How to Plan a Big Family Trip Without Becoming the Griswold’s

Research shows that spending money on experiences often brings more lasting joy than buying more “stuff.” Now imagine the joy and connection that comes from planning a big family vacation—one that creates memories for generations to come. I believe Clark Griswold knew the value of such trips, but he clearly had trouble pulling it off.  While getting everyone aligned may feel challenging, it’s also what makes the journey worthwhile. Let’s go over some key steps to ensure your family adventure is one for the books.

Open the Dialogue Early

Nobody enjoys being dragged along on someone else’s vacation. The key to a successful family trip is making sure everyone feels included from the start. Whether some family members are retired with flexible schedules or others are balancing school, work, and activities, it’s important to consider everyone’s situation.

Start by agreeing who is the ‘champion’ of the planning overall.  Someone must be responsible for organizing the communicating the plans.  Then start gathering input from everyone—use a group video chat, shared document, or a family meeting to talk through options. This gives everyone a chance to voice what works for them and helps you find common ground. Collaboration early on can make all the difference in pulling off a trip everyone enjoys.  Obviously this will look different if you are traveling with younger kids, but you know that they have opinions too!

Balance Togetherness and Individual Time

When planning a vacation for a large group, it’s crucial to strike the right balance between shared experiences and personal space. Not everyone will want to do the same activities, and that’s okay. Whether it’s golfers heading out for a round while others enjoy a spa day or different groups exploring different sights, the key is flexibility.

Plan a few moments for everyone to be together—like beach time or family dinners—but also allow space for each person to pursue what excites them. This balance will help everyone enjoy the trip in their own way without feeling overwhelmed or restricted.

Be Clear About the Budget

Few things create tension faster than money talk, especially in a family setting. If each family is paying their way, aim to pick a destination that fits most people’s budgets. If one person is paying for it all (ie, mom and dad), be totally clear about that from the beginning.  This ensures everyone can enjoy the trip without feeling financially strained.  Or worse, living in the uncertainty of ‘who is paying for what’?

If you are generously covering the cost, having a clear budget in place is even more important. Setting limits upfront helps ensure you don’t overstretch yourself financially, allowing you to fully enjoy this special experience with your loved ones.

Thinking ahead about your travel budget and ensuring that this family vacation fits within your broader financial goals will allow you to focus on making memories instead of managing costs.  This is what it is all about!

 

I have a Lump Sum in Cash – Should I Invest It Right Away?

Whether it’s a work bonus, inheritance, or proceeds from selling a business, receiving a large sum of money can leave you wondering, “What do I do with it now?” It’s natural to feel a bit stuck—especially with the market going through its usual ups and downs. Do you invest it all at once, or spread it out over time?

This is a common question, and honestly, it’s understandable. We all worry about making the wrong move—invest too soon and the market might drop; wait too long and you could miss a rally. But there’s no need to over-complicate it. Let’s break down your options.

Start with Your Goals

Before diving into the numbers, ask yourself: What do I want this money to do for me?

If you’ve got short-term goals, like paying for your kid’s college tuition in the next few years, you may want to lean toward more stable, less risky investments—think bonds, bond funds, or CDs. These are less likely to be impacted by the market’s short-term swings.

On the other hand, if this money is for long-term goals, like retirement, then putting it into the stock market might make sense. Over the long haul, markets tend to rise, despite the short-term ups and downs.

Lump-Sum vs. Dollar-Cost Averaging

Now, should you invest all the cash at once or spread it out?

Lump-sum investing gets all your money into the market right away, which could be great if the market’s on the rise. But no one can predict the future, and there’s always a chance the market dips right after you invest. If that possibility stresses you out, dollar-cost averaging (DCA) might be more your speed.

With DCA, you invest a set amount regularly—say, $1,000 a month for a year. When prices are high, you buy fewer shares; when prices drop, you buy more. It’s a steady approach that smooths out market fluctuations over time.

However, here’s the kicker: research shows that lump-sum investing tends to outperform dollar-cost averaging about 68% of the time. So, if your main goal is maximizing returns, lump-sum might be the way to go. That said, the difference in returns between the two strategies isn’t massive, so if dollar-cost averaging helps you sleep better at night, it’s worth considering. After all, the last thing you want is to panic and sell when the market dips.

The Bottom Line—Don’t Wait

Whether you go with lump-sum investing or dollar-cost averaging, the most important thing is not to delay. Holding onto cash means missing out on potential growth from stocks and bonds. And trying to time the market? That’s a tough game to win.

In fact, studies show that average investors who attempt to time the market often miss out—by as much as 5.5% compared to just sticking with the S&P 500. So, whatever you decide, get started. Both approaches will help you benefit from the market’s long-term upward trend, which is key to achieving your financial goals.

Need help figuring out which approach works best for you? Reach out, and we’ll walk through it together.