How to find your Dream Job

March 4, 2021 Avthar Sewrathan

Finding fulfilling work is a conundrum of modern life. We want work that's financially lucrative, but also stimulating and purposeful.

I’d like to share 3 big ideas which helped me navigate my own search for career fulfillment:

Examine and align your motives
Taste many things
Deepen your mastery

Together, these ideas will help you find your dream job.

Or more precisely, “How can you find the right role(s) for you which is aligned with your life vision and uses your unique strengths?”

1. Examine Your Motives

You must examine and accept your motives in life. Just like you have to take stock of and accept the things you’re more skilled and less skilled at, you must examine what you really want and why, both from your career and your life as a whole.

Understanding your motivation is important because it provides a compass with which to navigate opportunities, partnerships and major decisions in your career and life.

Here are some questions that I’ve found useful for you to meditate and reflect on in order to examine your motives

Take an afternoon. Sit in a quiet room. Put some classical music on. And reflect on these questions.

They will help you understand your definition of success, your motives for succeeding and the role of work in your life.

What does success look like for you?
Why do you want to be successful?
What does a “good life” look like to you?
What is work? Why work? What is the role of work in your life?
What defines good or worthwhile work?
What do you really desire? Why do you want what you want?
Are your desires your own or are they influenced by others?
Who or what are you afraid to disappoint?
What are you willing to sacrifice for success? What are you not?

I’ve written previously about living with an internal scorecard, which talked about the importance of defining success and living in accordance with your values. Answering these questions will help you avoid the trap of living life according to society’s definition of success.

Examining your motives will also help you avoid the anxiety that comes with “keeping up with the Joneses” and save you from comparing yourself to others who are running different races than you.

You’ll have your own convictions for success and why you want to achieve it.

You must both examine and accept your motives. Change what you can and accept what you can’t change. It’s better to be aware of what you desire and what’s driving you to prove yourself to the world and lean into that, than to blindly chase success in the hopes that it will fulfill you and finally make you happy.

Motives and Alignment

You can filter roles that you take on and the people you work with through your motives, discarding those that don’t align with your motivations and pursuing those that do.

Take the case of Shiv, who wants to start his own business:

After examining his motivations and the role of work in his life, Shiv came to the conclusion that he wants to work for himself for the independence and also that he isn’t willing to sacrifice time with his family and thus isn’t willing to work nights and weekends. It would be unwise for Shiv to partner with Vish, someone who also wants to start their own business but whose goal is to become as rich and powerful as possible and become the next Jeff Bezos, since their motives are woefully misaligned. Shiv should pursue a bootstrapped business, while Vish might want to pursue a high growth startup.

Understanding your motives allows you to partner with people whose motives are aligned with your own.

Moreover, understanding why you want a certain job and how it fits into your life is important. Sometimes it's okay to take a job that doesn’t light you on fire straight away, if you understand the role it plays at your stage in life. Most often, this takes the form of jobs providing financial stability and as a source of capital to use for future projects, which can bring you more freedom later in your life.

2. Taste Many Things

There's a saying I heard often while growing up in South Africa: “You can't be a doctor, if you've never seen a doctor.”

What this means is that if you've never been exposed to a certain career or industry, you can’t imagine yourself doing it because it’s outside your mental model of how the world works.

In order to find the right role for you, you must taste many different roles and industries in order to find which ones resonate with.

This will help broaden your mental model of what’s out there and help you make the best decision.

Let your strengths and curiosity guide you as you experiment and try different things out. This process of iteration creates more opportunities to find the people and ideas that resonate with you the most.

Often, it takes a mentor, manager or someone you trust to point out possible paths for you to explore.

The story of how I ended up in a role that uses my unique strengths, a Developer Advocate, is a prime example of this:

My boss was a Developer Advocate himself for many years, noticed my skills and experience and thought I’d be a natural at the role. I was hesitant at first, as I had never heard of this role before, but decided to try it out to see if I liked it. Others can expose us to possible paths, but it is up to us to explore them and see if they resonate with us.

