thrown out when you check out is wasteful and counterproductive.

How can you make small talk more interesting or meaningful?

Lead with big, direct questions (like asking what's the best part of someone's day) rather than generic small talk, even if it occasionally overwhelms the other person.

What should you do when you make an embarrassing mistake while speaking (e.g. mispronouncing a word)?

Commit fully to the mistake, say it confidently, and own it rather than trying to backtrack or hide it.

How should you handle currency conversion when travelling so you don't overspend?

Josh advises doubling euro amounts as a conservative estimate to get a realistic sense of the Australian dollar cost, arguing you should never treat foreign currency as equivalent one-for-one to home currency.

What's a better way to judge prices abroad than constant currency conversion?

Tommy suggests comparing relative local prices (e.g., treating a local coffee price as roughly equivalent to what you'd pay at home) rather than converting every single purchase, since doing so for every item becomes a 'nightmare'.

How can I get the exact hotel pillow or bed I loved on a trip?

Take a photo of the pillow or bed's brand and exact model while you're staying there, then order the same one online for your own home.

How can listeners support the podcast?

Rate the show 5 stars on iTunes/podcast apps, and leave a written review at the same time as rating it, since you can't go back and add a review after rating alone.

How can I navigate overseas without relying on mobile data?

In the Google Maps app, type 'OK Maps' to bring up a selectable region, resize it to cover the area you need (up to roughly a state-sized area), and download it so you can navigate offline without phone reception.

What should I be careful about when travelling internationally through different countries?

Be careful about what's in your pockets or bags (even residue), avoid volunteering information about filming/work to border officials since it can lead to extra scrutiny, and know that passport stamps from certain countries like Israel can cause issues entering other countries later.

How can I stop leaving my belongings scattered everywhere while travelling?

Use the 'invisible box method': designate one consistent spot (no tape or markers needed, just a mental square) in each hotel room for your wallet, keys, and phone so you always know where they are and don't leave things behind.

How should I behave as a guest in someone else's home (e.g. Airbnb)?

Keep toiletries and belongings contained in a bag and confined to your own room rather than spreading them around shared or host spaces, to avoid being an imposing guest.

How do people get into business-class airport lines/lounges without proper checks?

Tommy suggests walking up confidently and acting like you belong, noting that staff often don't actually verify business status or tickets.

How much gear should you pack for a filming-focused trip abroad?

Don't overthink it or overpack — travelling with heavy, bulky camera gear (like a big DSLR with multiple lenses) becomes exhausting and often goes underused; work within the limitation of a smaller camera to force better storytelling.

Does expensive equipment matter more than storytelling for online content?

Look at what performs well online — plenty of creators have massive impact despite using basic, low-production-value gear, suggesting the story itself matters more than the camera used to capture it.

When should you tip at a restaurant in Australia?

Josh says he tips at good restaurants but not at others, reasoning that at nicer places staff are often well-paid already but tipping is still a way to acknowledge good service and conditions.

How can I improve my sleep?

Get adequate sleep, turn your phone off or put it on do-not-disturb, and avoid drugs that disrupt sleep.

What's the best type of luggage for traveling through Europe?

Use a backpack (front and back) rather than a roller suitcase, since many European destinations like the Amalfi Coast have cobblestone streets and limited vehicle access that make rolling luggage impractical.

What should you do before traveling overseas with credit cards?

Call your credit card companies ahead of international travel to notify them, otherwise they may flag and cancel your card while you're abroad.