Driven through Discontentment

Are you satisfied?

Do you feel content with how your life is going? Is there a thought constantly bugging the back of your mind, but you don't know where it's coming from?

I know that feeling. I've recently been reading a lot of books about motivation, productivity, and career. Never Enough by Andrew Wilkinson, the billionaire, is a book that I finished recently. It's a book that talks about how he navigated his career and what his childhood was like. He ties everything together with the main thread surrounding his relationship with finances impacting many of the decisions he had made. "When will it ever be enough?" is the question that is most often repeated in the book.

I've been living in the Bay Area, a place that is chock full of highly intelligent people who are making a great living. Some are working at a tech company, and others are entrepreneurs trying to make it big with a venture of theirs. There are a lot of highly ambitious people who have big goals and dreams, perhaps as a byproduct of the environment in which they are in–a highly career-oriented space.

One of the key drivers of what motivates people to achieve great sums of money through their career is the feeling of having "never enough". Regardless of how much money someone has made, there's the lingering feeling that remains. As is discussed in Andrew Wilkinson's book, this feeling typically comes from childhood experiences that impact decisions made in adulthood. Be it from having parents who fought over money and the lack of it, or feeling inadequate compared to peers who had more, there's a consistent feeling of not having enough or being successful enough–a discontentment that sticks around.

In my 2.5 years of working in the corporate world, I've learned a lot about the world of business and what makes a successful business. And what I mean by "successful", is a business that is reliably generating profit. It doesn't have to be a corporation and grow infinitely (which is usually what a public company, or VC-funded startup) aims to have, but a business that lasts and is providing the necessary revenue to pay staff and employees as well as the owners or leadership.

For a lot of these highly ambitious people, some whom I personally know, they grew up surrounded by models of wealth. If it wasn't directly through the career success of their parents, it would be their classmates' parents. Frankly, growing up in the Bay Area with its Silicon Valley embeds a value system that prioritizes corporate wealth. These people have personal goals of achieving financial comfort, described by the ability to not worry about money. Essentially, they desire having more than enough for their own desires.

Risk Tolerance

Some of these people that I know are able to quickly execute on their dreams, soon after the dreams form. Some are more hesitant, still debating their own personal values. I've personally found that the ability to execute is often correlated with the individual's risk tolerance. There are multiple paths to this financial comfort. For those who are startup founders, there's an opportunity to leverage undergrad and university eHubs as a starting point. For other founders, they start their ventures later in their careers, after building a family. Some folks even execute on their ideas on the side, in parallel with their main 9-5 job.

The difference between each of those examples is a combination of what life goals they have and their risk tolerance. Risk averse people feel they have everything to lose, even if they have so much to gain. Thus, they typically aim for a stable job and establish a corporate career before taking the step to work on their ideas. For those who are more okay with risk, they are more comfortable with taking chances seeing as they aren't losing much. The investment and risk in itself is a net-positive on their life.

Risk averse people feel they have everything to lose, even if they have so much to gain.

Source of Drive

Being tolerant to risk is one enabler to achieving ambition goals, but, on its own, it can't sustain the momentum. I've written a past blog in which I mention Ikigai, a Japanese concept about achieving career satisfaction. I find that the more satisfied and content I feel about life, the less rushed I am to execute on various projects. The mindset I have instead is that "if it happens, it happens". In essence, I am satisfied with the current state and the envisioned future state is a "nice to have" rather than a survival necessity.

In certain cases, there can be a sustained drive if the ambition itself is focused on an external goal. This can be solving a problem given a solution gap in the market. For example, many founders of social good companies are motivated by the problem they are addressing – feeling the "if not me, then who else?" Given the set of unique experiences and skills an individual has acquired, they are able to harness them for a singular purpose. A mission or a life's calling, perhaps. The more spiritual might call this their dharma.

Compared to the first source of drive, "survival necessity", this second form of drive, sourced from an urgency to solve an external problem allows room for both personal satisfaction and this consistent drive to coexist. The former source of drive is rather unhealthy. This mindset of never having enough won't actually be solved because at any wealth number, there will always be more wealth that can be generated.

Personally, I'm satisfied and content with how my life is going. I have a job that pays me enough, I have a rented place of my own, plenty of hobbies, and a decent social life. I often grapple with the thought of wanting to achieve more either due to a desire to escape a corporate lifestyle chained to a 9-5 or to reach a metric of personal success. Despite this, I know that I am okay with where I am and that even though I may desire various changes and work towards them, I am savoring each step of the journey.