When is it OK to Pursue Our Dreams?

I don’t think I would ever get a tattoo, but if I were to get one, it’d almost definitely be a hollowed-out pyramid of Maslow’s Hierarchy of Needs.

Take a moment to indulge your flashbacks of Psych 1000

It’s a cool geometric shape. It’s quirky enough to improve my sense of individuality and my ability to start conversations. I would probably get the tattoo on one of my calves to bring more attention to how massive they are.

Abraham Maslow, whose calves were undoubtedly smaller than mine, was a psychologist that published this theory of motivation back in the 1940s.

Related image

You can’t see them here, but you just get the sense that they’re not very large

Maslow’s widespread theory of motivation ranks the order in which people naturally tend to pursue goals, ranging from immediate physical needs to personally fulfilling ambitions.

The first four categories (Physiological, Safety, Love and Esteem) represent deficiency needs that are said to arise due to deprivation. The fifth and final category of Self-Actualization is said to stem from one’s desire to grow as a person. Maslow essentially lays out a satisfaction tier list, with the presumed eventual goal of pursuing self-actualization.

In practice, it’s hard to blindly use the hierarchy as an ultimate north star for decision making.

Of course, people are complex and what’s immediately important is often circumstantial. But I’ve found that as I’ve grown up, it has become harder and harder to not think about self-actualization.

Humans may have spent the first thousands of years of humanity climbing the physiological rungs of the ladder, but in the span of a few short generations, those born into the first world can now wholly occupy themselves with the pursuit of esteem and meaning if they choose to.

Annoyingly, the goals seem to become more and more abstract as you progress up the hierarchy, which makes it difficult for those goals to ever feel completed. Securing enough water is a relatively quantifiable task, but goals like securing enough status and feeling satisfied with your accomplishments are flimsy and blurry targets.

My question, as it relates to designing our own lives, is: is there a point of financial comfort in which we should begin to devote our lives to self-discovery?

Is there a certain threshold of quality of life – at which incremental money or status begins to confer marginal utility – when it becomes our duty to seek out what is most enriching to us?

The Elusive Rung of Esteem

One of my favorite social surveys, conducted by professor Michael Norton at the prestigious Harvard Business School (a leading educational institution), surveyed millionaires in order to delineate the relationship between happiness and wealth.

They surveyed 2,000+ people with a net worth of $1M+ (including people with far greater net worths). They asked these millionaires how happy they were on a scale of 1-10 and how much more money they needed to get to a “10 out of 10” in happiness.

All the way up the income-wealth spectrum, basically everyone says they’d need two or three times as much to be perfectly happy… Predictions of the amount of wealth needed to increase happiness were similar across wealth levels.

The Happiness of Millionaires (Harvard Business School, University of Mannheim)
The Reason Many Ultrarich People Aren’t Satisfied With Their Wealth via The Atlantic

Regardless of one’s net worth, virtually everyone either has a feeling of financial discomfort or carries the notion that more money will lead to more happiness. It doesn’t matter if you’re rich or poor; just about everyone wants slightly more.

The honest instinct to improve one’s self is generally a productive trait, but when combined with the tendency to compare ourselves to others, it can leave us feeling perpetually inadequate. An addiction to financial excess can prevent us from ever pursuing things that feel personally meaningful.

I’ve found time and time again that the frustrating difficulty with the rung of Esteem is that we are generally disposed to feel like we have never satisfied it. No one except yourself can fully ease your desire for respect or recognition. And so, we rarely give ourselves permission to pursue the things that we find most intoxicating.

Money as an Outlet for Self Actualization

This is also all not to say that the pursuit of money or status is necessarily mutually exclusive of self-actualization. I think it is incredibly common and understandable for wealth and empire-building to be the most interesting games for someone to play. It is quite reasonable for someone to reflect and decide that their path to self-actualization is to build a huge business or become wildly financially successful.

Money and prestige are clear and highly visible scorekeepers, and for some people, that’s the right construct. For one, unlike money and prestige, parents tend not to brag to their friends about how woke their son is.

For some, there is no greater mission to being the majority owner of a sports team, being the top earning person at a firm, or making enormous philanthropic impact.

I think those are perfectly fine goals, they just aren’t the games for me.

The Impracticality of a Dream

So what’s the reasonable alternative then? Quit your job and start writing about psychological frameworks?

As romantic as it may be to drop everything and chase your wildest childhood dreams, I still don’t think it’s wise or practical to do so. A daydream or backpacking fantasy is not even a close substitute for a plan.

A key issue with the relentless pursuit of self-actualization is that unless you’ve permanently solved the money problem, you will likely eventually start struggling with the foundational pillars of Maslow’s hierarchy. If your self-actualization process is unprofitable, like most passion-bait interests tend to be, a happy medium simply may not exist. Unfortunately, if you work a traditional career in a job you don’t enjoy, the best chance you have at feeling fulfilled could be to sheepishly tend to a hobby in the scant crevices of your weekend.

KSHMR, a modern music legend (probably the most important electronic music production teacher in the world, and the producer behind Like a G6), quips the following about the security-passion trade-off:

Be broke. Be broke for as long as you can. Spend all your time making music and just live like a bum. See, bums don’t owe anything to anybody. No mortgage, no car payments, no responsibility. Everything that you are responsible for is going to suck your energy. And if you got a dream, you got to know that achieving it is giving everything you have. When you reach a certain age, it’s not cute to be broke any more… Giving up is subtle, we give up when we choose safety, when we trade our dreams for comfort.

KSHMR Full Masterclass at the Amsterdam Dance Event (video has since been taken down by YouTube)

KSHMR asserts that we need to forego the earlier rungs of shelter and esteem in order to achieve our passion, particularly in a competitive world like music.

It is perhaps true that in order to earn outsized returns in an intense field – the career ladder, sports, music, having the world’s largest collection of miniature ceramic Pokemon collectibles – you must have an unwavering focus on your goal. Some arenas in life are simply so competitive or zero-sum that only the most committed will succeed.

…But you know what, despite one of my music idols saying that you have to go all in, I still think it’s reasonable and possible to concurrently pursue financial success and personal success as non-dependent goals.

And after half a year of a sabbatical, my plan and goal is still to work 25 hours a week and spend the rest of the time on things that feel intrinsically fulfilling. Having unstructured free time off has only further affirmed how awesome control and autonomy are.

Time and time again, I come back to the two scenarios in my mind I feel like I’ve, at least in part, chosen between: is it more ambitious to have personal financial independence and a sense of fulfillment or to help found a successful company?


If you don’t have insane wealth goals, I think you can achieve partial financial independence by your mid 30s and then back-weight your 30s and 40s with something that feels intrinsically fulfilling. I think the compounding effect of money highlights the urgency of building wealth when you are young, but it seems even more important to have personal outlets that keep life interesting.

From my experience, I don’t think an obsessive focus on just one arena in your life is what leads to a sustainable and enjoyable sense of balance.

And well, I choose balance.

One thought on “When is it OK to Pursue Our Dreams?

  1. Another great article Matt,

    Reminds me of finite and infinite games by James Carse, you should check it out, very interesting book.

    P.s I haven’t actually read the actual book yet but I’ve read many book summaries and it covers a lot of similar themes you bring up in this post.

Leave a Reply

Your email address will not be published.