Finding the Perfect Job - Two Factors to Consider

Over the course of my rather colorful career, I’ve had the good fortune of being exposed to a wide range of big and small companies across the globe. Recently I got the opportunity to give career advice to a YouTube subscriber who was in the middle of transitions, which made me reflect on what makes me stay with a company and drives me to bounce. My conclusion is that:

A job must first be FULFILLING, second be SUSTAINABLE.

When these two criteria are met, you’ll continue to grow and be satisfied in your role. If work is fulfilling, but not sustainable, you’ll burn out or run out of money. If it’s sustainable, but not fulfilling, you’ll get bored and your performance will dip. Either way will eventually lead you to leave, which isn’t good for you or the company that just lost good talent.

Fulfilling

What does it mean to be fulfilled at work?

First is progress. Two-time NBA MVP Steph Curry once said,

“No matter where you are in your progression, we’re in the same boat. The time is now for you to start your journey to find ways to get better. That’s why we’re all here.”

The key to fulfillment is to have a purpose and meaningful challenges that give us opportunities to make progress. Purpose is having a future vision that you want to become reality - it is your ideal version of the future, be it for ourselves or the world. Working towards it and smashing goals along the way is what gives us meaning. The opposite, boredom and nihilism, happens when we lose that vision, don’t have opportunities, and encounter defeat repeatedly.

You can think of career growth as closing feedback loops. 

In machine learning, feedback loops enables the computer to learn from cause and effect and become smarter through trial and error. Startups operate in a similar way beginning with a value hypothesis. It then launches a prototype known as a minimum viable product (MVP) to create a feedback loop with the market that either proves or disproves its demand and business model. Growth happens when feedback loops close successfully and you learn works and what doesn’t. The more frequently these loops close, the faster your growth.

The same applies to our jobs. No matter what we do, we’re always working on some sort of project. If you start a project and aren’t around to see the results, you effectively have not learned anything. This is especially true for young people just starting out in large companies with slow turnaround times and many moving parts and stakeholders. They get menial tasks without clear impact and leave within a year or two without seeing the final outcome of their work, if it were visible in the first place.

That’s one reason why I like startups and their rapid rate of experimentation and change i.e. fast feedback loops. Even with the most delayed timelines and longest sales cycles, I’ll at least get to launch the damn product to market or close a deal or two and leave my mark before leaving the company.

The fastest feedback loops occur when you’re running the show. As a content creator, I’m learning from every video I produce, every article I write, every workshop I give, and every person I meet. As Seneca says, people “learn as they teach.”

The real benefit of closing successful feedback loops, however, is building your confidence. Confidence is a general super power that determines how often and how well you jump into novel scenarios. The more positive feedback loops you close the more confident you become. For instance, one of my financial manager friends is very confident in his career because he’s closed literally hundreds of feedback loops with many clients. This confidence not only allows him to take risks in related domains such as one day opening his own practice, but also manifests in his personal life and leadership in his community.

Similarly, I’ve grown confident enough to work in any role at high risk startups thanks to the last decade spent in the trenches. Though it’s a mix of positive and negative feedback loops, they still contribute to my confidence because, like vaccines, my failures inoculate me from fear of future failures, having lived through their consequences and realized that 1) it’s really not that bad and 2) the outcomes are rarely binary good and bad. Instead, it’s a spectrum. Each failed attempt increases my chances of success the next time I play. Every time I jump into a new company, I’m not starting at ground zero anymore. Instead I come with all the other mindsets, skill sets, and network carried over from my previous roles.

If the work itself is not fulfilling, sometimes it’s a matter of determining the parts that can be outsourced so you can focus on the things that you’re uniquely suited for. When I was starting to lag at my last startup, the CEO offered to hire an associate to help me offload partner operations, so that I can focus on strategy, fundraising, and growing the business. This was a win-win scenario that unlocked valuable activities for the company while making the work more fulfilling for me. It was a smart move that retained my services with the company for an extra year.

Sustainable

The three major factors to job sustainability are 1) Health, 2) Time and 3) Money. In that priority. Though in practice, we tend to reverse the order.

Health is number one because it influences everything we do, think, and feel and how long we go on for. Health can be broken up into three subcategories of body, mind and emotion.

First is physical health, which in turn can be divided into sleep, diet, and exercise. These are consistently my top goals in every 2-week sprint because all else lies on top of our bodily health. Getting to bed by 10pm, waking up at 5:30am, cycling or calisthenics for an hour, and not eating after 8pm are routines that ensure I have a solid vehicle to drive my work.

Second is mental health, which is influenced by the pressure and friction we feel on the job. Having launched many products over the years, I’m familiar with the stress of creation. Even writing this article gives me a certain level of stress. Then again, going to the gym is hard on our bodies, but it’s good for us. As Nassim Taleb says in Antifragile, we are designed for stress. Take all of it away and we’ll gradually weaken and decay.

The key is knowing the difference between healthy mental challenges and unhealthy mental breakdown. This means when I feel a bad case of writer’s block coming on, rather than banging my head against the screen, I’ll peel myself away from the keyboard and go for a walk (preferably around sunset). This allows my mind to rest in between sets and let my subconscious work on the problem, which is sometimes more effective than thinking intentionally about it. Many of my breakthroughs have also come from meditation and free flowing mind mapping and conversations with others.

Third is emotional health, which improves when work aligns with your values and interests, but degrades when you’re stuck in a toxic environment of blame and disrespect. The two greatest fears of human beings are death and being ostracized by others. We’re social creatures and therefore working together supercharges our meaning by holding us accountable and giving us a purpose beyond ourselves. Everything feels right when you’re connected to what you do and who you do it with. It sounds simple, but I’m astounded by how many people I meet who choose to stay in crappy working environments with bad management. And this is during a labor shortage folks!

Then there’s Time - for yourself and others. Time for yourself not only means looking after the three health areas, but also discovering and pursuing your personal interests outside of work. I’m not saying that everyone MUST have hobbies, but having interests draws clear boundaries in the form of opportunity costs for work itself.

The same thing goes for family and friends. While closing the blinds to focus on a mission critical project is sometimes necessary and prudent, if you find yourself not having enough time for your personal interests or show up for people supposedly important in your life for prolonged periods, then it’s a sign to slow down and consider sustainability. Even if you’re like me and see work as an important source of meaning and purpose, doing it for years at the cost of personal sacrifices will burn you out.

Work can also slow down or even disappear if you’re laid off or the business dies. If your sources of meaning aren’t diversified, well, then you could face what I described in last week’s article on the 2-day work week:

I realized that I had tied my identity and sense of purpose to my job. The busy-ness of the business kept me running on a hamster wheel of self-perpetuating self-worth. It didn’t even matter who I worked for or what I worked on, for I was constantly on the move for as long as I could remember. From one company to another, changing roles and teams, hopping around continents, all the while thinking that I was the linchpin. Even more insidious was how this constant movement distracted me from focusing on my relationships and personal growth. After 10 years of hustling in the tech industry, I had little community and purpose outside of the projects I led. I was afraid of stopping because it meant facing who I was and what I was lacking.

So find some interests and make time for people will ya?

Finally, I’ll end on Money. If we can’t make a living, then it’s not sustainable no matter how fulfilling the work is. If we can’t make enough to save, then we can’t build wealth for our future and buy time back. Even as an artist, I’m not a professional until I get paid. Instead I’ll always be an amateur dabbling in the arts. Money isn’t everything, but it is the most common way for others to respect our time and talents. We deserve that regardless of what we do.

📺 For the video folks, here’s the YouTube episode.

This is Mind Map that helped frame my thinking for this piece.