One reason we don’t explore the possible space of careers enough is because we’re memetic creatures: we outsource our thinking and often want things because others desire them.

When we don’t have a rich picture of all the different roles that are suitable to our strengths, we end up choosing our path based on what others are doing, rather than our own convictions.

I saw this during my time at Princeton University, where many students chose to go into management consulting, banking or even software engineering because they saw other people doing it, and felt fear of missing out (FOMO), rather than because of their own convictions. Many people who follow the crowd end up hating their job and leave after a few years. Tasting many things and finding those that resonate helps you not fall into the same trap and waste precious years of your life.

Finding roles and industries that resonate with you is not one off process: it’s a continuous process of adaptation and iteration.

It’s not something you do only in college, or only in your 20s. It’s a lifelong process to find who and what needs you the most and what aligns with your unique strengths at each stage of your life.

Practical Tips to Find What Resonates With You

While actually doing a job is the best indicator of whether you’re well suited for it, there are ways that you can test different roles and industries to decide if they deserve further exploration.

The key here is to figure out the smallest experiment you can do in order to see if you like something.

Here are some ideas for experiments you can run:

Tip 1: Side projects

Side projects are a low-risk way of testing your proclivity toward a role or industry.

Doing projects on nights and weekends in order to test hypotheses you have about roles you enjoy or to learn about new industry trends is a great way to continue learning and refining your fit while keeping a full-time job. Don’t be afraid to start, abandon and pick up new projects. Sustained interest over time is a good indicator of whether something is a good fit for you. Moreover, these projects don’t have to be solo efforts, they’re a great opportunity to taste different things and work with different sorts of people and learn about yourself in the process.

Tip 2: Empathy Interviews

Reach out to people who are doing the things you think you want to do. Build relationships with them. Find out what is it, functionally, that they do? Are you suited for that? Can you see yourself doing that?

If you’re a student you could reach out to alumni from your school, if you’re in the working world, reach out to others at your company, connect through your network or through Twitter and cold email.

Tip 3: Books, Courses and Classes

Thanks to the internet its easier than ever to learn about the functions of a role or trends in an industry. So many people are writing, tweeting or podcasting about it. Moreover, there are many courses you can take in order to test out a career hypothesis you have. Course and other groups are a great way to meet like-minded people who can help you refine your search.

3. Deepen Your Mastery

In line with the theme of finding and doubling down on your strengths:

Your dream job is one that will help refine your strengths and push you toward mastery.

By doing the job, you’ll become world class at your strengths

Here are some factors to evaluate if a role can help increase your level of mastery:

Can the role help you become world-class at your strengths?

An ideal role will be one in which you can showcase and refine your strengths.

To understand if the role uses your strengths, deconstruct the role into its functional parts.

Understanding exactly what someone does in a particular job is much more useful to decide if it's right for you, than judging it by the name alone.

This is where the Empathy Interviews I mentioned above shine. You can reach out to people doing jobs you think you might like or want to move into and learn about what exactly they do, the skills they use and the functions they perform.

Who can you learn from?

You want to be an environment where you can learn from the people around you.

Learning could be in the form of traditional mentoring from your boss or those in senior positions. It could also be learning from the example and experience of working with peers who are top performers.

Many people find themselves in good jobs’, but around people they can’t relate to and aren’t learning from. However, you should try your best to be proactive and find people who you align with in an organization and work with them as much as you can.

Evaluating who you can learn from in a job is perhaps the most difficult thing to judge before you join a company, but it is possible to gauge from speaking to current employees and during your interview process.

Does the industry knowledge deepen your personal monopoly?

For some, an ideal role is one that helps them use and deepen industry-specific knowledge.

Industry-specific knowledge could be understanding a certain target audience (e.g software developers, millennials) or how deals are done in an industry (e.g healthcare) or navigating challenges specific to a product type (e.g consumer social apps, AI regulation).

These kinds of industry-specific knowledge often translates across companies and the experience could be helpful in future endeavours or when tackling similar problems.

Jobs in certain industries you’re passionate about or want to become an expert in can help you learn more about an industry and cement that knowledge as part of your personal monopoly.