Wealthsimple makes powerful financial tools to help you grow and manage your money. This is the latest installment of our "Dear Ms. Etiquette" series, in this edition The Financial Diet guest-answers your money questions.

Dear TFD,

Somehow I found myself as the de facto “leader” of a group of close friends who are planning a vacation this summer. But everyone has wildly different budgets and incomes. I’m confused: if I gear it for the person with the smallest budget, a bunch of people will be super bummed. If I don’t, I’m making it so the folks with less money can’t come. Help!


Sincerely,
Mr. Reluctant Budgeter

Dear Reluctant,

First and foremost, apologies for having become the guy in charge of all the plans, as the term “de facto” implies that this is not something you sought out. Speaking as the friend who actually enjoys assuming the Chairman of the Social Activities Board role (and who gets a visceral thrill from sending out highly-detailed spreadsheets of hotel and flight options) I know that even as a purposely elected official the task can be daunting. So doing it as a reluctant appointment is probably maddening. I don’t know if it’ll make you feel better, but it's normal to feel a little anxious, since an unwritten part of the job description here is helping to figure out and then resolve amicably the inevitable disagreement or unspoken resentment between factions. And they are inevitable. So my advice to start is: understand you’ll probably end up trying to be both guidance counselor and referee (without offending any party) — a delicate social tightrope to walk. Heavy is the head looking over the spreadsheet but the fact that you’re even thoughtful enough to ask this question means you’re already ahead of the game.

#1: It’s Not You. It’s Money. The question of money on a group trip where everyone is coming from varied financial situations is intrinsically uncomfortable. Because in just about any social group, money is still a highly taboo topic and most people have a hard time confronting it head-on. So don't think you're being weak by not wanting to make someone feel singled out or self-conscious about their inability to afford something — you’re being considerate. Give yourself a pat on the back for not being sadistic.

#2: Have the Conversation Early. That being said, the truth is that one must preempt this issue as early and effectively as possible. Vacations are like a kind of low-key, unfilmed reality show where people are essentially trapped in a hotbox of social pressure for a week, and money issues won’t make it easier, that’s for sure. If you don’t face the reality that people have varying budgets before you make plans, you'll help ensure some people won't be swiping their credit card for things they can’t afford, or forced to make the uncomfortable announcement mid-vacation that these dinners at lavish restaurants are coming into conflict with their ability to pay rent this month. It’s frankly cruel to put someone in that position. So be budget-inclusive when planning the trip — travel, lodging, group activities. Ask everyone individually what they can afford so no one feels embarrassed. Then present the best option to the group. If people with more money don’t want to shack up at the place people with less money can afford — well, maybe it’s not a group that should vacation together.

#3: When in Doubt, Debt is Worse Than Lack of a Pool. While it’s true that people have the right to vacation in the manner they prefer, you also have to account for a simple financial truism: the worry of your wealthier friends not feeling “super bummed” by a budget-friendly agenda is trumped by not putting your less-wealthy friends in a position where they feel required to go into debt in order to be friends with you. This is a really important idea, whether you’re going on vacation or out for dinner: no one should feel ashamed of their budget. We all make different amounts of money, and unless you only want to be friends with people in your income bracket, we all have to take that into account. We should always be deferential to the people who are in a less privileged financial position, not only because it’s ethically the right thing to do, but because it’s the only way to ensure that everyone can actually participate and hang out together. And even if financial well-being wasn’t paramount, if folks go along with something they can’t afford out of some sense of obligation, the subtle resentment and anxiety radiating off of those people overextending themselves is guaranteed to bring the entire trip down. And rightfully so.

#4: Not Everyone Needs to Take Exactly the Same Trip. There are still ways to make it possible for everyone to have the vacation they want. First: make sure that the basics of attending the trip — the travel, the lodging, a few key group meals and activities — are financially accessible to all participants. Then, because some of your luxe friends might feel incredibly deprived if they’re not able to have a shopping afternoon montage set to Hoku’s “Perfect Day,” leave space in the agenda for people to have totally optional activities at increased price points. Think things like after-dinner cocktail bars, afternoons where several sub-groups can break apart, or even an evening where everyone does dinner on their own terms. Allowing everyone to sort of curate the “extras” they feel comfortable with while being able to participate in the most important group moments will help people stick to their financial comfort zone. And frankly, any group vacation is always better with several explicit windows of time for people to do whatever the hell they want. Some people may indeed end up going out and buying oil paintings, but others (say: me) may end up preferring to stay in their room, not talk to anyone, and watch SVU on their laptop for an hour or so.

Long story short, your job here is to make sure that no one ends up regretting this trip because it messed up their financial future. It might feel like a lot to balance at first, but in my experience, you’ll find that the trip will be so much more fun when you know that everyone can comfortably enjoy it.

And as de facto leader of this friend trip, you don’t want to end up getting de facto guillotined when the revolutionaries come for whoever enabled some overly expensive and tedious agenda.

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