What We Can Learn from a Teenage Pop Star

How people who excel at their craft go about their business is something I’ve always found fascinating. Lately, my deep dive into the creative process has me on a music kick as I’ve watched The Head and the Heart, Notorious BIG, and Billie Eilish documentaries. (As evidenced by my musical tastes, my embrace of diversification clearly extends far beyond investment strategy!)

The Head and the Heart doc highlighted the powerful combination of good fortune and hard work while the Biggie doc brought me back to anthems of my teenage years. But I was surprised that the Billie Eilish doc, someone I knew little about and just happened to stumble upon, made the biggest impression.

At one point towards the end of the documentary, Eilish, still just a teenager herself, is asked in reference to her music, “Why be so transparent?” Here’s her answer:

“Why is that so shocking? I’m telling you about how I am as a human, like why is that weird?”

Ah, to be young again!

If that was your initial reaction, I totally get it. That was my reaction as well. However, that brought another question to the surface that I began to chew on.

Why do we become less transparent – with ourselves and others – as we get older?

I think the simple answer is that becoming less transparent can be the default. As we get older, life becomes more complex and the more complex life gets, the less time we have/make for self-evaluation. In the absence of self-evaluation, we take the shortcut of absorbing our social and financial norms from the people around us.

This default approach tends to produce a lot of what I call surface-level happiness.

Solid jobs with a nice house in a good school district? Check.
Saving for college and retirement? Check.
Regular family vacations? Check.

On the surface, everything looks great. Most people would happily trade places with you and you do feel quite grateful. And yet, it can still feel like something is missing.

How do we explain that feeling? Is it just something we have to learn to live with?

Without self-evaluation, we tend to lack clarity around our personal values and default to societal values instead. Absent our own personal values, our financial decisions also tend to default to social norms. This disconnect explains why it can always feel like something is missing when everything on the surface looks great.

The good news is that this is fixable. The bad news is that the solution requires vulnerability and introspection that will feel uncomfortable at first. However I can assure you that this discomfort is well worth it for your own future well being.

We can start by committing to being transparent with ourselves again. This also means learning to accept that what really matters to us might be different than what society tells us SHOULD matter to us. Luckily, we grow more comfortable with this disconnect once we’ve aligned our financial lives with what matters most to us. That low-grade angst is replaced with the intestinal fortitude of knowing that your personal values and finances are now aligned.

Again, I’m not suggesting that it is an easy leap to make. It will require some hard work on your end. That’s why it can help to reflect on past experiences where you struggled initially — only to preserve and overcome. When we look back on these experiences, we remind ourselves what we’re capable of and the pride we now feel in overcoming those challenges.

There’s no better time than now to be more transparent with yourself, start to figure out what you personally value, and begin aligning your money and life with what matters most to you. For my money, it’s the best return on investment I know of.

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