How much do you give your kids?

My wife and I just got back from vacation with our kids. It was a great vacation–surprisingly so, since whenever traveling with little kids, we anticipate having a change in scenery more than a vacation per se. The place we stayed is located on a stretch of beach that is known for its many resorts, some of which are quite exclusive. In our pre-kid days, those are the places we would have stayed… we wouldn’t have even considered anything but the best of the best. With tykes in tow, however, a different mentality took over, and we opted for a place that we found on the internet that was cheaper, less exclusive, and that none of our well-traveled friends had ever heard of before…

The resort we chose turned out to be fine. Actually, it was better than fine… it was great. Our hotel was part of a 2 hotel + residences complex with seven restaurants (the food was surprisingly good), six or more pools (I lost count after five), live entertainment every night, an incredible beach, access to the local town, condos instead of rooms (that were unexpectedly high end), and refreshingly good service.

Still and all, once you’ve honeymooned at a Four Seasons resort, you’re pretty much spoiled for life. Look at the first line in the last paragraph to see what I mean: my first instinct was to describe the place as “fine,” when in fact it was great. But because it wasn’t the Four Seasons, I felt compelled to ding it. Regardless of how I like to view myself, or how well I think I take things in stride, that reaction means that, at least to some degree, I’m spoiled. I’ve had the best of the best; by comparison, everything else is–to paraphrase an entrepreneurial client of mine–just a different level of suck.

And hence the dilemma: when do I introduce my kids to the best of the best? As far as the resorts go, it’s a moot point–I don’t have the cash to make them relevant–but it may not always be moot, and in other areas of life, the question is real: Do I start them off with “good enough,” or launch them straight to the top? The latter risks spoiling them; the former means they grow up with less than they could have… and neither guarantees that they learn to appreciate money.

So how do I keep them from becoming spoiled? I’ve thrown the issue out to a number of people, and so far, it always seems to elicit a fast and clear response. A different fast and clear response, to be sure, but a fast and clear one nonetheless. Upon reflection, however, everyone I’ve engaged has backed off their initial positions and come to a place of some doubt. The thing that surprises those who say, “Start ‘em off with less” is the realization that, even at the “top” of the food chain, there is still a pecking order–those who drive Mercedes know the difference between the V12 SL500 and the V8 SL500, for instance–so it’s not like there is ever some pinnacle reached whereby the issue goes away. (Even for those born into F-U money, or who have sold enough books to earn it themselves–ahem–someone always has just a little bit more.) And on the other side, those who say, “If you’ve got it, spend it,” are stopped by the thought that they might be setting up their kids for future disappointment… can you imagine the pressure on a child who grows up with everything? How does that kid get excited about a job out of college earning $43,000 a year and the prospect of a long climb back to a place she had already spent her first 18 years? (Is it any wonder today’s young professionals are so disenchanted?)

We all know that money is not the measure of the man, but in a capitalist society, where we use money to price and therefore allocate scarce resources, we are mentally conditioned to think otherwise. It’s a tough mentality to break out of… if you live below your means, you can feel compelled to “cheat” a bit at the margins, to sneak some extra resources for yourself just to take the edge off, which pretty much defeats the purpose. If you stretch, then you expose your limits and risk having to come down with a hard “no” just as the party’s getting fired up. To be clear, this isn’t a question of financial discipline. It’s a question of emotional messiness, and it exists regardless of how much discipline you have or don’t have.

So where do I stand on the issue? I think the attitude my wife and I demonstrate in front of our kids is paramount. I think it’s not what you have, it’s the attitude you take toward what you have… not only to be grateful for it, but to be aware that material benefits are ephemeral, and to appreciate the moment for the people in it as opposed to the clothing worn during/location of/things used in the moment. The idea is to spend the money on things that will make them truly happier, as opposed to spending it because we can, or because someone will be impressed. There is a time to splurge, and a time not to. You’ve got to know the difference, and you’ve got to help your kids recognize it, too.

Sometimes, of course, money is an issue. To the extent possible, we try to constrain their choices to things that won’t bankrupt us through non-financial means. (“A pony? Really? Have you ever thought about how much a pony eats… and how much a pony poops? Do you really want a bunch of pony poop in the backyard where you like to play? What if you fall down in it? Yuck! I’d have to give you a shower with the hose before you came in the house because you’d be all stinky from the pony poop! What? You think maybe a goldfish instead? Hmm… that sounds like it could be a good idea…”) And if we can’t, we’re honest: “That would be fantastic; too bad we can’t afford it. OK, who wants dinner?”

Can you give your kids too much? Definitely. But I think that has more to do with a state of mind than with the actual quantity of stuff you give your kids. I don’t think it’s giving them the best of the best or less that makes the difference; it’s knowing when the best of the best is called for and doing it then. But we’ll find out. I’ll blog again in 20 years and let you know how if our parenting philosophy worked or not.

Jason Seiden is Co-founder and CEO of Ajax Social Media, a training company that shows professionals how use social media to work more effectively.