Unwinding Your Way to Contentment

The pursuit of more is a slippery slope. It starts innocent enough. We enter the real world and get our first place. We see how nice our friends’ place is, so we also get something nice. Maybe we’ve been driving a beater for a while, so we decide to get an upgrade. After all, we’ve been working hard and we’re finally making grown-up money. Then the new iPhone comes out and we realize ours is already a few years old……better get a new one. One small step, then another, then another. None of these are inherently bad. But without knowing it, we’ve set into motion the ever-alluring and never fulfilling pursuit of more. As I always say, the problem with more is that more is still, well, more.

Fast forward 15 years, we have a significantly higher income than we started out with……and an inflated lifestyle to match. Then, it dawns on us: we’re just as stressed and discontent now as we were back when we had almost nothing. This is the fork in the road. Down one path is the continued pursuit of more. Maybe we just haven’t gotten to the point where we have “enough” to actually be happy. Maybe we’re one promotion, one trip, one house upgrade, or one additional zero in our bank account away. The other path? The other path requires humility. It’s an acknowledgment that perhaps we’ve been seeking comfort and happiness in the wrong things, then deciding to unwind some of our past decisions.

Two clients have recently decided to pursue the latter path. These are families who have achieved much success. Incomes most of us will never have, and lifestyles to match. Truth is, they aren’t happy. Life is moving fast, they are overly busy, their marriages are strained, and they feel quite discontent. So what are they doing about it? They have humbly and painfully decided to take a few drastic steps:

• Sell their house and downsize (one is purchasing a much small house and the other will rent)

• Downgrade their vehicle situation to something a bit more practical.

• Start saying “no” to various activities, trips, and memberships. This is an effort to create margin in their family time.

• Dramatically increase how much they give, taking the focus off them and putting it on others.

• Downshift their careers to stop focusing on an upward trajectory and lean in on creating a healthier balance.

These are no doubt counter-cultural decisions. They’ve already started getting pushback from friends and family, which is how they know they are probably on the right track. Whenever the prevailing culture pushes back against you, it’s probably a sign you’re doing something right.

They haven’t even implemented all these changes and they are already feeling better about their situations. There’s something empowering about knowing you have the power to unwind past decisions. It’s a constant reminder that everything is on the table.

Ignorance is Bliss, Until It's a Nightmare

Whenever I start working with a new client, there’s a moment early on when they have more money stress and tension than they did before we started working together. On the surface, it seems like the coaching is counter-productive. After all, the whole point of this coaching concept is to make things better…..not worse. There’s a universal truth in all this. Ignorance is bliss. Many people have very little day-to-day tension and stress when it comes to money. It’s not because their finances are in a good place, but rather because, “out of sight, out of mind,” as the saying goes.

Digging into our finances and facing reality on reality’s terms can dredge up a lot of junk. It’s like looking into one of those ultra-magnifying mirrors you see in some hotel bathrooms. It’s scary to see yourself that close. ALL the blemishes become apparent. Money is much the same way. When we look close enough, we won’t always like what we see.

This idea hit home recently when I had two contrasting conversations. The first conversation was with a friend who is somewhat critical of my work. by the way, I love when people I care about can engage me in conversations like this. It shows trust in each other, and I always learn something from them. His main point was he and his wife spend almost zero time talking about money in their marriage. They “just live life,” as he put it. He went on to explain they don’t really worry about what they spend, they don’t worry about saving, and they don’t worry about the future. Life is good, live in the moment, and it will all work out in the end. In some ways, I’m jealous of their approach to life. I wish I could be more like that at times. On the other hand, based on what he shared with me, I have a feeling where some of this will go a few decades down the road……and it’s not good.

In a subsequent conversation, I talked to a couple who was a few decades older than the guy I just mentioned. They explained how they used to handle finances, or rather how they didn’t handle them. The way they portrayed their younger selves sounded a lot like the man above. Fast forward a few decades, and they are freaking out. They lived a financially stress-free life, but now stress is barreling down on them. They are starting to realize social security isn’t nearly enough to support them, they didn’t adequately save on their own, and the clock is ticking. The reality is they will HAVE to work well into their 70s (or beyond). I don’t personally believe in traditional retirement and I hope to be working into my 80s, but it breaks my heart to see a couple work so hard for many decades, only to find themselves in a position with very limited options.

They gave me permission to anonymously share this story with you because, as they put it, they “wouldn’t wish this upon their worst enemy.” Harsh words. I feel for them, I truly do. So if I can give you any advice on this topic, it would be this: be willing to endure some financial stress and tension today (getting it right), because it’s so much better than what’s coming down the road. This couple deserves better, and so do you!